Pronethalol

Pronethalol
Clinical data
Trade names	Alderlin
Other names	Nethalide; Pronetalol; Naphthylisoproterenol; ICI-38174; ICI38174; Compound 38174; AY-6204; AY6204
Routes of; administration	Oral
Drug class	Beta blocker
ATC code	None;
Legal status
Legal status	Withdrawn;
Identifiers
	IUPAC name 1-(naphthalen-2-yl)-2-(propan-2-ylamino)ethanol;
CAS Number	54-80-8 ;
PubChem CID	4930;
ChemSpider	4761;
UNII	XBP4RT1IMQ;
KEGG	C11707;
ChEBI	CHEBI:8463;
ChEMBL	ChEMBL16476;
CompTox Dashboard (EPA)	DTXSID8021193 ;
Chemical and physical data
Formula	C15H19NO
Molar mass	229.323 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES CC(C)NCC(C1=CC2=CC=CC=C2C=C1)O;
	InChI InChI=1S/C15H19NO/c1-11(2)16-10-15(17)14-8-7-12-5-3-4-6-13(12)9-14/h3-9,11,15-17H,10H2,1-2H3; Key:HRSANNODOVBCST-UHFFFAOYSA-N;

Pronethalol, sold under the brand name Alderlin, was an early non-selective beta blocker. 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.^[1]

However, it was never used widely due to carcinogenicity in mice, which was thought to result from formation of a carcinogenic naphthalene epoxide metabolite,^[2] and was superseded by propranolol from 1965 onward.^[1]

References

1 2 Quirke V (January 2006). "Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978". Med Hist. 50 (1): 69–92. doi:10.1017/s0025727300009455. PMC 1369014. PMID 16502872.
↑ Stapleton MP (1997). "Sir James Black and propranolol. The role of the basic sciences in the history of cardiovascular pharmacology". Texas Heart Institute Journal. 24 (4): 336–42. PMC 325477. PMID 9456487.

[Quirke-1] 1 2 Quirke V (January 2006). "Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978". Med Hist. 50 (1): 69–92. doi:10.1017/s0025727300009455. PMC 1369014. PMID 16502872.

[2] Stapleton MP (1997). "Sir James Black and propranolol. The role of the basic sciences in the history of cardiovascular pharmacology". Texas Heart Institute Journal. 24 (4): 336–42. PMC 325477. PMID 9456487.

[1]

[2]

See also

References