Hexoprenaline

Hexoprenaline

Systematic (IUPAC) name
(±)-4,4'-{Hexane-1,6-diylbis[imino(1-hydroxyethane-2,1-diyl)]}dibenzene-1,2-diol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral (tablets), IV
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	5–11% (Tmax = 2 hours)
Metabolism	COMT (slow O-methylation)
Biological half-life	~50 minutes (if taken orally)
Excretion	Feces (~90%)[1]
Identifiers
CAS Number	3215-70-1
ATC code	R03AC06 (WHO) R03CC05
PubChem	CID 3609
DrugBank	DB08957
ChemSpider	3483
UNII	G9L6B3W684
KEGG	D08039
Synonyms	4-[2-[6-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]hexylamino]-1-hydroxyethyl]benzene-1,2-diol
Chemical data
Formula	C22H32N2O6
Molar mass	420.499 g/mol
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 Key:OXLZNBCNGJWPRV-UHFFFAOYSA-N
(what is this?)  (verify)

Hexoprenaline (HEX-oh-PREN-a-leen, INN) is a selective β₂ adrenergic receptor agonist used in the treatment of asthma.^[2] Hexoprenaline is also used in some countries (such as Russia) as a tocolytic agent (i.e., labor suppressant), with the most common trade name being Gynipral.^[3] It is not approved by U.S. FDA.

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, ™; Avery, GS (July 1977). "Hexoprenaline". Drugs 14 (1): 1–28. doi:10.2165/00003495-197714010-00001. PMID 195789.
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.