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Identification
NameBupranolol
Accession NumberDB08808
TypeSmall Molecule
GroupsApproved
Description

Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Its potency is similar to propranolol.

Structure
Thumb
Synonyms
Bupranol
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BetadrenolDesma
OphtoreninWinzer (Germany)
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Bupranolol hydrochloride
15148-80-8
Thumb
  • InChI Key: WJUUZHQWGKSLIJ-UHFFFAOYSA-N
  • Monoisotopic Mass: 307.1105844
  • Average Mass: 308.24
DBSALT000905
Categories
UNII858YGI5PIT
CAS number14556-46-8
WeightAverage: 271.783
Monoisotopic: 271.13390666
Chemical FormulaC14H22ClNO2
InChI KeyInChIKey=HQIRNZOQPUAHHV-UHFFFAOYSA-N
InChI
InChI=1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3
IUPAC Name
1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
SMILES
CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1
Taxonomy
ClassificationNot classified
Pharmacology
IndicationUsed to manage hypertension and tachycardia. Also used to treat glaucoma.
PharmacodynamicsBupranolol is a competitive, nonselective beta-blocker similar to propanolol without intrinsic sympathomimetic activity.
Mechanism of actionBupranolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension.
Related Articles
AbsorptionQuickly and completely absorbed from the gut with less than 10% oral bioavailability.
Volume of distributionNot Available
Protein binding76%
Metabolism

Over 90% undergo first-pass metabolism. The main metabolite is carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid, of which 88% are eliminated renally within 24 hours.

SubstrateEnzymesProduct
Bupranolol
Not Available
carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acidDetails
Route of eliminationNot Available
Half life2-4 hours
ClearanceNot Available
ToxicitySymptoms of overdose include bradycardia, cardiac failure, hypotension, and brochospasm.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Bupranolol Action PathwayDrug actionSMP00670
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9784
Blood Brain Barrier-0.7572
Caco-2 permeable+0.5576
P-glycoprotein substrateSubstrate0.6384
P-glycoprotein inhibitor INon-inhibitor0.6857
P-glycoprotein inhibitor IINon-inhibitor0.8993
Renal organic cation transporterNon-inhibitor0.8713
CYP450 2C9 substrateNon-substrate0.8011
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.6373
CYP450 1A2 substrateInhibitor0.5416
CYP450 2C9 inhibitorNon-inhibitor0.8165
CYP450 2D6 inhibitorInhibitor0.6045
CYP450 2C19 inhibitorNon-inhibitor0.7218
CYP450 3A4 inhibitorNon-inhibitor0.8424
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5726
Ames testNon AMES toxic0.9025
CarcinogenicityNon-carcinogens0.8249
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4441 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9455
hERG inhibition (predictor II)Non-inhibitor0.6443
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.143 mg/mLALOGPS
logP3.14ALOGPS
logP2.99ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity74.86 m3·mol-1ChemAxon
Polarizability30.35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Kunz, W., Jacobi, H., Koch, C. and Geus, R.J.; U.S. Patent 3,309,406; March 14, 1967.

General ReferencesNot Available
External Links
ATC CodesC07AA19
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Receptor signaling protein activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
References
  1. Zelaszczyk D, Kozlowska H, Baranowska U, Baranowska M, Reutelsterz A, Kiec-Kononowicz K, Malinowska B, Schlicker E: Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors. J Physiol Pharmacol. 2009 Mar;60(1):51-60. [PubMed:19439807 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Lenard NR, Gettys TW, Dunn AJ: Activation of beta2- and beta3-adrenergic receptors increases brain tryptophan. J Pharmacol Exp Ther. 2003 May;305(2):653-9. Epub 2003 Jan 24. [PubMed:12606631 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name:
ADRB3
Uniprot ID:
P13945
Molecular Weight:
43518.615 Da
References
  1. Lenard NR, Gettys TW, Dunn AJ: Activation of beta2- and beta3-adrenergic receptors increases brain tryptophan. J Pharmacol Exp Ther. 2003 May;305(2):653-9. Epub 2003 Jan 24. [PubMed:12606631 ]
  2. Matsushita M, Horinouchi T, Tanaka Y, Tsuru H, Koike K: Characterization of beta 3-adrenoceptor-mediated relaxation in rat abdominal aorta smooth muscle. Eur J Pharmacol. 2003 Dec 15;482(1-3):235-44. [PubMed:14660028 ]
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Drug created on October 20, 2010 15:45 / Updated on May 01, 2016 21:55