Saquinavir mesylateProduct ingredient for Saquinavir
- Name
- Saquinavir mesylate
- Drug Entry
- Saquinavir
Saquinavir is an HIV-1 protease inhibitor used in combination with ritonavir and other antiretrovirals for the treatment of human immunodeficiency virus-1 (HIV-1) infection. In 1995 it became the first protease inhibitor approved by the FDA, followed shortly by ritonavir in 1996, and remains in clinical use today due to a relatively benign adverse effect profile as compared to other antiretroviral therapies.2 While its efficacy was initially limited by exceptionally poor oral bioavailability (approximately 4%),6 its current indications require the co-administration of ritonavir - a potent enzyme inhibitor - that increases the bioavailability and subsequent serum concentrations of saquinavir, thus dramatically improving antiviral activity.2,6,7
- Accession Number
- DBSALT002836
- Structure
- Synonyms
- Saquinavir mesilate / Saquinavir mesylate / Saquinavir monomethanesulfonate salt / SQV
- External IDs
- RO 31-8959/003 / RO-31-8959/003 / RO-318959003
- UNII
- UHB9Z3841A
- CAS Number
- 149845-06-7
- Weight
- Average: 766.96
Monoisotopic: 766.372383897 - Chemical Formula
- C39H54N6O8S
- InChI Key
- IRHXGOXEBNJUSN-YOXDLBRISA-N
- InChI
- InChI=1S/C38H50N6O5.CH4O3S/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;1-5(2,3)4/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);1H3,(H,2,3,4)/t26-,27+,30-,31-,32-,33+;/m0./s1
- IUPAC Name
- (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(quinolin-2-yl)formamido]butanediamide; methanesulfonic acid
- SMILES
- CS(O)(=O)=O.[H][C@@]12CCCC[C@]1([H])CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(N)=O)NC(=O)C1=NC3=C(C=CC=C3)C=C1)[C@@H](C2)C(=O)NC(C)(C)C
- External Links
- KEGG Drug
- D01160
- KEGG Compound
- C12560
- ChemSpider
- 54902
- ChEBI
- 32121
- ChEMBL
- CHEMBL282042
- Wikipedia
- Saquinavir
- Predicted Properties
Property Value Source Water Solubility 0.00247 mg/mL ALOGPS logP 4.04 ALOGPS logP 3.16 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 13.61 Chemaxon pKa (Strongest Basic) 8.47 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 166.75 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 186.67 m3·mol-1 Chemaxon Polarizability 73.81 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon