Hexoprenaline

Identification

Name
Hexoprenaline
Accession Number
DB08957
Type
Small Molecule
Groups
Approved, Withdrawn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
Structured Indications
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
DrugInteractionDrug group
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
Benzylpenicilloyl PolylysineHexoprenaline may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Hexoprenaline.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Hexoprenaline.Investigational
BunazosinBunazosin may decrease the vasoconstricting activities of Hexoprenaline.Investigational
CabergolineCabergoline may increase the hypertensive activities of Hexoprenaline.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Hexoprenaline.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Hexoprenaline.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Hexoprenaline.Approved
DuloxetineDuloxetine may increase the tachycardic activities of Hexoprenaline.Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Hexoprenaline.Approved
ErgonovineErgonovine may increase the hypertensive activities of Hexoprenaline.Approved
ErgotamineErgotamine may increase the hypertensive activities of Hexoprenaline.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Hexoprenaline.Withdrawn
LabetalolLabetalol may decrease the vasoconstricting activities of Hexoprenaline.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Hexoprenaline.Approved
MethylergometrineMethylergometrine may increase the hypertensive activities of Hexoprenaline.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Hexoprenaline.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Hexoprenaline.Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Hexoprenaline.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Hexoprenaline.Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
TerazosinTerazosin may decrease the vasoconstricting activities of Hexoprenaline.Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Hexoprenaline.Experimental
UrapidilUrapidil may decrease the vasoconstricting activities of Hexoprenaline.Investigational
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Hexoprenaline.Approved
VenlafaxineVenlafaxine may increase the tachycardic activities of Hexoprenaline.Approved
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
R03CC05 — HexoprenalineR03AC06 — 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 December 01, 2017 17:19