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Approved, Withdrawn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
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
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Hexoprenaline.Experimental
AcebutololAcebutolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Investigational
AcepromazineAcepromazine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Vet Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Withdrawn
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Hexoprenaline.Illicit, Withdrawn
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Hexoprenaline.Approved
AmitriptylinoxideThe risk or severity of adverse effects can be increased when Amitriptylinoxide is combined with Hexoprenaline.Approved, Investigational
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Hexoprenaline.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Hexoprenaline.Approved, Illicit, Investigational
AripiprazoleAripiprazole may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
AsenapineAsenapine may decrease the vasoconstricting activities of Hexoprenaline.Approved
AtenololAtenolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
AtomoxetineAtomoxetine may increase the tachycardic activities of Hexoprenaline.Approved
AtosibanThe risk or severity of adverse effects can be increased when Hexoprenaline is combined with Atosiban.Approved, Investigational
AzosemideHexoprenaline may increase the hypokalemic activities of Azosemide.Investigational
BendroflumethiazideHexoprenaline may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Hexoprenaline.Withdrawn
BenzthiazideHexoprenaline may increase the hypokalemic activities of Benzthiazide.Approved
Benzylpenicilloyl PolylysineHexoprenaline may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Hexoprenaline can be decreased when used in combination with Betahistine.Approved, Investigational
BetaxololBetaxolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Investigational
BevantololBevantolol may decrease the vasoconstricting activities of Hexoprenaline.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
BrexpiprazoleBrexpiprazole may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
BrofaromineThe risk or severity of adverse effects can be increased when Brofaromine is combined with Hexoprenaline.Experimental
BromocriptineBromocriptine may increase the hypertensive and vasoconstricting activities of Hexoprenaline.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Hexoprenaline.Investigational
BumetanideHexoprenaline may increase the hypokalemic activities of Bumetanide.Approved
BunazosinBunazosin may decrease the vasoconstricting activities of Hexoprenaline.Investigational
BupranololBupranolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
ButriptylineThe risk or severity of adverse effects can be increased when Butriptyline is combined with Hexoprenaline.Approved
CabergolineCabergoline may increase the hypertensive and vasoconstricting activities of Hexoprenaline.Approved
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Hexoprenaline.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Investigational
ChlorothiazideHexoprenaline may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorpromazineChlorpromazine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational, Vet Approved
ChlorthalidoneHexoprenaline may increase the hypokalemic activities of Chlorthalidone.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Hexoprenaline.Approved, Investigational, Vet Approved
CloranololCloranolol may decrease the bronchodilatory activities of Hexoprenaline.Experimental
ClozapineClozapine may decrease the vasoconstricting activities of Hexoprenaline.Approved
CyclopenthiazideHexoprenaline may increase the hypokalemic activities of Cyclopenthiazide.Experimental
DapiprazoleDapiprazole may decrease the vasoconstricting activities of Hexoprenaline.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Hexoprenaline.Approved, Investigational
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Hexoprenaline.Approved, Investigational
DextroamphetamineDextroamphetamine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Illicit
DibenzepinThe risk or severity of adverse effects can be increased when Dibenzepin is combined with Hexoprenaline.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive and vasoconstricting activities of Hexoprenaline.Approved, Investigational
DimetacrineThe risk or severity of adverse effects can be increased when Dimetacrine is combined with Hexoprenaline.Approved, Withdrawn
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Hexoprenaline.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Hexoprenaline.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Hexoprenaline.Approved, Investigational
DoxofyllineThe risk or severity of adverse effects can be increased when Doxofylline is combined with Hexoprenaline.Approved, Investigational
DronedaroneDronedarone may decrease the vasoconstricting activities of Hexoprenaline.Approved
DroperidolDroperidol may decrease the vasoconstricting activities of Hexoprenaline.Approved, Vet Approved
DuloxetineDuloxetine may increase the tachycardic activities of Hexoprenaline.Approved
EpinephrineEpinephrine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Vet Approved
EpitizideHexoprenaline may increase the hypokalemic activities of Epitizide.Experimental
Ergoloid mesylateErgoloid mesylate may increase the hypertensive and vasoconstricting activities of Hexoprenaline.Approved
ErgonovineErgonovine may increase the hypertensive and vasoconstricting activities of Hexoprenaline.Approved
ErgotamineErgotamine may increase the hypertensive and vasoconstricting activities of Hexoprenaline.Approved
EscitalopramEscitalopram may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
Etacrynic acidHexoprenaline may increase the hypokalemic activities of Etacrynic acid.Approved, Investigational
FlupentixolFlupentixol may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational, Withdrawn
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Hexoprenaline.Approved, Investigational, Vet Approved
FurosemideHexoprenaline may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Hexoprenaline.Experimental
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Hexoprenaline.Experimental
HydrochlorothiazideHexoprenaline may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideHexoprenaline may increase the hypokalemic activities of Hydroflumethiazide.Approved, Investigational
IloperidoneIloperidone may decrease the vasoconstricting activities of Hexoprenaline.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Hexoprenaline.Approved
IndapamideHexoprenaline may increase the hypokalemic activities of Indapamide.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Hexoprenaline.Withdrawn
IprindoleThe risk or severity of adverse effects can be increased when Iprindole is combined with Hexoprenaline.Experimental
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Hexoprenaline.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Hexoprenaline.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Hexoprenaline.Approved
LabetalolLabetalol may decrease the vasoconstricting activities of Hexoprenaline.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Hexoprenaline.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
LofepramineThe risk or severity of adverse effects can be increased when Lofepramine is combined with Hexoprenaline.Experimental
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Hexoprenaline.Withdrawn
MelitracenThe risk or severity of adverse effects can be increased when Melitracen is combined with Hexoprenaline.Experimental, Investigational
MepindololMepindolol may decrease the bronchodilatory activities of Hexoprenaline.Experimental
MethotrimeprazineMethotrimeprazine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
MethyclothiazideHexoprenaline may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Hexoprenaline.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive and vasoconstricting activities of Hexoprenaline.Approved
MetolazoneHexoprenaline may increase the hypokalemic activities of Metolazone.Approved
MetoprololMetoprolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of Hexoprenaline.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Hexoprenaline.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Hexoprenaline.Approved, Investigational
NadololNadolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
NebivololNebivolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Investigational
NefazodoneNefazodone may decrease the vasoconstricting activities of Hexoprenaline.Approved, Withdrawn
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Hexoprenaline.Withdrawn
NicardipineNicardipine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
NicergolineNicergoline may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
NiguldipineNiguldipine may decrease the vasoconstricting activities of Hexoprenaline.Experimental
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Hexoprenaline.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Hexoprenaline.Withdrawn
OlanzapineOlanzapine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Hexoprenaline.Investigational
OxprenololOxprenolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
PaliperidonePaliperidone may decrease the vasoconstricting activities of Hexoprenaline.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Hexoprenaline.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Investigational
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Hexoprenaline.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Hexoprenaline.Withdrawn
PhenoxybenzaminePhenoxybenzamine may decrease the vasoconstricting activities of Hexoprenaline.Approved
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Hexoprenaline.Withdrawn
PhentolaminePhentolamine may decrease the vasoconstricting activities of Hexoprenaline.Approved
PindololPindolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Investigational
PiretanideHexoprenaline may increase the hypokalemic activities of Piretanide.Approved
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Hexoprenaline.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Hexoprenaline.Withdrawn
PizotifenPizotifen may decrease the vasoconstricting activities of Hexoprenaline.Approved
PolythiazideHexoprenaline may increase the hypokalemic activities of Polythiazide.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Hexoprenaline.Approved
ProcaineThe risk or severity of adverse effects can be increased when Procaine is combined with Hexoprenaline.Approved, Investigational, Vet Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Hexoprenaline.Approved, Investigational
PromazinePromazine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Vet Approved
PropericiazinePropericiazine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
PropiomazinePropiomazine may decrease the vasoconstricting activities of Hexoprenaline.Approved
PropiverinePropiverine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
PropranololPropranolol may decrease the bronchodilatory activities of Hexoprenaline.Approved, Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Hexoprenaline.Approved
QuetiapineQuetiapine may decrease the vasoconstricting activities of Hexoprenaline.Approved
QuinethazoneHexoprenaline may increase the hypokalemic activities of Quinethazone.Approved
QuinidineQuinidine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
RacepinephrineRacepinephrine may decrease the vasoconstricting activities of Hexoprenaline.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Hexoprenaline.Approved
RisperidoneRisperidone may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Hexoprenaline.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Hexoprenaline.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Hexoprenaline.Approved
SotalolSotalol may decrease the bronchodilatory 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
TertatololTertatolol may decrease the bronchodilatory activities of Hexoprenaline.Experimental
ThioproperazineThioproperazine may decrease the vasoconstricting activities of Hexoprenaline.Approved
ThioridazineThioridazine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Withdrawn
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Hexoprenaline.Approved, Investigational
TimololTimolol may decrease the bronchodilatory activities of Hexoprenaline.Approved
TolazolineTolazoline may decrease the vasoconstricting activities of Hexoprenaline.Approved, Vet Approved
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Hexoprenaline.Approved
TorasemideHexoprenaline may increase the hypokalemic activities of Torasemide.Approved
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Hexoprenaline.Approved, Investigational
TrazodoneTrazodone may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
TrichlormethiazideHexoprenaline may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrifluoperazineTrifluoperazine may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
TrimazosinTrimazosin may decrease the vasoconstricting activities of Hexoprenaline.Experimental
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Hexoprenaline.Approved
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
VerapamilVerapamil may decrease the vasoconstricting activities of Hexoprenaline.Approved
ZiprasidoneZiprasidone may decrease the vasoconstricting activities of Hexoprenaline.Approved
ZuclopenthixolZuclopenthixol may decrease the vasoconstricting activities of Hexoprenaline.Approved, Investigational
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 July 02, 2018 20:41