hexoprenaline

Hexoprenaline is a selective β2 adrenergic receptor agonist used in the treatment of asthma. Hexoprenaline is also used in some countries (such as Russia and Switzerland) as a tocolytic agent (i.e., labor suppressant), with the most common trade name being Gynipral. It is not approved by the United States Food and Drug Administration.

Key facts

Drug.ATC_prefix: R03
Drug.ATC_suffix: AC06
Drug.PubChem: 3609
Drug.DrugBank: DB08957
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 444541801
Drug.IUPAC_name: (±)-4,4'-{Hexane-1,6-diylbis[imino(1-hydroxyethane-2,1-diyl)]}dibenzene-1,2-diol
Drug.image: Hexoprenaline.svg
Drug.image_class: skin-invert-image
Drug.width: 225px
Drug.chirality: Racemic mixture
Drug.legal_AU: S4
Drug.legal_status: Rx-only
Drug.routes_of_administration: Oral (tablets), IV
Drug.bioavailability: 5–11% (Tmax = 2 hours)
Drug.metabolism: COMT (slow O-methylation)
Drug.elimination_half life: ~50 minutes (if taken orally)

via Wikipedia infobox

Chemical data

Formula: C22H32N2O6
Molecular weight: 420.5 g/mol
IUPAC name: 4-[2-[6-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]hexylamino]-1-hydroxyethyl]benzene-1,2-diol

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule
Indications: Airway obstruction

via ChEMBL · EBI

Research

207 papers

Hexoprenaline Compared with Atosiban as Tocolytic Treatment for Preterm Labor.Geburtshilfe und Frauenheilkunde · 2022
Hexoprenaline--a new bronchodilator.South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde · 1972
Hexoprenaline activates potassium channels of human myometrial myocytes.Archives of gynecology and obstetrics · 1993
Beta-adrenergic bronchodilators.Pediatric clinics of North America · 1975
A prospective randomised trial of atosiban versus hexoprenaline for acute tocolysis and intrauterine resuscitation.BJOG : an international journal of obstetrics and gynaecology · 2004

via PubMed

Wikidata facts

Mass: 420.226

Show 5 more facts

chemical formula: C₂₂H₃₂N₂O₆
World Health Organisation international non-proprietary name: hexoprenaline
canonical SMILES: C1=CC(=C(C=C1C(CNCCCCCCNCC(C2=CC(=C(C=C2)O)O)O)O)O)O
defined daily dose: 1.5
Commons category: Hexoprenaline

Sources (3)

via Wikidata · CC0

~3 min read

Article

3 sections

Contents

Contraindications
Drug-drug interactions
References

{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444541801 | IUPAC_name = (±)-4,4'-{Hexane-1,6-diylbis[imino(1-hydroxyethane-2,1-diyl)]}dibenzene-1,2-diol | image = Hexoprenaline.svg | image_class = skin-invert-image | width = 225px | chirality = Racemic mixture