Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB08808
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
- Beta-1 adrenergic receptorAntagonist
- Beta-1 adrenergic receptor
Identification
- Generic Name
- Bupranolol
- DrugBank Accession Number
- DB08808
- Background
Bupranolol is a non-selective beta blocker with potency similar to propanolol. It does not have intrinsic sympathomimetic activity (ISA), but does have strong membrane stabilizing activity.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Bupranolol (DB08808)
- Weight
- Average: 271.783
Monoisotopic: 271.13390666 - Chemical Formula
- C14H22ClNO2
- Synonyms
- Bupranolol
- Bupranololum
Pharmacology
- Indication
Used to manage hypertension and tachycardia. Also used to treat glaucoma.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Bupranolol is a competitive, nonselective beta-blocker similar to propanolol without intrinsic sympathomimetic activity.
- Mechanism of action
Bupranolol 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.
Target Actions Organism ABeta-1 adrenergic receptor antagonistHumans UBeta-2 adrenergic receptor antagonistHumans UBeta-3 adrenergic receptor antagonistHumans - Absorption
Quickly and completely absorbed from the gut with less than 10% oral bioavailability.
- Volume of distribution
Not Available
- Protein binding
76%
- Metabolism
Over 90% undergoes 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.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
2-4 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include bradycardia, cardiac failure, hypotension, and brochospasm.
- Pathways
Pathway Category Bupranolol Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide Abaloparatide may increase the hypotensive activities of Bupranolol. Abatacept The metabolism of Bupranolol can be increased when combined with Abatacept. Abiraterone The metabolism of Bupranolol can be decreased when combined with Abiraterone. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Bupranolol. Acebutolol Acebutolol may increase the arrhythmogenic activities of Bupranolol. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bupranolol hydrochloride DTC2G3GDPL 15148-80-8 WJUUZHQWGKSLIJ-UHFFFAOYSA-N - International/Other Brands
- Betadrenol (Desma) / Ophtorenin (Winzer (Germany))
Categories
- ATC Codes
- C07AA19 — Bupranolol
- Drug Categories
- Adrenergic Agents
- Adrenergic Antagonists
- Adrenergic beta-Antagonists
- Agents causing hyperkalemia
- Alcohols
- Amines
- Amino Alcohols
- Antiarrhythmic agents
- Antihypertensive Agents
- Beta Blocking Agents, Non-Selective
- Bradycardia-Causing Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Neurotransmitter Agents
- Phenoxypropanolamines
- Potential QTc-Prolonging Agents
- Propanolamines
- Propanols
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Phenoxy compounds / Toluenes / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Organochlorides show 1 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Ether / Halobenzene show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 858YGI5PIT
- CAS number
- 14556-46-8
- InChI Key
- 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
References
- Synthesis Reference
Kunz, W., Jacobi, H., Koch, C. and Geus, R.J.; U.S. Patent 3,309,406; March 14, 1967.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015697
- KEGG Drug
- D07590
- PubChem Compound
- 2475
- PubChem Substance
- 99445278
- ChemSpider
- 2381
- BindingDB
- 25765
- 1817
- ChEBI
- 135123
- ChEMBL
- CHEMBL305380
- PharmGKB
- PA165958426
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Bupranolol
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.143 mg/mL ALOGPS logP 3.14 ALOGPS logP 2.99 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 14.09 Chemaxon pKa (Strongest Basic) 9.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 41.49 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 74.86 m3·mol-1 Chemaxon Polarizability 30.35 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9784 Blood Brain Barrier - 0.7572 Caco-2 permeable + 0.5576 P-glycoprotein substrate Substrate 0.6384 P-glycoprotein inhibitor I Non-inhibitor 0.6857 P-glycoprotein inhibitor II Non-inhibitor 0.8993 Renal organic cation transporter Non-inhibitor 0.8713 CYP450 2C9 substrate Non-substrate 0.8011 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Non-substrate 0.6373 CYP450 1A2 substrate Inhibitor 0.5416 CYP450 2C9 inhibitor Non-inhibitor 0.8165 CYP450 2D6 inhibitor Inhibitor 0.6045 CYP450 2C19 inhibitor Non-inhibitor 0.7218 CYP450 3A4 inhibitor Non-inhibitor 0.8424 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5726 Ames test Non AMES toxic 0.9025 Carcinogenicity Non-carcinogens 0.8249 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4441 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9455 hERG inhibition (predictor II) Non-inhibitor 0.6443
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4r-9410000000-4fb6e56fbfc20d328e01 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-2190000000-ae015cadc9e93a4139e6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00bc-2920000000-4453847d05d1dd30814e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05fr-9410000000-e6f6771075dde90980d0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-4900000000-d51d2af0671fd6202015 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9600000000-fa84d69484eaf2237a3e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9400000000-2bc14332a353a560ccab Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 165.2940728 predictedDarkChem Lite v0.1.0 [M-H]- 163.24641 predictedDeepCCS 1.0 (2019) [M+H]+ 165.9130728 predictedDarkChem Lite v0.1.0 [M+H]+ 165.60442 predictedDeepCCS 1.0 (2019) [M+Na]+ 165.2340728 predictedDarkChem Lite v0.1.0 [M+Na]+ 171.69757 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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. Involved in the regulation of sleep/wake behaviors (PubMed:31473062)
- Specific Function
- alpha-2A adrenergic receptor binding
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51222.97 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General 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
- Specific Function
- adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General 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
- Specific Function
- beta-3 adrenergic receptor binding
- Gene Name
- ADRB3
- Uniprot ID
- P13945
- Uniprot Name
- Beta-3 adrenergic receptor
- Molecular Weight
- 43518.615 Da
References
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [Article]
- Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
- Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [Article]
Drug created at October 20, 2010 21:45 / Updated at November 09, 2024 06:13