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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
Molecular Formula C27H36N4O3
Molecular Weight 464.5997
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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
238
Curator's Comment: # Merck & Co

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Evaluation of an International Pharmacopoeia method for the analysis of indinavir sulfate by liquid chromatography.
2006-09-11
Determination of indinavir, potassium sorbate, methylparaben, and propylparaben in aqueous pediatric suspensions.
1999-04
Species differences in the pharmacokinetics and metabolism of indinavir, a potent human immunodeficiency virus protease inhibitor.
1996-10
Patents

Patents

WO2006050964
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:19:58 GMT 2025
Edited
by admin
on Mon Mar 31 22:19:58 GMT 2025
Record UNII
4L1DMF47VA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDINAVIR LACTONE
Common 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
Preferred 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
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 Mon Mar 31 22:19:58 GMT 2025 , Edited by admin on Mon Mar 31 22:19:58 GMT 2025
PRIMARY
CAS
913293-57-9
Created by admin on Mon Mar 31 22:19:58 GMT 2025 , Edited by admin on Mon Mar 31 22:19:58 GMT 2025
PRIMARY
PUBCHEM
72941947
Created by admin on Mon Mar 31 22:19:58 GMT 2025 , Edited by admin on Mon Mar 31 22:19:58 GMT 2025
PRIMARY
Related Record Type Details
Structure of INDINAVIR SULFATE ETHANOLATE
PARENT -> IMPURITY
Structure of INDINAVIR SULFATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
NIH
NCATS
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