Saquinavir mesylate (CHEM016947)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:48:27 UTC
Update Date2016-11-09 01:15:30 UTC
Accession NumberCHEM016947
Identification
Common NameSaquinavir mesylate
ClassSmall Molecule
DescriptionSaquinavir, 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 patented in 1988 and first sold in 1995. 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.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Saquinavir mesilateKegg
InviraseKegg
Saquinavir mesilic acidGenerator
Saquinavir mesylic acidGenerator
Saquinavir monomethanesulfonateMeSH
Monomethanesulfonate, saquinavirMeSH
SaquinavirMeSH
SaquinivirMeSH
Chemical FormulaC39H54N6O8S
Average Molecular Mass766.960 g/mol
Monoisotopic Mass766.372 g/mol
CAS Registry Number149845-06-7
IUPAC Name(2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butyl-C-hydroxycarbonimidoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(quinolin-2-yl)formamido]butanediimidic acid; methanesulfonic acid
Traditional Nameinvirase; methanesulfonic acid
SMILESCS(O)(=O)=O.[H][C@@](O)(CN1C[C@@]2([H])CCCC[C@@]2([H])C[C@@]1([H])C(O)=NC(C)(C)C)[C@]([H])(CC1=CC=CC=C1)N=C(O)[C@]([H])(CC(O)=N)NC(=O)C1=NC2=CC=CC=C2C=C1
InChI IdentifierInChI=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
InChI KeyIRHXGOXEBNJUSN-YOXDLBRISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassHalohydrins
Sub ClassChlorohydrins
Direct ParentChlorohydrins
Alternative Parents
Substituents
  • Chlorohydrin
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0076 g/LALOGPS
logP3.96ALOGPS
logP-0.53ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-0.96ChemAxon
pKa (Strongest Basic)12.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area174.72 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity198.65 m³·mol⁻¹ChemAxon
Polarizability74.25 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-0cf34e5ca3aa1cabaa8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-0cf34e5ca3aa1cabaa8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0000000900-0cf34e5ca3aa1cabaa8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-c5b70513d21499cd5a1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000000900-c5b70513d21499cd5a1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0000000900-c5b70513d21499cd5a1aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSaquinavir
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID60934
Kegg Compound IDC12560
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available