SEMOTIADIL FUMARATE

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

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.COC1=CC=C(OCCCN(C)CCOC2=CC3=C(OCO3)C=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

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564235 | https://www.ncbi.nlm.nih.gov/pubmed/8720589 | https://adisinsight.springer.com/drugs/800000198

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	8720589
Pharmacological profile of semotiadil fumarate, a novel calcium antagonist, in rat experimental angina model.	1995-09	8564235
Effects of semotiadil fumarate (SD-3211) on renal hemodynamics and function in dogs.	1992-08-06	1425946
Tissue selectivity of the novel calcium antagonist sesamodil fumarate in isolated smooth muscles and cardiac muscles.	1990-03	2112000

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:03:27 GMT 2025` Edited by `admin` on `Mon Mar 31 19:03:27 GMT 2025`
Record UNII	48E2Q389VX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SEMOTIADIL FUMARATE

Common Name

English

SD-3211

Preferred Name

English

2H-1,4-BENZOTHIAZIN-3(4H)-ONE, 2-(2-(3-((2-(1,3-BENZODIOXOL-5-YLOXY)ETHYL)METHYLAMINO)PROPOXY)-5-METHOXYPHENYL)-4-METHYL-, (R)-, (E)-2-BUTENEDIOATE (1:1)

Systematic Name

English

2H-1,4-BENZOTHIAZIN-3(4H)-ONE, 2-(2-(3-((2-(1,3-BENZODIOXOL-5-YLOXY)ETHYL)METHYLAMINO)PROPOXY)-5-METHOXYPHENYL)-4-METHYL-, (2R)-, (2E)-2-BUTENEDIOATE (1:1)

Systematic Name

English

SEMOTIADIL FUMARATE [JAN]

Common Name

English

SD3211

Code

English

SESAMODIL FUMARATE

Common Name

English

SEMOTIADIL FUMARATE [MI]

Common Name

English

Code System Code Type Description

CAS

116476-14-3