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
Thumb
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
KEGG Drug
D01160
KEGG Compound
C12560
ChemSpider
54902
ChEBI
32121
ChEMBL
CHEMBL282042
Wikipedia
Saquinavir
Predicted Properties
PropertyValueSource
Water Solubility0.00247 mg/mLALOGPS
logP4.04ALOGPS
logP3.16ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)8.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area166.75 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity186.67 m3·mol-1ChemAxon
Polarizability73.81 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon