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
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
| 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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
Edited
Wed Apr 02 09:37:04 GMT 2025
by
admin
on
Wed Apr 02 09:37:04 GMT 2025
|
| Record UNII |
DGN08QZ30G
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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
|
PRIMARY | |||
|
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
|
PRIMARY | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
|