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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H28N2O5
Molecular Weight 376.4467
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of (2S)-1-((2S)-2-(((1R)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)PROPANOYL)PYRROLIDINE-2-CARBOXYLIC ACID

SMILES

CCOC(=O)[C@@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(O)=O

InChI

InChIKey=GBXSMTUPTTWBMN-UAGQMJEPSA-N
InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16+,17-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H28N2O5
Molecular Weight 376.4467
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

(2S)-1-((2S)-2-(((1R)-1-(Ethoxycarbonyl)-3-Phenylpropyl)Amino)Propanoyl)Pyrrolidine-2-Carboxylic Acid is an epimer and synthetic impurity of Enalpril which is an angiotensin-converting-enzyme (ACE) inhibitor used in the treatment of hypertension, diabetic nephropathy, and some types of chronic heart failure.

Originator

Curator's Comment: # Merck

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
User-Friendly HPLC Method Development and Validation for Determination of Enalapril Maleate and Its Impurities in Enalapril Tablets.
2017 Nov 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 Sat Dec 16 05:44:29 UTC 2023
Edited
by admin
on Sat Dec 16 05:44:29 UTC 2023
Record UNII
S7IJ7OBG9V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(2S)-1-((2S)-2-(((1R)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)PROPANOYL)PYRROLIDINE-2-CARBOXYLIC ACID
Systematic Name English
ENALAPRIL MALEATE IMPURITY A [EP IMPURITY]
Common Name English
ENALAPRIL IMPURITY A
Common Name English
(S, S, R)-ENALAPRIL
Common Name English
L-PROLINE, N-((1R)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)-L-ALANYL-
Systematic Name English
Code System Code Type Description
PUBCHEM
5362032
Created by admin on Sat Dec 16 05:44:29 UTC 2023 , Edited by admin on Sat Dec 16 05:44:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID601181936
Created by admin on Sat Dec 16 05:44:29 UTC 2023 , Edited by admin on Sat Dec 16 05:44:29 UTC 2023
PRIMARY
CAS
76420-74-1
Created by admin on Sat Dec 16 05:44:29 UTC 2023 , Edited by admin on Sat Dec 16 05:44:29 UTC 2023
PRIMARY
FDA UNII
S7IJ7OBG9V
Created by admin on Sat Dec 16 05:44:29 UTC 2023 , Edited by admin on Sat Dec 16 05:44:29 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY