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Pronethalol: Difference between revisions

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{{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=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| legal_status = Withdrawn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''' (codenamed '''ICI 38174''' and also known as '''nethalide''') was an early [[beta blocker]] clinical candidate. It was never used clinically due to [[carcinogenicity]] in mice.<ref>{{cite journal |author=Stapleton MP |title=Sir James Black and propranolol. The role of the basic sciences in the history of cardiovascular pharmacology |journal=Tex Heart Inst J |volume=24 |issue=4 |pages=336–42 |year=1997 |pmid=9456487 |pmc=325477}}</ref>▼
 
'''Pronethalol''' (also known as '''nethalide''' or '''compound 38,174'''; trade name '''Alderlin''') was an early non-selective [[beta blocker]] clinical candidate. It was the first beta blocker to be developed by [[James Black (pharmacologist)|James Black]] and associates at [[Imperial Chemical Industries]], and the first to enter clinical use, in November 1963.<ref name=Quirke>{{cite journal |vauthors=Quirke V |title=Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978 |journal=Med Hist |volume=50 |issue=1 |pages=69–92 |date=January 2006 |pmid=16502872 |pmc=1369014 |doi=10.1017/s0025727300009455}}</ref>
==References==▼
 
▲'''Pronethalol'''However, (codenamedit '''ICIwas 38174'''never andused alsowidely knowndue as '''nethalide''') was an earlyto [[beta blockercarcinogenicity]] clinicalin candidate.mice, Itwhich was neverthought usedto clinicallyresult duefrom toformation of a carcinogenic [[carcinogenicitynaphthalene epoxide]] in mice.metabolite,<ref>{{cite journal |author vauthors = Stapleton MP | title = Sir James Black and propranolol. The role of the basic sciences in the history of cardiovascular pharmacology | journal =Tex Texas Heart InstInstitute JJournal | 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/>
 
== See also ==
* [[Beta blocker]]
* [[Discovery and development of beta-blockers]]
 
▲== References ==
{{Reflist}}
{{-}}
 
{{Adrenergics}}
[[Category:Beta blockers]]▼
{{Phenethylamines}}
 
▲[[Category:Beta blockers]]
[[Category:2-Naphthyl compounds]]
[[Category:Phenylethanolamines]]
 
{{pharmaantihypertensive-stub}}
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