DANEGAPTIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H17N3O4
Molecular Weight	291.3025
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCC(=O)N1C[C@@H](C[C@H]1C(O)=O)NC(=O)C2=CC=CC=C2

InChI

InChIKey=BIZKIHUJGMSVFD-MNOVXSKESA-N

InChI=1S/C14H17N3O4/c15-7-12(18)17-8-10(6-11(17)14(20)21)16-13(19)9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,19)(H,20,21)/t10-,11+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C14H17N3O4
Molecular Weight	291.3025
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19175320 | https://www.ncbi.nlm.nih.gov/pubmed/29602883

Danegaptide (GAP-134) is a small dipeptide gap junction modifier, developed by Wyeth and Zealand Pharma. Danegaptide works by re-establishing of gap junction intercellular communications in adjacent cardiomyocytes, thus reversing cardiac conduction slowing and electrical heterogeneity thought to be responsible for arrhythmias. In a canine model of acute sterile pericarditis, Danegaptide significantly reduced AF duration and overall AF burden. Danegaptide was investigated in phase 2 clinical trial in patients with ST-segment elevation myocardial infarction (STEMI). It was found that administrations danegaptide to patients with STEMI did not improve myocardial salvage, and development of the drug was discontinued.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
gap junction assembly 3 Target ID: GO:0016264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19252062	Modulator 828

PubMed

Title	Date	PubMed
Discovery of (2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid hydrochloride (GAP-134)13, an orally active small molecule gap-junction modifier for the treatment of atrial fibrillation.	2009 Feb 26	19175320
GAP-134 ([2S,4R]-1-[2-aminoacetyl]4-benzamidopyrrolidine-2-carboxylic acid) prevents spontaneous ventricular arrhythmias and reduces infarct size during myocardial ischemia/reperfusion injury in open-chest dogs.	2009 Sep	19721133

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:33:23 UTC 2023` Edited by `admin` on `Fri Dec 15 16:33:23 UTC 2023`
Record UNII	PA0Y7735AT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DANEGAPTIDE

Official Name

English

GAP-134

Code

English

GLYCYL-(4R)-4-(BENZOYLAMINO)-L-PROLINE

Systematic Name

English

ZP-1609

Code

English

L-PROLINE, GLYCYL-4-(BENZOYLAMINO)-, (4R)-

Systematic Name

English

DANEGAPTIDE [USAN]

Common Name

English

(2S,4R)-1-(AMINOACETYL)-4-(BENZOYLAMINO)PYRROLIDINE-2-CARBOXYLIC ACID

Systematic Name

English

ZP1609

Code

English

Danegaptide [WHO-DD]

Common Name

English

danegaptide [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47793