Details of the Drug

General Information of Drug (ID: DMXB9RS)

Drug Name
ROTIGAPTIDE
Synonyms GAP-486; Rotigaptide < USAN; ZP-123; N-Acetyl-D-tyrosyl-D-prolyl-4(S)-hydroxy-D-prolyl-glycyl-D-alanyl-glycinamide
Indication
Disease Entry ICD 11 Status REF
Cardiac arrhythmias BC9Z Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 617.7
Logarithm of the Partition Coefficient (xlogp) -2.3
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 7
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C28H39N7O9
IUPAC Name
(2R,4S)-1-[(2R)-1-[(2R)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]-N-[2-[[(2R)-1-[(2-amino-2-oxoethyl)amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-4-hydroxypyrrolidine-2-carboxamide
Canonical SMILES
C[C@H](C(=O)NCC(=O)N)NC(=O)CNC(=O)[C@H]1C[C@@H](CN1C(=O)[C@H]2CCCN2C(=O)[C@@H](CC3=CC=C(C=C3)O)NC(=O)C)O
InChI
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
InChIKey
GFJRASPBQLDRRY-TWTQBQJDSA-N
Cross-matching ID
PubChem CID
9938933
CAS Number
355151-12-1
DrugBank ID
DB13067
TTD ID
D0C4QN

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Gap junction protein (GJP) TTJO6E9 NOUNIPROTAC Modulator [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00137332) Study Evaluating GAP-486 on Heart Rhythm in Patients With Coronary Artery Disease. U.S. National Institutes of Health.
2 The antiarrhythmic peptide rotigaptide (ZP123) increases gap junction intercellular communication in cardiac myocytes and HeLa cells expressing connexin 43. Br J Pharmacol. 2006 Mar;147(5):486-95.