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Details

Stereochemistry RACEMIC
Molecular Formula C18H23NO3
Molecular Weight 301.3801
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOXSUPRINE

SMILES

C[C@H](COC1=CC=CC=C1)N[C@H](C)[C@@H](O)C2=CC=C(O)C=C2

InChI

InChIKey=BMUKKTUHUDJSNZ-HBUWYVDXSA-N
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/t13-,14-,18-/m1/s1

HIDE SMILES / InChI

Description
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.

Originator

Sources: Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1956), 75, 1215-20.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.48 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Soft tissue necrosis with noradrenaline and its prevention with isoxsuprine.
1967 Apr
Effects of phentolamine, dihydroergocristine and isoxsuprine on the blood pressure and heart rate in normotensive, hypotensive and hypertensive rats.
1975
Effect of intravenous infusion of betasympathomimetic agents on plasma renin activity during pregnancy.
1978 Nov
Myotonic muscular dystrophy associated with ritodrine tocolysis.
1985 Jan 1
Transient electrocardiographic changes suggesting myocardial ischaemia in newborn infants following tocolysis with beta-sympathomimetics.
1990 Jul
Therapeutic effects of high-dose isoxsuprine in the management of mixed-type impotence.
2001 Jul
Tricuspid regurgitation in a pair of twins at birth secondary to antenatal indomethacin.
2001 Oct
Isoxsuprine hydrochloride in the horse: a review.
2002 Apr
Fluorimetric determination of isoxsuprine hydrochloride in pharmaceuticals and biological fluids.
2002 Apr 15
A simple kinetic spectrophotometric method for the determination of isoxsuprine in dosage forms.
2002 Aug
Enantioseparation of chiral vasodilator drug isoxsuprine in high-performance liquid chromatography and capillary electrophoresis.
2002 Jan 1
The history of tocolysis.
2003 Apr
A comparative study between nifedipine and isoxsuprine in the suppression of preterm labour.
2003 Apr-Jun
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.
2004 Apr 21
Infectious and uterus related complications during pregnancy and development of atopic and nonatopic asthma in children.
2004 Jan
A GC-MS method for the determination of isoxsuprine in biological fluids of the horse utilizing electron impact ionization.
2004 Jan-Feb
Evaluation of MISPE for the multi-residue extraction of beta-agonists from calves urine.
2004 May 5
An analgesic evaluation of isoxsuprine in horses.
2004 Sep-Oct
Search of chemical scaffolds for novel antituberculosis agents.
2005 Apr
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
Qualitative and quantitative analysis of illicit drug mixtures on paper currency using Raman microspectroscopy.
2005 Dec
Determination of beta-agonists in liver and retina by liquid chromatography-tandem mass spectrometry.
2005 Jan-Feb
Determination of beta-agonist residues in bovine urine using liquid chromatography-tandem mass spectrometry.
2005 Jan-Feb
Determination of isoxsuprine hydrochloride by sequential injection visible spectrophotometry.
2005 Jun-Jul
Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol.
2005 May 4
Synthesis and evaluation of uterine relaxant activity for a novel series of substituted p-hydroxyphenylethanolamines.
2006 Oct 1
Use of isoxsuprine for treatment of clinical signs associated with presumptive atherosclerosis in a yellow-naped Amazon parrot (Amazona ochrocephala auropalliata).
2007 Sep
Effects of alcohols on CE enantioseparation of basic drugs with native gamma-CD as chiral selector.
2008 Aug
[Multi-residue analysis of 10 beta2-agonists in animal tissues using gas chromatography-mass spectrometry].
2008 Jan
A highly sensitive assay for ritodrine in human serum by hydrophilic interaction chromatography-tandem mass spectrometry.
2008 Jan 1
Prophylactic oral betamimetics for preventing preterm labour in singleton pregnancies.
2008 Jan 23
Pharmacokinetics of isoxsuprine hydrochloride administered orally and intramuscularly to female healthy volunteers.
2009
Rapid determination of ractopamine residues in edible animal products by enzyme-linked immunosorbent assay: development and investigation of matrix effects.
2009
Drugs to treat Alzheimer's disease.
2009 Apr
Rapid classification of simulated street drug mixtures using Raman spectroscopy and principal component analysis.
2009 Jul
Molecularly imprinted polymer for the determination of trace ractopamine in pork using SPE followed by HPLC with fluorescence detection.
2009 May
Ritodrine and isoxsuprine in management of preterm labor.
2009 Oct-Dec
Use of isoxsuprine hydrochloride as a tocolytic agent in the treatment of preterm labour: a systematic review of previous literature.
2010
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
Management of pregnant female with meningioma for craniotomy.
2010 Jan
Simultaneous determination of ritodrine and isoxsuprine using coupling technique of synchronous fluorimetry and H-point standard addition method.
2010 Jan
Investigation of ractopamine-imprinted polymer for dispersive solid-phase extraction of trace beta-agonists in pig tissues.
2010 Jul
Use of N, N-diethyl-p-phenylenediamine sulphate for the spectrophotometric determination of some phenolic and amine drugs.
2010 Jun
Determination of beta-agonists in pig feed, pig urine and pig liver using capillary electrophoresis with electrochemical detection.
2010 Jun
Spectrophotometric determination of isoxsuprine hydrochloride using 3-methyl-2-benzothiazolinone hydrazone hydrochloride in spiked human urine and pharmaceuticals.
2010 Jun 15
Investigation of ractopamine molecularly imprinted stir bar sorptive extraction and its application for trace analysis of beta2-agonists in complex samples.
2010 May 28
Development and validation of fixed-time method for the determination of isoxsuprine hydrochloride in commercial dosages forms.
2010 Sep
Discovery of novel CDK1 inhibitors by combining pharmacophore modeling, QSAR analysis and in silico screening followed by in vitro bioassay.
2010 Sep
Patents

Patents

Sample Use Guides

Oral: 10 to 20 mg, three or four times daily.
Route of Administration: Oral
In Vitro Use Guide
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
Name Type Language
ISOXSUPRINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BENZYL ALCOHOL, P-HYDROXY-ALPHA-(1-((1-METHYL-2-PHENOXYETHYL)AMINO)ETHYL)-
Common Name English
Isoxsuprine [WHO-DD]
Common Name English
DILATOR
Brand Name English
isoxsuprine [INN]
Common Name English
BENZENEMETHANOL, 4-HYDROXY-ALPHA-(1-((1-METHYL-2-PHENOXYETHYL)AMINO)ETHYL)-
Systematic Name English
ISOXSUPRINE [MI]
Common Name English
ISOXSUPRINE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
WHO-ATC C04AA01
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
WHO-VATC QC04AA01
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
Code System Code Type Description
SMS_ID
100000082839
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
NCI_THESAURUS
C61795
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
INN
773
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
CAS
395-28-8
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL1197051
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023178
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
PUBCHEM
11779629
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
MERCK INDEX
m6555
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY Merck Index
FDA UNII
R15UI3245N
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
DRUG BANK
DB08941
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
MESH
D007556
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
DAILYMED
R15UI3245N
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
WIKIPEDIA
ISOXSUPRINE
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
RXCUI
6066
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
1510
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-898-2
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY
EVMPD
SUB08345MIG
Created by admin on Fri Dec 15 15:11:37 UTC 2023 , Edited by admin on Fri Dec 15 15:11:37 UTC 2023
PRIMARY