Betaxolol

Title: Betaxolol
CAS Registry Number: 63659-18-7
CAS Name: 1-[4-[2-(Cyclopropylmethoxy)ethyl]-phenoxy]-3-[(1-methylethyl)amino]-2-propanol
Additional Names: (±)-1-(isopropylamino)-3-[p-(cyclopropylmethoxyethyl)phenoxy]-2-propanol
Molecular Formula: C18H29NO3
Molecular Weight: 307.43
Percent Composition: C 70.32%, H 9.51%, N 4.56%, O 15.61%
Literature References: Cardioselective b1-adrenergic blocker. Prepn: P. M. J. Manoury et al., DE 2649605; eidem, US 4252984 (1977, 1981 both to Synthelabo). Blood concn and pharmacodynamic effects: S. J. Warrington et al., Br. J. Clin. Pharmacol. 10, 449 (1980). Pharmacokinetics: G. Bianchetti et al., Arzneim.-Forsch. 30, 1912 (1980). Cardiovascular effects in normal volunteers: P. J. Cadigan et al., Br. J. Clin. Pharmacol. 9, 569 (1980). Efficacy and pharmacokinetics: K. Balnave et al., ibid. 11, 171 (1981). Use in treatment of glaucoma: A. R. Berrospi, H. M. Leibowitz, Arch. Ophthalmol. 100, 943 (1982). Antihypertensive effect: M. Pathe et al., Therapie 37, 75 (1982). Book: Betaxolol and Other b1-Adrenoceptor Antagonists, P. L. Morselli et al., Eds. (Raven Press, New York, 1983) 385 pp.
Properties: Crystals from petr ether, mp 70-72°.
Melting point: mp 70-72°
Derivative Type: Hydrochloride
CAS Registry Number: 63659-19-8
Manufacturers' Codes: SLD-212; SL-75.212
Trademarks: Betoptic (Alcon); Betoptima (Alcon); Kerlone (Synthelabo)
Molecular Formula: C18H29NO3.HCl
Molecular Weight: 343.89
Percent Composition: C 62.87%, H 8.79%, N 4.07%, O 13.96%, Cl 10.31%
Properties: Crystals from acetone, mp 116°. LD50 in mice (mg/kg): 944 orally; 37 i.v. (Manoury).
Melting point: mp 116°
Toxicity data: LD50 in mice (mg/kg): 944 orally; 37 i.v. (Manoury)
Therap-Cat: Antihypertensive; antiglaucoma.
Keywords: ?Adrenergic Blocker; Antiglaucoma; Antihypertensive; Aryloxypropanolamine Derivatives.
Betazole Betel Bethanechol Chloride Bethanidine Betonicine

Betaxolol
Betaxolol structure.svg
Betaxolol ball-and-stick.png
Systematic (IUPAC) name
(RS)-1-{4-[2-(cyclopropylmethoxy)ethyl]-
phenoxy}-3-(isopropylamino)propan-2-ol
Clinical data
Trade names Kerlone
AHFS/Drugs.com monograph
MedlinePlus a609023
Pregnancy cat. C (AU) C (US)
Legal status Prescription only
Routes oral, ocular
Pharmacokinetic data
Bioavailability 89%
Metabolism Hepatic
Half-life 14–22 hours
Excretion Renal (20%)
Identifiers
CAS number 63659-18-7 YesY
ATC code C07AB05 S01ED02
PubChem CID 2369
IUPHAR ligand 549
DrugBank DB00195
ChemSpider 2279 YesY
UNII O0ZR1R6RZ2 YesY
KEGG D07526 YesY
ChEBI CHEBI:3082 YesY
ChEMBL CHEMBL423 YesY
Chemical data
Formula C18H29NO3 
Mol. mass 307.428 g/mol
 YesY (what is this?)  (verify)

Betaxolol (trade names Betoptic, Betoptic S, Lokren, Kerlone) is a selective beta1 receptor blocker used in the treatment of hypertension and glaucoma. 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 affininty 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.

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.