(2S)-N-[(2S,3R)-4-[(3S)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinolin-2-ylformamido)butanediamide

• ChemBase ID: 1101
• Molecular Formular: C38H50N6O5
• Molecular Mass: 670.8408
• Monoisotopic Mass: 670.38426873
• SMILES: O=C(NC(C)(C)C)[C@H]1N(CC2C(C1)CCCC2)C[C@@H](O)[C@@H](NC(=O)[C@@H](NC(=O)c1nc2c(cc1)cccc2)CC(=O)N)Cc1ccccc1
• Canonical SMILES: NC(=O)C[C@@H](C(=O)N[C@H]([C@@H](CN1CC2CCCCC2C[C@H]1C(=O)NC(C)(C)C)O)Cc1ccccc1)NC(=O)c1ccc2c(n1)cccc2
• 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
• InChIKey: QWAXKHKRTORLEM-LINFGICFSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: saquinavir
• Brand Name: Fortovase; Invirase; ROC
• Synonyms: Saquinavir Mesylate; SQV; saquinavir; Saquinavir

Database IDs

• CAS Number: 127779-20-8
• PubChem SID: 46508726; 160964564
• PubChem CID: 60787

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.608145
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 0.2937352
• LogD (pH = 7.4): 2.0477285
• Log P: 3.1554067
• Molar Refractivity: 186.6732 cm^3
• Polarizability: 74.205475 Å^3
• Polar Surface Area: 166.75 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.04
• LOG S: -5.43
• Solubility (Water): 2.47e-03 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble
• Hydrophobicity(logP): 3.8

DETAILS

DrugBank - DB01232

• Drug Groups: approved; investigational
• Description: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases. [PubChem]
• Indication: For the treatment of HIV-1 with advanced immunodeficiency together with antiretroviral nucleoside analogues.
• Pharmacology: Saquinavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Saquinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.
• Toxicity: Probably experience pain in the throat
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Hepatic
• Absorption: Absolute bioavailability averages 4%
• Protein Binding: 98%
• Elimination: In vitro studies using human liver microsomes have shown that the metabolism of saquinavir is cytochrome P450 mediated with the specific isoenzyme, CYP3A4, responsible for more than 90% of the hepatic metabolism. Only 1% of saquinavir is excreted in the urine, so the impact of renal impairment on saquinavir elimination should be minimal.
• Distribution: * 700 L
• Clearance: * 1.14 L/h/kg [Healthy volunteers receiving IV doses of 6, 36, and 72 mg]
• References: Forestier F, de Renty P, Peytavin G, Dohin E, Farinotti R, Mandelbrot L: Maternal-fetal transfer of saquinavir studied in the ex vivo placental perfusion model. Am J Obstet Gynecol. 2001 Jul;185(1):178-81. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Forestier F, de Renty P, Peytavin G, Dohin E, Farinotti R, Mandelbrot L: Maternal-fetal transfer of saquinavir studied in the ex vivo placental perfusion model. Am J Obstet Gynecol. 2001 Jul;185(1):178-81. Pubmed