Bupranolol

Bupranolol
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral, topical (eye drops)
ATC code
Pharmacokinetic data
Bioavailability< 10%
Protein binding76%
MetabolismFirst pass elimination > 90%
Elimination half-life2-4 hours (plasma)
Excretion> 88% renal (as carboxybupranolol)
Identifiers
IUPAC name
  • (RS)-1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H22ClNO2
Molar mass271.79 g·mol−1
3D model (JSmol)
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 checkY
  • Key:HQIRNZOQPUAHHV-UHFFFAOYSA-N checkY
 ☒NcheckY (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

    Further reading

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