Indinavir

Indinavir
Clinical data
Trade names	Crixivan
AHFS/Drugs.com	Monograph
MedlinePlus	a696028
License data	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 ;
PubChem CID	5362440;
DrugBank	DB00224 ;
ChemSpider	4515036 ;
UNII	9MG78X43ZT;
KEGG	C07051 ;
ChEBI	CHEBI:44032 ;
ChEMBL	ChEMBL540914 ;
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 ; Key:CBVCZFGXHXORBI-PXQQMZJSSA-N ;
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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]

It is no longer 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] on March 13 by the United States Food and Drug Administration,^[3] on October 1 by the Australian Therapeutic Goods Administration^[4] and on October 4 by the European Medicines Agency.^[5]

^ "Indinavir". PubChem. U.S. National Library of Medicine. Retrieved October 22, 2018.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 509. ISBN 9783527607495.
^ "NDA 20-685 Crivivan™ (inidinavir sulfate) Capsules" (PDF). Food and Drug Administration. March 13, 1996. Archived from the original (PDF) on December 11, 2020. Retrieved March 4, 2025.
^ "New drug: Indinavir sulfate". Australian Prescriber. 19 (4): 108–111. October 1, 1996. doi:10.18773/austprescr.1996.098.
^ "Crixivan". European Medicines Agency. Retrieved March 4, 2025.

[PubChem-1] "Indinavir". PubChem. U.S. National Library of Medicine. Retrieved October 22, 2018.

[Fis2006-2] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 509. ISBN 9783527607495.

[3] "NDA 20-685 Crivivan™ (inidinavir sulfate) Capsules" (PDF). Food and Drug Administration. March 13, 1996. Archived from the original (PDF) on December 11, 2020. Retrieved March 4, 2025.

[4] "New drug: Indinavir sulfate". Australian Prescriber. 19 (4): 108–111. October 1, 1996. doi:10.18773/austprescr.1996.098.

[5] "Crixivan". European Medicines Agency. Retrieved March 4, 2025.

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