MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 326751 | Name: Mibefradil

Description:

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

Mibefradil, also known as Ro 405967 or Ro 40-5967, is a drug for the treatment of hypertension and chronic angina pectoris. It belongs to a group known as calcium channel blockers. The mechanism of action of mibefradil is characterized by the selective blockade of transient, low-voltage-activated (T-type) calcium channels over long-lasting, high-voltage-activated (L-type) calcium channels, which is probably responsible for many of its unique properties. It is nonselective. On June 8, 1998, Roche announced the voluntary withdrawal of the drug from the market, one year after approval by the FDA, due to the potential for drug interactions, some of them deadly, which may occur when it is taken together with some other medications.

Chemical Structure

Mibefradil
Mibefradil
CAS#116644-53-2 (free base)

Theoretical Analysis

MedKoo Cat#: 326751

Name: Mibefradil

CAS#: 116644-53-2 (free base)

Chemical Formula: C29H38FN3O3

Exact Mass: 495.2897

Molecular Weight: 495.64

Elemental Analysis: C, 70.28; H, 7.73; F, 3.83; N, 8.48; O, 9.68

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 #
116644-53-2 (bfree ase) 116666-63-8 (2HCl)
Synonym
Ro 405967; Ro-405967; Ro405967; Ro 40-5967; Ro-40-5967; Ro40-5967; Mibefradil; trade name: Posicor.
IUPAC/Chemical Name
(1S,2S)-2-(2-((3-(1H-benzo[d]imidazol-2-yl)propyl)(methyl)amino)ethyl)-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl 2-methoxyacetate
InChi Key
HBNPJJILLOYFJU-VMPREFPWSA-N
InChi Code
InChI=1S/C29H38FN3O3/c1-20(2)28-23-12-11-22(30)18-21(23)13-14-29(28,36-27(34)19-35-4)15-17-33(3)16-7-10-26-31-24-8-5-6-9-25(24)32-26/h5-6,8-9,11-12,18,20,28H,7,10,13-17,19H2,1-4H3,(H,31,32)/t28-,29-/m0/s1
SMILES Code
O=C(O[C@@]1(CCN(CCCC2=NC3=CC=CC=C3N2)C)[C@@H](C(C)C)C4=C(C=C(F)C=C4)CC1)COC
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

Preparing Stock Solutions

The following data is based on the product molecular weight 495.64 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.

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: Reimer EN, Walenda G, Seidel E, Scholl UI. CACNA1H(M1549V) mutant calcium channel causes autonomous aldosterone production in HAC15 cells and is inhibited by Mibefradil. Endocrinology. 2016 Jun 3:en20161170. [Epub ahead of print] PubMed PMID: 27258646. 2: Gomez-Lagunas F, Carrillo E, Pardo LA, Stühmer W. Gating Modulation of the Tumor-Related Kv10.1 Channel by Mibefradil. J Cell Physiol. 2016 Jun 3. doi: 10.1002/jcp.25448. [Epub ahead of print] PubMed PMID: 27255432. 3: Li HH, Xie LJ, Xiao TT, Huang M, Shen J. Mibefradil suppresses the proliferation of pulmonary artery smooth muscle cells. J Investig Med. 2016 Jan;64(1):45-9. doi: 10.1136/jim-d-15-00167. PubMed PMID: 26755813. 4: Krouse AJ, Gray L, Macdonald T, McCray J. Repurposing and Rescuing of Mibefradil, an Antihypertensive, for Cancer: A Case Study. Assay Drug Dev Technol. 2015 Dec;13(10):650-3. doi: 10.1089/adt.2015.29014.ajkdrrr. PubMed PMID: 26690767. 5: Schäfer S, Ferioli S, Hofmann T, Zierler S, Gudermann T, Chubanov V. Mibefradil represents a new class of benzimidazole TRPM7 channel agonists. Pflugers Arch. 2016 Apr;468(4):623-34. doi: 10.1007/s00424-015-1772-7. Epub 2015 Dec 16. PubMed PMID: 26669310. 6: Chen YL, Tsaur ML, Wang SW, Wang TY, Hung YC, Lin CS, Chang YF, Wang YC, Shiue SJ, Cheng JK. Chronic intrathecal infusion of mibefradil, ethosuximide and nickel attenuates nerve ligation-induced pain in rats. Br J Anaesth. 2015 Jul;115(1):105-11. doi: 10.1093/bja/aev198. PubMed PMID: 26089446. 7: Huang W, Lu C, Wu Y, Ouyang S, Chen Y. T-type calcium channel antagonists, mibefradil and NNC-55-0396 inhibit cell proliferation and induce cell apoptosis in leukemia cell lines. J Exp Clin Cancer Res. 2015 May 21;34:54. doi: 10.1186/s13046-015-0171-4. PubMed PMID: 25989794; PubMed Central PMCID: PMC4443536. 8: Fernández-Morales JC, Fernando Padín J, Vestring S, Musial DC, de Diego AM, García AG. Blockade by NNC 55-0396, mibefradil, and nickel of calcium and exocytotic signals in chromaffin cells: implications for the regulation of hypoxia-induced secretion at early life. Eur J Pharmacol. 2015 Mar 15;751:1-12. doi: 10.1016/j.ejphar.2015.01.025. Epub 2015 Jan 23. PubMed PMID: 25622555. 9: Lee JE, Kwon TH, Gu SJ, Lee DH, Kim BM, Lee JY, Lee JK, Seo SH, Pae AN, Keum G, Cho YS, Min SJ. Efficient synthesis of mibefradil analogues: an insight into in vitro stability. Org Biomol Chem. 2014 Aug 14;12(30):5669-81. doi: 10.1039/c4ob00504j. Epub 2014 Jun 25. PubMed PMID: 24964394. 10: Obradovic ALj, Hwang SM, Scarpa J, Hong SJ, Todorovic SM, Jevtovic-Todorovic V. CaV3.2 T-type calcium channels in peripheral sensory neurons are important for mibefradil-induced reversal of hyperalgesia and allodynia in rats with painful diabetic neuropathy. PLoS One. 2014 Apr 4;9(4):e91467. doi: 10.1371/journal.pone.0091467. eCollection 2014. PubMed PMID: 24705276; PubMed Central PMCID: PMC3976247. 11: Lu Y, Long M, Zhou S, Xu Z, Hu F, Li M. Mibefradil reduces blood glucose concentration in db/db mice. Clinics (Sao Paulo). 2014 Jan;69(1):61-7. doi: 10.6061/clinics/2014(01)09. PubMed PMID: 24473561; PubMed Central PMCID: PMC3870312. 12: Sheehan JP, Xu Z, Popp B, Kowalski L, Schlesinger D. Inhibition of glioblastoma and enhancement of survival via the use of mibefradil in conjunction with radiosurgery. J Neurosurg. 2013 Apr;118(4):830-7. doi: 10.3171/2012.11.JNS121087. Epub 2012 Nov 30. PubMed PMID: 23198803. 13: Hong da H, Yang D, Choi IW, Son YK, Jung WK, Kim DJ, Han J, Na SH, Park WS. The T-type Ca²⁺ channel inhibitor mibefradil inhibits voltage-dependent K⁺ channels in rabbit coronary arterial smooth muscle cells. J Pharmacol Sci. 2012;120(3):196-205. Epub 2012 Oct 27. PubMed PMID: 23117866. 14: Keir ST, Friedman HS, Reardon DA, Bigner DD, Gray LA. Mibefradil, a novel therapy for glioblastoma multiforme: cell cycle synchronization and interlaced therapy in a murine model. J Neurooncol. 2013 Jan;111(2):97-102. doi: 10.1007/s11060-012-0995-0. Epub 2012 Oct 20. PubMed PMID: 23086436. 15: Sekiguchi N, Kato M, Takada M, Watanabe H, Takata S, Mitsui T, Aso Y, Ishigai M. Quantitative prediction of mechanism-based inhibition caused by mibefradil in rats. Drug Metab Dispos. 2011 Jul;39(7):1255-62. doi: 10.1124/dmd.110.037903. Epub 2011 Apr 7. PubMed PMID: 21474682. 16: Foti RS, Rock DA, Pearson JT, Wahlstrom JL, Wienkers LC. Mechanism-based inactivation of cytochrome P450 3A4 by mibefradil through heme destruction. Drug Metab Dispos. 2011 Jul;39(7):1188-95. doi: 10.1124/dmd.111.038505. Epub 2011 Mar 29. PubMed PMID: 21447734. 17: Quesada A, Bui PH, Homanics GE, Hankinson O, Handforth A. Comparison of mibefradil and derivative NNC 55-0396 effects on behavior, cytochrome P450 activity, and tremor in mouse models of essential tremor. Eur J Pharmacol. 2011 May 20;659(1):30-6. doi: 10.1016/j.ejphar.2011.01.004. Epub 2011 Jan 21. PubMed PMID: 21256842; PubMed Central PMCID: PMC3988263. 18: Bancila M, Copin JC, Daali Y, Schatlo B, Gasche Y, Bijlenga P. Two structurally different T-type Ca 2+ channel inhibitors, mibefradil and pimozide, protect CA1 neurons from delayed death after global ischemia in rats. Fundam Clin Pharmacol. 2011 Aug;25(4):469-78. doi: 10.1111/j.1472-8206.2010.00879.x. Epub 2010 Oct 6. PubMed PMID: 21039820. 19: Lee JH, Kim JU, Kim C, Min CK. Inhibitory actions of mibefradil on steroidogenesis in mouse Leydig cells: involvement of Ca(2+) entry via the T-type Ca(2+) channel. Asian J Androl. 2010 Nov;12(6):807-13. doi: 10.1038/aja.2010.51. Epub 2010 Aug 9. PubMed PMID: 20694017; PubMed Central PMCID: PMC3739071. 20: Bui PH, Quesada A, Handforth A, Hankinson O. The mibefradil derivative NNC55-0396, a specific T-type calcium channel antagonist, exhibits less CYP3A4 inhibition than mibefradil. Drug Metab Dispos. 2008 Jul;36(7):1291-9. doi: 10.1124/dmd.107.020115. Epub 2008 Apr 14. PubMed PMID: 18411403; PubMed Central PMCID: PMC2927974.

View History

Micarosyl protylonolide

Micarosyl protylonolide