Identification
- Generic Name
- Hexoprenaline
- DrugBank Accession Number
- DB08957
- Background
Hexoprenaline is a stimulant of beta 2 adrenergic receptors. It is used as a bronchodilator, antiasthmatic, and tocolytic agent.
- Type
- Small Molecule
- Groups
- Experimental, Withdrawn
- Structure
Structure for Hexoprenaline (DB08957)
- Weight
- Average: 420.4993
Monoisotopic: 420.226036766 - Chemical Formula
- C22H32N2O6
- Synonyms
- Hexoprenaline
- External IDs
- ST 1512/504
Pharmacology
- Indication
Not Available
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- 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 softwareAcebutolol The therapeutic efficacy of Hexoprenaline can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Hexoprenaline. Acemetacin The risk or severity of hypertension can be increased when Hexoprenaline is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Hexoprenaline. Aclidinium The risk or severity of Tachycardia can be increased when Aclidinium is combined with Hexoprenaline. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Hexoprenaline. Alclofenac The risk or severity of hypertension can be increased when Hexoprenaline is combined with Alclofenac. Alfentanil The risk or severity of hypertension can be increased when Alfentanil is combined with Hexoprenaline. Alfuzosin The therapeutic efficacy of Hexoprenaline can be decreased when used in combination with Alfuzosin. Aliskiren Hexoprenaline may decrease the antihypertensive activities of Aliskiren. 
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- 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 Hexoprenaline sulfate U851S9102C 32266-10-7 GTDCHGNGVGRHQY-UHFFFAOYSA-N - International/Other Brands
- Argocian (Biol) / Etoscol (DCPC) / Gynipral (Alkaloid) / Hexoline (Shou Chan) / Ipradol (Nycomed) / Taicopin (DCPC)
Categories
- ATC Codes
- R03AC06 — Hexoprenaline
- R03AC — Selective beta-2-adrenoreceptor agonists
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics for Systemic Use
- Adrenergics, Inhalants
- Agents producing tachycardia
- Agents that produce hypertension
- Amines
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Drugs for Obstructive Airway Diseases
- Ethylamines
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Phenethylamines
- Reproductive Control Agents
- Respiratory System Agents
- Selective Beta 2-adrenergic Agonists
- Tocolytic Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Benzenediols
- Direct Parent
- Catechols
- Alternative Parents
- Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Catechol / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- G9L6B3W684
- CAS number
- 3215-70-1
- InChI Key
- OXLZNBCNGJWPRV-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H32N2O6/c25-17-7-5-15(11-19(17)27)21(29)13-23-9-3-1-2-4-10-24-14-22(30)16-6-8-18(26)20(28)12-16/h5-8,11-12,21-30H,1-4,9-10,13-14H2
- IUPAC Name
- 4-{2-[(6-{[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino}hexyl)amino]-1-hydroxyethyl}benzene-1,2-diol
- SMILES
- OC(CNCCCCCCNCC(O)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1
References
- Synthesis Reference
U.S. Patent 3,329,709.
- General References
- Pinder RM, Brogden RN, Speight TM, Avery GS: Hexoprenaline: a review of its pharmacological properties and therapeutic efficacy with particular reference to asthma. Drugs. 1977 Jul;14(1):1-28. [Article]
- External Links
- PubChem Compound
- 3609
- PubChem Substance
- 310264922
- ChemSpider
- 3483
- BindingDB
- 50239967
- 5307
- ChEMBL
- CHEMBL1589896
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Hexoprenaline
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 10 µg/2ml Injection, solution, concentrate Parenteral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 222-228 U.S. Patent 3,329,709. - Predicted Properties
Property Value Source Water Solubility 0.199 mg/mL ALOGPS logP 1.14 ALOGPS logP 0.22 ChemAxon logS -3.3 ALOGPS pKa (Strongest Acidic) 8.69 ChemAxon pKa (Strongest Basic) 10.18 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 145.44 Å2 ChemAxon Rotatable Bond Count 13 ChemAxon Refractivity 115.2 m3·mol-1 ChemAxon Polarizability 45.96 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at May 28, 2014 20:02 / Updated at January 02, 2022 12:00