Saquinavir

Saquinavir
Clinical data
Trade names	Invirase, Fortovase
Other names	SQV
AHFS/Drugs.com	Monograph
MedlinePlus	a696001
License data	EU EMA: by INN; US DailyMed: Saquinavir;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
ATC code	J05AE01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	~4% (without ritonavir boosting)
Protein binding	98%
Metabolism	Liver, mainly by CYP3A4
Elimination half-life	9–15 hours
Excretion	feces (81%) and urine (3%)
Identifiers
	IUPAC name (2S)-N-[(2S,3R)-4-[(3S)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinolin-2-ylformamido)butanediamide;
CAS Number	127779-20-8 ;
PubChem CID	441243;
IUPHAR/BPS	4813;
DrugBank	DB01232 ;
ChemSpider	390016 ;
UNII	L3JE09KZ2F;
KEGG	D00429 ;
ChEMBL	ChEMBL114 ;
NIAID ChemDB	000640;
PDB ligand	ROC (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID6044012 ;
Chemical and physical data
Formula	C38H50N6O5
Molar mass	670.855 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N)C[C@H](NC(=O)c1nc2c(cc1)cccc2)C(=O)N[C@@H](Cc3ccccc3)[C@H](O)CN5[C@H](C(=O)NC(C)(C)C)C[C@@H]4CCCC[C@@H]4C5;
	InChI InChI=1S/C38H50N6O5/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49)/t26-,27+,30-,31-,32-,33+/m0/s1 ; Key:QWAXKHKRTORLEM-UGJKXSETSA-N ;
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Saquinavir, sold under the brand name Invirase among others, is an antiretroviral medication used together with other medications to treat or prevent HIV/AIDS. Typically it is used with ritonavir or lopinavir/ritonavir to increase its effect. It is taken by mouth.

Common side effects include nausea, vomiting, diarrhea, and feeling tired. More serious side effects include problems with QT prolongation, heart block, high blood lipids, and liver problems. It appears to be safe in pregnancy. It is in the protease inhibitor class and works by blocking the HIV protease.

Saquinavir was patented in 1988 and first sold in 1995.

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