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MedKoo Cat#: 534029 | Name: Monatepil HCl

Description:

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

Monatepil is a calcium channel blocker and α1-adrenergic receptor antagonist used as an antihypertensive. At concentrations of 2 x 10(-5) M, monatepil increased the binding (248 +/- 43%; mean +/- SD), internalization (374 +/- 18%), and degradation (145 +/- 2%) of 125I-LDL in human skin fibroblasts (n = 3, p < 0.05). Monatepil maleate (30 mg/kg/day for 6 months, orally) inhibited the increases of ACAT activity and esterified cholesterol content by 51% and 71%, respectively. In in vitro experiments, monatepil maleate inhibited ACAT activity in a concentration-dependent manner, whereas it did not affect 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase activity.

Chemical Structure

Monatepil HCl
Monatepil HCl
CAS#103379-02-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 534029

Name: Monatepil HCl

CAS#: 103379-02-8 (HCl)

Chemical Formula: C28H31ClFN3OS

Exact Mass: 0.0000

Molecular Weight: 512.08

Elemental Analysis: C, 65.67; H, 6.10; Cl, 6.92; F, 3.71; N, 8.21; O, 3.12; S, 6.26

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 #
103377-41-9 (free base) 103379-03-9 (maleate) 132046-06-1 (delated) 103379-02-8 (HCl)
Synonym
Monatepil HCl; AJ 2615; AJ2615; AJ-2615;
IUPAC/Chemical Name
1-Piperazinebutanamide, N-(6,11-dihydrodibenzo(b,E)thiepin-11-yl)-4-(4-fluorophenyl), hydrochloride
InChi Key
SJLXYQPZWXMNNW-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H30FN3OS.ClH/c29-22-11-13-23(14-12-22)32-18-16-31(17-19-32)15-5-10-27(33)30-28-24-7-2-1-6-21(24)20-34-26-9-4-3-8-25(26)28;/h1-4,6-9,11-14,28H,5,10,15-20H2,(H,30,33);1H
SMILES Code
O=C(NC1C2=CC=CC=C2SCC3=CC=CC=C13)CCCN4CCN(C5=CC=C(F)C=C5)CC4.Cl
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 512.08 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.

Recalculate based on batch purity %
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: Liu MH, Floten SH, Yang Q, He GW. Inhibition of vasoconstriction by AJ-2615, a novel calcium antagonist with alpha(1)-adrenergic receptor blocking activity in human conduit arteries used as bypass grafts. Br J Clin Pharmacol. 2001 Sep;52(3):279-87. doi: 10.1046/j.0306-5251.2001.01444.x. PMID: 11560560; PMCID: PMC2014550. 2: Singh NK, Goyal RK. New classes of antihypertensive drugs: therapeutic potentials. Clin Exp Hypertens. 1999 Jan-Feb;21(1-2):137-43. doi: 10.3109/10641969909068656. PMID: 10052649. 3: Ikeno A, Sumiya T, Minato H, Fujitani B, Masuda Y, Hosoki K, Kurono M, Yasuba M. Effects of monatepil maleate, a new Ca2+ channel antagonist with alpha1-adrenoceptor antagonistic activity, on cholesterol absorption and catabolism in high cholesterol diet-fed rabbits. Jpn J Pharmacol. 1998 Nov;78(3):303-12. doi: 10.1254/jjp.78.303. PMID: 9869264. 4: Matsunaga A, Inoue T, Koga T, Mori K, Kugi M, Sasaki J, Arakawa K. Effects of monatepil, a novel calcium antagonist with alpha 1-adrenergic blocking activity, on the low-density lipoprotein receptor in human skin fibroblasts. Cardiovasc Drugs Ther. 1997 Dec;11(6):747-50. doi: 10.1023/a:1007710123290. PMID: 9512869. 5: Sumiya T, Ikeno A, Kato H, Fujitani B, Masuda Y, Hosoki K, Miyazaki M. Inhibitory effect of monatepil maleate on acyl-CoA:cholesterol acyltransferase activity in the liver of cholesterol-fed Japanese monkeys. Am J Hypertens. 1997 Jul;10(7 Pt 1):779-85. doi: 10.1016/s0895-7061(97)00066-6. PMID: 9234833. 6: Kurono M, Suzuki K, Yoshida K, Naruto S. Simultaneous determination of a novel calcium entry blocker, monatepil maleate, and its metabolites in rat plasma by means of solid-phase extraction and reversed-phase liquid chromatography with electrochemical detection. J Chromatogr B Biomed Sci Appl. 1997 Feb 21;689(2):427-32. doi: 10.1016/s0378-4347(96)00346-5. PMID: 9080333. 7: Hayashi K, Kuga Y, Nomura S, Okura Y, Tanaka K, Yasunobu Y, Nomura K, Shingu T, Kuwashima J, Kajiyama G. Inhibition of lipid hydroperoxidation of low density lipoprotein by the Ca(2+)-channel and alpha 1-adrenoceptor antagonist monatepil maleate. Arzneimittelforschung. 1996 Apr;46(4):378-81. PMID: 8740082. 8: Takeuchi H, Araki Y, Emaduddin M, Zhang W, Han XY, Salunga TL, Wong SM. Identifiable Achatina giant neurones: their localizations in ganglia, axonal pathways and pharmacological features. Gen Pharmacol. 1996 Jan;27(1):3-32. doi: 10.1016/0306-3623(95)00113-1. PMID: 8742492. 9: Nagata S, Hosoki K, Karasawa T. Long-lasting antagonistic effects of monatepil on Ca2+ current in guinea-pig ventricular cells. Arzneimittelforschung. 1995 Oct;45(10):1061-3. PMID: 8595058. 10: Honda Y, Masuda Y, Yoshida T, Sato F, Kurokawa M, Hosoki K. Studies on calcium antagonistic and alpha 1-adrenergic receptor blocking activities of monatepil maleate, its metabolites and their enantiomers. Arzneimittelforschung. 1995 Oct;45(10):1057-60. PMID: 8595057. 11: Gregoire JR, Sheps SG. Newer antihypertensive drugs. Curr Opin Cardiol. 1995 Sep;10(5):445-9. doi: 10.1097/00001573-199509000-00002. PMID: 7496051. 12: Sugimoto T, Hosoki K, Karasawa T. Relative contribution of alpha 1-adrenoceptor blocking activity to the hypotensive effect of the novel calcium antagonist monatepil. J Cardiovasc Pharmacol. 1995 Jul;26(1):55-60. doi: 10.1097/00005344-199507000-00009. PMID: 7564365. 13: Notake M, Kondo Y, Nomura H, Nakano K, Hosoki K, Miyazaki M. Up-regulation of hepatic LDL receptor gene expression by monatepil, a novel calcium antagonist, in high cholesterol diet-fed Japanese monkeys. Am J Hypertens. 1994 Nov;7(11):1026-30. doi: 10.1093/ajh/7.11.1026. PMID: 7848617. 14: Sasaki J, Ogihara T, Yokoyama M, Kajiyama G, Mashiba H, Sunaga T, Nonaka K, Shichiri M, Tanaka N, Arakawa K. Comparative effects of monatepil, a novel calcium antagonist with alpha 1-adrenergic-blocking activity, and nitrendipine on lipoprotein and carbohydrate metabolism in patients with hypertension. Am J Hypertens. 1994 Oct;7(10 Pt 2):161S-166S. doi: 10.1093/ajh/7.10.161s. PMID: 7826567. 15: Tsushima M, Koh H, Suzuki M, Kyotani S, Waki M, Nishioeda Y, Harano Y, Omae T. Noninvasive quantitative evaluation of early atherosclerosis and the effect of monatepil, a new antihypertensive agent. An interim report. Am J Hypertens. 1994 Oct;7(10 Pt 2):154S-160S. doi: 10.1093/ajh/7.10.154s. PMID: 7826566. 16: Ishii M, Iimura O, Yoshinaga K, Abe K, Inagaki Y, Yagi S, Kuramoto K, Kajiwara N, Saruta T, Kuramochi M, et al. The efficacy of monatepil, a new calcium antagonist, in the treatment of essential hypertension. Am J Hypertens. 1994 Oct;7(10 Pt 2):141S-145S. doi: 10.1093/ajh/7.10.141s. PMID: 7826564. 17: Miyazaki M. Antihypertensive, antiatherosclerotic, and plasma lipid-lowering effects of monatepil, a novel calcium antagonist with alpha 1-adrenoceptor- blocking activity in experimental animals. Am J Hypertens. 1994 Oct;7(10 Pt 2):131S-40S. doi: 10.1093/ajh/7.10.131s. PMID: 7826563. 18: Nayler WG. New therapeutic trends in calcium antagonism. Are they meaningful? Am J Hypertens. 1994 Oct;7(10 Pt 2):126S-130S. doi: 10.1093/ajh/7.10.126s. PMID: 7826562. 19: Yamamoto T, Hosoki K, Kikuta C, Karasawa T. Preventive effect of monatepil on thromboxane A2 agonist-induced myocardial ischemia in rats. Arzneimittelforschung. 1994 Jun;44(6):712-4. PMID: 8053969. 20: Miyazaki M, Hosoki K, Okunishi H, Ishii K, Ikeno A, Okazaki Y. Anti- atherosclerotic and plasma lipid lowering effects of the novel calcium blocker with alpha 1-adrenoceptor antagonistic activity, monatepil, in high cholesterol diet-fed Japanese Macaca fuscata monkeys. Arzneimittelforschung. 1994 Mar;44(3):288-97. PMID: 8192692.

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