Bupranolol

Bupranolol
Systematic (IUPAC) name

(RS)-1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, topical (eye drops)
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
CAS Number	23284-25-5^N
ATC code	C07AA19
PubChem	CID 2475
IUPHAR/BPS	550
DrugBank	DB08808^Y
ChemSpider	2381^Y
UNII	858YGI5PIT^Y
KEGG	D07590^N
ChEMBL	CHEMBL305380^Y
Chemical data
Formula	C₁₄H₂₂ClNO₂
Molar mass	271.78298 g/mol
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?) (verify)

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. 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.

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.

Adverse effects, contraindications, interactions

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

References

Dinnendahl, V, Fricke, U, ed. (2007). Arzneistoff-Profile (in German) 2 (21 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.

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 Metoprolol Nebivolol Practolol S-Atenolol Talinolol

β₂-selective	Butaxamine

α₁- + β-selective	Carvedilol Labetalol

^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

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