U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ISOXSUPRINE HYDROCHLORIDE

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

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
[Multi-residue analysis of 10 beta2-agonists in animal tissues using gas chromatography-mass spectrometry].
2008 Jan
Prophylactic oral betamimetics for preventing preterm labour in singleton pregnancies.
2008 Jan 23
Ritodrine and isoxsuprine in management of preterm labor.
2009 Oct-Dec
Use of N, N-diethyl-p-phenylenediamine sulphate for the spectrophotometric determination of some phenolic and amine drugs.
2010 Jun
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 HYDROCHLORIDE
EP   HSDB   JAN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
Common Name English
ISOXSUPRINE HCL
Common Name English
ISOXSUPRINE HYDROCHLORIDE [MART.]
Common Name English
VASOTRAN
Brand Name English
ISOXSUPRINE HYDROCHLORIDE [HSDB]
Common Name English
DILAVASE
Brand Name English
ISOXSUPRINE HYDROCHLORIDE [MI]
Common Name English
ISOXSUPRINE HYDROCHLORIDE [VANDF]
Common Name English
ISOXSUPRINE HYDROCHLORIDE [USP-RS]
Common Name English
VADOSILAN
Brand Name English
DUVADILAN
Brand Name English
P-HYDROXY-.ALPHA.-(1-((1-METHYL-2-PHENOXYETHYL)AMINO)ETHYL)BENZYL ALCOHOL HYDROCHLORIDE
Common Name English
ISOXSUPRINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
NAVILOX
Brand Name English
DUVICULINE
Brand Name English
ISOXSUPRINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
VASODILAN
Brand Name English
ISOXSUPRINE HYDROCHLORIDE [JAN]
Common Name English
SUPRILENT
Brand Name English
NSC-757067
Code English
(±)-(.ALPHA.R*)-P-HYDROXY-.ALPHA.-((1S*)-1-(((1S*)-1-METHYL-2-PHENOXYETHYL)AMINO)ETHYL)BENZYL ALCOHOL HYDROCHLORIDE
Common Name English
Isoxsuprine hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 15:01:21 GMT 2023 , Edited by admin on Fri Dec 15 15:01:21 GMT 2023
Code System Code Type Description
RXCUI
82033
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PRIMARY RxNorm
PUBCHEM
73415938
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PRIMARY
HSDB
3106
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PRIMARY
FDA UNII
V74TEQ36CO
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PRIMARY
ChEMBL
CHEMBL1197051
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PRIMARY
SMS_ID
100000086440
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PRIMARY
EPA CompTox
DTXSID1045328
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PRIMARY
ECHA (EC/EINECS)
209-443-6
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PRIMARY
RS_ITEM_NUM
1354003
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PRIMARY
CAS
579-56-6
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DRUG BANK
DBSALT001553
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PRIMARY
MERCK INDEX
m6555
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PRIMARY Merck Index
NSC
757067
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PRIMARY
NCI_THESAURUS
C47576
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PRIMARY
DAILYMED
V74TEQ36CO
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PRIMARY
EVMPD
SUB02808MIG
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PRIMARY