| Betaxolol is a selective beta1 receptor blocker used in the treatment of hypertension and angina. It is also a adrenergic blocker with no partial agonist action and minimal membrane stabilizing activity. 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. |
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Read full article at Wikipedia
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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 |
| NWIUTZDMDHAVTP-UHFFFAOYSA-N |
| CC(C)NCC(O)COc1ccc(CCOCC2CC2)cc1 |
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
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sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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View more via ChEBI Ontology
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1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-(propan-2-ylamino)propan-2-ol
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betaxolol
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ChemIDplus
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betaxolol
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WHO MedNet
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bétaxolol
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WHO MedNet
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betaxololum
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ChemIDplus
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1-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-2-propanol
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ChemIDplus
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1-(isopropylamino)-3-[p-(cyclopropylmethoxyethyl)phenoxy]-2-propanol
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ChEBI
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1991268
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Reaxys Registry Number
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Reaxys
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63659-18-7
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CAS Registry Number
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ChemIDplus
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Vaz RJ, Nayeem A, Santone K, Chandrasena G, Gavai AV (2005)
A 3D-QSAR model for CYP2D6 inhibition in the aryloxypropanolamine series.
Bioorganic & medicinal chemistry letters 15, 3816-3820 (Source: ChEMBL) [PubMed:15993593]
[show Abstract]
A comparative molecular similarity index analysis (CoMSiA) has been performed for cytochrome P450 2D6 inhibition on a series of aryloxypropanolamines to determine the factors contributing to this activity. The model is in agreement with a CYP2D6 homology model constructed on the basis of the mammalian CYP2C5 crystal structure. The energy minimized conformations were generated using the systematic search methodology in Sybyl 6.7. The model not only elucidated the relationship between structure and biological activity but, more importantly, provided useful strategies to modulate CYP2D6 affinity in the aryloxypropanolamine series. | Lombardo F, Obach RS, Shalaeva MY, Gao F (2004)
Prediction of human volume of distribution values for neutral and basic drugs. 2. Extended data set and leave-class-out statistics.
Journal of medicinal chemistry 47, 1242-1250 (Source: ChEMBL) [PubMed:14971904]
[show Abstract]
We present an extension and confirmation of our previously published method (J. Med. Chem. 2002, 45, 2867-2876) for the prediction of volume of distribution (VD) in humans for neutral and basic compounds. It is based on two experimentally determined physicochemical parameters, ElogD(7.4) and f(i(7.4)), the latter being the fraction of compound ionized at pH 7.4, and on the fraction of free drug in plasma (fu). By regressing the fraction unbound in tissues, fut, vs the above parameters, we demonstrate the ruggedness of the method in predicting VD through the Oie-Tozer equation, via the use of several testing approaches. A comparison is also presented between several methods based on animal pharmacokinetic data, using the same set of proprietary compounds, and it lends further support for the use of this method, as opposed to methods that require the gathering of pharmacokinetic data in laboratory animals. The reduction in the use of animals and the overall faster and cheaper accessibility of the parameters used make this method highly attractive for prospectively predicting the VD of new chemical entities in humans. | Yoshida F, Topliss JG (2000)
QSAR model for drug human oral bioavailability.
Journal of medicinal chemistry 43, 2575-2585 (Source: ChEMBL) [PubMed:10891117]
[show Abstract]
The quantitative structure-bioavailability relationship of 232 structurally diverse drugs was studied to evaluate the feasibility of constructing a predictive model for the human oral bioavailability of prospective new medicinal agents. The oral bioavailability determined in human adults was assigned one of four ratings and analyzed in relation to physicochemical and structural factors by the ORMUCS (ordered multicategorical classification method using the simplex technique) method. A systematic examination of various physicochemical parameters relating primarily to absorption, and structural elements which could influence metabolism, was carried out to analyze their effects on the bioavailabilty classification of drugs in the data set. Lipophilicity, expressed as the distribution coefficient at pH 6.5, was found to be a significant factor influencing bioavailability. The observation that acids generally had better bioavailability characteristics than bases, with neutral compounds between, led to the formulation of a new parameter, Delta log D (log D(6.5) - log D(7.4)), which proved to be an important contributor in improving the classification results. The addition of 15 structural descriptors relating primarily to well-known metabolic processes yielded a satisfactory QSAR equation which had a correct classification rate of 71% (97% within one class) and a Spearman rank correlation coefficient (R(s)) of 0.851, despite the diversity of structure and pharmacological activity in the compound set. In leave-one-out tests, an average of 67% of drugs were correctly classified (96% within one class) with an R(s) of 0.812. The relationship formulated identified significant factors influencing bioavailability and assigned them quantitative values expressing their contribution. The predictive power of the model was evaluated using a separate test set of 40 compounds, of which 60% (95% within one class) were correctly classified. Since the necessary physicochemical parameters can be calculated or estimated and the structural descriptors are obtained from an inspection of the structure, the model enables a rough estimate to be made of the prospective human oral bioavailability of unsynthesized compounds. Also, the model has the advantage of transparency in that it indicates which factors may affect bioavailabilty and the extent of that effect. This could be useful in designing compounds which are more bioavailable. Refinement of the model is possible as more bioavailability data becomes available. Potential uses are in drug design, prioritization of compounds for synthesis, and selection for detailed studies of early compound leads in drug discovery programs. | Ball JB, Nero TL, Iakovidis D, Tung L, Jackman G, Louis WJ (1992)
Computer-aided mapping of the beta-adrenoceptor. 1. Explanation for effect of para substitution on blocking activity at the beta-1-adrenoceptor.
Journal of medicinal chemistry 35, 4676-4682 (Source: ChEMBL) [PubMed:1361581]
[show Abstract]
Anomalously low affinities for the beta-1-adrenoceptor are seen for members of a series of para-substituted N-isopropylphenoxypropanolamines in which the substituent is able to conjugate with the aromatic ring. The energy of conjugation was calculated using the AM1 semiempirical molecular orbital method and appears to correlate with the loss of binding energy, and hence affinity for the receptor. This suggests that binding is associated with movement of the substituent out of the plane of the aromatic ring due to steric interference with the receptor. A previously unrecognized binding site for aromatic groups off the para position is also identified. | Stagni G, Davis PJ, Ludden TM (1991)
Human pharmacokinetics of betaxolol enantiomers.
Journal of pharmaceutical sciences 80, 321-324 [PubMed:1865331]
[show Abstract]
Betaxolol is a cardioselective beta-adrenergic antagonist effective in the treatment of hypertension. The pharmacokinetic behavior of betaxolol enantiomers in healthy male subjects is reported. Betaxolol enantiomer concentrations were determined in samples collected up to 48 h after iv administration of a 10-mg dose over a 30-min period by constant-rate infusion in 12 subjects and after oral administration of 40-mg capsules to eight of the same subjects. Betaxolol extracted from whole blood was reacted with (+) or (-)-1-naphthylethyl isocyanate. The resulting diastereoisomeric derivatives were analyzed by reversed-phase HPLC with fluorimetric detection. Following the iv dose, there were no differences in clearance or volume of distribution for the two enantiomers (15.6 +/- 4.4 versus 16.4 +/- 4.1 L/h and 342 +/- 62 versus 340 +/- 65 L, respectively). Likewise, after the oral dose, there were no differences in the maximum concentration, time of maximum concentration, bioavailability, or apparent absorption rate constant (41.0 +/- 8.6 versus 42.0 +/- 7.0 ng/mL, 214 +/- 59 versus 215 +/- 56 min, 0.89 +/- 0.26 versus 0.94 +/- 0.23, and 1.0 +/- 0.6 versus 1.2 +/- 0.6 h-1, respectively). Thus, the pharmacokinetic behavior of racemic betaxolol accurately reflects the behavior of betaxolol enantiomers in this subject group. | Goldberg I (1989)
Betaxolol.
Australian and New Zealand journal of ophthalmology 17, 9-13 [PubMed:2569884]
[show Abstract]
Drugs classified as beta-blockers have proved to be valuable in the treatment of patients with glaucoma. Timolol has become the most widely used ocular hypotensive agent. Actual and potential side effects associated with its non-selective beta-blockade have prevented its use in patients with reactive airways disease, and to a lesser extent, with various cardiovascular conditions. Betaxolol is a relatively selective beta-1 blocker which in most patients is almost as effective as timolol in lowering intraocular pressure, and may be partly additive with dipivefrin. It is probably safer in patients unable to tolerate non-selective beta-blockers. However, it needs to be used with caution in these patients, who are unpredictably susceptible to systemic side effects. |
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2014-04-30
