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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H23FN4O2
Molecular Weight 394.442
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIMACALIB

SMILES

C[C@H](C1=NOC(NC(=N)N2CCOCC2)=C1)C3=CC=C(C(F)=C3)C4=CC=CC=C4

InChI

InChIKey=MYTIJGWONQOOLC-HNNXBMFYSA-N
InChI=1S/C22H23FN4O2/c1-15(17-7-8-18(19(23)13-17)16-5-3-2-4-6-16)20-14-21(29-26-20)25-22(24)27-9-11-28-12-10-27/h2-8,13-15H,9-12H2,1H3,(H2,24,25)/t15-/m0/s1

HIDE SMILES / InChI
Rimacalib (SMP 114) is a prostaglandin E2 antagonist that has been evaluated for use in rheumatoid arthritis. This orally bioavailable compound is a CaMKII inhibitor developed for human use. A phase II clinical trial to compare the effects of rimacalib to placebo in patients with rheumatoid arthritis has been terminated in 2009. Rimacalib also reduces SR Ca2+ leak and was therefore suggested as a candidate drug to treat proarrhythmogenic events in human atrial cardiomyocytes and cardiomyocytes from patients with heart failure.

Approval Year

Patents
Name Type Language
SMP-114
Preferred Name English
RIMACALIB
INN  
INN  
Official Name English
4-MORPHOLINECARBOXIMIDAMIDE, N-(3-((1S)-1-(2-FLUORO(1,1'-BIPHENYL)-4-YL)ETHYL)-5-ISOXAZOLYL)-
Systematic Name English
N-(3-((1S)-1-(2-FLUOROBIPHENYL-4-YL)ETHYL)-1,2-OXAZOL-5-YL)MORPHOLINE-4-CARBOXIMIDAMIDE
Systematic Name English
rimacalib [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL2107772
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY
INN
8597
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY
NCI_THESAURUS
C87325
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID401351185
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY
CAS
215174-50-8
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY
FDA UNII
BZ76J3N815
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY
PUBCHEM
9800765
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY
DRUG BANK
DB12571
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY
SMS_ID
100000175055
Created by admin on Mon Mar 31 18:44:15 GMT 2025 , Edited by admin on Mon Mar 31 18:44:15 GMT 2025
PRIMARY