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Revision as of 13:34, 1 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit Latest revision as of 06:03, 18 March 2024 edit undoWhywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,153 editsm script-assisted date audit and style fixes per MOS:NUM 
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{{Short description|Chemical compound}}
{{Use dmy dates|date=March 2024}}
{{drugbox {{drugbox
| Verifiedfields = changed
| IUPAC_name = Acetyl-YTSLIHSLIEESQNQ QEKNEQELLELDKWASLWNWF-amide
| Watchedfields = changed
| verifiedrevid = 399917793
| width = 280 | width = 280
| image = Enfuvirtide.svg
| InChI = 1/C204H301N51O64/c1-20-102(15)166(253-195(310)137(75-100(11)12)239-200(315)150(93-258)251-190(305)143(82-112-90-215-95-219-112)248-203(318)167(103(16)21-2)254-196(311)138(76-101(13)14)240-201(316)151(94-259)252-204(319)168(105(18)260)255-197(312)139(221-106(19)261)78-108-45-47-113(262)48-46-108)202(317)233-131(58-68-164(280)281)178(293)228-130(57-67-163(278)279)182(297)250-149(92-257)198(313)232-125(52-62-155(210)266)179(294)245-145(84-157(212)268)191(306)229-124(51-61-154(209)265)175(290)224-122(49-59-152(207)263)173(288)226-126(53-63-159(270)271)176(291)222-120(43-31-33-69-205)172(287)244-144(83-156(211)267)192(307)231-127(54-64-160(272)273)177(292)225-123(50-60-153(208)264)174(289)227-128(55-65-161(274)275)180(295)235-134(72-97(5)6)185(300)237-133(71-96(3)4)184(299)230-129(56-66-162(276)277)181(296)236-135(73-98(7)8)187(302)247-147(86-165(282)283)194(309)223-121(44-32-34-70-206)171(286)241-140(79-109-87-216-117-40-28-25-37-114(109)117)183(298)220-104(17)170(285)249-148(91-256)199(314)238-136(74-99(9)10)186(301)242-142(81-111-89-218-119-42-30-27-39-116(111)119)189(304)246-146(85-158(213)269)193(308)243-141(80-110-88-217-118-41-29-26-38-115(110)118)188(303)234-132(169(214)284)77-107-35-23-22-24-36-107/h22-30,35-42,45-48,87-90,95-105,120-151,166-168,216-218,256-260,262H,20-21,31-34,43-44,49-86,91-94,205-206H2,1-19H3,(H2,207,263)(H2,208,264)(H2,209,265)(H2,210,266)(H2,211,267)(H2,212,268)(H2,213,269)(H2,214,284)(H,215,219)(H,220,298)(H,221,261)(H,222,291)(H,223,309)(H,224,290)(H,225,292)(H,226,288)(H,227,289)(H,228,293)(H,229,306)(H,230,299)(H,231,307)(H,232,313)(H,233,317)(H,234,303)(H,235,295)(H,236,296)(H,237,300)(H,238,314)(H,239,315)(H,240,316)(H,241,286)(H,242,301)(H,243,308)(H,244,287)(H,245,294)(H,246,304)(H,247,302)(H,248,318)(H,249,285)(H,250,297)(H,251,305)(H,252,319)(H,253,310)(H,254,311)(H,255,312)(H,270,271)(H,272,273)(H,274,275)(H,276,277)(H,278,279)(H,280,281)(H,282,283)/t102-,103-,104-,105+,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,166-,167-,168-/m0/s1
| alt =
| InChIKey = PEASPLKKXBYDKL-FXEVSJAOBV

| smiles = CCC(C)C(C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CO)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)O)C(=O)NC(CCCCN)C(=O)NC(Cc1cc2c1cccc2)C(=O)NC(C)C(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NC(Cc3cc4c3cccc4)C(=O)NC(CC(=O)N)C(=O)NC(Cc5cc6c5cccc6)C(=O)NC(Cc7ccccc7)C(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(Cc8cnc8)NC(=O)C(C(C)CC)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(Cc9ccc(cc9)O)NC(=O)C
<!--Clinical data-->
| StdInChI = 1S/C204H301N51O64/c1-20-102(15)166(253-195(310)137(75-100(11)12)239-200(315)150(93-258)251-190(305)143(82-112-90-215-95-219-112)248-203(318)167(103(16)21-2)254-196(311)138(76-101(13)14)240-201(316)151(94-259)252-204(319)168(105(18)260)255-197(312)139(221-106(19)261)78-108-45-47-113(262)48-46-108)202(317)233-131(58-68-164(280)281)178(293)228-130(57-67-163(278)279)182(297)250-149(92-257)198(313)232-125(52-62-155(210)266)179(294)245-145(84-157(212)268)191(306)229-124(51-61-154(209)265)175(290)224-122(49-59-152(207)263)173(288)226-126(53-63-159(270)271)176(291)222-120(43-31-33-69-205)172(287)244-144(83-156(211)267)192(307)231-127(54-64-160(272)273)177(292)225-123(50-60-153(208)264)174(289)227-128(55-65-161(274)275)180(295)235-134(72-97(5)6)185(300)237-133(71-96(3)4)184(299)230-129(56-66-162(276)277)181(296)236-135(73-98(7)8)187(302)247-147(86-165(282)283)194(309)223-121(44-32-34-70-206)171(286)241-140(79-109-87-216-117-40-28-25-37-114(109)117)183(298)220-104(17)170(285)249-148(91-256)199(314)238-136(74-99(9)10)186(301)242-142(81-111-89-218-119-42-30-27-39-116(111)119)189(304)246-146(85-158(213)269)193(308)243-141(80-110-88-217-118-41-29-26-38-115(110)118)188(303)234-132(169(214)284)77-107-35-23-22-24-36-107/h22-30,35-42,45-48,87-90,95-105,120-151,166-168,216-218,256-260,262H,20-21,31-34,43-44,49-86,91-94,205-206H2,1-19H3,(H2,207,263)(H2,208,264)(H2,209,265)(H2,210,266)(H2,211,267)(H2,212,268)(H2,213,269)(H2,214,284)(H,215,219)(H,220,298)(H,221,261)(H,222,291)(H,223,309)(H,224,290)(H,225,292)(H,226,288)(H,227,289)(H,228,293)(H,229,306)(H,230,299)(H,231,307)(H,232,313)(H,233,317)(H,234,303)(H,235,295)(H,236,296)(H,237,300)(H,238,314)(H,239,315)(H,240,316)(H,241,286)(H,242,301)(H,243,308)(H,244,287)(H,245,294)(H,246,304)(H,247,302)(H,248,318)(H,249,285)(H,250,297)(H,251,305)(H,252,319)(H,253,310)(H,254,311)(H,255,312)(H,270,271)(H,272,273)(H,274,275)(H,276,277)(H,278,279)(H,280,281)(H,282,283)/t102-,103-,104-,105+,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,166-,167-,168-/m0/s1
| tradename = Fuzeon
| StdInChIKey = PEASPLKKXBYDKL-FXEVSJAOSA-N
| Drugs.com = {{drugs.com|monograph|enfuvirtide}}
| CAS_number = 159519-65-0
| MedlinePlus = a603023
| DailyMedID = Enfuvirtide
| pregnancy_AU = B2
| pregnancy_AU_comment = <ref name="Fuzeon PI" />
| routes_of_administration = ]
| ATC_prefix = J05 | ATC_prefix = J05
| ATC_suffix = AX07 | ATC_suffix = AX07
| ATC_supplemental = | ATC_supplemental =

| PubChem = 16130199
| legal_AU = S4
| ChemSpiderID=16743716
| legal_AU_comment =<ref name="Fuzeon PI">{{cite web | website=guildlink.com.au | url=https://www.guildlink.com.au/gc/ws/ro/pi.cfm?product=ropfuzeo10315 | title=Product | access-date=8 January 2023 | archive-date=8 January 2023 | archive-url=https://web.archive.org/web/20230108233513/https://www.guildlink.com.au/gc/ws/ro/pi.cfm?product=ropfuzeo10315 | url-status=dead }}</ref>
| DrugBank = DB00109
| legal_CA = Rx-only
| C=202 | H=298 | N=50 | O=64
| legal_UK = POM
| molecular_weight = 4492.1 g/mol
| legal_US = Rx-only
| bioavailability = 84.3% (])
| legal_status =

<!--Pharmacokinetic data-->
| bioavailability = 84.3% (])
| protein_bound = 92% | protein_bound = 92%
| metabolism = Hepatic | metabolism = ]
| elimination_half-life = 3.8 hours | elimination_half-life = 3.8 hours
| excretion = unknown | excretion = unknown
| pregnancy_category = B2 <small>(])</small>, B <small>(])</small>
| legal_status = S4 <small>(Au)</small>, POM <small>(])</small>, ℞-only <small>(U.S.)</small>
| routes_of_administration = ] (SC)
}}
'''Enfuvirtide''' (]) is an ] ], the first of a novel class of ]s used in ] for the treatment of ]-1 infection. It is marketed under the trade name '''Fuzeon''' (]).


<!--Identifiers-->
Enfuvirtide therapy costs an estimated USD$25,000 per year in the United States. Its cost and inconvenient dosing regimen are factors behind its use as a reserve, for "salvage" therapy in patients with multi-drug resistant HIV.
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 159519-65-0
| PubChem = 16130199
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00109
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16743716
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 19OWO1T3ZE
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D02499
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 608828
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 525076
| NIAID_ChemDB = 059486


<!--Chemical data-->
==Structural formula==
| C=204 | H=301 | N=51 | O=64
]
| smiles = CC(C)(C(=O)N(CCC(=O)O)C(=O)N(CCC(=O)O)C(=O)N(CO)C(=O)N(CCC(=O)N)C(=O)N(CC(=O)N)C(=O)N(CCC(=O)N)C(=O)N(CCC(=O)N)C(=O)N(CCC(=O)O)C(=O)N(CCCCN)C(=O)N(CC(=O)N)C(=O)N(CCC(=O)O)C(=O)N(CCC(=O)N)C(=O)N(CCC(=O)O)C(=O)N(CC(C)C)C(=O)N(CC(C)C)C(=O)N(CCC(=O)O)C(=O)N(CC(C)C)C(=O)N(CC(=O)O)C(=O)N(CCCCN)C(=O)N(Cc1cc2c1cccc2)C(=O)N(C)C(=O)N(CO)C(=O)N(CC(C)C)C(=O)N(Cc3cc4c3cccc4)C(=O)N(CC(=O)N)C(=O)N(Cc5cc6c5cccc6)C(=O)N(Cc7ccccc7)C(=O)N)NC(=O)(CC(C)C)NC(=O)(CO)NC(=O)(Cc8cnc8)NC(=O)((C)CC)NC(=O)(CC(C)C)NC(=O)(CO)NC(=O)((C)O)NC(=O)(Cc9ccc(cc9)O)NC(=O)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C204H301N51O64/c1-20-102(15)166(253-195(310)137(75-100(11)12)239-200(315)150(93-258)251-190(305)143(82-112-90-215-95-219-112)248-203(318)167(103(16)21-2)254-196(311)138(76-101(13)14)240-201(316)151(94-259)252-204(319)168(105(18)260)255-197(312)139(221-106(19)261)78-108-45-47-113(262)48-46-108)202(317)233-131(58-68-164(280)281)178(293)228-130(57-67-163(278)279)182(297)250-149(92-257)198(313)232-125(52-62-155(210)266)179(294)245-145(84-157(212)268)191(306)229-124(51-61-154(209)265)175(290)224-122(49-59-152(207)263)173(288)226-126(53-63-159(270)271)176(291)222-120(43-31-33-69-205)172(287)244-144(83-156(211)267)192(307)231-127(54-64-160(272)273)177(292)225-123(50-60-153(208)264)174(289)227-128(55-65-161(274)275)180(295)235-134(72-97(5)6)185(300)237-133(71-96(3)4)184(299)230-129(56-66-162(276)277)181(296)236-135(73-98(7)8)187(302)247-147(86-165(282)283)194(309)223-121(44-32-34-70-206)171(286)241-140(79-109-87-216-117-40-28-25-37-114(109)117)183(298)220-104(17)170(285)249-148(91-256)199(314)238-136(74-99(9)10)186(301)242-142(81-111-89-218-119-42-30-27-39-116(111)119)189(304)246-146(85-158(213)269)193(308)243-141(80-110-88-217-118-41-29-26-38-115(110)118)188(303)234-132(169(214)284)77-107-35-23-22-24-36-107/h22-30,35-42,45-48,87-90,95-105,120-151,166-168,216-218,256-260,262H,20-21,31-34,43-44,49-86,91-94,205-206H2,1-19H3,(H2,207,263)(H2,208,264)(H2,209,265)(H2,210,266)(H2,211,267)(H2,212,268)(H2,213,269)(H2,214,284)(H,215,219)(H,220,298)(H,221,261)(H,222,291)(H,223,309)(H,224,290)(H,225,292)(H,226,288)(H,227,289)(H,228,293)(H,229,306)(H,230,299)(H,231,307)(H,232,313)(H,233,317)(H,234,303)(H,235,295)(H,236,296)(H,237,300)(H,238,314)(H,239,315)(H,240,316)(H,241,286)(H,242,301)(H,243,308)(H,244,287)(H,245,294)(H,246,304)(H,247,302)(H,248,318)(H,249,285)(H,250,297)(H,251,305)(H,252,319)(H,253,310)(H,254,311)(H,255,312)(H,270,271)(H,272,273)(H,274,275)(H,276,277)(H,278,279)(H,280,281)(H,282,283)/t102-,103-,104-,105+,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,166-,167-,168-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PEASPLKKXBYDKL-FXEVSJAOSA-N
}}


'''Enfuvirtide''' (]), sold under the brand name '''Fuzeon''', is an ] ], the first of a class of ]s used in ] for the treatment of ].
]-]-]-]-]-]-]-Ser-Leu-
Ile-]-Glu-Ser-]-]-Gln-Gln-Glu-
]-Asn-Glu-Gln-Glu-Leu-Leu-Glu-
Leu-]-]-]-]-Ser-Leu-Trp-]-
Trp-]-]


==History== == Medical uses ==
Enfuvirtide is ] for the treatment of HIV-1 infection, in ] with other antiretrovirals, in people where all other treatments have failed.<ref name="AMH2006">{{cite book | veditors = Rossi S | title =Australian Medicines Handbook | location = Adelaide | publisher = Australian Medicines Handbook Pty Ltd | date = 2006 | isbn = 0-9757919-2-3 | title-link =Australian Medicines Handbook }}</ref>
Enfuvirtide originated at ], where researchers formed a pharmaceutical company known as Trimeris. Trimeris began development on enfuvirtide in 1996 and initially designated it '''T-20'''. In 1999, Trimeris entered into partnership with ] to complete the development of the drug. It was approved by the U.S. ] (FDA) on March 13, 2003 <!-- or was it march 15? --> as the first HIV ], a new class of antiretroviral drugs. It was approved on the basis of two studies (TORO 1 and TORO 2) which compared the effect of optimized regimens of antiretroviral medication with and without the addition of enfuvirtide on serum ].

==Adverse effects==
Common ]s (≥1% of patients) associated with enfuvirtide therapy include: injection site reactions (pain, hardening of skin, ], ]s, ]s, itch; experienced by nearly all patients, particularly in the first week), ], ], ], cough, ], ], ], infections (including bacterial ]) and/or ]. Various ] reactions occur infrequently (0.1–1% of patients), symptoms of which include ], ], ], ], ], rigors, ], elevated hepatic ]s; and possibly more severe reactions including ], ] and/or ] – ] is not recommended.<ref name="AMH2006" />


==Pharmacology== ==Pharmacology==

===Mechanism of action=== ===Mechanism of action===
Enfuvirtide works by disrupting the ]-1 molecular machinery at the final stage of ] with the target ], preventing uninfected cells from becoming infected. A ] ], enfuvirtide was designed to mimic components of the ]-1 fusion machinery and displace them, preventing normal fusion. Drugs that disrupt fusion of ] and target ] are termed ] or ]s. Enfuvirtide works by disrupting the ]-1 molecular machinery at the final stage of ] with the target ], preventing uninfected cells from becoming infected. A ] ], enfuvirtide was designed to mimic components of the ]-1 fusion machinery and displace them, preventing normal fusion. Drugs that disrupt fusion of ] and target ] are termed ] or ]s.{{cn|date=April 2021}}

HIV binds to the host CD4+ cell receptor via the viral protein gp120; gp41, a viral ], then undergoes a ] that assists in the fusion of the viral membrane to the host cell membrane. Enfuvirtide binds to gp41 preventing the creation of an entry pore for the capsid of the virus, keeping it out of the cell.<ref>{{cite journal | vauthors = Lalezari JP, Eron JJ, Carlson M, Cohen C, DeJesus E, Arduino RC, Gallant JE, Volberding P, Murphy RL, Valentine F, Nelson EL, Sista PR, Dusek A, Kilby JM | display-authors = 6 | title = A phase II clinical study of the long-term safety and antiviral activity of enfuvirtide-based antiretroviral therapy | journal = AIDS | volume = 17 | issue = 5 | pages = 691–8 | date = March 2003 | pmid = 12646792 | doi = 10.1097/00002030-200303280-00007 | s2cid = 32014873 | doi-access = free }}</ref>


Enfuvirtide is also an activator of the chemotactic factor receptor, formyl peptide receptor 1, and thereby activates phagocytes and presumably other cells bearing this receptor (see ]).<ref name="pmid10339497">{{cite journal | vauthors = Su SB, Gong WH, Gao JL, Shen WP, Grimm MC, Deng X, Murphy PM, Oppenheim JJ, Wang JM | display-authors = 6 | title = T20/DP178, an ectodomain peptide of human immunodeficiency virus type 1 gp41, is an activator of human phagocyte N-formyl peptide receptor | journal = Blood | volume = 93 | issue = 11 | pages = 3885–92 | date = June 1999 | pmid = 10339497 | doi = 10.1182/blood.V93.11.3885 }}</ref> The physiological significance of this activation is unknown.{{cn|date=January 2023}}
HIV binds to the host CD4+ cell receptor via the viral protein gp120; gp41, a viral ], then undergoes a ] that assists in the fusion of the viral membrane to the host cell membrane. Enfuvirtide binds to gp41 preventing the creation of an entry pore for the capsid of the virus, keeping it out of the cell.<ref>Lalezari JP, Eron JJ, Carlson M, et al. A phase II clinical study of the long-term safety and antiviral activity of enfuvirtide-based antiretroviral therapy. AIDS 2003;17:691—8.</ref>


===Microbiology=== ===Microbiology===
Enfuvirtide is considered to be active against HIV-1 only. Low activity against HIV-2 isolates has been demonstrated '']''.<ref name="FuzeonPI">Roche Products Pty Ltd. Fuzeon (Australian Approved Product Information). Dee Why (NSW): Roche; 2005.</ref> Enfuvirtide is considered to be active against HIV-1 only. Low activity against HIV-2 isolates has been demonstrated '']''.<ref name="FuzeonPI">Roche Products Pty Ltd. Fuzeon (Australian Approved Product Information). Dee Why (NSW): Roche; 2005.</ref>


Variable susceptibility to enfuvirtide has been observed in clinical isolates, with ] the result of a mutated 10 ] motif in viral gp41. ], however, has yet to be observed.<ref name="Greenberg2004">Greenberg ML, Cammack N. Resistance to enfuvirtide, the first HIV fusion inhibitor. J Antimicrob Chemother 2004;54(2):333-40. PMID 15231762</ref> Variable susceptibility to enfuvirtide has been observed in clinical isolates, with ] the result of a mutated 10 ] motif in viral gp41. ], however, has yet to be observed.<ref name="Greenberg2004">{{cite journal | vauthors = Greenberg ML, Cammack N | title = Resistance to enfuvirtide, the first HIV fusion inhibitor | journal = The Journal of Antimicrobial Chemotherapy | volume = 54 | issue = 2 | pages = 333–40 | date = August 2004 | pmid = 15231762 | doi = 10.1093/jac/dkh330 | doi-access = free }}</ref>


==Clinical use== ===Structural formula===
Enfuvirtide is a 36-amino acid peptide with the following sequence:<ref>{{cite journal | vauthors = Wild C, Greenwell T, Shugars D, Rimsky-Clarke L, Matthews T | title = The Inhibitory Activity of an HIV Type 1 Peptide Correlates with Its Ability to Interact with a Leucine Zipper Structure | journal = AIDS Research and Human Retroviruses | volume = 11 | issue = 3 | pages = 323–25 | year = 1995 | doi = 10.1089/aid.1995.11.323| pmid = 7786578 }}</ref><ref>{{cite journal | vauthors = De Clercq E | title = Toward Improved Anti-HIV Chemotherapy: Therapeutic Strategies for Intervention with HIV Infections | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 14 | pages = 2491–2517 | date = July 1995 | doi = 10.1021/jm00014a001| pmid = 7543152 }}</ref>
===Indications===
Enfuvirtide is indicated for the treatment of HIV-1 infection, in ] with other antiretrovirals, in patients where all other treatments have failed.<ref name="AMH2006">Rossi S, editor. ] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3</ref>


]-]-]-]-]-]-]-Ser-Leu-Ile-]-Glu-Ser-]-]-Gln-Gln-Glu-]-Asn-Glu-Gln-Glu-Leu-Leu-Glu-Leu-]-]-]-]-Ser-Leu-Trp-]-Trp-]-] (Ac-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNWF-NH<sub>2</sub>)
===Dosage forms===
By virtue of its peptide nature, enfuvirtide is marketed in injectable form. The lyophilised enfuvirtide powder must be reconstituted by the patient and administered twice daily by ] injection.


==History==
===Adverse effects===
Enfuvirtide originated at ], where researchers formed a pharmaceutical company known as Trimeris. Trimeris began development on enfuvirtide in 1996 and initially designated it '''T-20'''. In 1999, Trimeris entered into partnership with ] to complete the development of the drug. It was approved by the U.S. ] (FDA) on 13 March 2003<ref>{{cite web |title=Drugs@FDA: FDA Approved Drug Products – Fuzeon (Click on 'Approval Date(s) and History, Letters, Labels, Reviews for NDA 021481') |url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=021481 |website=accessdata.fda.gov |publisher=United States Food and Drug Administration |access-date=6 January 2019 |archive-date=28 June 2017 |archive-url=https://web.archive.org/web/20170628150059/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=021481 |url-status=live }}</ref> as the first HIV ], a new class of antiretroviral drugs. It was approved on the basis of two studies which compared the effect of optimized regimens of antiretroviral medication with and without the addition of enfuvirtide on serum ].{{cn|date=April 2021}}
Common ]s (≥1% of patients) associated with enfuvirtide therapy include: injection site reactions (pain, hardening of skin, ], ]s, ]s, itch; experienced by nearly all patients, particularly in the first week), ], ], ], cough, ], ], ], infections (including bacterial ]) and/or ]. Various ] reactions occur infrequently (0.1–1% of patients), symptoms of which include rash, fever, nausea, vomiting, chills, rigors, ], elevated hepatic ]s; and possibly more severe reactions including ], ] and/or ] – ] is not recommended.<ref name="AMH2006" />


==References== == References ==
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{{Antiretroviral drug}}
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