Saquinavir

Saquinavir

Clinical data
Trade names	Invirase, Fortovase
AHFS/Drugs.com	Monograph
MedlinePlus	a696001
Pregnancy category	B1 (Australia)
ATC code	J05AE01 (WHO)
Pharmacokinetic data
Bioavailability	~4% (without ritonavir boosting)
Protein binding	98%
Metabolism	Hepatic, mainly by CYP3A4
Biological 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 Y
PubChem CID	441243
IUPHAR/BPS	4813
DrugBank	DB01232 Y
ChemSpider	390016 Y
UNII	L3JE09KZ2F
KEGG	D00429 Y
ChEMBL	CHEMBL114 Y
NIAID ChemDB	000640
Chemical and physical data
Formula	C38H50N6O5
Molar mass	670.841 g/mol
3D model (Jmol)	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 Y Key:QWAXKHKRTORLEM-UGJKXSETSA-N Y

Saquinavir, sold under the brand names Invirase and Fortovase, is an antiretroviral drug 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 first sold in 1995. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. As of 2015 it is not available as a generic medication in the United States and is expensive. The wholesale cost in the developing world is about 4.50 USD per day.

Saquinavir is used together with other medications to treat or prevent HIV/AIDS. Typically it is used with ritonavir or lopinavir/ritonavir to increase its effect.

The most frequent adverse events with saquinavir in either formulation are mild gastrointestinal symptoms, including diarrhea, nausea, loose stools & abdominal discomfort. Invirase is better tolerated than Fortovase.

Saquinavir, in the Invirase formulation, has a low and variable oral bioavailability, when given alone. The Fortovase formulation at the standard dosage delivers approximately eightfold more active drug than Invirase, also at the standard dosage.