Isoxsuprine

Isoxsuprine
Clinical data

Pronunciation	eye-SOCK-syoo-preen
Trade names	Duvadilan, Vasodilan
MedlinePlus	a682831
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral (tablets)
ATC code	C04AA01 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	~100% (humans),^[1] 2.2% (horses; oral)^[2]
Onset of action	1 hour
Biological half-life	<3 hours (horses)^[3]
Excretion	Mainly renal
Identifiers
IUPAC name 4-{1-Hydroxy-2-[(1-methyl-2-phenoxyethyl)amino]propyl}phenol
CAS Number	395-28-8
PubChem (CID)	3783
DrugBank	DB08941
ChemSpider	3651^Y
UNII	R15UI3245N^Y
KEGG	D08092^Y
ChEMBL	CHEMBL1197051^N
ECHA InfoCard	100.006.272
Chemical and physical data
Formula	C₁₈H₂₃NO₃
Molar mass	301.39 g·mol⁻¹
3D model (Jmol)	Interactive image
SMILES O(c1ccccc1)CC(NC(C)C(O)c2ccc(O)cc2)C
InChI InChI=1S/C18H23NO3/c1-13(12-22-17-6-4-3-5-7-17)19-14(2)18(21)15-8-10-16(20)11-9-15/h3-11,13-14,18-21H,12H2,1-2H3^Y Key:BMUKKTUHUDJSNZ-UHFFFAOYSA-N^Y

Isoxsuprine (used as isoxsuprine hydrochloride) is a drug used as a vasodilator^[4] in humans (under the trade name Duvadilan) and equines. Isoxsuprine is a β₂ adrenoreceptor agonist that causes direct relaxation of uterine and vascular smooth muscle via β₂ receptors.^[5]

Use

In humans

Isoxsuprine it is used in humans for treatment of premature labor, i.e. a tocolytic,^[6] and as a vasodilator for the treatment of cerebral vascular insufficiency, Raynaud's phenomenon, and other conditions.^[7]

Isoxsuprine may increase the heart rate, cause changes in blood pressure, and irritate the GI tract. It should therefore be used with caution if combined with other drugs that affect blood pressure, such as sedatives and anesthetic drugs.

In horses

Isoxsuprine is most commonly used to treat hoof-related problems in the horse, most commonly for laminitis and navicular disease, as its effects as a vasodilator are thought to increase circulation within the hoof to help counteract the problems associated with these conditions. Isoxsuprine is given orally, and many horses find the pills quite palatable.^[8] Isoxsuprine is a prohibited class B drug in FEI-regulated competition, and is often prohibited by other equine associations. It may be detected in the urine for several weeks or months following administration. It is therefore important to check the drug-rules within an animal's given competitive organization, before administering the drug.

Because it is a vasodilator, it should not be used in horses that are bleeding, or in mares following foaling.

References

↑ McGuigan, Michael A.; Whyte, Ian MacGregor; Dawson, Andrew H.; Seifert, Steven A.; Schonwald, Seth; Yip, Luke; Keyes, Daniel C.; Hurlbut, Katherine M.; Erdman, Andrew R.; Dart, Richard C. (2004). "125. Vasodilators". In Dart, Richard C. Medical Toxicology (3rd ed.). Philadelphia [u.a.]: Lippincott Williams & Wilkins. p. 718. ISBN 0781728452.
↑ Erkert, RS; Macallister, CG (April 2002). "Isoxsuprine hydrochloride in the horse: a review". Journal of veterinary pharmacology and therapeutics. 25 (2): 81–7. doi:10.1046/j.1365-2885.2002.00386.x. PMID 12000527.
↑ Cole, Cynthia; Bentz, Bradford; Maxwell, Lara, eds. (2014). "13. Clinical pharmacology of the equine musculoskeletal system". Equine pharmacology. Wiley—Blackwell. p. 224. ISBN 978-0-8138-2262-4.
↑ Gozo EG, Yebes RB (November 1984). "Hemodynamic effects of isoxsuprine in cardiac failure". Chest. 86 (5): 736–40. doi:10.1378/chest.86.5.736. PMID 6488912.
↑ Falkay, G.; Kovács, L. (1986). "Affinity of tocolytic agents on human placental and myometrial beta-adrenergic receptors". Journal of perinatal medicine. 14 (2): 109–113. doi:10.1515/jpme.1986.14.2.109. PMID 2874205.
↑ Giorgino, F. L.; Egan, C. G. (2010). "Use of isoxsuprine hydrochloride as a tocolytic agent in the treatment of preterm labour: A systematic review of previous literature". Arzneimittel-Forschung. 60 (7): 415–20. doi:10.1055/s-0031-1296305. PMID 20712130.
↑ Drugs.com: Isoxsuprine
↑ Forney, Barbara C (2007). Equine Medications. Lexington, KY: Blood Horse Publications.

Adrenergic receptor modulators

α₁

Agonists 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline

Antagonists Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone) Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride) Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Nefazodone Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin Silodosin Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Trazodone Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine) Trimazosin Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Urapidil WB-4101 Zolertine

α₂

Agonists (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rilmenidine Romifidine Talipexole Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil XP21279 Xylazine Xylometazoline

Antagonists 1-PP Adimolol Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine) Azapirones (e.g., buspirone, tandospirone) BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine

Agonists Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol

Antagonists Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

See also: Dopaminergics

Melatonergics

Serotonergics

Monoamine reuptake and release modulators

Monoamine metabolism modulators

Monoamine neurotoxins

Peripheral vasodilators (C04)

Phenylethanolamine derivatives	Isoxsuprine Buphenine Bamethan

Alpha blockers	Non-selective Tolazoline Phentolamine Selective α₁-blockers Alfuzosin Doxazosin Prazosin Silodosin Tamsulosin Terazosin

Niacin and derivatives	Niacin Nicotinyl alcohol Inositol nicotinate Ciclonicate

Purine derivatives	Pentifylline Xantinol nicotinate Pentoxifylline Etofylline nicotinate

Ergot alkaloids	Ergoloid Nicergoline Dihydroergocristine

Other peripheral vasodilators	Cyclandelate Phenoxybenzamine Vincamine Moxisylyte Bencyclane Vinburnine Sulcotidil Buflomedil Naftidrofuryl Butalamine Visnadine Cetiedil Cinepazide Ifenprodil Azapetine Fasudil

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