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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO3.C4H4O4
Molecular Weight 531.5962
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ZAMIFENACIN FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.C(CC1=CC2=C(OCO2)C=C1)N3CCC[C@H](C3)OC(C4=CC=CC=C4)C5=CC=CC=C5

InChI

InChIKey=PMHKTAIGYOVZEZ-ZHWJIHCSSA-N
InChI=1S/C27H29NO3.C4H4O4/c1-3-8-22(9-4-1)27(23-10-5-2-6-11-23)31-24-12-7-16-28(19-24)17-15-21-13-14-25-26(18-21)30-20-29-25;5-3(6)1-2-4(7)8/h1-6,8-11,13-14,18,24,27H,7,12,15-17,19-20H2;1-2H,(H,5,6)(H,7,8)/b;2-1+/t24-;/m1./s1

HIDE SMILES / InChI
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE
Molecular Formula C27H29NO3
Molecular Weight 415.5241
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Zamifenacin, also known as UK-76654, a selective muscarinic M3 receptor antagonist, was studied in patients with irritable bowel syndrome (IBS). This drug participated in clinical trials for the IBS phase III in the USA and phase II in the UK, but these studies were discontinued.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Muscarinic acetylcholine receptor M3
159
Target ID: P20309
Gene ID: 1131.0
Gene Symbol: CHRM3
Target Organism: Homo sapiens (Human)
Antagonist
2778
 8.52 null [pKi]
PubMed

PubMed

TitleDatePubMed
Characterization of the interaction of zamifenacin at muscarinic receptors in vitro.
1995 Oct 16
In vitro toxicity of zamifenacin (UK-76,654) and metabolites in primary hepatocyte cultures.
1998 Sep
Patents

Patents

20050004155
2
JPH07157469A
2

Sample Use Guides

In Vivo Use Guide
single dose of zamifenacin 10 mg or 40 mg on both fasting (30 min) and fed (60 min)
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:30:17 GMT 2023
Edited
by admin
on Sat Dec 16 08:30:17 GMT 2023
Record UNII
YCS9BM2UNR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZAMIFENACIN FUMARATE
Common Name English
UK-76654-2
Code English
PIPERIDINE, 1-(2-(1,3-BENZODIOXOL-5-YL)ETHYL)-3-(DIPHENYLMETHOXY)-, (3R)-, (2E)-2-BUTENEDIOATE (1:1)
Systematic Name English
(R)-3-(BENZHYDRYLOXY)-1-(2-(BENZO(D)(1,3)DIOXOL-5-YL)ETHYL)PIPERIDINE FUMARATE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID9049037
Created by admin on Sat Dec 16 08:30:17 GMT 2023 , Edited by admin on Sat Dec 16 08:30:17 GMT 2023
PRIMARY
PUBCHEM
60196362
Created by admin on Sat Dec 16 08:30:17 GMT 2023 , Edited by admin on Sat Dec 16 08:30:17 GMT 2023
PRIMARY
CAS
127308-98-9
Created by admin on Sat Dec 16 08:30:17 GMT 2023 , Edited by admin on Sat Dec 16 08:30:17 GMT 2023
PRIMARY
FDA UNII
YCS9BM2UNR
Created by admin on Sat Dec 16 08:30:17 GMT 2023 , Edited by admin on Sat Dec 16 08:30:17 GMT 2023
PRIMARY
Related Record Type Details
Structure of ZAMIFENACIN
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NIH
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