Hexoprenaline

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.

Hexoprenaline

Clinical data
Pronunciation	/ˌhɛksoʊˈprɛnəliːn/ HEKS-oh-PREN-ə-leen
Other names	4-[2-[6-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]hexylamino]-1-hydroxyethyl]benzene-1,2-diol
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral (tablets), IV
ATC code	R03AC06 (WHO) R03CC05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	5–11% (Tmax = 2 hours)
Metabolism	COMT (slow O-methylation)
Elimination half-life	~50 minutes (if taken orally)
Excretion	Feces (~90%)[1]
Identifiers
IUPAC name (±)-4,4'-{Hexane-1,6-diylbis[imino(1-hydroxyethane-2,1-diyl)]}dibenzene-1,2-diol
CAS Number	3215-70-1 Y
PubChem CID	3609
DrugBank	DB08957 N
ChemSpider	3483 N
UNII	G9L6B3W684
KEGG	D08039 N
CompTox Dashboard (EPA)	DTXSID7048322
Chemical and physical data
Formula	C22H32N2O6
Molar mass	420.506 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic 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
NY (what is this?)  (verify)

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. "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. S2CID 43775455.
3. "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.