Bupranolol

Bupranolol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, topical (eye drops)
ATC code	C07AA19 (WHO) ;
Pharmacokinetic data
Bioavailability	< 10%
Protein binding	76%
Metabolism	First pass elimination > 90%
Elimination half-life	2-4 hours (plasma)
Excretion	> 88% renal (as carboxybupranolol)
Identifiers
	show IUPAC name
CAS Number	14556-46-8 ;
PubChem CID	2475;
IUPHAR/BPS	550;
DrugBank	DB08808 ;
ChemSpider	2381 ;
UNII	858YGI5PIT;
KEGG	D07590 ;
ChEMBL	ChEMBL305380 ;
CompTox Dashboard (EPA)	DTXSID7022704 ;
Chemical and physical data
Formula	C14H22ClNO2
Molar mass	271.79 g·mol−1
3D model (JSmol)	Interactive image;
	show SMILES
	show InChI
	(what is this?)

Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Its potency is similar to propranolol.

Uses and dosage[]

Like other beta blockers, oral bupranolol can be used to treat hypertension and tachycardia.^{[citation needed]} The initial dose is 50 mg two times a day. It can be increased to 100 mg four times a day. Bupranolol eye drops (0.05%-0.5%) are used against glaucoma.^{[citation needed]}

Pharmacology[]

Bupranolol is quickly and completely absorbed from the gut. Over 90% undergo first-pass metabolism. Bupranolol has a plasma half life of about two to four hours, with levels never reaching 1 µg/l in therapeutic doses. The main metabolite is carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid – that is, the methyl group at the benzene ring is oxidized to a carboxyl group –, of which 88% are eliminated renally within 24 hours.^{[citation needed]}

Adverse effects, contraindications, interactions[]

Adverse effects, contraindications and interactions are similar to other beta blockers.^{[citation needed]}

show v t Beta blockers (C07)
β, non-selective	Alprenolol Bopindolol Bupranolol Carteolol Cloranolol Mepindolol Nadolol Oxprenolol Penbutolol Pindolol/Iodopindolol Propranolol^# Sotalol Tertatolol Timolol^#
β₁-selective	Acebutolol Atenolol Betaxolol Bevantolol Bisoprolol^# Celiprolol Epanolol Esmolol Landiolol Metoprolol Nebivolol Practolol Talinolol
β₂-selective	Butaxamine
α₁- + β-selective	Arotinolol Carvedilol Labetalol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Bupranolol

Contents

Uses and dosage[]

Pharmacology[]

Adverse effects, contraindications, interactions[]

References[]

Further reading[]

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, topical (eye drops)
ATC code	C07AA19 (WHO)
Pharmacokinetic data
Bioavailability	< 10%
Protein binding	76%
Metabolism	First pass elimination > 90%
Elimination half-life	2-4 hours (plasma)
Excretion	> 88% renal (as carboxybupranolol)
Identifiers
show IUPAC name (RS)-1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
CAS Number	14556-46-8^N
PubChem CID	2475
IUPHAR/BPS	550
DrugBank	DB08808^Y
ChemSpider	2381^Y
UNII	858YGI5PIT
KEGG	D07590^N
ChEMBL	ChEMBL305380^Y
CompTox Dashboard (EPA)	DTXSID7022704
Chemical and physical data
Formula	C₁₄H₂₂ClNO₂
Molar mass	271.79 g·mol⁻¹
3D model (JSmol)	Interactive image
show SMILES CC1=CC(=C(C=C1)Cl)OCC(CNC(C)(C)C)O
show InChI InChI=1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3^Y Key:HQIRNZOQPUAHHV-UHFFFAOYSA-N^Y
^NY (what is this?)