Mibefradil: Difference between revisions

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Mibefradil
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a607007
Routes of; administration	Oral
ATC code	C08CX01 (WHO) ;
Legal status
Legal status	Withdrawn from market;
Pharmacokinetic data
Bioavailability	70 %
Protein binding	> 99 %
Metabolism	Hepatic
Elimination half-life	17-25 h
Identifiers
	IUPAC 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;
CAS Number	116644-53-2 ;
PubChem CID	60662;
DrugBank	DB01388 ;
ChemSpider	54673 ;
UNII	27B90X776A;
KEGG	D08217 ;
ChEMBL	ChEMBL45816 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C29H38FN3O3
Molar mass	495.63 g/mol
3D model (JSmol)	Interactive image;
Melting point	128 °C (262.4 °F) (dihydrochloride salt)
	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;
	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 ; Key:HBNPJJILLOYFJU-VMPREFPWSA-N ;
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VisualWikitext

Latest revision as of 19:24, 8 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Mibefradil (Posicor) is a drug for the treatment of hypertension and chronic angina pectoris. It belongs to a group known as calcium channel blockers.

It is nonselective.^[1]

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. ^[2]

Synthesis

References

↑ Bezprozvanny I, Tsien RW (September 1995). "Voltage-dependent blockade of diverse types of voltage-gated Ca2+ channels expressed in Xenopus oocytes by the Ca2+ channel antagonist mibefradil (Ro 40-5967)". Mol. Pharmacol. 48 (3): 540–9. PMID 7565636.
↑ Heart Drug Withdrawn as Evidence Shows It Could Be Lethal: http://www.nytimes.com/1998/06/09/us/heart-drug-withdrawn-as-evidence-shows-it-could-be-lethal.html

Template:Membrane transport modulators

[pmid7565636-1] Bezprozvanny I, Tsien RW (September 1995). "Voltage-dependent blockade of diverse types of voltage-gated Ca2+ channels expressed in Xenopus oocytes by the Ca2+ channel antagonist mibefradil (Ro 40-5967)". Mol. Pharmacol. 48 (3): 540–9. PMID 7565636.

[2] Heart Drug Withdrawn as Evidence Shows It Could Be Lethal: http://www.nytimes.com/1998/06/09/us/heart-drug-withdrawn-as-evidence-shows-it-could-be-lethal.html

[1]

[2]

@@ Line 1: / Line 1: @@
+{{Drugbox
+| Verifiedfields = changed
+| Watchedfields = changed
+| verifiedrevid = 407797796
+| IUPAC_name = (1''S'',2''S'')-2-(2-((3-(1''H''-benzo[''d'']imidazol-2-yl)propyl) (methyl)amino)ethyl)-6-fluoro-1-isopropyl- 1,2,3,4-tetrahydronaphthalen-2-yl 2-methoxyacetate
+| image = Mibefradil.png
+<!--Clinical data-->
+| tradename =
+| Drugs.com = {{drugs.com|CONS|mibefradil}}
+| MedlinePlus = a607007
+| pregnancy_category =
+| legal_status = Withdrawn from market
+| routes_of_administration = Oral
+<!--Pharmacokinetic data-->
+| bioavailability = 70 %
+| protein_bound = > 99 %
+| metabolism = [[Hepatic]]
+| elimination_half-life =  17-25 h
+| excretion =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 116644-53-2
+| ATC_prefix = C08
+| ATC_suffix = CX01
+| PubChem = 60662
+| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
+| DrugBank = DB01388
+| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII = 27B90X776A
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D08217
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 45816
+| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
+| ChemSpiderID      = 54673
+<!--Chemical data-->
+| C=29 | H=38 | F=1 | N=3 | O=3
+| molecular_weight = 495.63 g/mol
+| 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
+| InChI             = 1/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
+| InChIKey          = HBNPJJILLOYFJU-VMPREFPWBB
+| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChI          = 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
+| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChIKey       = HBNPJJILLOYFJU-VMPREFPWSA-N
+| melting_point = 128
+| melting_notes = (dihydrochloride salt)
+}}
+__NOTOC__
 {{SI}}
-{{EH}}
+{{CMG}}
+==Overview==
+'''Mibefradil''' ('''Posicor''') is a drug for the treatment of [[hypertension]] and chronic [[angina pectoris]].  It belongs to a group known as [[calcium channel blockers]].
+It is nonselective.<ref name="pmid7565636">{{cite journal |author=Bezprozvanny I, Tsien RW |title=Voltage-dependent blockade of diverse types of voltage-gated Ca2+ channels expressed in Xenopus oocytes by the Ca2+ channel antagonist mibefradil (Ro 40-5967) |journal=Mol. Pharmacol. |volume=48 |issue=3 |pages=540–9 |date=September 1995 |pmid=7565636 |doi= |url=http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7565636}}</ref>
+On June 8, 1998, [[Hoffmann–La Roche|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. <ref>Heart Drug Withdrawn as Evidence Shows It Could Be Lethal: http://www.nytimes.com/1998/06/09/us/heart-drug-withdrawn-as-evidence-shows-it-could-be-lethal.html </ref>
+==Synthesis==
+[[File:Mibefradil1.png|thumb|600px|center|Mibefradil synthesis]]
+==References==
+{{Reflist|2}}
-==Mibefradil==
+{{Membrane transport modulators}}
-Mibefradil is a drug used to treat [[Angina pectoris|angina]] and high blood pressure.
-{{SIB}}
+[[Category:Calcium channel blockers]]
-[[Category:Drugs]]
+[[Category:Withdrawn drugs]]
-{{WH}}
+[[Category:Benzimidazoles]]
-{{WikiDoc Sources}}
+[[Category:Organofluorides]]
+[[Category:Ethers]]
+[[Category:Amines]]
+[[Category:Drug]]

Mibefradil: Difference between revisions

Latest revision as of 19:24, 8 April 2015

Overview

Synthesis

References

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