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Line 1: {{Short description\|Chemical compound}} ~~{{chembox~~ {{Drugbox \|ImageFile=Pronethalol.svg▼ \| IUPAC_name = 1-(naphthalen-2-yl)-2-(propan-2-ylamino)ethanol ~~\|ImageSize=~~ ▲\|~~ImageFile~~ image = Pronethalol.svg ~~\|IUPACName=(''RS'')-2-(isopropylamino)-1-(2-naphthyl)ethanol~~ \| chirality = [[Racemic mixture]] ~~\|OtherNames=~~ \| drug_name = ~~\|Section1={{Chembox Identifiers~~ <!--Clinical data--> \| CASNo=54-80-8▼ \| tradename = \| PubChem=4930▼ \| pregnancy_category = \| SMILES=CC(C)NCC(C1=CC2=CC=CC=C2C=C1)O▼ \| legal_status = Withdrawn ~~\| MeSHName=Pronethalol~~ \| routes_of_administration = Oral }} ~~\|Section2={{Chembox Properties~~ <!--Pharmacokinetic data--> ~~\| Formula=C<sub>15</sub>H<sub>19</sub>NO~~ \| bioavailability = ~~\| MolarMass=229.31746~~ \| metabolism = ~~\| Appearance=~~ \| elimination_half-life = ~~\| Density=~~ \| excretion = ~~\| MeltingPt=~~ ~~\| BoilingPt=~~ <!--Identifiers--> ~~\| Solubility=~~ \| CAS_number_Ref = {{cascite\|correct\|CAS}} }} ▲\| CAS_number ~~CASNo~~= 54-80-8 ~~\|Section3={{Chembox Hazards~~ \| ATC_prefix = none ~~\| MainHazards=~~ \| ATC_suffix = ~~\| FlashPt=~~ ▲\| PubChem = 4930 ~~\| Autoignition=~~ \| ChemSpiderID = 4761 }} \| ChEMBL = 16476 \| UNII_Ref = {{fdacite\|correct\|FDA}} \| UNII = XBP4RT1IMQ <!--Chemical data--> \| C=15 \| H=19 \| N=1 \| O=1 ▲\| smiles ~~SMILES~~= CC(C)NCC(C1=CC2=CC=CC=C2C=C1)O }} '''Pronethalol''' (also known as '''~~Alderlin~~nethalide''' or '''compound 38,174'''; trade name '''~~Nethalide~~Alderlin''') was an early non-selective [[beta blocker]] clinical candidate. It was ~~never~~the ~~used~~first ~~clinically~~beta ~~due~~blocker to be developed by [[~~carcinogenicity~~James Black (pharmacologist)\|James Black]] inand ~~mice,~~associates ~~which~~at ~~was~~[[Imperial ~~thought~~Chemical toIndustries]], ~~result~~and ~~from~~the ~~formation~~first ofto aenter ~~carcinogenic~~clinical ~~[[naphthalene~~use, ~~epoxide]]~~in ~~metabolite~~November 1963.<ref name=Quirke>{{cite journal \|~~author~~vauthors=~~Stapleton~~Quirke MPV \|title=~~Sir~~Putting ~~James~~theory ~~Black~~into ~~and~~practice: ~~propranolol.~~James ~~The~~Black, ~~role~~receptor oftheory and the ~~basic~~development ~~sciences in~~of the ~~history~~beta-blockers ofat ~~cardiovascular~~ICI, ~~pharmacology~~1958-1978 \|journal=~~Tex Heart Inst~~Med JHist \|volume=2450 \|issue=41 \|pages=~~336–42~~69–92 \|~~year~~date=~~1997~~January 2006 \|pmid=~~9456487~~16502872 \|pmc=~~325477~~1369014 \|doi=10.1017/s0025727300009455}}</ref> However, it was never used widely due to [[carcinogenicity]] in mice, which was thought to result from formation of a carcinogenic [[naphthalene epoxide]] metabolite,<ref>{{cite journal \| vauthors = Stapleton MP \| title = Sir James Black and propranolol. The role of the basic sciences in the history of cardiovascular pharmacology \| journal = Texas Heart Institute Journal \| volume = 24 \| issue = 4 \| pages = 336–42 \| year = 1997 \| pmid = 9456487 \| pmc = 325477 }}</ref> and was superseded by [[propranolol]] from 1965 onward.<ref name=Quirke/> {{antihypertensive-stub}}▼ == See also == * [[Beta blocker]] * [[Discovery and development of beta-blockers]] == References == {{Reflist}} {{Adrenergics}} {{Phenethylamines}} [[Category:Beta blockers]] [[Category:2-Naphthyl compounds]] [[Category:Phenylethanolamines]] ▲{{antihypertensive-stub}}