Bupranolol
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| Systematic (IUPAC) name | |
| (RS)-1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | ? |
| Legal status | ? |
| Routes | Oral, topical (eye drops) |
| Pharmacokinetic data | |
| Bioavailability | < 10% |
| Protein binding | 76% |
| Metabolism | First pass elimination > 90% |
| Half-life | 2-4 hours (plasma) |
| Excretion | > 88% renal (as carboxybupranolol) |
| Identifiers | |
| CAS number | 23284-25-5  |
| ATC code | C07AA19 |
| PubChem | CID 2475 |
| IUPHAR ligand | 550 |
| DrugBank | DB08808 |
| ChemSpider | 2381  |
| UNII | 858YGI5PIT |
| KEGG | D07590 |
| ChEMBL | CHEMBL305380 |
| Chemical data | |
| Formula | C14H22ClNO2 |
| Mol. mass | 271.78298 g/mol |
| SMILES | eMolecules & PubChem |
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Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Its potency is similar to propranolol.
Contents |
[edit] 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.
[edit] 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.
[edit] Adverse effects, contraindications, interactions
Adverse effects, contraindications and interactions are similar to other beta blockers.
[edit] References
- Dinnendahl, V, Fricke, U, ed (2007) (in German). Arzneistoff-Profile. 2 (21 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-98-46-3.
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