Sesamodil | CAS#116476-13-2 | CAS#116476-14-3 | Calcium Channel Antagonist

MedKoo Cat#: 328111 | Name: Sesamodil

Description:

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

Sesamodil is a calcium channel antagonist potentially used for the treatment of angina pectoris and hypertension. Results suggest that Sesamodil exerts a potent and long-lasting Ca2+ antagonistic effect on isolated arteries, possessing pharmacological properties diverse from those of known Ca2+ antagonists with respect to tissue selectivity, i.e., it is more vasoselective than diltiazem and verapamil, and more cardioselective than nifedipine and nicardipine.

Chemical Structure

Sesamodil

CAS#116476-13-2 (free base)

Theoretical Analysis

MedKoo Cat#: 328111

Name: Sesamodil

CAS#: 116476-13-2 (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.

Bulk Inquiry

Related CAS #

116476-14-3 (fumarate) 116476-13-2 (free base)

Synonym

Sesamodil; Sesamodil fumarate; SD 3211; SD-3211; SD3211; DS-4823; DS 4823; DS4823; Semotiadil

IUPAC/Chemical Name

(R)-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-MUUNZHRXSA-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-/m1/s1

SMILES Code

O=C1[C@@H](C2=CC(OC)=CC=C2OCCCN(CCOC3=CC=C(OCO4)C4=C3)C)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

>2 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

2934.99.9001

More Info

Related CAS# 116476-13-2 (Sesamodil free base); 116476-14-3 (Sesamodil fumarate)

Instruction

View handling instruction

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

1: Morishima K, Tahara R, Horiuchi M. Determination of a new calcium antagonist, sesamodil fumarate (SD-3211), and its metabolite in plasma by liquid chromatography with electrochemical detection. J Chromatogr. 1990 May 18;527(2):381-8. PubMed PMID: 2387885. 2: Nishimura K, Miyawaki N, Yamauchi H, Iso T. Tissue selectivity of the novel calcium antagonist sesamodil fumarate in isolated smooth muscles and cardiac muscles. Arzneimittelforschung. 1990 Mar;40(3):244-8. PubMed PMID: 2112000. 3: 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. 4: 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. 5: 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. 6: 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. 7: Nakajima M, Suzuki M, Yamaji R, Takashina H, Shimada N, Yamazaki H, Yokoi T. Isoform selective inhibition and inactivation of human cytochrome P450s by methylenedioxyphenyl compounds. Xenobiotica. 1999 Dec;29(12):1191-202. PubMed PMID: 10647906. 8: 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. 9: 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. 10: 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.