pronethalol

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 1-(naphthalen-2-yl)-2-(propan-2-ylamino)ethanol

| image = Pronethalol.svg

| chirality = Racemic mixture

| drug_name =

| tradename =

| pregnancy_category =

| legal_status = Withdrawn

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 54-80-8

| ATC_prefix = none

| ATC_suffix =

| PubChem = 4930

| ChemSpiderID = 4761

| ChEMBL = 16476

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = XBP4RT1IMQ

| C=15 | H=19 | N=1 | O=1

| smiles = CC(C)NCC(C1=CC2=CC=CC=C2C=C1)O

}}

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 and associates at Imperial Chemical Industries, and the first to enter clinical use, in November 1963.{{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}}

However, it was never used widely due to carcinogenicity in mice, which was thought to result from formation of a carcinogenic naphthalene epoxide metabolite,{{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Institute Journal | volume = 24 | issue = 4 | pages = 336–42 | year = 1997 | pmid = 9456487 | pmc = 325477 }} and was superseded by propranolol from 1965 onward.