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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H36N4O3
Molecular Weight 464.5997
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDINAVIR LACTONE

SMILES

CC(C)(C)NC(=O)[C@@H]1CN(CC2=CC=CN=C2)CCN1C[C@@H]3C[C@@H](CC4=CC=CC=C4)C(=O)O3

InChI

InChIKey=MEAYEAZWSJPITC-SGNDLWITSA-N
InChI=1S/C27H36N4O3/c1-27(2,3)29-25(32)24-19-30(17-21-10-7-11-28-16-21)12-13-31(24)18-23-15-22(26(33)34-23)14-20-8-5-4-6-9-20/h4-11,16,22-24H,12-15,17-19H2,1-3H3,(H,29,32)/t22-,23+,24+/m1/s1

HIDE SMILES / InChI

Description

Indinavir lactone is a product of the primary degradation pathway for indinavir, which is the primary active ingredient in the HIV anti-retroviral therapy Crixivan. Degradation of Indinavir occurs when exposed to moisture or elevated temperature.

Originator

Merck
216
Curator's Comment: # Merck & Co

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Species differences in the pharmacokinetics and metabolism of indinavir, a potent human immunodeficiency virus protease inhibitor.
1996 Oct
Determination of indinavir, potassium sorbate, methylparaben, and propylparaben in aqueous pediatric suspensions.
1999 Apr
Evaluation of an International Pharmacopoeia method for the analysis of indinavir sulfate by liquid chromatography.
2006 Sep 11
Patents

Patents

WO2006050964
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
INDINAVIR LACTONE
Common Name English
(3R,5S)-3-BENZYL-5-(((2S)-2-((1,1-DIMETHYLETHYL)CARBAMOYL)-4-(PYRIDIN-3-YLMETHYL)PIPERAZIN-1-YL)METHYL)-4,5-DIHYDROFURAN-2(3H)-ONE
Systematic Name English
(S)-1-(((2S,4R)-4-BENZYL-5-OXOTETRAHYDROFURAN-2-YL)METHYL)-N-TERT-BUTYL-4-(PYRIDIN-3-YLMETHYL)PIPERAZINE-2-CARBOXAMIDE
Systematic Name English
D-ERYTHRO-PENTONIC ACID, 2,3,5-TRIDEOXY-5-((2S)-2-(((1,1-DIMETHYLETHYL)AMINO)CARBONYL)-4-(3-PYRIDINYLMETHYL)-1-PIPERAZINYL)-2-(PHENYLMETHYL)-, .GAMMA.-LACTONE
Common Name English
INDINAVIR SULFATE IMPURITY D [EP IMPURITY]
Common Name English
INDINAVIR SULFATE IMPURITY, INDINAVIR LACTONE- [USP IMPURITY]
Common Name English
Code System Code Type Description
FDA UNII
4L1DMF47VA
Created by admin on Sat Dec 16 08:50:07 GMT 2023 , Edited by admin on Sat Dec 16 08:50:07 GMT 2023
PRIMARY
CAS
913293-57-9
Created by admin on Sat Dec 16 08:50:07 GMT 2023 , Edited by admin on Sat Dec 16 08:50:07 GMT 2023
PRIMARY
PUBCHEM
72941947
Created by admin on Sat Dec 16 08:50:07 GMT 2023 , Edited by admin on Sat Dec 16 08:50:07 GMT 2023
PRIMARY
SUBSTANCE RECORD
Structure of INDINAVIR LACTONE
NIH
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