Betaxolol

Betaxolol
Clinical data
Trade names	Kerlone
AHFS/Drugs.com	Monograph
MedlinePlus	a609023
Pregnancy; category	AU: C;
Routes of; administration	oral, ocular
ATC code	C07AB05 (WHO) S01ED02 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	89%
Metabolism	Liver
Elimination half-life	14–22 hours
Excretion	Kidney (20%)
Identifiers
	IUPAC name (RS)-1-{4-[2-(cyclopropylmethoxy)ethyl]-; phenoxy}-3-(isopropylamino)propan-2-ol;
CAS Number	63659-18-7 ;
PubChem CID	2369;
IUPHAR/BPS	549;
DrugBank	DB00195 ;
ChemSpider	2279 ;
UNII	O0ZR1R6RZ2;
KEGG	D07526 ;
ChEBI	CHEBI:3082 ;
ChEMBL	ChEMBL423 ;
CompTox Dashboard (EPA)	DTXSID2022674 ;
ECHA InfoCard	100.113.058
Chemical and physical data
Formula	C18H29NO3
Molar mass	307.434 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O(CCc1ccc(OCC(O)CNC(C)C)cc1)CC2CC2;
	InChI InChI=1S/C18H29NO3/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3 ; Key:NWIUTZDMDHAVTP-UHFFFAOYSA-N ;
	(verify)

Betaxolol is a selective beta₁ receptor blocker used in the treatment of hypertension and glaucoma.^[1] Being selective for beta₁ receptors, it typically has fewer systemic side effects than non-selective beta-blockers, for example, not causing bronchospasm (mediated by beta₂ receptors) as timolol may. Betaxolol also shows greater affinity for beta₁ receptors than metoprolol. In addition to its effect on the heart, betaxolol reduces the pressure within the eye (intraocular pressure). This effect is thought to be caused by reducing the production of the liquid (which is called the aqueous humor) within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the optic nerve and loss of vision in patients with elevated intraocular pressure due to glaucoma.

It was patented in 1975 and approved for medical use in 1983.^[2]

Medical uses

Oral: for the management of hypertension
Ophthalmic: for the management of glaucoma
the drug seems to have an effect of neuroprotection in glaucoma treatment

Contraindications

Hypersensitivity to the drug
Patients with sinus bradycardia, heart block greater than first degree, cardiogenic shock, and overt cardiac failure

Side effects

History

Betaxolol was approved by the U.S. Food and Drug Administration (FDA) for ocular use as a 0.5% solution (Betoptic) in 1985 and as a 0.25% solution (Betoptic S) in 1989.

Brand names

Brand names include Betoptic, Betoptic S, Lokren, Kerlone.

References

^ Buckley MM, Goa KL, Clissold SP (July 1990). "Ocular betaxolol. A review of its pharmacological properties, and therapeutic efficacy in glaucoma and ocular hypertension". Drugs. 40 (1): 75–90. doi:10.2165/00003495-199040010-00005. PMID 2202584. S2CID 46962082.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 461. ISBN 9783527607495.

External links

Kerlone prescribing information

[1] Buckley MM, Goa KL, Clissold SP (July 1990). "Ocular betaxolol. A review of its pharmacological properties, and therapeutic efficacy in glaucoma and ocular hypertension". Drugs. 40 (1): 75–90. doi:10.2165/00003495-199040010-00005. PMID 2202584. S2CID 46962082.

[2] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 461. ISBN 9783527607495.

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