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

Molecular Formula C29H32N2O6S
Molecular Weight 536.639
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Semotiadil improves survival of rats with monocrotaline-induced pulmonary hypertension: comparison with diltiazem.
1996-01-11
Pharmacological profile of semotiadil fumarate, a novel calcium antagonist, in rat experimental angina model.
1995-09
Effects of semotiadil fumarate (SD-3211) on renal hemodynamics and function in dogs.
1992-08-06
Tissue selectivity of the novel calcium antagonist sesamodil fumarate in isolated smooth muscles and cardiac muscles.
1990-03
Patents
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:37:04 GMT 2025
Edited
by admin
on Wed Apr 02 09:37:04 GMT 2025
Record UNII
DGN08QZ30G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SEMOTIADIL [MI]
Preferred Name English
SEMOTIADIL
INN   MI  
INN  
Official Name English
SESAMODIL
Common Name English
semotiadil [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
Code System Code Type Description
CAS
116476-13-2
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
MERCK INDEX
m9855
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY Merck Index
INN
6706
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
NCI_THESAURUS
C72624
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
PUBCHEM
65929
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
EVMPD
SUB10481MIG
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
SMS_ID
100000084091
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
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MESH
C064356
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
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WIKIPEDIA
SESAMODIL
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID30869602
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
FDA UNII
DGN08QZ30G
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
ChEMBL
CHEMBL2107501
Created by admin on Wed Apr 02 09:37:04 GMT 2025 , Edited by admin on Wed Apr 02 09:37:04 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> ENANTIOMER
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY