Halofuginone Hydrobromide | prolyl-tRNA synthetase inhibitor | 1217623-74-9

MedKoo Cat#: 124421 | Name: Halofuginone hydrochloride

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Halofuginone Hydrobromide is a potent prolyl-tRNA synthetase inhibitor.

Chemical Structure

Halofuginone hydrochloride

CAS#1217623-74-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 124421

Name: Halofuginone hydrochloride

CAS#: 1217623-74-9 (HCl)

Chemical Formula: C16H18BrCl2N3O3

Exact Mass: 0.0000

Molecular Weight: 451.14

Elemental Analysis: C, 42.60; H, 4.02; Br, 17.71; Cl, 15.72; N, 9.31; O, 10.64

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

55837-20-2 (free base) 64924-67-0 (HBr) 1217623-74-9 (HCl) 82186-71-8 (lactate)

Synonym

Halofuginone hydrochloride; Halofuginone (hydrochloride); Halofuginone HCl;

IUPAC/Chemical Name

7-bromo-6-chloro-3-(3-((2S,3R)-3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one hydrochloride

InChi Key

XFFYBQUXAJOKAL-LDXVYITESA-N

InChi Code

InChI=1S/C16H17BrClN3O3.ClH/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14;/h5-6,8,14-15,19,23H,1-4,7H2;1H/t14-,15+;/m0./s1

SMILES Code

O=C1N(C=NC2=C1C=C(C(Br)=C2)Cl)CC(C[C@@H]3NCCC[C@H]3O)=O.[H]Cl

Appearance

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 451.14 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.

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

1: Pines M, Spector I. Halofuginone - The Multifaceted Molecule. Molecules. 2015 Jan 5;20(1):573-594. Review. PubMed PMID: 25569515. 2: Pines M. Halofuginone for fibrosis, regeneration and cancer in the gastrointestinal tract. World J Gastroenterol. 2014 Oct 28;20(40):14778-86. doi: 10.3748/wjg.v20.i40.14778. PubMed PMID: 25356039; PubMed Central PMCID: PMC4209542. 3: Guo LW, Wang B, Goel SA, Little C, Takayama T, Shi XD, Roenneburg D, DiRenzo D, Kent KC. Halofuginone stimulates adaptive remodeling and preserves re-endothelialization in balloon-injured rat carotid arteries. Circ Cardiovasc Interv. 2014 Aug;7(4):594-601. doi: 10.1161/CIRCINTERVENTIONS.113.001181. Epub 2014 Jul 29. PubMed PMID: 25074254; PubMed Central PMCID: PMC4140988. 4: Park MK, Park JS, Park EM, Lim MA, Kim SM, Lee DG, Baek SY, Yang EJ, Woo JW, Lee J, Kwok SK, Kim HY, Cho ML, Park SH. Halofuginone ameliorates autoimmune arthritis in mice by regulating the balance between Th17 and Treg cells and inhibiting osteoclastogenesis. Arthritis Rheumatol. 2014 May;66(5):1195-207. doi: 10.1002/art.38313. PubMed PMID: 24782183. 5: Bodanovsky A, Guttman N, Barzilai-Tutsch H, Genin O, Levy O, Pines M, Halevy O. Halofuginone improves muscle-cell survival in muscular dystrophies. Biochim Biophys Acta. 2014 Jul;1843(7):1339-47. doi: 10.1016/j.bbamcr.2014.03.025. Epub 2014 Apr 2. PubMed PMID: 24703880. 6: McLaughlin NP, Evans P, Pines M. The chemistry and biology of febrifugine and halofuginone. Bioorg Med Chem. 2014 Apr 1;22(7):1993-2004. doi: 10.1016/j.bmc.2014.02.040. Epub 2014 Mar 1. Review. PubMed PMID: 24650700. 7: Petermann J, Paraud C, Pors I, Chartier C. Efficacy of halofuginone lactate against experimental cryptosporidiosis in goat neonates. Vet Parasitol. 2014 May 28;202(3-4):326-9. doi: 10.1016/j.vetpar.2014.02.027. Epub 2014 Feb 22. PubMed PMID: 24636788. 8: Kapoor S. Reduction of burn scar formation by halofuginone-eluting silicone gel sheets: a controlled study on nude mice. Ann Plast Surg. 2014 Apr;72(4):489. doi: 10.1097/SAP.0b013e318281ad59. PubMed PMID: 24618743. 9: Carlson TJ, Pellerin A, Djuretic IM, Trivigno C, Koralov SB, Rao A, Sundrud MS. Halofuginone-induced amino acid starvation regulates Stat3-dependent Th17 effector function and reduces established autoimmune inflammation. J Immunol. 2014 Mar 1;192(5):2167-76. doi: 10.4049/jimmunol.1302316. Epub 2014 Jan 31. PubMed PMID: 24489094; PubMed Central PMCID: PMC3936195. 10: Jin C, Jia Y, Jin C, Dong H, Cheng P, Zhou J, Wang Y, Zheng B, Liu F. Therapeutic effect of Halofuginone on ITP mice by regulating the differentiation of Th cell subsets. Int Immunopharmacol. 2014 Feb;18(2):213-6. doi: 10.1016/j.intimp.2013.12.013. Epub 2013 Dec 22. PubMed PMID: 24368123. 11: Liang J, Zhang B, Shen RW, Liu JB, Gao MH, Li Y, Li YY, Zhang W. Preventive effect of halofuginone on concanavalin A-induced liver fibrosis. PLoS One. 2013 Dec 16;8(12):e82232. doi: 10.1371/journal.pone.0082232. eCollection 2013. PubMed PMID: 24358159; PubMed Central PMCID: PMC3864948. 12: Jin ML, Park SY, Kim YH, Park G, Lee SJ. Halofuginone induces the apoptosis of breast cancer cells and inhibits migration via downregulation of matrix metalloproteinase-9. Int J Oncol. 2014 Jan;44(1):309-18. doi: 10.3892/ijo.2013.2157. Epub 2013 Oct 31. PubMed PMID: 24173318. 13: Son J, Lee EH, Park M, Kim JH, Kim J, Kim S, Jeon YH, Hwang KY. Conformational changes in human prolyl-tRNA synthetase upon binding of the substrates proline and ATP and the inhibitor halofuginone. Acta Crystallogr D Biol Crystallogr. 2013 Oct;69(Pt 10):2136-45. doi: 10.1107/S0907444913020556. Epub 2013 Sep 20. PubMed PMID: 24100331. 14: Zeplin PH. Halofuginone down-regulates Smad3 expression and inhibits the TGFbeta-induced expression of fibrotic markers in human corneal fibroblasts. Ann Plast Surg. 2014 Apr;72(4):489. doi: 10.1097/SAP.0b013e31828a49e3. PubMed PMID: 23845969. 15: Almawly J, Prattley D, French NP, Lopez-Villalobos N, Hedgespeth B, Grinberg A. Utility of halofuginone lactate for the prevention of natural cryptosporidiosis of calves, in the presence of co-infection with rotavirus and Salmonella Typhimurium. Vet Parasitol. 2013 Oct 18;197(1-2):59-67. doi: 10.1016/j.vetpar.2013.04.029. Epub 2013 Apr 24. PubMed PMID: 23707392. 16: Chu TL, Guan Q, Nguan CY, Du C. Halofuginone suppresses T cell proliferation by blocking proline uptake and inducing cell apoptosis. Int Immunopharmacol. 2013 Aug;16(4):414-23. doi: 10.1016/j.intimp.2013.04.031. Epub 2013 May 16. PubMed PMID: 23685128. 17: Keidel J, Daugschies A. Integration of halofuginone lactate treatment and disinfection with p-chloro-m-cresol to control natural cryptosporidiosis in calves. Vet Parasitol. 2013 Sep 23;196(3-4):321-6. doi: 10.1016/j.vetpar.2013.03.003. Epub 2013 Mar 14. PubMed PMID: 23561324. 18: Yavas G, Calik M, Calik G, Yavas C, Ata O, Esme H. The effect of Halofuginone in the amelioration of radiation induced-lung fibrosis. Med Hypotheses. 2013 Apr;80(4):357-9. doi: 10.1016/j.mehy.2013.01.001. Epub 2013 Jan 23. PubMed PMID: 23352286. 19: Halevy O, Genin O, Barzilai-Tutsch H, Pima Y, Levi O, Moshe I, Pines M. Inhibition of muscle fibrosis and improvement of muscle histopathology in dysferlin knock-out mice treated with halofuginone. Histol Histopathol. 2013 Feb;28(2):211-26. PubMed PMID: 23275304. 20: JuÃ¡rez P, Mohammad KS, Yin JJ, Fournier PG, McKenna RC, Davis HW, Peng XH, Niewolna M, Javelaud D, Chirgwin JM, Mauviel A, Guise TA. Halofuginone inhibits the establishment and progression of melanoma bone metastases. Cancer Res. 2012 Dec 1;72(23):6247-56. doi: 10.1158/0008-5472.CAN-12-1444. Epub 2012 Sep 20. PubMed PMID: 23002206.