Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H32N2O6S.C4H4O4 |
Molecular Weight | 652.711 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C(O)=O.COC1=CC=C(OCCCN(C)CCOC2=CC=C3OCOC3=C2)C(=C1)[C@H]4SC5=CC=CC=C5N(C)C4=O
InChI
InChIKey=DIEJEELGDWGUCV-CNTJLTAHSA-N
InChI=1S/C29H32N2O6S.C4H4O4/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;5-3(6)1-2-4(7)8/h4-5,7-12,17-18,28H,6,13-16,19H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/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 |
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
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 |
---|---|---|
Tissue selectivity of the novel calcium antagonist sesamodil fumarate in isolated smooth muscles and cardiac muscles. | 1990 Mar |
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Effects of semotiadil fumarate (SD-3211) on renal hemodynamics and function in dogs. | 1992 Aug 6 |
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Semotiadil improves survival of rats with monocrotaline-induced pulmonary hypertension: comparison with diltiazem. | 1996 Jan 11 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:07:35 GMT 2023
by
admin
on
Fri Dec 15 18:07:35 GMT 2023
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Record UNII |
48E2Q389VX
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Record Status |
Validated (UNII)
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Record Version |
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m9855
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PARENT -> SALT/SOLVATE |
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PARENT -> SALT/SOLVATE |
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