Isoxsuprine HCl
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MedKoo CAT#: 531027

CAS#: 579-56-6 (HCl)

Description: Isoxsuprine is a beta 2-adrenergic agonist and NR2B subtype-selective N-methyl-D-aspartate (NMDA) receptor antagonist used for the treatment of pre-term labor and dysmenorrhea. Isoxsuprine affects the vascular smooth muscle and results in peripheral vascular dilation. Isoxsuprine also relaxes the uterine smooth muscles. Isoxsuprine elevated the blood flow volume in the umbilical arteries. Veterinary treatment of cows with isoxsuprine may temporarily lead to low levels of isoxsuprine in the hair of their newborn calves, which promotes growth.

Chemical Structure

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Isoxsuprine HCl
CAS# 579-56-6 (HCl)
Instruction

Theoretical Analysis

MedKoo Cat#: 531027
Name: Isoxsuprine HCl
CAS#: 579-56-6 (HCl)
Chemical Formula: C18H24ClNO3
Exact Mass: 301.17
Molecular Weight: 337.844
Elemental Analysis: C, 63.99; H, 7.16; Cl, 10.49; N, 4.15; O, 14.21

Price and Availability

Size Price Availability Quantity
5g USD 250 2 Weeks
10g USD 450 2 Weeks
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Related CAS #: 395-28-8 (free)   579-56-6 (HCl)   58379-21-8 (lactate)  

Synonym: Isoxsuprine, Isoxsuprine HCl, Isoxsuprine hydrochloride, Isoxsuprine lactate, Dilavase, Vasodilian

IUPAC/Chemical Name: 4-(1-hydroxy-2-((1-phenoxypropan-2-yl)amino)propyl)phenol hydrochloride

InChi Key: QVPSGVSNYPRFAS-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: OC1=CC=C(C(O)C(NC(C)COC2=CC=CC=C2)C)C=C1.[H]Cl

Appearance: White crystalline solid.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 337.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hill JW, Thompson JF, Carter MB, Edwards BS, Sklar LA, Rosenberg GA. Identification of isoxsuprine hydrochloride as a neuroprotectant in ischemic stroke through cell-based high-throughput screening. PLoS One. 2014 May 7;9(5):e96761. doi: 10.1371/journal.pone.0096761. eCollection 2014. PubMed PMID: 24804769; PubMed Central PMCID: PMC4013073.

2: Costa W, Silva AL, Costa GR, Vidigal PV, Pereira FH. Analysis of effect isoxsuprine hydrochloride and nicotine in the Transverse Rectus Abdominis Myocutaneous flap (TRAM) in rats. Acta Cir Bras. 2015 Jul;30(7):497-502. doi: 10.1590/S0102-865020150070000008. PubMed PMID: 26270142.

3: Waldvogel D, Bleul U. Effect of xylazine, isoxsuprine, and lidocaine on Doppler sonographic uterine and umbilical blood flow measurements in cows during the last month of pregnancy. Theriogenology. 2014 Apr 15;81(7):993-1003. doi: 10.1016/j.theriogenology.2014.01.031. Epub 2014 Jan 31. PubMed PMID: 24581585.

4: Bhadage CJ, Umarji HR, Shah K, Välimaa H. Vasodilator isoxsuprine alleviates symptoms of oral submucous fibrosis. Clin Oral Investig. 2013 Jun;17(5):1375-82. doi: 10.1007/s00784-012-0824-z. Epub 2012 Aug 15. PubMed PMID: 22893038.

5: Alavi A, Rajaee M, Amirian M, Mahboobi H, Jahanshahi KA, Faghihi A. Effect of Maintenance Therapy with Isoxsuprine in the Prevention of Preterm Labor: Randomized controlled trial. Electron Physician. 2015 Aug 10;7(4):1144-9. doi: 10.14661/2015.1144-1149. eCollection 2015 Aug. PubMed PMID: 26396726; PubMed Central PMCID: PMC4578532.

6: Groot MJ, Lasaroms JJ, Van Hende J, Nielen MW. Veterinary treatment of cows with isoxsuprine for a caesarian section may temporarily lead to residues in hair of both cow and calf. Drug Test Anal. 2012 Jun;4(6):515-8. doi: 10.1002/dta.272. Epub 2011 Mar 5. PubMed PMID: 21381222.

7: Giorgino FL, Egan CG. Use of isoxsuprine hydrochloride as a tocolytic agent in the treatment of preterm labour: a systematic review of previous literature. Arzneimittelforschung. 2010;60(7):415-20. doi: 10.1055/s-0031-1296305. PubMed PMID: 20712130.

8: Bhushan R, Nagar H. Resolution and isolation of enantiomers of (±)-isoxsuprine using thin silica gel layers impregnated with L-glutamic acid, comparison of separation of its diastereomers prepared with chiral derivatizing reagents having L-amino acids as chiral auxiliaries. Biomed Chromatogr. 2015 Mar;29(3):357-65. doi: 10.1002/bmc.3284. Epub 2014 Jul 7. PubMed PMID: 25044026.

9: Vural HA, Koenhemsi L, Gonul R, Yardibi HD, Gulyasar T, Or E, Hosturk GT, Barutcu B, Balci H. Effects of isoxsuprine hydrochloride on electrocardiographic and trace element status in sheeps. J Pak Med Assoc. 2016 Aug;66(8):938-42. PubMed PMID: 27524523.

10: Kim-Egloff C, Hässig M, Bruckmaier R, Bleul U. Doppler sonographic examination of uterine and placental perfusion in cows in the last month of gestation and effects of epidural anesthesia and isoxsuprine. Theriogenology. 2016 Mar 15;85(5):986-98. doi: 10.1016/j.theriogenology.2015.11.010. Epub 2015 Nov 22. PubMed PMID: 26739532.

11: Kretschy N, Teichmann M, Kopf S, Atanasov AG, Saiko P, Vonach C, Viola K, Giessrigl B, Huttary N, Raab I, Krieger S, Jäger W, Szekeres T, Nijman SM, Mikulits W, Dirsch VM, Dolznig H, Grusch M, Krupitza G. In vitro inhibition of breast cancer spheroid-induced lymphendothelial defects resembling intravasation into the lymphatic vasculature by acetohexamide, isoxsuprine, nifedipin and proadifen. Br J Cancer. 2013 Feb 19;108(3):570-8. doi: 10.1038/bjc.2012.580. Epub 2013 Jan 8. PubMed PMID: 23299527; PubMed Central PMCID: PMC3593542.

12: Yogol NS, Shakya R, Thapa P. Ritodrine and isoxsuprine in management of preterm labor. JNMA J Nepal Med Assoc. 2009 Oct-Dec;48(176):265-8. PubMed PMID: 21105546.

13: Shiri F, Shahraki S, Shahriyar A, Majd MH. Exploring isoxsuprine hydrochloride binding with human serum albumin in the presence of folic acid and ascorbic acid using multispectroscopic and molecular modeling methods. J Photochem Photobiol B. 2017 May;170:152-163. doi: 10.1016/j.jphotobiol.2017.04.007. Epub 2017 Apr 11. PubMed PMID: 28432945.

14: Marzo A, Zava D, Coa K, Dal Bo L, Ismaili S, Tavazzi S, Cantoni V. Pharmacokinetics of isoxsuprine hydrochloride administered orally and intramuscularly to female healthy volunteers. Arzneimittelforschung. 2009;59(9):455-60. doi: 10.1055/s-0031-1296425. PubMed PMID: 19856793.

15: Ogata ES. Isoxsuprine infusion in the rat: alterations in maternal, fetal and neonatal glucose homeostasis. J Perinat Med. 1981;9(6):293-301. PubMed PMID: 7035644.

16: Belloli C, Badino P, Carcano R, Odore R, Arioli F, Caloni F, Re G. Investigations on the stereoselective action of isoxsuprine on alpha- and beta-adrenoceptors in equine common digital artery. Pharmacol Res. 1999 Aug;40(2):177-82. PubMed PMID: 10433878.

17: Erkert RS, Macallister CG. Isoxsuprine hydrochloride in the horse: a review. J Vet Pharmacol Ther. 2002 Apr;25(2):81-7. Review. PubMed PMID: 12000527.

18: Briones-Garduño JC, González-Alvarez R. [Isoxsuprine in hypertension during pregnancy]. Gac Med Mex. 1997 Sep-Oct;133(5):403-6. Spanish. PubMed PMID: 9580102.

19: Psomadakis C, Kallerghi G, Bourantas C, Papageorgiou J. Experience with isoxsuprine in the treatment of sickle cell crisis: a proposed mechanism of action. Angiology. 1981 Apr;32(4):249-56. PubMed PMID: 7224235.

20: Das B, Dutta S, Nayak AK, Nanda U. Zinc alginate-carboxymethyl cashew gum microbeads for prolonged drug release: development and optimization. Int J Biol Macromol. 2014 Sep;70:506-15. doi: 10.1016/j.ijbiomac.2014.07.030. Epub 2014 Jul 22. PubMed PMID: 25062990.