Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:51:58 UTC |
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HMDB ID | HMDB0015417 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Fosphenytoin |
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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. | Read more...
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Structure | OP(O)(=O)OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1 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) |
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Synonyms | Value | Source |
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(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 |
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Chemical Formula | C16H15N2O6P |
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Average Molecular Weight | 362.2739 |
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Monoisotopic Molecular Weight | 362.066772734 |
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IUPAC Name | [(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methoxy]phosphonic acid |
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Traditional Name | fosphenytoin |
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CAS Registry Number | 93390-81-9 |
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SMILES | OP(O)(=O)OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1 |
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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) |
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InChI Key | XWLUWCNOOVRFPX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Diphenylmethanes |
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Direct Parent | Diphenylmethanes |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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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 |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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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 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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, 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 | 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, 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 |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01320 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01320 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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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 |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB01320 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 50839 |
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KEGG Compound ID | C07840 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Fosphenytoin |
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METLIN ID | Not Available |
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PubChem Compound | 56339 |
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PDB ID | Not Available |
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ChEBI ID | 775287 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
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