(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide

• ChemBase ID: 109
• Molecular Formular: C36H47N5O4
• Molecular Mass: 613.78948
• Monoisotopic Mass: 613.36280501
• SMILES: O[C@H](CN1[C@@H](CN(CC1)Cc1cccnc1)C(=O)NC(C)(C)C)C[C@H](C(=O)N[C@@H]1[C@H](O)Cc2c1cccc2)Cc1ccccc1
• Canonical SMILES: O[C@H](CN1CCN(C[C@H]1C(=O)NC(C)(C)C)Cc1cccnc1)C[C@H](C(=O)N[C@@H]1[C@H](O)Cc2c1cccc2)Cc1ccccc1
• InChI: InChI=1S/C36H47N5O4/c1-36(2,3)39-35(45)31-24-40(22-26-12-9-15-37-21-26)16-17-41(31)23-29(42)19-28(18-25-10-5-4-6-11-25)34(44)38-33-30-14-8-7-13-27(30)20-32(33)43/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45)/t28-,29+,31+,32-,33+/m1/s1
• InChIKey: CBVCZFGXHXORBI-PXQQMZJSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide
• IUPAC Traditional name: indinavir
• Brand Name: Crixivan
• Synonyms: Indinavir sulfate; Compound J; Indinavir

Database IDs

• CAS Number: 150378-17-9
• PubChem SID: 46506442; 160963572
• PubChem CID: 5362440

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.191399
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.94212973
• LogD (pH = 7.4): 2.5233755
• Log P: 2.8099308
• Molar Refractivity: 175.8941 cm^3
• Polarizability: 68.852844 Å^3
• Polar Surface Area: 118.03 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.26
• LOG S: -4.11
• Solubility (Water): 4.82e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.015 mg/ml
• Hydrophobicity(logP): 2.9

DETAILS

DrugBank - DB00224

• Drug Groups: approved
• Description: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability. [PubChem]
• Indication: Indinavir is an antiretroviral drug for the treatment of HIV infection.
• Pharmacology: Indinavir 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. Indinavir 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: Symptoms of overdose include myocardial infarction and angina pectoris.
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Hepatic. Seven metabolites have been identified, one glucuronide conjugate and six oxidative metabolites. In vitro studies indicate that cytochrome P-450 3A4 (CYP3A4) is the major enzyme responsible for formation of the oxidative metabolites.
• Absorption: Rapidly absorbed
• Half Life: 1.8 (± 0.4) hours
• Protein Binding: 60%
• Elimination: Less than 20% of indinavir is excreted unchanged in the urine.
• External Links: Wikipedia; RxList; Drugs.com