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2D Structure
Also known as: 116644-53-2, Mibefradil [inn:ban], Ro 40-5967, Mibefradil (inn), Mibefradil hcl, [(1s,2s)-2-[2-[3-(1h-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1h-naphthalen-2-yl] 2-methoxyacetate
Molecular Formula
C29H38FN3O3
Molecular Weight
495.6  g/mol
InChI Key
HBNPJJILLOYFJU-VMPREFPWSA-N
FDA UNII
27B90X776A

A benzimidazoyl-substituted tetraline that selectively binds and inhibits CALCIUM CHANNELS, T-TYPE.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(1S,2S)-2-[2-[3-(1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] 2-methoxyacetate
2.1.2 InChI
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
2.1.3 InChI Key
HBNPJJILLOYFJU-VMPREFPWSA-N
2.1.4 Canonical SMILES
CC(C)C1C2=C(CCC1(CCN(C)CCCC3=NC4=CC=CC=C4N3)OC(=O)COC)C=C(C=C2)F
2.1.5 Isomeric SMILES
CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=CC=CC=C4N3)OC(=O)COC)C=C(C=C2)F
2.2 Other Identifiers
2.2.1 UNII
27B90X776A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Mibefradil Dihydrochloride

2. Posicor

3. Ro 40 5967

4. Ro 40-5967

5. Ro 405967

2.3.2 Depositor-Supplied Synonyms

1. 116644-53-2

2. Mibefradil [inn:ban]

3. Ro 40-5967

4. Mibefradil (inn)

5. Mibefradil Hcl

6. [(1s,2s)-2-[2-[3-(1h-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1h-naphthalen-2-yl] 2-methoxyacetate

7. Chembl45816

8. Chebi:6920

9. 27b90x776a

10. Mibefradil [inn]

11. Acetic Acid, Methoxy-, (1s,2s)-2-[2-[[3-(1h-benzimidazol-2-yl)propyl]methylamino]ethyl]-6-fluoro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2-naphthalenyl Ester

12. Acetic Acid, Methoxy-, 2-(2-((3-(1h-benzimidazol-2-yl)propyl)methylamino)ethyl)-6-fluoro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2-naphthalenyl Ester, (1s-cis)-

13. Mls001056800

14. Mibefradil Dihydrochloride Hydrate

15. (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

16. (1s,2s)-2-(2-{[3-(1h-benzimidazol-2-yl)propyl](methyl)amino}ethyl)-6-fluoro-1-(propan-2-yl)-1,2,3,4-tetrahydronaphthalen-2-yl Methoxyacetate

17. Ac1l1toe

18. Smr000326970

19. Lopac-m-5441

20. Ro 405967

21. Ro 40 5967

22. Unii-27b90x776a

23. Mibefradil [mi]

24. Mibefradil [vandf]

25. Mibefradil [who-dd]

26. Lopac0_000748

27. Schembl39551

28. (1s-cis)-2-(2-((3-(1h-benzimidazol-2-yl)propyl)methylamino)ethyl)-6-fluoro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2-naphthalenyl Methoxyacetate

29. 2-(2-((3-(1h-benzimidazol-2-yl)propyl)methylamino)ethyl)-6-fluoro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2-naphthalenyl Methoxyacetate (1s-cis)-

30. Mibefradildihydrochloride

31. Gtpl2522

32. Dtxsid1023318

33. Bdbm78934

34. Cid_16746591

35. Bcp09875

36. Ro40-5967

37. Zinc3782486

38. Bdbm50117922

39. Nsc760798

40. Akos022185482

41. Ccg-204833

42. Cs-1218

43. Db01388

44. Nsc-760798

45. Sdccgsbi-0050726.p002

46. Ncgc00015683-01

47. Ncgc00161420-01

48. Ncgc00161420-03

49. Ncgc00161420-04

50. Ncgc00161420-12

51. (1s,2s)-(2-((3-(2-benzimidazolyl)propyl)methylamino)ethyl)-6-fluoro-1,2,3,4-tetrahydro-1-isopropyl-2-naphthyl Methoxyacetate

52. Hy-15553

53. Ro-405967-001

54. C07222

55. D08217

56. Q6827783

57. Brd-k09549677-300-01-8

58. (1s,2s)-2-(2-{[3-(1h-benzimidazol-2-yl)propyl](methyl)amino}ethyl)-6-fluoro-1-(1-methylethyl)-1,2,3,4-tetrahydronaphthalen-2-yl (methyloxy)acetate

59. (1s,2s)-2-[2-{[3-(1h-benzimidazol-2-yl)propyl]-methylamino }ethyl]-6-fluoro- 1-isopropyl- 1,2,3,4-tetrahydronaphthalen-2-yl Methoxyacetate

60. (1s,2s)-2-[2-{[3-(1h-benzimidazol-2-yl)propyl]-methylamino}ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl Methoxyacetate

61. (1s,2s)-2-[2-{[3-(1h-benzimidazol-2-yl)propyl]methylamino}ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl Methoxyacetate

62. [(1s,2s)-2-[2-[3-(1h-benzimidazol-2-yl)propyl-methyl-amino]ethyl]-6-fluoranyl-1-propan-2-yl-3,4-dihydro-1h-naphthalen-2-yl] 2-methoxyethanoate;hydrate;hydrochloride

63. [(1s,2s)-2-[2-[3-(1h-benzimidazol-2-yl)propyl-methyl-amino]ethyl]-6-fluoro-1-isopropyl-tetralin-2-yl] 2-methoxyacetate

64. [(1s,2s)-2-[2-[3-(1h-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1h-naphthalen-2-yl] 2-methoxyacetate;hydrate;hydrochloride

65. 2-{2-[3-(1h-benzoimidazol-2-yl)-propylamino]-ethyl}-6-fluoro-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl Ester(mibefradil)methoxy-acetic Acid

66. 2-methoxyacetic Acid [(1s,2s)-2-[2-[3-(1h-benzimidazol-2-yl)propyl-methyl-amino]ethyl]-6-fluoro-1-isopropyl-tetralin-2-yl] Ester;hydrate;hydrochloride

67. 2-methoxyacetic Acid [(1s,2s)-2-[2-[3-(1h-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1h-naphthalen-2-yl] Ester;hydrate;hydrochloride

68. Methoxy-acetic Acid (1s,2s)-2-(2-{[3-(1h-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-6-fluoro-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl Ester

69. Methoxy-acetic Acid 2-(2-{[3-(1h-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-6-fluoro-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl Ester

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 495.6 g/mol
Molecular Formula C29H38FN3O3
XLogP35.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count12
Exact Mass495.28972024 g/mol
Monoisotopic Mass495.28972024 g/mol
Topological Polar Surface Area67.4 Ų
Heavy Atom Count36
Formal Charge0
Complexity709
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For the treatment of angina and high blood pressure.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Mibefradil belongs to a group of medicines called calcium channel blocking agents, or, more commonly, calcium channel blockers. Calcium channel blocking agents affect the movement of calcium into the cells of the heart and blood vessels. As a result, they relax blood vessels and increase the supply of blood and oxygen to the heart while reducing its workload. Mibefradil is a benzimidazoyl-substituted tetraline that selectively binds and inhibits T-type calcium channels.


5.2 MeSH Pharmacological Classification

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)


Cytochrome P-450 CYP1A2 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)


Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


5.3 ATC Code

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CX - Other selective calcium channel blockers with mainly vascular effects

C08CX01 - Mibefradil


5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability after a single dose is 70%. After multiple dosing, the proportion of mibefradil undergoing first-pass metabolism is reduced, resulting in a steady state bioavailability of approximately 90%. Food does not affect the rate or extent of absorption of mibefradil.


5.5 Metabolism/Metabolites

The two metabolic pathways that mibefradil undergoes are esterase-catalyzed hydrolysis of the ester side chain (producing an alcohol metabolite) and cytochrome P450 3A4-catalyzed oxidation (that becomes less important during chronic dosing). The pharmacologic effect of the metabolite is approximately 10% of that of the parent mibefradil.


5.6 Biological Half-Life

17 to 25 hours at steady state.


5.7 Mechanism of Action

Mibefradil is a tetralol calcium channel blocking agent that inhibits the influx of calcium ions across both the T (low-voltage) and L (high-voltage) calcium channels of cardiac and vascular smooth muscle, with a greater selectivity for T channels. Vasodilation occurs in vascular smooth muscle, causing a decrease in peripheral vascular resistance and a resulting decrease in blood pressure. Mibefradil causes a slight increase in cardiac output during chronic dosing. Mibefradil slows sinus and atrioventricular (AV) node conduction, producing a slight reduction in heart rate and a slight increase in the PR interval. It has also been shown to slightly lengthen the corrected sinus node recovery time and AH interval and to raise the Wenckebach point. The mechanism by which mibefradil reduces angina is not known, but is thought to be attributed to a reduction in heart rate, total peripheral resistance (afterload), and the heart rate–systolic blood pressure product at any given level of exercise. The result of these effects is a decrease in cardiac workload and myocardial oxygen demand.