Home > Compound List > Compound details
150378-17-9 molecular structure
click picture or here to close

(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 and InChIs

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

Cite this record

CBID:109 http://www.chembase.cn/molecule-109.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
150378-17-9
PubChem SID
46506442
160963572
PubChem CID
5362440

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.191399  H Acceptors
H Donor LogD (pH = 5.5) 0.94212973 
LogD (pH = 7.4) 2.5233755  Log P 2.8099308 
Molar Refractivity 175.8941 cm3 Polarizability 68.852844 Å3
Polar Surface Area 118.03 Å2 Rotatable Bonds 12 
Lipinski's Rule of Five false 
Log P 3.26  LOG S -4.11 
Solubility (Water) 4.82e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
0.015 mg/ml expand Show data source
Hydrophobicity(logP)
2.9 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00224 external link
Item Information
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
    No data available
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle