NAV

Hexoprenaline

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Experimental, Withdrawn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
3D
Similar Structures
Weight
Average: 420.4993
Monoisotopic: 420.226036766
Chemical Formula
C22H32N2O6
Synonyms
  • Hexoprenaline
External IDs
  • ST 1512/504
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofPremature labour•••••••••••••••••••••• •••••••••• ••••••••• •••••••••••
Contraindications & Blackbox Warnings
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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
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AcebutololThe therapeutic efficacy of Hexoprenaline can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Hexoprenaline.
AcemetacinThe risk or severity of hypertension can be increased when Hexoprenaline is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Hexoprenaline.
AclidiniumThe risk or severity of Tachycardia can be increased when Aclidinium is combined with Hexoprenaline.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Hexoprenaline sulfateU851S9102C32266-10-7GTDCHGNGVGRHQY-UHFFFAOYSA-N
International/Other Brands
Argocian (Biol) / Etoscol (DCPC) / Gynipral (Alkaloid) / Hexoline (Shou Chan) / Ipradol (Nycomed) / Taicopin (DCPC)

Categories

ATC Codes
R03AC06 — HexoprenalineR03CC05 — Hexoprenaline
Drug Categories
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
  1. 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]
PubChem Compound
3609
PubChem Substance
310264922
ChemSpider
3483
BindingDB
50239967
RxNav
5307
ChEMBL
CHEMBL1589896
Drugs.com
Drugs.com Drug Page
Wikipedia
Hexoprenaline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntravenous10 µg/2ml
Injection, solution, concentrateParenteral25 µg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)222-228U.S. Patent 3,329,709.
Predicted Properties
PropertyValueSource
Water Solubility0.199 mg/mLALOGPS
logP1.14ALOGPS
logP0.22Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.69Chemaxon
pKa (Strongest Basic)10.18Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area145.44 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity115.2 m3·mol-1Chemaxon
Polarizability45.96 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-0920000000-63257fa3faea4c075a19
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0033900000-cf9f902d760a1f91ac0c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uy0-0610900000-abc6265b860d30d9b160
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0wml-0098400000-4a7d2c978faab008584a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pc0-0309300000-d0fa269b201a957241f2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ei-1940000000-279668c80ef06cbaf636
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05ci-0509000000-792b51d978ce49ba6e6e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.72685
predicted
DeepCCS 1.0 (2019)
[M+H]+208.42183
predicted
DeepCCS 1.0 (2019)
[M+Na]+217.05196
predicted
DeepCCS 1.0 (2019)

Drug created at May 28, 2014 20:02 / Updated at December 02, 2023 07:01