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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

Molecular Formula C18H23NO3
Molecular Weight 301.3801
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Effects of phentolamine, dihydroergocristine and isoxsuprine on the blood pressure and heart rate in normotensive, hypotensive and hypertensive rats.
1975
Isoxsuprine hydrochloride in the horse: a review.
2002 Apr
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
Determination of beta-agonist residues in bovine urine using liquid chromatography-tandem mass spectrometry.
2005 Jan-Feb
[Multi-residue analysis of 10 beta2-agonists in animal tissues using gas chromatography-mass spectrometry].
2008 Jan
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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:11:37 GMT 2023
Edited
by admin
on Fri Dec 15 15:11:37 GMT 2023
Record UNII
R15UI3245N
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
WHO-ATC C04AA01
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
WHO-VATC QC04AA01
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
Code System Code Type Description
SMS_ID
100000082839
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
NCI_THESAURUS
C61795
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
INN
773
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
CAS
395-28-8
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL1197051
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID9023178
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
PUBCHEM
11779629
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
MERCK INDEX
m6555
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY Merck Index
FDA UNII
R15UI3245N
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
DRUG BANK
DB08941
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
MESH
D007556
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
DAILYMED
R15UI3245N
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
WIKIPEDIA
ISOXSUPRINE
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
RXCUI
6066
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
1510
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-898-2
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
EVMPD
SUB08345MIG
Created by admin on Fri Dec 15 15:11:37 GMT 2023 , Edited by admin on Fri Dec 15 15:11:37 GMT 2023
PRIMARY
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