Nelfinavir

Nelfinavir
Clinical data
Trade names	Viracept
Other names	NFV
AHFS/Drugs.com	Monograph
MedlinePlus	a697034
License data	US DailyMed: Nelfinavir;
Routes of; administration	By mouth
ATC code	J05AE04 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	Uncertain; increases when taking with food
Protein binding	>98%
Metabolism	Liver by CYP including CYP3A4 and CYP2C19
Elimination half-life	3.5–5 hours
Excretion	feces (87%), urine (1–2%)
Identifiers
	IUPAC name (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide;
CAS Number	159989-64-7 ;
PubChem CID	64143;
DrugBank	DB00220 ;
ChemSpider	57718 ;
UNII	HO3OGH5D7I;
KEGG	D08259 ;
ChEBI	CHEBI:7496 ;
ChEMBL	ChEMBL1159655 ;
NIAID ChemDB	028590;
CompTox Dashboard (EPA)	DTXSID5035080 ;
Chemical and physical data
Formula	C32H45N3O4S
Molar mass	567.79 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	349.94 °C (661.89 °F)
	SMILES O=C(c1cccc(O)c1C)N[C@@H](CSc2ccccc2)[C@H](O)CN4[C@H](C(=O)NC(C)(C)C)C[C@@H]3CCCC[C@@H]3C4;
	InChI InChI=1S/C32H45N3O4S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39)/t22-,23+,26-,27-,29+/m0/s1 ; Key:QAGYKUNXZHXKMR-HKWSIXNMSA-N ;
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Nelfinavir, sold under the brand name Viracept, is an antiretroviral medication used in the treatment of HIV/AIDS. Nelfinavir belongs to the class of drugs known as protease inhibitors (PIs) and like other PIs is almost always used in combination with other antiretroviral drugs.

Nelfinavir is an orally bioavailable human immunodeficiency virus HIV-1 protease inhibitor (K_i = 2 nM) and is widely prescribed in combination with HIV reverse transcriptase inhibitors for the treatment of HIV infection.^[2]

It was patented in 1992 and approved for medical use in 1997.^[3]

^ "Viracept (nelfinavir mesylate) Tablets and Oral Powder, for Oral Use. Full Prescribing Information" (PDF). ViiV Healthcare Company. Research Triangle Park, NC 27709. Retrieved 23 November 2015.
^ Zhang KE, Wu E, Patick AK, Kerr B, Zorbas M, Lankford A, et al. (April 2001). "Circulating metabolites of the human immunodeficiency virus protease inhibitor nelfinavir in humans: structural identification, levels in plasma, and antiviral activities". Antimicrobial Agents and Chemotherapy. 45 (4): 1086–1093. doi:10.1128/AAC.45.4.1086-1093.2001. PMC 90428. PMID 11257019.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 510. ISBN 9783527607495.

[1] "Viracept (nelfinavir mesylate) Tablets and Oral Powder, for Oral Use. Full Prescribing Information" (PDF). ViiV Healthcare Company. Research Triangle Park, NC 27709. Retrieved 23 November 2015.

[2] Zhang KE, Wu E, Patick AK, Kerr B, Zorbas M, Lankford A, et al. (April 2001). "Circulating metabolites of the human immunodeficiency virus protease inhibitor nelfinavir in humans: structural identification, levels in plasma, and antiviral activities". Antimicrobial Agents and Chemotherapy. 45 (4): 1086–1093. doi:10.1128/AAC.45.4.1086-1093.2001. PMC 90428. PMID 11257019.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 510. ISBN 9783527607495.

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