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Revision as of 06:08, 14 January 2011 editPashihiko (talk | contribs)Extended confirmed users3,559 editsNo edit summary← Previous edit		Latest revision as of 23:54, 22 October 2023 edit undoKimen8 (talk | contribs)Extended confirmed users5,112 edits change generic short description
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			{{Short description|Withdrawn antihypertensive drug of the calcium channel blocker class}}
	{{Drugbox|		{{Drugbox
⚫	|IUPAC_name = (1''S'',2''S'')-2-(2-((3-(1''H''-benzoimidazol-2-yl)propyl) (methyl)amino)ethyl)-6-fluoro-1-isopropyl- 1,2,3,4-tetrahydronaphthalen-2-yl 2-methoxyacetate
			| Verifiedfields = changed
⚫	| image = Mibefradil.png
			| Watchedfields = changed
⚫	| CAS_number=116644-53-2
			| verifiedrevid = 407797796
	| CAS_supplemental=
		⚫	| IUPAC_name = (1''S'',2''S'')-2-(2-((3-(1''H''-benzoimidazol-2-yl)propyl) (methyl)amino)ethyl)-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl 2-methoxyacetate
⚫	| ATC_prefix=C08
		⚫	| image = Mibefradil.svg
⚫	| ATC_suffix=CX01
			| width = 275
	| ATC_supplemental=
⚫	| PubChem=60662
			<!--Clinical data-->
⚫	| DrugBank=
			| tradename = Posicor
			| Drugs.com = {{drugs.com|CONS|mibefradil}}
			| MedlinePlus = a607007
		⚫	| pregnancy_category =
		⚫	| legal_status = Withdrawn from market
			| routes_of_administration = ] (])
			<!--Pharmacokinetic data-->
		⚫	| bioavailability = 70%
			| protein_bound = >99%
		⚫	| metabolism = ] (])
		⚫	| elimination_half-life = 17–25 hours
		⚫	| excretion =
			<!--Identifiers-->
			| IUPHAR_ligand = 2522
			| 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		| KEGG = D08217
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 45816
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 54673
			| PDB_ligand = MWV
			<!--Chemical data-->
	| C=29 | H=38 | F=1 | N=3 | O=3		| C=29 | H=38 | F=1 | N=3 | O=3
			| smiles = CC(C)1C2=C(CC1(CCN(C)CCCC3=NC4=CC=CC=C4N3)OC(=O)COC)C=C(C=C2)F
	| molecular_weight = 495.63 g/mol
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫	| bioavailability=
			| 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
⚫	| metabolism =
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫	| elimination_half-life=
			| StdInChIKey = HBNPJJILLOYFJU-VMPREFPWSA-N
⚫	| excretion =
			| melting_point = 128
⚫	| pregnancy_category =
			| melting_notes = (dihydrochloride salt)
⚫	| legal_status = Withdrawn from market
	| routes_of_administration= Oral
	}}		}}
		⚫	'''Mibefradil''' (trade name '''Posicor''') was a ] used for the treatment of ] and chronic ]. It is a nonselective ]. It was voluntary pulled from the market ten months after FDA approval, citing potential serious health hazards shown in post release studies.<ref name="pmid7565636">{{cite journal |vauthors=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 |url=http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7565636}}</ref>
	'''Mibefradil''' ('''Posicor''') is a drug for the treatment of ] and chronic ]. It belongs to a group known as ].
			The mechanism of action of mibefradil is characterized by the selective blockade of transient, low-voltage-activated (]) calcium channels over long-lasting, high-voltage-activated (]) calcium channels,<ref name="pmid7565636" /> which is probably responsible for many of its unique properties.{{fact|date=April 2022}}
⚫	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 |year=1995 |month=September |pmid=7565636 |doi= |url=http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7565636}}</ref>
	On June 8, 1998, ] announced the voluntary withdrawal of the drug from the market,<ref>Letter from Roche Laboratories: http://www.fda.gov/medwatch/SAFETY/1998/poscor.htm </ref> due to the potential for drug interactions, some of them serious, which may occur when it is taken together with some other medications.		On June 8, 1998, ] 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 name="Stolberg 1998">{{cite web | last=Stolberg | first=Sheryl Gay | title=Heart Drug Withdrawn as Evidence Shows It Could Be Lethal | website=The New York Times | date=1998-06-09 | url=https://www.nytimes.com/1998/06/09/us/heart-drug-withdrawn-as-evidence-shows-it-could-be-lethal.html | access-date=2019-01-12}}</ref>
			==Synthesis==
			]
	==References==		==References==
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	{{Membrane transport modulators}}		{{Membrane transport modulators}}
		⚫	]
	]
⚫	]
	]		]
	]		]
			]
			]
	]		]
	]		]
	]		]
			]
			]
	{{cardiovascular-drug-stub}}		{{cardiovascular-drug-stub}}