Hexoprenaline

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Hexoprenaline
Hexoprenaline.svg
Clinical data
Pronunciation/ˌhɛksoʊˈprɛnəliːn/ HEKS-oh-PREN-ə-leen
Other names4-[2-[6-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]hexylamino]-1-hydroxyethyl]benzene-1,2-diol
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral (tablets), IV
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability5–11% (Tmax = 2 hours)
MetabolismCOMT (slow O-methylation)
Elimination half-life~50 minutes (if taken orally)
ExcretionFeces (~90%)[1]
Identifiers
  • (±)-4,4'-{Hexane-1,6-diylbis[imino(1-hydroxyethane-2,1-diyl)]}dibenzene-1,2-diol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H32N2O6
Molar mass420.506 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • C1=CC(=C(C=C1C(CNCCCCCCNCC(C2=CC(=C(C=C2)O)O)O)O)O)O
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 ☒N
  • Key:OXLZNBCNGJWPRV-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  

Hexoprenaline is a selective β2 adrenergic receptor agonist used in the treatment of asthma.[2] 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.[3][4] It is not approved by the United States Food and Drug Administration.

Contraindications[]

When used as a tocolytic, hexoprenaline is contraindicated in:

  • Hyperthyroidism
  • Cardiovascular diseases, e.g. cardiac arrhythmias, tachycardia, myocarditis, mitral valve disease and aortic stenosis
  • Ischemic heart disease
  • Hypertension
  • Angle-closure glaucoma
  • Placental abruption, vaginal bleeding and inflammatory diseases of internal genitalia (such as endometritis)
  • Shock
  • First trimester of pregnancy
  • Breastfeeding[1][3]

It should be used with caution in people with gestational diabetes.

Drug-drug interactions[]

When concomitantly administered:

  • Beta blockers reduce or neutralize therapeutic effects of hexoprenaline
  • Methylxanthines (caffeine, theobromine, theophylline) increase its action
  • General anaesthetics (e.g., halothane) and adrenergic receptor agonists may increase the risk of cardiovascular side effects, such as arrhythmia

Hexoprenaline is contraindicated for use with monoamine oxidase inhibitors (MAOIs), tricyclic antidepressant (TCAs), ergot alkaloids, and dihydrotachysterol.[3]

References[]

  1. ^ a b "Gynipral (hexoprenaline) Full Prescribing Information". Russian State Register of Medicinal Products (in Russian). Nycomed Austria GmbH. St. Peter-Straße 25, A-4020, Linz, Austria. Retrieved 19 March 2016.
  2. ^ Pinder RM, Brogden RN, Speight TM, Avery GS (July 1977). "Hexoprenaline: a review of its pharmacological properties and therapeutic efficacy with particular reference to asthma". Drugs. 14 (1): 1–28. doi:10.2165/00003495-197714010-00001. PMID 195789.
  3. ^ a b c "Gynipral (hexoprenaline) Tablets 0.5 mg, Solution for Intravenous Infusion 5 μg/mL (0.0005%)". "RLS" (РЛС): Russian Register of Medical Products (in Russian). Retrieved 19 March 2016.
  4. ^ "GYNIPRAL Inj Lös 10 mcg/2ml". "Compendium": Swiss Register of Medical Products (in German). Retrieved 3 April 2017.
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