Levosemotiadil | CAS#116476-16-5 | antiarrhythmic agent

MedKoo Cat#: 598746 | Name: Levosemotiadil

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levosemotiadil is an antiarrhythmic agent with vasodilator properties.

Chemical Structure

Levosemotiadil

CAS#116476-16-5 (free base)

Theoretical Analysis

MedKoo Cat#: 598746

Name: Levosemotiadil

CAS#: 116476-16-5 (free base)

Chemical Formula: C29H32N2O6S

Exact Mass: 536.1981

Molecular Weight: 536.64

Elemental Analysis: C, 64.91; H, 6.01; N, 5.22; O, 17.89; S, 5.97

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

116476-17-6 (fumarate) 116476-16-5 (free base)

Synonym

Levosemotiadil;

IUPAC/Chemical Name

(S)-2-(2-(3-((2-(benzo[d][1,3]dioxol-5-yloxy)ethyl)(methyl)amino)propoxy)-5-methoxyphenyl)-4-methyl-2H-benzo[b][1,4]thiazin-3(4H)-one

InChi Key

RKXVEXUAWGRFNP-NDEPHWFRSA-N

InChi Code

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

SMILES Code

O=C1[C@H](C2=CC(OC)=CC=C2OCCCN(C)CCOC3=CC(OCO4)=C4C=C3)SC5=CC=CC=C5N1C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Levosemotiadil is an antiarrhythmic agent with vasodilator properties.

In vitro activity:

TBD

In vivo activity:

Negative chronotropic effect of levosemotiadil was examined using the heart rate response to isoproterenol and comparing it with response to propranolol. Levosemotiadil prevented VF in 64% (7 of 11) of the high-risk dogs. Heart rate responses to myocardial ischemia and to graded doses of isoproterenol were blunted by the high dose of levosemotiadil. Reference: J Cardiovasc Pharmacol. 2003 May;41(5):665-70. https://pubmed.ncbi.nlm.nih.gov/12717095/

Preparing Stock Solutions

The following data is based on the product molecular weight 536.64 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Adamson PB, Vanoli E, Shibano T, Foreman RD, Schwartz PJ. Combined sodium and calcium channel blockade in prevention of lethal arrhythmias. J Cardiovasc Pharmacol. 2003 May;41(5):665-70. doi: 10.1097/00005344-200305000-00001. PMID: 12717095.

In vitro protocol:

TBD

In vivo protocol:

1: Adamson PB, Vanoli E, Shibano T, Foreman RD, Schwartz PJ. Combined sodium and calcium channel blockade in prevention of lethal arrhythmias. J Cardiovasc Pharmacol. 2003 May;41(5):665-70. PubMed PMID: 12717095. 2: Ueda K, Yamaoka K, Rodriguez ME, Shibukawa A, Nakagawa T. Enantioselective local disposition of semotiadil (R-enantiomer) and levosemotiadil (S-enantiomer) in perfused rat liver. Drug Metab Dispos. 1997 Mar;25(3):281-6. PubMed PMID: 9172944. 3: Rodriguez Rosas ME, Shibukawa A, Yoshikawa Y, Kuroda Y, Nakagawa T. Binding study of semotiadil and levosemotiadil with alpha(1)-acid glycoprotein using high-performance frontal analysis. Anal Biochem. 1999 Oct 1;274(1):27-33. PubMed PMID: 10527493. 4: Rodriguez Rosas ME, Shibukawa A, Ueda K, Nakagawa T. Enantioselective protein binding of semotiadil and levosemotiadil determined by high-performance frontal analysis. J Pharm Biomed Anal. 1997 Jun;15(9-10):1595-601. PubMed PMID: 9226594. 5: Sasaki S, Nakagawa M. [Calcium channel blocker for therapy of patients with hypertension]. Nihon Rinsho. 1997 Aug;55(8):2061-6. Review. Japanese. PubMed PMID: 9284424. 6: Fujiki A, Tani M, Hayashi H, Mizumaki K, Inoue H, Uemura H, Nakaya H. Electrophysiologic effects of SD-3212, a new class I antiarrhythmic drug, on canine atrial flutter and atrial action-potential characteristics. J Cardiovasc Pharmacol. 1997 Apr;29(4):471-5. PubMed PMID: 9156356. 7: Wolfram RM, Kritz H, Oguogho A, Sinzinger H. Antiplatelet activity of semotiadil fumarate. Thromb Res. 2002 May 15;106(4-5):187-90. PubMed PMID: 12297124. 8: Nishiyama A, Tamaki T, Masumura H, He H, Kiyomoto H, Aki Y, Yamamoto A, Iwao H, Abe Y. Effects of semotiadil fumarate (SD-3211) on renal hemodynamics and function in dogs. Eur J Pharmacol. 1992 Aug 6;218(2-3):311-7. PubMed PMID: 1425946. 9: Takahashi N, Ito M, Ishida S, Fujino T, Maruyama T, Saikawa T. Electrophysiological effects of SD-3212, a novel antiarrhythmic agent, on rabbit hearts in vivo and in vitro. J Cardiovasc Pharmacol. 1995 Jun;25(6):1006-11. PubMed PMID: 7564327. 10: Koidl B, Miyawaki N, Tritthart HA. A novel benzothiazine Ca2+ channel antagonist, semotiadil, inhibits cardiac L-type Ca2+ currents. Eur J Pharmacol. 1997 Mar 19;322(2-3):243-7. PubMed PMID: 9098694. 11: Hirasawa A, Haruno A, Matsuzaki T, Hashimoto K. Effects of a new antiarrhythmic drug, SD-3212, on canine ventricular arrhythmia models. Jpn Heart J. 1992 Nov;33(6):851-61. PubMed PMID: 1299746. 12: Tomita K, Tomidokoro A, Tamaki Y, Araie M, Matsubara M, Fukaya Y. Effects of semotiadil, a novel calcium antagonist, on the retina and optic nerve head circulation. J Ocul Pharmacol Ther. 2000 Jun;16(3):231-9. PubMed PMID: 10872920. 13: Fujimura K, Ota A, Kawashima Y. Quantitative structure-activity relationships of Ca(2+)-antagonistic semotiadil congeners. Chem Pharm Bull (Tokyo). 1996 Mar;44(3):542-6. PubMed PMID: 8882451. 14: Kodama I, Suzuki R, Maruyama K, Toyama J. Electrophysiological effects of SD-3212, a new antiarrhythmic agent with vasodilator action, on guinea-pig ventricular cells. Br J Pharmacol. 1995 Jan;114(2):503-9. PubMed PMID: 7881749; PubMed Central PMCID: PMC1510254. 15: Miyawaki N, Furuta T, Shigei T, Yamauchi H, Iso T. Electrophysiological properties of SD-3211, a novel putative Ca2+ antagonist, in isolated guinea pig and rabbit hearts. J Cardiovasc Pharmacol. 1990 Nov;16(5):769-75. PubMed PMID: 1703599. 16: Mori T, Ishigai Y, Fukuzawa A, Chiba K, Shibano T. Pharmacological profile of semotiadil fumarate, a novel calcium antagonist, in rat experimental angina model. Br J Pharmacol. 1995 Sep;116(1):1668-72. PubMed PMID: 8564235; PubMed Central PMCID: PMC1908907. 17: Takahashi T, Kanda T, Imai S, Suzuki T, Kobayashi I, Murata K. Semotiadil inhibits the development of right ventricular hypertrophy and medial thickening of pulmonary arteries in a rat model of pulmonary hypertension. Cardiovasc Drugs Ther. 1995 Dec;9(6):809-14. PubMed PMID: 8850386. 18: Stark G, Kasper K, Stark U, Miyawaki N, Decrinis M, Tritthart HA. Effects of semotiadil, a novel Ca2+ channel antagonist, on the electrical activity of Langendorff-perfused guinea pig hearts in comparison with diltiazem, amlodipine and nifedipine. Eur J Pharmacol. 1995 Nov 3;286(1):71-8. PubMed PMID: 8566153. 19: Tsuchiya Y, Ohno H, Satoh H, Sugawara T, Kajimura T, Nomura M. Thyroid hypertrophic effect of semotiadil fumarate, a new calcium antagonist, in rats. J Toxicol Sci. 2000 May;25(2):121-30. PubMed PMID: 10845190. 20: Nakayama K, Nozawa Y, Fukuta Y. Allosteric interaction of semotiadil fumarate, a novel benzothiazine, with 1,4-dihydropyridines, phenylalkylamines, and 1,5-benzothiazepines at the Ca(2+)-channel antagonist binding sites in canine skeletal muscle membranes. J Cardiovasc Pharmacol. 1994 May;23(5):731-40. PubMed PMID: 7521455.