Hexoprenaline

Identification

Name
Hexoprenaline
Accession Number
DB08957
Type
Small Molecule
Groups
Experimental, Withdrawn
Description

Hexoprenaline is a stimulant of beta 2 adrenergic receptors. It is used as a bronchodilator, antiasthmatic, and tocolytic agent.

Structure
Thumb
Synonyms
Not Available
External IDs
ST 1512/504
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
UNII
G9L6B3W684
CAS number
3215-70-1
Weight
Average: 420.4993
Monoisotopic: 420.226036766
Chemical Formula
C22H32N2O6
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid is combined with Hexoprenaline.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Hexoprenaline.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Hexoprenaline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Hexoprenaline is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Hexoprenaline.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Hexoprenaline.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of hypertension can be increased when Hexoprenaline is combined with 5-methoxy-N,N-dimethyltryptamine.
AbediterolThe risk or severity of adverse effects can be increased when Hexoprenaline is combined with Abediterol.
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.
Food Interactions
Not Available

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. [PubMed:195789]
External Links
PubChem Compound
3609
PubChem Substance
310264922
ChemSpider
3483
ChEMBL
CHEMBL1589896
Drugs.com
Drugs.com Drug Page
Wikipedia
Hexoprenaline
ATC Codes
R03AC06 — HexoprenalineR03CC05 — Hexoprenaline

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Secondary amine / Secondary aliphatic amine / Aromatic alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on May 28, 2014 14:02 / Updated on November 02, 2018 08:46