Indinavir

Indinavir

Clinical data
Trade names	Crixivan
AHFS/Drugs.com	Monograph
MedlinePlus	a696028
License data	EU EMA: by INN US FDA: Indinavir
Routes of administration	Oral
ATC code	J05AE02 (WHO)
Pharmacokinetic data
Bioavailability	~65%
Protein binding	60%
Metabolism	Hepatic via CYP3A4
Elimination half-life	1.8 ± 0.4 hours
Identifiers
IUPAC name (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide
CAS Number	150378-17-9 Y
PubChem CID	5362440
DrugBank	DB00224 Y
ChemSpider	4515036 Y
UNII	9MG78X43ZT
KEGG	C07051 Y
ChEBI	CHEBI:44032 Y
ChEMBL	ChEMBL540914 N
NIAID ChemDB	005824
PDB ligand	MK1 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID4043802
Chemical and physical data
Formula	C36H47N5O4
Molar mass	613.803 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)(C)NC(=O)[C@@H]1CN(CCN1C[C@H](C[C@@H](Cc2ccccc2)C(=O)N[C@H]3c4ccccc4C[C@H]3O)O)Cc5cccnc5
InChI InChI=1S/C36H47N5O4/c1-36(2,3)39-35(45)31-24-40(22-26-12-9-15-37-21-26)16-17-41(31)23-29(42)19-28(18-25-10-5-4-6-11-25)34(44)38-33-30-14-8-7-13-27(30)20-32(33)43/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45)/t28-,29+,31+,32-,33+/m1/s1 Y Key:CBVCZFGXHXORBI-PXQQMZJSSA-N Y
NY (what is this?)  (verify)

Indinavir (IDV; trade name Crixivan, made by Merck) is a protease inhibitor used as a component of highly active antiretroviral therapy to treat HIV/AIDS. It is soluble white powder administered orally in combination with other antiviral drugs. The drug prevents protease from functioning normally. Consequently, HIV viruses cannot reproduce, causing a decrease in the viral load. Commercially sold indinavir is indinavir anhydrous, which is indinavir with an additional amine in the hydroxyethylene backbone. This enhances its solubility and oral bioavailability, making it easier for users to intake. It was synthetically produced for the purpose of inhibiting the protease in the HIV virus.^[1]

Currently, it is not recommended for use in HIV/AIDS treatment due to its side effects. Furthermore, it is controversial for many reasons starting from its development to its usage.

It was patented in 1991 and approved for medical use in 1996.^[2]