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@@H]2SC3=C(C=CC=C3)N(C)C2=O)=C(OCCCN(C)CCOC4=CC5=C(OCO5)C=C4)C=C1
InChI
InChIKey=DIEJEELGDWGUCV-NQTKYQIASA-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-;/m0./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 |
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 |
|---|---|---|
| Binding study of semotiadil and levosemotiadil with alpha(1)-acid glycoprotein using high-performance frontal analysis. | 1999 Oct 1 |
|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 05:12:39 GMT 2023
by
admin
on
Sat Dec 16 05:12:39 GMT 2023
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1GVF558KQJ
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| Record Status |
Validated (UNII)
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