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
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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| Pharmacological profile of semotiadil fumarate, a novel calcium antagonist, in rat experimental angina model. | 1995 Sep |
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| Semotiadil improves survival of rats with monocrotaline-induced pulmonary hypertension: comparison with diltiazem. | 1996 Jan 11 |
Patents
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116476-14-3
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6437846
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m9855
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48E2Q389VX
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DTXSID201034884
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
