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- Experimental, Withdrawn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
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.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Premature labour •••••••••••• •••••••••• •••••••••• ••••••••• ••••••••••• - 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
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. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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. - 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 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
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 10 µg/2ml Injection, solution, concentrate Parenteral 25 µg - 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 splash10-000i-0920000000-63257fa3faea4c075a19 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0uk9-0033900000-cf9f902d760a1f91ac0c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0uy0-0610900000-abc6265b860d30d9b160 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0wml-0098400000-4a7d2c978faab008584a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0pc0-0309300000-d0fa269b201a957241f2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00ei-1940000000-279668c80ef06cbaf636 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05ci-0509000000-792b51d978ce49ba6e6e 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]- 205.72685 predictedDeepCCS 1.0 (2019) [M+H]+ 208.42183 predictedDeepCCS 1.0 (2019) [M+Na]+ 217.05196 predictedDeepCCS 1.0 (2019)
Drug created at May 28, 2014 20:02 / Updated at December 02, 2023 07:01