Saquinavir

Saquinavir
Clinical data
Trade namesInvirase, Fortovase
Other namesSQV
AHFS/Drugs.comMonograph
MedlinePlusa696001
License data
Pregnancy
category
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~4% (without ritonavir boosting)[3]
Protein binding98%
MetabolismLiver, mainly by CYP3A4
Elimination half-life9–15 hours
Excretionfeces (81%) and urine (3%)
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC38H50N6O5
Molar mass670.855 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:QWAXKHKRTORLEM-UGJKXSETSA-N checkY
  (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]

  1. ^ "Saquinavir Use During Pregnancy". Drugs.com. 20 March 2018. Retrieved 28 January 2020.
  2. ^ Roche Products Pty Limited (6 November 2018). "Invirase® (Saquinavir mesilate)". Australian Product Information – via MedAdvisor International Pty Ltd.
  3. ^ "Invirase- saquinavir mesylate capsule INVIRASE- saquinavir mesylate tablet, film coated". DailyMed. 26 December 2019. Retrieved 28 January 2020.
  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.
  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.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 509. ISBN 9783527607495.