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%
Biological half-life	2-4 hours (plasma)
Excretion	> 88% renal (as carboxybupranolol)
Identifiers
IUPAC name (RS)-1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
CAS Number	23284-25-5 N
PubChem CID	2475
IUPHAR/BPS	550
DrugBank	DB08808 Y
ChemSpider	2381 Y
UNII	858YGI5PIT
KEGG	D07590 N
ChEMBL	CHEMBL305380 Y
Chemical and physical data
Formula	C14H22ClNO2
Molar mass	271.78298 g/mol
3D model (Jmol)	Interactive image
SMILES CC1=CC(=C(C=C1)Cl)OCC(CNC(C)(C)C)O
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?)

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

Like other beta blockers, oral bupranolol can be used to treat hypertension and tachycardia. 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.

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.

Adverse effects, contraindications and interactions are similar to other beta blockers.