LEVOSEMOTIADIL

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 Search

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-NDEPHWFRSA-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-/m0/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

Description
Sources: https://adisinsight.springer.com/drugs/800000187 | https://www.ncbi.nlm.nih.gov/pubmed/12717095 | https://www.ncbi.nlm.nih.gov/pubmed/9172944 | https://www.ncbi.nlm.nih.gov/pubmed/9226594

Levosemotiadil is an S-enantiomer of semotiadil. It is an antiarrhythmic drug with sodium and calcium channel blocking action, as well as potassium blocking activity. Levosemotiadil is bound strongly and enantioselectively to human serum albumin and human alpha1-acid glycoprotein. Since levosemotiadil is hydrophobic basic drug, it is likely that this drug is also bound to lipoprotein in human plasma. Levosemotiadil might be effective in prevention of lethal arrhythmias. It was shown, that levosemotiadil prevented ventricular fibrillation in 64% of the high-risk animals. Heart rate responses to myocardial ischemia and to graded doses of isoproterenol were blunted by the high dose of levosemotiadil. Levosemotiadil had been in phase II clinical trials by Santen Pharmaceutical for the treatment of arrhythmias. However, this study was discontinued.

Approval Year

PubMed

Title	Date	PubMed
Enantioselective protein binding of semotiadil and levosemotiadil determined by high-performance frontal analysis.	1997 Jun	9226594
Enantioselective local disposition of semotiadil (R-enantiomer) and levosemotiadil (S-enantiomer) in perfused rat liver.	1997 Mar	9172944
Binding study of semotiadil and levosemotiadil with alpha(1)-acid glycoprotein using high-performance frontal analysis.	1999 Oct 1	10527493
Efficient identification of photolabelled amino acid residues by combining immunoaffinity purification with MS: revealing the semotiadil-binding site and its relevance to binding sites for myristates in domain III of human serum albumin.	2002 Apr 15	11931649
Antiplatelet activity of semotiadil fumarate.	2002 May 15	12297124
Combined sodium and calcium channel blockade in prevention of lethal arrhythmias.	2003 May	12717095

Sample Use Guides

In Vivo Use Guide

15 and 30 mg/kg/day for 7 days

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:38:13 GMT 2023` Edited by `admin` on `Fri Dec 15 16:38:13 GMT 2023`
Record UNII	9VDH1G55NC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVOSEMOTIADIL

Official Name

English

levosemotiadil [INN]

Common Name

English

(-)-(S)-2-(5-METHOXY-2-(3-(METHYL(2-(3,4-(METHYLENEDIOXY)PHENOXY)ETHYL)AMINO)PROPOXY)PHENYL)-4-METHYL-2H-1,4-BENZOTHIAZIN-3(4H)-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29707