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63659-18-7 molecular structure
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(3-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-2-hydroxypropyl)(propan-2-yl)amine

ChemBase ID: 80
Molecular Formular: C18H29NO3
Molecular Mass: 307.42776
Monoisotopic Mass: 307.21474379
SMILES and InChIs

SMILES:
O(CC1CC1)CCc1ccc(OCC(O)CNC(C)C)cc1
Canonical SMILES:
OC(COc1ccc(cc1)CCOCC1CC1)CNC(C)C
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
InChIKey:
NWIUTZDMDHAVTP-UHFFFAOYSA-N

Cite this record

CBID:80 http://www.chembase.cn/molecule-80.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-2-hydroxypropyl)(propan-2-yl)amine
1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-[(propan-2-yl)amino]propan-2-ol
IUPAC Traditional name
1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-(isopropylamino)propan-2-ol
betaxolol
Brand Name
Betaxon
Betoptic
Betoptic S
Kerlone
Synonyms
Betazolol
Betaxolol HCL
Betaxololum [INN-Latin]
Betaxolol (Betoptic)
1-[4-(2-(Cyclopropylmethyloxy)ethyl]-phenoxy]-3-[(1-methylethyl)amino]-2-propanol
(+/-)-1-(Isopropylamino)-3-[p-(cyclopropylmethoxyethyl)phenoxy]-2-propanol
Betaxolol
CAS Number
63659-18-7
659-18-7
PubChem SID
46506041
160963543
PubChem CID
2369

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.087972  H Acceptors
H Donor LogD (pH = 5.5) -0.65399736 
LogD (pH = 7.4) 0.31399572  Log P 2.5392344 
Molar Refractivity 88.6396 cm3 Polarizability 35.132854 Å3
Polar Surface Area 50.72 Å2 Rotatable Bonds 11 
Lipinski's Rule of Five true 
Log P 3.0  LOG S -4.01 
Solubility (Water) 2.98e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
451 mg/L expand Show data source
Acetone expand Show data source
Chloroform expand Show data source
Apperance
White Solid expand Show data source
Melting Point
61-63°C expand Show data source
Hydrophobicity(logP)
2.4 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Target
Adrenergic Receptor expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00195 external link
Item Information
Drug Groups approved
Description A cardioselective beta-1-adrenergic antagonist with no partial agonist activity. [PubChem]
Indication For the management of hypertension.
Pharmacology 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.
Toxicity Oral LD50s are 350 to 400 mg betaxolol/kg in mice and 860 to 980 mg/kg in rats. Predicted symptoms of overdose include bradycardia, congestive heart failure, hypotension, bronchospasm, and hypoglycemia.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic. Approximately 15% of the dose administered is excreted as unchanged drug, the remainder being metabolites whose contribution to the clinical effect is negligible.
Absorption Absorption of an oral dose is complete. There is a small and consistent first-pass effect resulting in an absolute bioavailability of 89% ± 5% that is unaffected by the concomitant ingestion of food or alcohol.
Half Life 14-22 hours
Protein Binding 50%
References
Canotilho J, Castro RA: The structure of betaxolol studied by infrared spectroscopy and natural bond orbital theory. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Aug;76(3-4):395-400. Epub 2010 Apr 4. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - B328000 external link
Cardioselective β1-adrenergic blocker. An antihypertensive; antiglaucoma.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Canotilho J, Castro RA: The structure of betaxolol studied by infrared spectroscopy and natural bond orbital theory. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Aug;76(3-4):395-400. Epub 2010 Apr 4. Pubmed
  • • Cadigan, P.J., et al.: Br. J. Clin. Pharmacol., 9, 569 (1980)
  • • Pathe, M., et al.: Therapie, 37, 75 (1980)
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PATENTS

PATENTS

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INTERNET

INTERNET

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