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Revision as of 14:29, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456652821 of page Fosphenytoin for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').  Latest revision as of 19:57, 20 December 2023 edit JJMC89 bot III (talk | contribs)Bots, Administrators3,685,221 editsm Moving Category:Pfizer brands to Category:Drugs developed by Pfizer per Misplaced Pages:Categories for discussion/Log/2023 December 9#Category:AstraZeneca brands 
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{{Short description|Anti-epileptic drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 402134440 | verifiedrevid = 461113778
⚫ | IUPAC_name = (2,5-dioxo-4,4-diphenyl-imidazolidin-1-yl)methoxyphosphonic acid
| image = Fosphenytoin.svg | image = Fosphenytoin.svg
| width = 250 | width = 175
| alt =
| image2 = Fosphenytoin3d.png | image2 = Fosphenytoin 3D ball.png
| alt2 =


<!--Clinical data--> <!--Clinical data-->
| tradename = Cerebyx | tradename = Cerebyx, Pro-Epanutin
| Drugs.com = {{drugs.com|monograph|cerebyx}} | Drugs.com = {{drugs.com|monograph|fosphenytoin-sodium}}
| MedlinePlus = a604036 | MedlinePlus = a604036
| DailyMedID = Fosphenytoin
| pregnancy_US = D | pregnancy_US = D
| legal_US = Rx-only
| legal_status = Rx-only | legal_status = Rx-only
| routes_of_administration = ], ] | routes_of_administration = ], ]
⚫ | ATC_prefix = N03
⚫ | ATC_suffix = AB05


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 100% (]) | bioavailability = 100% (])
| protein_bound = 95 to 99% | protein_bound = 95–99%
| metabolism = ] | metabolism = ]
| elimination_half-life = 15 minutes to convert to phenytoin | elimination_half-life = 15 minutes to convert to ]
| excretion = ] (as phenytoin) | excretion = ] (as phenytoin)


<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 93390-81-9 | CAS_number = 93390-81-9
⚫ | ATC_prefix = N03
⚫ | ATC_suffix = AB05
| PubChem = 56339 | PubChem = 56339
| IUPHAR_ligand = 7190
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01320 | DrugBank = DB01320
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B4SF212641 | UNII = B4SF212641
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07993 | KEGG = D07993
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 919 --> | ChEMBL = 919

<!--Chemical data-->
⚫ | IUPAC_name = (2,5-Dioxo-4,4-diphenyl-imidazolidin-1-yl)methoxyphosphonic acid
| C=16 | H=15 | N=2 | O=6 | P=1 | C=16 | H=15 | N=2 | O=6 | P=1
| molecular_weight = 362.274 g/mol
| smiles = O=C3N(C(=O)C(c1ccccc1)(c2ccccc2)N3)COP(=O)(O)O | smiles = O=C3N(C(=O)C(c1ccccc1)(c2ccccc2)N3)COP(=O)(O)O
| InChI = 1/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)
| InChIKey = XWLUWCNOOVRFPX-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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) | StdInChI = 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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| StdInChIKey = XWLUWCNOOVRFPX-UHFFFAOYSA-N | StdInChIKey = XWLUWCNOOVRFPX-UHFFFAOYSA-N
}} }}

'''Fosphenytoin''', also known as fosphenytoin ], and sold under the brand name '''Cerebyx''' among others, is a water-soluble ] ] that is administered intravenously to deliver phenytoin, potentially more safely than intravenous ]. It is used in the acute treatment of convulsive ].

<!-- History, society, and culture -->
Fosphenytoin was developed in 1996.<ref>{{cite book| vauthors = Pitkänen A, Schwartzkroin PA, Moshé SL |title=Models of Seizures and Epilepsy.|date=2005|publisher=Elsevier|location=Burlington|isbn=9780080457024|page=539|url=https://books.google.com/books?id=Qw6KqLjwtZQC&pg=PA539}}</ref> On 18 November 2004, Sicor (a subsidiary of ]) received a tentative approval letter from the ] for a generic version of fosphenytoin.<ref name=generic>{{cite web | url=http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Label_ApprovalHistory#apphist | title=Fosphenytoin Sodium Approval History | access-date=20 October 2005 }}</ref>

== Medical uses ==
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,<ref name=approved_use>{{cite web|author=Parke-Davis |year=2001 |title=Cerebyx: Fosphenytoin Sodium Injection - Labeling Revision |work=Cerebyx Approval History |publisher=Warner-Lambert Company |url=https://www.fda.gov/cder/foi/label/2001/20450s4s5lbl.pdf |access-date=20 October 2005 |url-status=dead |archive-url=https://web.archive.org/web/20031017163732/https://www.fda.gov/CDER/foi/label/2001/20450s4s5lbl.pdf |archive-date=October 17, 2003 }}</ref> such as ], ] or some other type of repeated seizures; cluster seizure, vomiting, and/or the patient is unalert or not awake or both.<ref name=when_to_use_fosphenytoin>{{cite journal |vauthors=Johnson J, Wrenn K | title=Inappropriate fosphenytoin use in the ED | journal=American Journal of Emergency Medicine | volume=19 | issue=4 | year=2001 | pages=293–4 | pmid=11447516 | doi=10.1053/ajem.2001.24471}}</ref>

=== Other ===
In 2003, it was reported that even though ]s are often very effective in ], and acute mania requires rapid treatment, fosphenytoin had no antimanic effect.<ref name=not_an_antimanic>{{cite journal | doi=10.4088/JCP.v64n0408 |vauthors=Applebaum J, Levine J, Belmaker RH | title=Intravenous fosphenytoin in acute mania | journal=Journal of Clinical Psychiatry | volume=64 | issue=4 | year=2003 | pages=408–9 | pmid=12716241 }}</ref>

== Metabolism ==
One ]] of phenytoin is produced for every millimole of fosphenytoin administered; the ] of fosphenytoin also yields ] and ], the latter of which is subsequently metabolized to ], which is in turn metabolized by a folate dependent mechanism.<ref name=approved_use />

== Side effects ==
Side effects are similar to intravenous phenytoin and include hypotension, cardiac ], CNS adverse events (], dizziness, sedation/somnolence, ] and ]), and local dermatological reactions. ] probably occurs with fosphenytoin but possibly at lower frequency than with intravenous phenytoin. Fosphenytoin can cause ] in end-stage ] patients.<ref name=not_in_kidney_failure>{{cite journal |vauthors=McBryde KD, Wilcox J, Kher KK | title=Hyperphosphatemia due to fosphenytoin in a pediatric ESRD patient | journal=Pediatric Nephrology (Berlin, Germany) | volume=20 | issue=8 | year=2005 | pages=1182–5 | pmid=15965770 | doi=10.1007/s00467-005-1947-0| s2cid=6664220 }}</ref>

==History==
Phenytoin, in both its acidic and sodium salt forms, is erratically bioavailable whether it is injected or taken orally due to its high ], weak ], and its being only sparingly ] in water.<ref name=erratic>{{cite journal |vauthors=Yamaoka Y, Roberts RD, Stella VJ |title=Low-melting phenytoin prodrugs as alternative oral delivery modes for phenytoin: a model for other high-melting sparingly water-soluble drugs |journal=J Pharm Sci |volume=72 |issue=4 |pages=400–5 |date=April 1983 |pmid=6864479 |doi=10.1002/jps.2600720420 }}</ref> Simply putting patients on other drugs is not always an option; this was especially true before 1993, when the number of ]s available was much more limited.<ref name=pre-1993>{{cite web | vauthors = Tuen C | url = http://neuroland.com/sz/anticon/before_93.htm | title = Anticonvulsants before 1993 | work = Neuroland | archive-url = https://web.archive.org/web/20190804174151/https://neuroland.com/sz/anticon/before_93.htm | archive-date = 4 August 2019 }} </ref> One solution was to develop a prodrug that did not have these drawbacks.

Fosphenytoin was approved by the ] (FDA) on August 5, 1996, for use in epilepsy.<ref name=approval>{{cite web | url=http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Label_ApprovalHistory | title=Cerebyx Approval History | access-date=20 October 2005 }}</ref>

==See also==
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==References==
{{Reflist}}

== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/fosphenytoin | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Fosphenytoin }}
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/fosphenytoin%20sodium | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Fosphenytoin sodium }}

{{Anticonvulsants}}
{{Portal bar | Medicine}}

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