U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C28H39N7O9
Molecular Weight 617.6508
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROTIGAPTIDE

SMILES

C[C@@H](NC(=O)CNC(=O)[C@H]1C[C@H](O)CN1C(=O)[C@H]2CCCN2C(=O)[C@@H](CC3=CC=C(O)C=C3)NC(C)=O)C(=O)NCC(N)=O

InChI

InChIKey=GFJRASPBQLDRRY-TWTQBQJDSA-N
InChI=1S/C28H39N7O9/c1-15(25(41)30-12-23(29)39)32-24(40)13-31-26(42)22-11-19(38)14-35(22)28(44)21-4-3-9-34(21)27(43)20(33-16(2)36)10-17-5-7-18(37)8-6-17/h5-8,15,19-22,37-38H,3-4,9-14H2,1-2H3,(H2,29,39)(H,30,41)(H,31,42)(H,32,40)(H,33,36)/t15-,19+,20-,21-,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula C28H39N7O9
Molecular Weight 617.6508
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Rotigaptide (previously known as ZP123) originally was developed by Zealand Pharma as a stable antiarrhythmic peptide analog, which maintains gap junction intercellular communication. Then this drug was licensed to Wyeth Pharmaceuticals where it studied in phase II clinical trials in patients with coronary artery disease and with atrial fibrillation. However, these researches have been discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
ZP123 increases gap junctional conductance and prevents reentrant ventricular tachycardia during myocardial ischemia in open chest dogs.
2003 May
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:00:17 GMT 2023
Edited
by admin
on Sat Dec 16 16:00:17 GMT 2023
Record UNII
GFA1W6KO7N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROTIGAPTIDE
INN   USAN  
USAN   INN  
Official Name English
ROTIGAPTIDE [USAN]
Common Name English
ZP-123 (ZEALAND)
Code English
ZP-123
Code English
rotigaptide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C152260
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
DRUG BANK
DB13067
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
WIKIPEDIA
ROTIGAPTIDE
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
USAN
RR-54
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
PUBCHEM
9938933
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
MESH
C477643
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL450656
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
CAS
355151-12-1
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID80189024
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
FDA UNII
GFA1W6KO7N
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
INN
8717
Created by admin on Sat Dec 16 16:00:17 GMT 2023 , Edited by admin on Sat Dec 16 16:00:17 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> ACTIVATOR
Rotigaptide has been shown to activate various protein kinase C (PKC) isoforms to cause the phosphorylation of Cx43, Rotigaptide (RG, ZP123) prevents of dephosphorylation and thereby uncoupling of 24 Connexin-43 (Cx43), possibly via action on unidentified protein phosphatases.
Related Record Type Details
ACTIVE MOIETY