Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H23NO3.ClH |
Molecular Weight | 337.841 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C[C@H](COC1=CC=CC=C1)N[C@H](C)[C@@H](O)C2=CC=C(O)C=C2
InChI
InChIKey=QVPSGVSNYPRFAS-BQZDIUEZSA-N
InChI=1S/C18H23NO3.ClH/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;1H/t13-,14-,18-;/m1./s1
DescriptionSources: https://www.drugs.com/cdi/isoxsuprine.htmlCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22893038 | https://www.ncbi.nlm.nih.gov/pubmed/16388203 | https://www.ncbi.nlm.nih.gov/pubmed/11445487 | https://www.ncbi.nlm.nih.gov/pubmed/2874205
Sources: https://www.drugs.com/cdi/isoxsuprine.html
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22893038 | https://www.ncbi.nlm.nih.gov/pubmed/16388203 | https://www.ncbi.nlm.nih.gov/pubmed/11445487 | https://www.ncbi.nlm.nih.gov/pubmed/2874205
Isoxsuprine (used as isoxsuprine hydrochloride) is a drug used as a vasodilator 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. Isoxsuprine it is used in humans for treatment of premature labor, i.e. a tocolytic, and as a vasodilator for the treatment of cerebral vascular insufficiency, Raynaud's phenomenon, and other conditions. 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. 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.
Approval Year
PubMed
Title | Date | PubMed |
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Soft tissue necrosis with noradrenaline and its prevention with isoxsuprine. | 1967 Apr |
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Effects of phentolamine, dihydroergocristine and isoxsuprine on the blood pressure and heart rate in normotensive, hypotensive and hypertensive rats. | 1975 |
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Effect of intravenous infusion of betasympathomimetic agents on plasma renin activity during pregnancy. | 1978 Nov |
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Myotonic muscular dystrophy associated with ritodrine tocolysis. | 1985 Jan 1 |
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Transient electrocardiographic changes suggesting myocardial ischaemia in newborn infants following tocolysis with beta-sympathomimetics. | 1990 Jul |
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Therapeutic effects of high-dose isoxsuprine in the management of mixed-type impotence. | 2001 Jul |
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Tricuspid regurgitation in a pair of twins at birth secondary to antenatal indomethacin. | 2001 Oct |
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Isoxsuprine hydrochloride in the horse: a review. | 2002 Apr |
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Fluorimetric determination of isoxsuprine hydrochloride in pharmaceuticals and biological fluids. | 2002 Apr 15 |
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A simple kinetic spectrophotometric method for the determination of isoxsuprine in dosage forms. | 2002 Aug |
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Enantioseparation of chiral vasodilator drug isoxsuprine in high-performance liquid chromatography and capillary electrophoresis. | 2002 Jan 1 |
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The history of tocolysis. | 2003 Apr |
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A comparative study between nifedipine and isoxsuprine in the suppression of preterm labour. | 2003 Apr-Jun |
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Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol. | 2004 Apr 21 |
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Infectious and uterus related complications during pregnancy and development of atopic and nonatopic asthma in children. | 2004 Jan |
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A GC-MS method for the determination of isoxsuprine in biological fluids of the horse utilizing electron impact ionization. | 2004 Jan-Feb |
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Evaluation of MISPE for the multi-residue extraction of beta-agonists from calves urine. | 2004 May 5 |
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An analgesic evaluation of isoxsuprine in horses. | 2004 Sep-Oct |
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Search of chemical scaffolds for novel antituberculosis agents. | 2005 Apr |
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Design, synthesis and evaluation of racemic 1-(4-hydroxyphenyl)-2-[3-(substituted phenoxy)-2-hydroxy-1-propyl]amino-1-propanol hydrochlorides as novel uterine relaxants. | 2005 Aug 1 |
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Qualitative and quantitative analysis of illicit drug mixtures on paper currency using Raman microspectroscopy. | 2005 Dec |
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Determination of beta-agonists in liver and retina by liquid chromatography-tandem mass spectrometry. | 2005 Jan-Feb |
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Determination of beta-agonist residues in bovine urine using liquid chromatography-tandem mass spectrometry. | 2005 Jan-Feb |
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Determination of isoxsuprine hydrochloride by sequential injection visible spectrophotometry. | 2005 Jun-Jul |
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Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol. | 2005 May 4 |
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Synthesis and evaluation of uterine relaxant activity for a novel series of substituted p-hydroxyphenylethanolamines. | 2006 Oct 1 |
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Use of isoxsuprine for treatment of clinical signs associated with presumptive atherosclerosis in a yellow-naped Amazon parrot (Amazona ochrocephala auropalliata). | 2007 Sep |
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Effects of alcohols on CE enantioseparation of basic drugs with native gamma-CD as chiral selector. | 2008 Aug |
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[Multi-residue analysis of 10 beta2-agonists in animal tissues using gas chromatography-mass spectrometry]. | 2008 Jan |
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A highly sensitive assay for ritodrine in human serum by hydrophilic interaction chromatography-tandem mass spectrometry. | 2008 Jan 1 |
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Prophylactic oral betamimetics for preventing preterm labour in singleton pregnancies. | 2008 Jan 23 |
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Pharmacokinetics of isoxsuprine hydrochloride administered orally and intramuscularly to female healthy volunteers. | 2009 |
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Rapid determination of ractopamine residues in edible animal products by enzyme-linked immunosorbent assay: development and investigation of matrix effects. | 2009 |
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Drugs to treat Alzheimer's disease. | 2009 Apr |
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Rapid classification of simulated street drug mixtures using Raman spectroscopy and principal component analysis. | 2009 Jul |
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Molecularly imprinted polymer for the determination of trace ractopamine in pork using SPE followed by HPLC with fluorescence detection. | 2009 May |
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Ritodrine and isoxsuprine in management of preterm labor. | 2009 Oct-Dec |
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Use of isoxsuprine hydrochloride as a tocolytic agent in the treatment of preterm labour: a systematic review of previous literature. | 2010 |
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Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories. | 2010 Apr |
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Management of pregnant female with meningioma for craniotomy. | 2010 Jan |
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Simultaneous determination of ritodrine and isoxsuprine using coupling technique of synchronous fluorimetry and H-point standard addition method. | 2010 Jan |
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Investigation of ractopamine-imprinted polymer for dispersive solid-phase extraction of trace beta-agonists in pig tissues. | 2010 Jul |
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Use of N, N-diethyl-p-phenylenediamine sulphate for the spectrophotometric determination of some phenolic and amine drugs. | 2010 Jun |
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Determination of beta-agonists in pig feed, pig urine and pig liver using capillary electrophoresis with electrochemical detection. | 2010 Jun |
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Development and validation of fixed-time method for the determination of isoxsuprine hydrochloride in commercial dosages forms. | 2010 Sep |
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Discovery of novel CDK1 inhibitors by combining pharmacophore modeling, QSAR analysis and in silico screening followed by in vitro bioassay. | 2010 Sep |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2874205
Human myometrial strips were obtained from uteri at the time of cesarean section. The tissues were homogenized in 10 volume of buffer containing 10 mM Tris. HC1 0.25 M sucrose, 1 mM EDTA and 3mM MgCk, pH 7.4, using an Ultra-Turrax PRUhomogenizer. The homogenate was passed through four layers of gauze and centrifuged at 600 x g for 10 min at 4 °C to remove unbroken cells and connective tissue. The supernatant was centrifuged twice at 48 000 χ g for 20 min, with washing of the intermediate pellet. The final pellet was resuspended in assay buffer (50 mM Tris. HC1, 3 mM MgCk, pH 7.4). The membrane preparations were stored in liquid nitrogen until used. 100 μΐ aliquots of the membrane fraction were prepared in triplicate and incubated with 6 nM [3H]-DHA and the increasing concentration of the displacing agent (Isoxsuprine) in a final volume of 300 μΐ assay buffer. After incubation for 20 min at 25 °C, 2 ml of icecold buffer were added and immediately filtered over glassfiber filters
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NCI_THESAURUS |
C29707
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ACTIVE MOIETY
SUBSTANCE RECORD