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 ;
	(verify)

Saquinavir, sold under the brand name Invirase among others, is an antiretroviral medication used together with other medications to treat or prevent HIV/AIDS.^[4] Typically it is used with ritonavir or lopinavir/ritonavir to increase its effect.^[4] It is taken by mouth.^[4]

Common side effects include nausea, vomiting, diarrhea, and feeling tired.^[4] More serious side effects include problems with QT prolongation, heart block, high blood lipids, and liver problems.^[4] It appears to be safe in pregnancy.^[4] It is in the protease inhibitor class and works by blocking the HIV protease.^[4]

Saquinavir was patented in 1988 and first sold in 1995.^[5]^[6]

^ "Saquinavir Use During Pregnancy". Drugs.com. 20 March 2018. Retrieved 28 January 2020.
^ Roche Products Pty Limited (6 November 2018). "Invirase® (Saquinavir mesilate)". Australian Product Information – via MedAdvisor International Pty Ltd.
^ "Invirase- saquinavir mesylate capsule INVIRASE- saquinavir mesylate tablet, film coated". DailyMed. 26 December 2019. Retrieved 28 January 2020.
^ ^a ^b ^c ^d ^e ^f ^g "Saquinavir". The American Society of Health-System Pharmacists. Archived from the original on 8 September 2015. Retrieved 5 September 2015.
^ Minor LK (2006). Handbook of Assay Development in Drug Discovery. Hoboken: CRC Press. p. 117. ISBN 9781420015706. Archived from the original on 31 March 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 509. ISBN 9783527607495.

[Drugs.com_pregnancy-1] "Saquinavir Use During Pregnancy". Drugs.com. 20 March 2018. Retrieved 28 January 2020.

[Invirase_PI-2] Roche Products Pty Limited (6 November 2018). "Invirase® (Saquinavir mesilate)". Australian Product Information – via MedAdvisor International Pty Ltd.

[Invirase_label-3] "Invirase- saquinavir mesylate capsule INVIRASE- saquinavir mesylate tablet, film coated". DailyMed. 26 December 2019. Retrieved 28 January 2020.

[AHFS2015-4] ^ ^a ^b ^c ^d ^e ^f ^g "Saquinavir". The American Society of Health-System Pharmacists. Archived from the original on 8 September 2015. Retrieved 5 September 2015.

[Min2006-5] Minor LK (2006). Handbook of Assay Development in Drug Discovery. Hoboken: CRC Press. p. 117. ISBN 9781420015706. Archived from the original on 31 March 2016.

[Fis2006-6] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 509. ISBN 9783527607495.

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