Betaxolol

HCID 2369CAS 63659-18-7

Basic information

Standard SMILES
CC(C)NCC(O)COc1ccc(CCOCC2CC2)cc1
InChIKey
NWIUTZDMDHAVTP-UHFFFAOYSA-N
Molecular formula
C18H29NO3
Average molar mass
307.4 g/mol
Monoisotopic mass
307.21474379

Overview

Betaxolol is a propanolamine that is 3-aminopropane-1,2-diol in which the hydrogen of the primary hydoxy is substituted by a 4-[2-(cyclopropylmethoxy)ethyl]phenyl group and one of the hydrogens attached to the amino group is substituted by isopropyl. It is a selective beta1-receptor blocker and is used in the treatment of glaucoma as well as hypertension, arrhythmias, and coronary heart disease. It is also used to reduce non-fatal cardiac events in patients with heart failure. It has a role as a beta-adrenergic antagonist, an antihypertensive agent and a sympatholytic agent.

Names & identifiers

Preferred name
Betaxolol
IUPAC
1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol
English name
Betaxolol
Molecular formula
C18H29NO3
Molecular weight
307.43

Names & synonyms

betaxolol63659-18-7BetaxololumDTXSID2022674SL 75212O0ZR1R6RZ21-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol1-(4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-2-propanolALO-140102 FREE BASE2-Propanol, 1-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-SL-7521210 FREE BASECHEBI:3082
Show more names
ZB-5C06849βxololBetaxololsBetoptic SBetaprololBetaxolol BaseBetaxolol, >=98%Betaxolol USP/EP/BP
DTXCID1026741-(isopropylamino)-3-[p-(cyclopropylmethoxyethyl)phenoxy]-2-propanol1-{4-[2-(Cyclopropylmethoxy)ethyl]phenoxy}-3-[(propan-2-yl)amino]propan-2-ol1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-(propan-2-ylamino)propan-2-ol1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-[(1-methylethyl)amino]-2-propanolbetaxololoOxodalBetoptic susp

Database identifiers

CAS
63659-18-7
PubChem CID
2369
DTXSID
DTXSID2022674
ChEMBL
CHEMBL423
ChEBI
CHEBI:3082
UNII
O0ZR1R6RZ2
EC Number
613-310-1
Nikkaji
J19.271F

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
50.7 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
11
Heavy atoms
22

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP · 2 items

2.4

2.81

Solubility2.98e-02 g/L
Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiglaucoma Agents; Antiarrhythmics

Pharmaceuticals

Melting Point · 2 items

70-72 °C

70 - 72 °C

Physical DescriptionSolid

Physicochemical properties

Melting point
61 · 61-63°C
Boiling point
448 · 448.0±40.0 °C(Predicted)
Density
1.067 · 1.067±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C Freezer
solubility
Chloroform (Slightly), Methanol (Slightly)
pka
9.21 · pKa 9.21 (Uncertain)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Hepatotoxicity · 1 item

Betaxolol therapy has been associated with a low rate of mild-to-moderate elevations of serum aminotransferase levels which are usually asymptomatic and transient and resolve even with continuation of therapy. There have been no well documented cases of clinically apparent, acute liver injury attributable to betaxolol. Thus, hepatotoxicity due to betaxolol must be very rare, if it occurs at all. Most commonly used beta-blockers have been linked to rare instances of clinically apparent liver injury, typically with onset within 2 to 12 weeks, a hepatocellular pattern of liver enzyme elevations, rapid recovery on withdrawal, and little evidence of hypersensitivity (rash, fever, eosinophilia) or autoantibody formation.

Adverse Effects · 1 item

Betaxolol has both local and systemic adverse effects. The ocular adverse drug reactions include transient irritation (25% to 40%), burning, pruritus, punctate keratitis, and blurry vision. Compared to topical timolol (a nonselective β-blocker), betaxolol showed a higher incidence of ocular adverse effects. Compared to nonselective topical β-adrenergic receptor blockers, betaxolol is less likely to cause adverse effects on pulmonary function. However, betaxolol use still requires caution in patients with underlying pulmonary disease. Symptomatic pulmonary obstruction due to betaxolol has been reported in patients with underlying asthma or chronic obstructive pulmonary disease. A post-marketing study in the United States identified 56 spontaneous adverse effect reports, with 8 cases requiring hospitalization due to asthma exacerbation.

Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

betaxolol

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

hs_code
29225090
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
Hazard statements
H361-H302-H412
Precautionary statements
P201-P202-P281-P308+P313-P405-P501-P264-P270-P301+P312-P330-P501-P273-P501

Chemistry & industry

Pharmacology

ATC Code · 5 items

S01ED02

C - Cardiovascular system

S - Sensory organs

QS - Sensory organs

QC - Cardiovascular system

Protein Binding50%
Pharmacodynamics · 1 item

Betaxolol is a competitive, beta(1)-selective (cardioselective) adrenergic antagonist. Betaxolol is used to treat hypertension, arrhythmias, coronary heart disease, glaucoma, and is also used to reduce non-fatal cardiac events in patients with heart failure. Activation of beta(1)-receptors (located mainly in the heart) by epinephrine increases the heart rate and the blood pressure, and the heart consumes more oxygen. Drugs such as betaxolol that block these receptors therefore have the reverse effect: they lower the heart rate and blood pressure and hence are used in conditions when the heart itself is deprived of oxygen. They are routinely prescribed in patients with ischemic heart disease. In addition, beta(1)-selective blockers prevent the release of renin, which is a hormone produced by the kidneys which leads to constriction of blood vessels. Betaxolol is lipophilic and exhibits no intrinsic sympathomimetic activity (ISA) or membrane stabilizing activity.

Mechanism of Action · 1 item

Betaxolol selectively blocks catecholamine stimulation of beta(1)-adrenergic receptors in the heart and vascular smooth muscle. This results in a reduction of heart rate, cardiac output, systolic and diastolic blood pressure, and possibly reflex orthostatic hypotension. Betaxolol can also competitively block beta(2)-adrenergic responses in the bronchial and vascular smooth muscles, causing bronchospasm.

Biological Half-Life14-22 hours
Metabolism/MetabolitesPrimarily hepatic. Approximately 15% of the dose administered is excreted as unchanged drug, the remainder being metabolites whose contribution to the clinical effect is negligible.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >100
Use ClassificationPharmaceuticals

Applications

UsesCardioselective 1-adrenergic blocker. An antihypertensive; antiglaucoma

UsesCardioselective β1-adrenergic blocker. An antihypertensive; antiglaucoma.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A propanolamine that is 3-aminopropane-1,2-diol in which the hydrogen of the primary hydoxy is substituted by a 4-[2-(cyclopropylmethoxy)ethyl]phenyl group and one of the hydrogens attached to the amino group is substituted by isopropyl. It is a selective beta1-receptor blocker and is used in the treatment of glaucoma as well as hypertension, arrhythmias, and coronary heart disease. It is also used to reduce non-fatal cardiac events in patients with heart failure.

Related reactions

9 records

Linked notes

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