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

Molecular Formula C22H23FN4O2
Molecular Weight 394.442
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:44:15 GMT 2025
Edited
by admin
on Mon Mar 31 18:44:15 GMT 2025
Record UNII
BZ76J3N815
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ACTIVE MOIETY