Ki16425 | CAS#355025-24-0 | LPA receptor antagonist

MedKoo Cat#: 526788 | Name: Ki16425

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Description:

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

Ki16425 is a LPA receptor antagonist with selectivity for LPA1 and LPA3. It exhibits Ki values of 0.34, 6.5, and 0.93 µM for the human LPA1, LPA2, and LPA3 receptors, respectively. Ki16425 reduces nerve growth factor-induced neurite outgrowth in pheochromocytoma 12 cells. ki16425 blunts abdominal and systemic inflammation in a mouse model of peritoneal sepsis.

Chemical Structure

Ki16425

CAS#355025-24-0

Theoretical Analysis

MedKoo Cat#: 526788

Name: Ki16425

CAS#: 355025-24-0

Chemical Formula: C23H23ClN2O5S

Exact Mass: 474.1016

Molecular Weight: 474.96

Elemental Analysis: C, 58.16; H, 4.88; Cl, 7.46; N, 5.90; O, 16.84; S, 6.75

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
250mg	USD 1,450.00	2 Weeks
500mg	USD 2,350.00	2 Weeks

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Synonym

Ki16425; Ki-16425; Ki 16425.

IUPAC/Chemical Name

3-((4-(4-(((1-(2-chlorophenyl)ethoxy)carbonyl)amino)-3-methylisoxazol-5-yl)benzyl)thio)propanoic acid

InChi Key

LLIFMNUXGDHTRO-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H23ClN2O5S/c1-14-21(25-23(29)30-15(2)18-5-3-4-6-19(18)24)22(31-26-14)17-9-7-16(8-10-17)13-32-12-11-20(27)28/h3-10,15H,11-13H2,1-2H3,(H,25,29)(H,27,28)

SMILES Code

O=C(O)CCSCC1=CC=C(C2=C(NC(OC(C3=CC=CC=C3Cl)C)=O)C(C)=NO2)C=C1

Appearance

Solid powder

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ki16425 (Debio 0719) is a subtype-selective, competitive antagonist of the EDG-family receptors, LPA1 and LPA3 with Kis of 0.34 μM and 0.93 μM, respectively.

In vitro activity:

Ki16425 reduced the LPA-induced activation of p42/p44 mitogen activated protein kinase (MAPK), while acting as a weak stimulator of p42/p44 MAPK on its own, properties typical of a protean agonist. Significantly, Ki16425 also reduced the NGF-induced stimulation of p42/p44 MAPK and inhibited NGF-stimulated neurite outgrowth. Reference: J Neurochem. 2006 Sep;98(6):1920-9. https://pubmed.ncbi.nlm.nih.gov/16945108/

In vivo activity:

The blockade of nerve injury-induced neuropathic pain by Ki-16425 was maximum as late as 3 h after the injury but not after this critical period. The administration of Ki-16425 at 3 h but not at 6 h after injury also blocked neurochemical changes, including up-regulation of voltage-gated calcium channel alpha(2)delta-1 subunit expression in dorsal root ganglion and reduction of substance P expression in the spinal dorsal horn. All of these results using Ki-16425 suggest that lysophosphatidic acid 1 receptor-mediated signaling which underlies the development of neuropathic pain works at an early stage of the critical period after nerve injury. Reference: J Neurochem. 2009 Apr;109(2):603-10. https://pubmed.ncbi.nlm.nih.gov/19222705/

	Solvent	mg/mL	mM
Solubility
	DMF	12.0	25.27
	DMSO	62.9	132.38
	DMSO:PBS (pH 7.2) (1:4)	0.2	0.42
	Ethanol	52.0	109.48

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 474.96 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

Formulation protocol:

1. Moughal NA, Waters CM, Valentine WJ, Connell M, Richardson JC, Tigyi G, Pyne S, Pyne NJ. Protean agonism of the lysophosphatidic acid receptor-1 with Ki16425 reduces nerve growth factor-induced neurite outgrowth in pheochromocytoma 12 cells. J Neurochem. 2006 Sep;98(6):1920-9. doi: 10.1111/j.1471-4159.2006.04009.x. PMID: 16945108. 2. Yamada T, Sato K, Komachi M, Malchinkhuu E, Tobo M, Kimura T, Kuwabara A, Yanagita Y, Ikeya T, Tanahashi Y, Ogawa T, Ohwada S, Morishita Y, Ohta H, Im DS, Tamoto K, Tomura H, Okajima F. Lysophosphatidic acid (LPA) in malignant ascites stimulates motility of human pancreatic cancer cells through LPA1. J Biol Chem. 2004 Feb 20;279(8):6595-605. doi: 10.1074/jbc.M308133200. Epub 2003 Dec 3. PMID: 14660630. 3. Ma L, Matsumoto M, Xie W, Inoue M, Ueda H. Evidence for lysophosphatidic acid 1 receptor signaling in the early phase of neuropathic pain mechanisms in experiments using Ki-16425, a lysophosphatidic acid 1 receptor antagonist. J Neurochem. 2009 Apr;109(2):603-10. doi: 10.1111/j.1471-4159.2009.05987.x. Epub 2009 Feb 13. PMID: 19222705. 4. Sánchez-Marín L, Ladrón de Guevara-Miranda D, Mañas-Padilla MC, Alén F, Moreno-Fernández RD, Díaz-Navarro C, Pérez-Del Palacio J, García-Fernández M, Pedraza C, Pavón FJ, Rodríguez de Fonseca F, Santín LJ, Serrano A, Castilla-Ortega E. Systemic blockade of LPA1/3 lysophosphatidic acid receptors by ki16425 modulates the effects of ethanol on the brain and behavior. Neuropharmacology. 2018 May 1;133:189-201. doi: 10.1016/j.neuropharm.2018.01.033. Epub 2018 Jan 31. PMID: 29378212.

In vitro protocol:

In vivo protocol:

1. Ma L, Matsumoto M, Xie W, Inoue M, Ueda H. Evidence for lysophosphatidic acid 1 receptor signaling in the early phase of neuropathic pain mechanisms in experiments using Ki-16425, a lysophosphatidic acid 1 receptor antagonist. J Neurochem. 2009 Apr;109(2):603-10. doi: 10.1111/j.1471-4159.2009.05987.x. Epub 2009 Feb 13. PMID: 19222705. 2. Sánchez-Marín L, Ladrón de Guevara-Miranda D, Mañas-Padilla MC, Alén F, Moreno-Fernández RD, Díaz-Navarro C, Pérez-Del Palacio J, García-Fernández M, Pedraza C, Pavón FJ, Rodríguez de Fonseca F, Santín LJ, Serrano A, Castilla-Ortega E. Systemic blockade of LPA1/3 lysophosphatidic acid receptors by ki16425 modulates the effects of ethanol on the brain and behavior. Neuropharmacology. 2018 May 1;133:189-201. doi: 10.1016/j.neuropharm.2018.01.033. Epub 2018 Jan 31. PMID: 29378212.

1: Zhao J, Wei J, Weathington N, Jacko AM, Huang H, Tsung A, Zhao Y. Lysophosphatidic acid receptor 1 antagonist ki16425 blunts abdominal and systemic inflammation in a mouse model of peritoneal sepsis. Transl Res. 2015 Jul;166(1):80-8. doi: 10.1016/j.trsl.2015.01.008. Epub 2015 Jan 31. PubMed PMID: 25701366; PubMed Central PMCID: PMC4458421. 2: Sato T, Sugimoto K, Inoue A, Okudaira S, Aoki J, Tokuyama H. Synthesis and biological evaluation of optically active Ki16425. Bioorg Med Chem Lett. 2012 Jul 1;22(13):4323-6. doi: 10.1016/j.bmcl.2012.05.012. Epub 2012 May 11. PubMed PMID: 22658556. 3: Kim K, Kim HL, Lee YK, Han M, Sacket SJ, Jo JY, Kim YL, Im DS. Lysophosphatidylserine induces calcium signaling through Ki16425/VPC32183-sensitive GPCR in bone marrow-derived mast cells and in C6 glioma and colon cancer cells. Arch Pharm Res. 2008 Mar;31(3):310-7. doi: 10.1007/s12272-001-1157-x. Epub 2008 Apr 13. PubMed PMID: 18409043. 4: Moughal NA, Waters CM, Valentine WJ, Connell M, Richardson JC, Tigyi G, Pyne S, Pyne NJ. Protean agonism of the lysophosphatidic acid receptor-1 with Ki16425 reduces nerve growth factor-induced neurite outgrowth in pheochromocytoma 12 cells. J Neurochem. 2006 Sep;98(6):1920-9. PubMed PMID: 16945108. 5: Ohta H, Sato K, Murata N, Damirin A, Malchinkhuu E, Kon J, Kimura T, Tobo M, Yamazaki Y, Watanabe T, Yagi M, Sato M, Suzuki R, Murooka H, Sakai T, Nishitoba T, Im DS, Nochi H, Tamoto K, Tomura H, Okajima F. Ki16425, a subtype-selective antagonist for EDG-family lysophosphatidic acid receptors. Mol Pharmacol. 2003 Oct;64(4):994-1005. PubMed PMID: 14500756.