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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015417

Secondary Accession Numbers

HMDB15417

Metabolite Identification

Common Name

Fosphenytoin

Description

Fosphenytoin, also known as cerebyx or HMPDP, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Fosphenytoin is a drug which is used for the control of generalized convulsive status epilepticus and prevention and treatment of seizures occurring during neurosurgery. it can also be substituted, short-term, for oral phenytoin. Fosphenytoin can cause hyperphosphatemia in end-stage renal failure patients. Fosphenytoin is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, fosphenytoin is involved in the metabolic disorder called the fosphenytoin (antiarrhythmic) metabolism pathway. Fosphenytoin is a potentially toxic compound. Fosphenytoin is approved in the United States for the short term (five days or fewer) treatment of epilepsy when more widely used means of phenytoin administration are not possible or are ill-advised, such as endotracheal intubation, status epilepticus or some other type of repeated seizures; vomiting, and/or the patient is unalert or not awake or both. One solution was to develop a prodrug that did not have these drawbacks. Fosphenytoin (fosphenytoin sodium, trade names Cerebyx, Parke-Davis; Prodilantin, Pfizer Holding France) is a water-soluble phenytoin prodrug that is administered intravenously to deliver phenytoin, potentially more safely than intravenous phenytoin. Side effects are similar to intravenous phenytoin and include hypotension, cardiac arrhythmias, CNS adverse events (nystagmus, dizziness, sedation/somnolence, ataxia and stupor), and local dermatological reactions. Purple glove syndrome probably occurs with fosphenytoin but possibly at lower frequency than with intravenous phenytoin. It is most commonly used in the acute treatment of convulsive status epilepticus. On 18 November 2004, Sicor (a subsidiary of Teva) received a tentative approval letter from the United States Food and Drug Administration for a generic version of fosphenytoin. One millimole of phenytoin is produced for every millimole of fosphenytoin administered; the hydrolysis of fosphenytoin also yields phosphate and formaldehyde, the latter of which is subsequently metabolized to formate, which is in turn metabolized by a folate dependent mechanism. Fosphenytoin was approved by the Food and Drug Administration (FDA) on August 5, 1996 for use in epilepsy. Simply putting patients on other drugs is not always an option; this was especially true before 1993, when the number of anticonvulsants available was much more limited. In 2003, it was reported that even though anticonvulsants are often very effective in mania, and acute mania requires rapid treatment, fosphenytoin had no antimanic effect.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0015417
     RDKit          3D
Fosphenytoin
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.0127   -1.2379    2.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2622   -0.5718    1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -0.1626    1.7601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6581    0.1688    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391    1.1158    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247    2.2611   -0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9935    3.0972    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957    2.7918    1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7181    1.6424    1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    0.8229    1.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134   -1.0999   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.1195   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -2.2720   -1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634   -3.4690   -1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6636   -3.4575    0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -2.2912    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    0.6345   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    1.4676   -1.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6463   -0.0629    0.2638 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101   -0.2025   -0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7948    0.8266   -0.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2217    0.5122   -0.9545 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9118   -0.3751   -2.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4032   -0.1717    0.0512 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8092    2.0315   -1.4745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5769   -0.1057    2.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2758    2.5631   -0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111    3.9939   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7027    3.4936    1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4326    1.4451    2.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -0.0689    2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763   -0.1868   -1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8050   -2.2842   -2.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6644   -4.3866   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028   -4.3961    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697   -2.3001    1.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491   -0.1898   -1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4131   -1.1657   -0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2813    0.0828   -0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7626    2.6267   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 19  2  1  0
 10  5  1  0
 16 11  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 20 37  1  0
 20 38  1  0
 24 39  1  0
 25 40  1  0
M  END

1320
  Mrv0541 02231215232D          

 25 27  0  0  0  0            999 V2000
    6.9218    1.8428    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.4110   -0.9262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1371    1.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5135    1.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6668    2.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7064    2.0978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1768    1.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8461    0.5259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1809    0.5259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010   -0.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9260   -0.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010   -1.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840   -0.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5135    1.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9656    0.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8155   -1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865   -1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761    0.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8155   -2.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1580   -1.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865   -2.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010   -2.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  2  0  0  0  0
  2 11  2  0  0  0  0
  3 15  1  0  0  0  0
  4 14  2  0  0  0  0
  8 10  1  0  0  0  0
  8 14  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 12 16  2  0  0  0  0
 12 18  1  0  0  0  0
 13 17  2  0  0  0  0
 13 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  2  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 25  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015417

> <DATABASE_NAME>
hmdb

> <SMILES>
OP(O)(=O)OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15N2O6P/c19-14-16(12-7-3-1-4-8-12,13-9-5-2-6-10-13)17-15(20)18(14)11-24-25(21,22)23/h1-10H,11H2,(H,17,20)(H2,21,22,23)

> <INCHI_KEY>
XWLUWCNOOVRFPX-UHFFFAOYSA-N

> <FORMULA>
C16H15N2O6P

> <MOLECULAR_WEIGHT>
362.2739

> <EXACT_MASS>
362.066772734

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.22664671818143

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methoxy]phosphonic acid

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
1.6680293453333337

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.057759222943897

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.460741206613097

> <JCHEM_PKA_STRONGEST_BASIC>
-9.658399928883057

> <JCHEM_POLAR_SURFACE_AREA>
116.17

> <JCHEM_REFRACTIVITY>
87.05370000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fosphenytoin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015417
     RDKit          3D
Fosphenytoin
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.0127   -1.2379    2.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2622   -0.5718    1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -0.1626    1.7601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6581    0.1688    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391    1.1158    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247    2.2611   -0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9935    3.0972    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957    2.7918    1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7181    1.6424    1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    0.8229    1.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134   -1.0999   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.1195   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -2.2720   -1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634   -3.4690   -1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6636   -3.4575    0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -2.2912    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    0.6345   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    1.4676   -1.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6463   -0.0629    0.2638 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101   -0.2025   -0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7948    0.8266   -0.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2217    0.5122   -0.9545 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9118   -0.3751   -2.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4032   -0.1717    0.0512 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8092    2.0315   -1.4745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5769   -0.1057    2.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2758    2.5631   -0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111    3.9939   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7027    3.4936    1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4326    1.4451    2.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -0.0689    2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763   -0.1868   -1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8050   -2.2842   -2.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6644   -4.3866   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028   -4.3961    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697   -2.3001    1.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491   -0.1898   -1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4131   -1.1657   -0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2813    0.0828   -0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7626    2.6267   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 19  2  1  0
 10  5  1  0
 16 11  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 20 37  1  0
 20 38  1  0
 24 39  1  0
 25 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1320                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0      12.921   3.440   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      10.101  -1.729   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.456   2.964   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.425   3.427   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      12.445   4.904   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      14.385   3.916   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.397   1.975   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       7.179   0.982   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.671   0.982   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.655  -0.483   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.195  -0.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.655  -2.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.130  -0.697   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.425   1.887   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.136   1.458   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.989  -2.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.553  -2.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.321  -2.793   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.182   0.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.989  -4.333   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.028  -2.339   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.321  -4.333   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.657   0.302   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.655  -5.103   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -1.126   0.000  0.00  0.00           C+0
CONECT    1    3    5    6    7                                             
CONECT    2   11                                                            
CONECT    3    1   15                                                       
CONECT    4   14                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8   10   14                                                       
CONECT    9   11   14   15                                                  
CONECT   10    8   11   12   13                                             
CONECT   11    2    9   10                                                  
CONECT   12   10   16   18                                                  
CONECT   13   10   17   19                                                  
CONECT   14    4    8    9                                                  
CONECT   15    3    9                                                       
CONECT   16   12   20                                                       
CONECT   17   13   21                                                       
CONECT   18   12   22                                                       
CONECT   19   13   23                                                       
CONECT   20   16   24                                                       
CONECT   21   17   25                                                       
CONECT   22   18   24                                                       
CONECT   23   19   25                                                       
CONECT   24   20   22                                                       
CONECT   25   21   23                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0015417
HETATM    1  O1  UNL     1       2.013  -1.238   2.317  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.262  -0.572   1.561  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.082  -0.163   1.760  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.658   0.169   0.472  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.739   1.116   0.682  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.925   2.261  -0.048  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.994   3.097   0.235  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.896   2.792   1.260  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.718   1.642   1.999  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.650   0.823   1.704  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.213  -1.100  -0.110  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.814  -1.119  -1.350  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.331  -2.272  -1.904  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.263  -3.469  -1.223  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.664  -3.458   0.018  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.141  -2.291   0.579  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.515   0.634  -0.269  1.00  0.00           C  
HETATM   18  O2  UNL     1       0.669   1.468  -1.208  1.00  0.00           O  
HETATM   19  N2  UNL     1       1.646  -0.063   0.264  1.00  0.00           N  
HETATM   20  C16 UNL     1       2.910  -0.203  -0.396  1.00  0.00           C  
HETATM   21  O3  UNL     1       3.795   0.827  -0.105  1.00  0.00           O  
HETATM   22  P1  UNL     1       5.222   0.512  -0.954  1.00  0.00           P  
HETATM   23  O4  UNL     1       4.912  -0.375  -2.123  1.00  0.00           O  
HETATM   24  O5  UNL     1       6.403  -0.172   0.051  1.00  0.00           O  
HETATM   25  O6  UNL     1       5.809   2.031  -1.475  1.00  0.00           O  
HETATM   26  H1  UNL     1      -0.577  -0.106   2.671  1.00  0.00           H  
HETATM   27  H2  UNL     1      -1.276   2.563  -0.852  1.00  0.00           H  
HETATM   28  H3  UNL     1      -3.111   3.994  -0.360  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.703   3.494   1.418  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.433   1.445   2.777  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.557  -0.069   2.311  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.876  -0.187  -1.900  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.805  -2.284  -2.882  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.664  -4.387  -1.643  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.603  -4.396   0.568  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.670  -2.300   1.562  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.749  -0.190  -1.490  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.413  -1.166  -0.172  1.00  0.00           H  
HETATM   39  H14 UNL     1       7.281   0.083  -0.344  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.763   2.627  -0.684  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   26
CONECT    4    5   11   17
CONECT    5    6    6   10
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   31
CONECT   11   12   12   16
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   36
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   37   38
CONECT   21   22
CONECT   22   23   23   24   25
CONECT   24   39
CONECT   25   40
END

HMDB0015417
     RDKit          3D
Fosphenytoin
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.0127   -1.2379    2.3166 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2622   -0.5718    1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -0.1626    1.7601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6581    0.1688    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391    1.1158    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247    2.2611   -0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9935    3.0972    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957    2.7918    1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7181    1.6424    1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    0.8229    1.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134   -1.0999   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.1195   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -2.2720   -1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634   -3.4690   -1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6636   -3.4575    0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -2.2912    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    0.6345   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    1.4676   -1.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6463   -0.0629    0.2638 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101   -0.2025   -0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7948    0.8266   -0.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2217    0.5122   -0.9545 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9118   -0.3751   -2.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4032   -0.1717    0.0512 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8092    2.0315   -1.4745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5769   -0.1057    2.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2758    2.5631   -0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111    3.9939   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7027    3.4936    1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4326    1.4451    2.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -0.0689    2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763   -0.1868   -1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8050   -2.2842   -2.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6644   -4.3866   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028   -4.3961    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697   -2.3001    1.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491   -0.1898   -1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4131   -1.1657   -0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2813    0.0828   -0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7626    2.6267   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 19  2  1  0
 10  5  1  0
 16 11  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 20 37  1  0
 20 38  1  0
 24 39  1  0
 25 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3-Phosphoryloxymethyl)phenytoin	HMDB
Cerebyx	HMDB
HMPDP	HMDB
3-(Hydroxymethyl)phenytoin disodium phosphate	HMDB
Fosphenytoin, disodium salt	HMDB
Prodilantin	HMDB
Fosphenytoin sodium	HMDB
3-(Hydroxymethyl)phenytoin phosphate ester	HMDB

Chemical Formula

C₁₆H₁₅N₂O₆P

Average Molecular Weight

362.2739

Monoisotopic Molecular Weight

362.066772734

IUPAC Name

[(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methoxy]phosphonic acid

Traditional Name

fosphenytoin

CAS Registry Number

93390-81-9

SMILES

OP(O)(=O)OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H15N2O6P/c19-14-16(12-7-3-1-4-8-12,13-9-5-2-6-10-13)17-15(20)18(14)11-24-25(21,22)23/h1-10H,11H2,(H,17,20)(H2,21,22,23)

InChI Key

XWLUWCNOOVRFPX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Alpha-amino acid or derivatives
N-acyl urea
Ureide
Monoalkyl phosphate
Imidazolinone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
2-imidazoline
Isourea
Azacycle
Carboxylic acid derivative
Carboximidamide
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazolidine-2,4-dione (CHEBI:5165 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015417)
Membrane (HMDB: HMDB0015417)

Source

Exogenous

Exogenous (HMDB: HMDB0015417)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fosphenytoin (Antiarrhythmic) Pathway (HMDB: HMDB0015417)
Fosphenytoin (Antiarrhythmic) Action Pathway (PathBank: SMP0000326)

Metabolic pathway

Fosphenytoin (Antiarrhythmic) Metabolism Pathway (PathBank: SMP0000618)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.08	ALOGPS
logP	1.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	1.46	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.17 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.05 m³·mol⁻¹	ChemAxon
Polarizability	33.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	181.857	31661259
DarkChem	[M-H]-	177.854	31661259
DeepCCS	[M+H]+	168.403	30932474
DeepCCS	[M-H]-	166.045	30932474
DeepCCS	[M-2H]-	199.109	30932474
DeepCCS	[M+Na]+	174.496	30932474
AllCCS	[M+H]+	181.5	32859911
AllCCS	[M+H-H2O]+	178.4	32859911
AllCCS	[M+NH4]+	184.4	32859911
AllCCS	[M+Na]+	185.2	32859911
AllCCS	[M-H]-	178.8	32859911
AllCCS	[M+Na-2H]-	178.5	32859911
AllCCS	[M+HCOO]-	178.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.98 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4139 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.67 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	122.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1547.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	230.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	137.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	354.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	478.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	179.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	767.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	395.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	965.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	295.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	167.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	128.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fosphenytoin	OP(O)(=O)OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	4203.1	Standard polar	33892256
Fosphenytoin	OP(O)(=O)OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	2763.6	Standard non polar	33892256
Fosphenytoin	OP(O)(=O)OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	3087.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fosphenytoin,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3127.2	Semi standard non polar	33892256
Fosphenytoin,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2915.8	Standard non polar	33892256
Fosphenytoin,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	4296.1	Standard polar	33892256
Fosphenytoin,1TMS,isomer #2	C[Si](C)(C)N1C(=O)N(COP(=O)(O)O)C(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	2854.8	Semi standard non polar	33892256
Fosphenytoin,1TMS,isomer #2	C[Si](C)(C)N1C(=O)N(COP(=O)(O)O)C(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	2870.8	Standard non polar	33892256
Fosphenytoin,1TMS,isomer #2	C[Si](C)(C)N1C(=O)N(COP(=O)(O)O)C(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	4455.3	Standard polar	33892256
Fosphenytoin,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	3107.1	Semi standard non polar	33892256
Fosphenytoin,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	2979.5	Standard non polar	33892256
Fosphenytoin,2TMS,isomer #1	C[Si](C)(C)OP(=O)(OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	3836.6	Standard polar	33892256
Fosphenytoin,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2891.7	Semi standard non polar	33892256
Fosphenytoin,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2872.9	Standard non polar	33892256
Fosphenytoin,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3866.7	Standard polar	33892256
Fosphenytoin,3TMS,isomer #1	C[Si](C)(C)OP(=O)(OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	2943.0	Semi standard non polar	33892256
Fosphenytoin,3TMS,isomer #1	C[Si](C)(C)OP(=O)(OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	2931.6	Standard non polar	33892256
Fosphenytoin,3TMS,isomer #1	C[Si](C)(C)OP(=O)(OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	3469.6	Standard polar	33892256
Fosphenytoin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3360.9	Semi standard non polar	33892256
Fosphenytoin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3129.5	Standard non polar	33892256
Fosphenytoin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	4404.6	Standard polar	33892256
Fosphenytoin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)N(COP(=O)(O)O)C(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	3163.9	Semi standard non polar	33892256
Fosphenytoin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)N(COP(=O)(O)O)C(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	3090.9	Standard non polar	33892256
Fosphenytoin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)N(COP(=O)(O)O)C(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	4395.0	Standard polar	33892256
Fosphenytoin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	3536.9	Semi standard non polar	33892256
Fosphenytoin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	3342.6	Standard non polar	33892256
Fosphenytoin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCN1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	4070.1	Standard polar	33892256
Fosphenytoin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3365.3	Semi standard non polar	33892256
Fosphenytoin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3268.9	Standard non polar	33892256
Fosphenytoin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3917.3	Standard polar	33892256
Fosphenytoin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	3514.4	Semi standard non polar	33892256
Fosphenytoin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	3480.2	Standard non polar	33892256
Fosphenytoin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	3653.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fosphenytoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ls-4941000000-7f020f5c4237af5bfb3c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fosphenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 10V, Positive-QTOF	splash10-03di-0019000000-801dc353a42886feac15	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 20V, Positive-QTOF	splash10-03dj-1019000000-954988a4832c09ddde71	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 40V, Positive-QTOF	splash10-0uy0-5931000000-a2e668ce8b6003249e52	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 10V, Negative-QTOF	splash10-03di-2009000000-f100b603f8bec4297f64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 20V, Negative-QTOF	splash10-004i-9100000000-974b8eaa512f665645c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 40V, Negative-QTOF	splash10-002f-9000000000-edcf929c72670ddaeafe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 10V, Positive-QTOF	splash10-03di-0029000000-80555bf6b08b1edde5ba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 20V, Positive-QTOF	splash10-014i-0191000000-7ba4d52b46cd24385200	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 40V, Positive-QTOF	splash10-0159-0920000000-be8b0958365f6e0346ab	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 10V, Negative-QTOF	splash10-03di-0009000000-cc4d0db2ee88412c5f88	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 20V, Negative-QTOF	splash10-0udi-0944000000-f5c9d9bf3cb087cf7685	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosphenytoin 40V, Negative-QTOF	splash10-00p0-5930000000-1c6b6a79ed38b9c1414a	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fosphenytoin (Antiarrhythmic) Action Pathway		Not Available
Fosphenytoin (Antiarrhythmic) Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01320	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01320	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01320

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

50839

KEGG Compound ID

C07840

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fosphenytoin

METLIN ID

Not Available

PubChem Compound

56339

PDB ID

Not Available

ChEBI ID

775287

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Browne TR, Kugler AR, Eldon MA: Pharmacology and pharmacokinetics of fosphenytoin. Neurology. 1996 Jun;46(6 Suppl 1):S3-7. [PubMed:8649612 ]
Johnson J, Wrenn K: Inappropriate fosphenytoin use in the ED. Am J Emerg Med. 2001 Jul;19(4):293-4. [PubMed:11447516 ]
Applebaum J, Levine J, Belmaker RH: Intravenous fosphenytoin in acute mania. J Clin Psychiatry. 2003 Apr;64(4):408-9. [PubMed:12716241 ]
McCleane GJ: Intravenous infusion of fosphenytoin produces prolonged pain relief: a case report. J Pain. 2002 Apr;3(2):156-8. [PubMed:14622802 ]
Luszczki JJ: Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions. Pharmacol Rep. 2009 Mar-Apr;61(2):197-216. [PubMed:19443931 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF: Drugs behave as substrates, inhibitors and inducers of human cytochrome P450 3A4. Curr Drug Metab. 2008 May;9(4):310-22. [PubMed:18473749 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Sahi J, Shord SS, Lindley C, Ferguson S, LeCluyse EL: Regulation of cytochrome P450 2C9 expression in primary cultures of human hepatocytes. J Biochem Mol Toxicol. 2009 Jan-Feb;23(1):43-58. doi: 10.1002/jbt.20264. [PubMed:19202563 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Goldstein JA: Clinical relevance of genetic polymorphisms in the human CYP2C subfamily. Br J Clin Pharmacol. 2001 Oct;52(4):349-55. [PubMed:11678778 ]
Klotz U: The role of pharmacogenetics in the metabolism of antiepileptic drugs: pharmacokinetic and therapeutic implications. Clin Pharmacokinet. 2007;46(4):271-9. [PubMed:17375979 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Anderson GD: Pharmacokinetic, pharmacodynamic, and pharmacogenetic targeted therapy of antiepileptic drugs. Ther Drug Monit. 2008 Apr;30(2):173-80. doi: 10.1097/FTD.0b013e318167d11b. [PubMed:18367977 ]
Hennessy S, Leonard CE, Freeman CP, Metlay JP, Chu X, Strom BL, Bilker WB: CYP2C9, CYP2C19, and ABCB1 genotype and hospitalization for phenytoin toxicity. J Clin Pharmacol. 2009 Dec;49(12):1483-7. doi: 10.1177/0091270009343006. Epub 2009 Jul 17. [PubMed:19617466 ]
Klotz U: The role of pharmacogenetics in the metabolism of antiepileptic drugs: pharmacokinetic and therapeutic implications. Clin Pharmacokinet. 2007;46(4):271-9. [PubMed:17375979 ]

Enzyme Details

4. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Wang H, Faucette S, Moore R, Sueyoshi T, Negishi M, LeCluyse E: Human constitutive androstane receptor mediates induction of CYP2B6 gene expression by phenytoin. J Biol Chem. 2004 Jul 9;279(28):29295-301. Epub 2004 Apr 28. [PubMed:15123723 ]
Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [PubMed:14977870 ]

Enzyme Details

5. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Kim KA, Park JY: Inhibitory effect of glyburide on human cytochrome p450 isoforms in human liver microsomes. Drug Metab Dispos. 2003 Sep;31(9):1090-2. [PubMed:12920163 ]

Enzyme Details

6. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Swadron SP, Rudis MI, Azimian K, Beringer P, Fort D, Orlinsky M: A comparison of phenytoin-loading techniques in the emergency department. Acad Emerg Med. 2004 Mar;11(3):244-52. [PubMed:15001403 ]
Mantegazza M, Curia G, Biagini G, Ragsdale DS, Avoli M: Voltage-gated sodium channels as therapeutic targets in epilepsy and other neurological disorders. Lancet Neurol. 2010 Apr;9(4):413-24. doi: 10.1016/S1474-4422(10)70059-4. [PubMed:20298965 ]
Lenkowski PW, Ko SH, Anderson JD, Brown ML, Patel MK: Block of human NaV1.5 sodium channels by novel alpha-hydroxyphenylamide analogues of phenytoin. Eur J Pharm Sci. 2004 Apr;21(5):635-44. [PubMed:15066664 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Fosphenytoin (HMDB0015417)

MOL for HMDB0015417 (Fosphenytoin)

3D MOL for HMDB0015417 (Fosphenytoin)

3D SDF for HMDB0015417 (Fosphenytoin)

3D-SDF for HMDB0015417 (Fosphenytoin)

PDB for HMDB0015417 (Fosphenytoin)

3D PDB for HMDB0015417 (Fosphenytoin)

SMILES for HMDB0015417 (Fosphenytoin)

INCHI for HMDB0015417 (Fosphenytoin)

Structure for HMDB0015417 (Fosphenytoin)

3D Structure for HMDB0015417 (Fosphenytoin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References