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

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H32N2O6S
Molecular Weight 536.639
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEMOTIADIL

SMILES

COC1=CC([C@H]2SC3=C(C=CC=C3)N(C)C2=O)=C(OCCCN(C)CCOC4=CC5=C(OCO5)C=C4)C=C1

InChI

InChIKey=RKXVEXUAWGRFNP-MUUNZHRXSA-N
InChI=1S/C29H32N2O6S/c1-30(14-16-34-21-10-12-25-26(18-21)37-19-36-25)13-6-15-35-24-11-9-20(33-3)17-22(24)28-29(32)31(2)23-7-4-5-8-27(23)38-28/h4-5,7-12,17-18,28H,6,13-16,19H2,1-3H3/t28-/m1/s1

HIDE SMILES / InChI
Semotiadil (also known as sesamodil or SD 3211) is a (+)-(R)-stereoisomer, the corresponding (−)-(S)-stereoisomer is called levosemotiadil. Semotiadil, a benzothiazine derivative was developed as a novel Ca2+ channel blocker with antiplatelet activity. Experiments on rodents have revealed that the drug had an advantage in the treatment of angina with regard to long-lasting action and selectivity for coronary artery and myocardium. In addition, semotiadil improved survival of rats with monocrotaline-induced pulmonary hypertension: comparison with diltiazem. Semotiadil was studied in phase II clinical trials for the treatment of angina pectoris and hypertension in Europe, and in Japan for the treatment of arrhythmias. However, the further development of semotiadil has now been discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Tissue selectivity of the novel calcium antagonist sesamodil fumarate in isolated smooth muscles and cardiac muscles.
1990 Mar
Effects of semotiadil fumarate (SD-3211) on renal hemodynamics and function in dogs.
1992 Aug 6
Pharmacological profile of semotiadil fumarate, a novel calcium antagonist, in rat experimental angina model.
1995 Sep
Semotiadil improves survival of rats with monocrotaline-induced pulmonary hypertension: comparison with diltiazem.
1996 Jan 11
Patents
Name Type Language
SEMOTIADIL
INN   MI  
INN  
Official Name English
SEMOTIADIL [MI]
Common Name English
SESAMODIL
Common Name English
semotiadil [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
Code System Code Type Description
CAS
116476-13-2
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
MERCK INDEX
m9855
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY Merck Index
INN
6706
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
NCI_THESAURUS
C72624
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
PUBCHEM
65929
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
EVMPD
SUB10481MIG
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
SMS_ID
100000084091
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
MESH
C064356
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
WIKIPEDIA
SESAMODIL
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID30869602
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
FDA UNII
DGN08QZ30G
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL2107501
Created by admin on Sat Dec 16 17:50:07 UTC 2023 , Edited by admin on Sat Dec 16 17:50:07 UTC 2023
PRIMARY