Hexoprenaline

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Hexoprenaline
Hexoprenaline.svg
Clinical data
Pronunciation/ˌhɛksˈprɛnəln/ 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
  • C1=CC(=C(C=C1C(CNCCCCCCNCC(C2=CC(=C(C=C2)O)O)O)O)O)O
  • 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?)  (verify)

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:

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

Drug-drug interactions

When concomitantly administered:

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.