KRP-203 HCl

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

MedKoo CAT#: 205775

CAS#: 509088-69-1 (HCl)

Description: KRP-203 is a selective Sphingosine-1-phosphate receptor agonist that has been shown to reduce peripheral lymphocyte infiltration and to prolong survival in rat transplant models. Sphingosine-1-phosphate (S1P) is a bioactive sphingolipid metabolite involved in many critical cellular processes including proliferation, survival, and migration, as well as angiogenesis and immune responses.

Chemical Structure

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KRP-203 HCl
CAS# 509088-69-1 (HCl)
Instruction

Theoretical Analysis

MedKoo Cat#: 205775
Name: KRP-203 HCl
CAS#: 509088-69-1 (HCl)
Chemical Formula: C24H27Cl2NO3S
Exact Mass: 0.00
Molecular Weight: 480.447
Elemental Analysis: C, 60.00; H, 5.66; Cl, 14.76; N, 2.92; O, 9.99; S, 6.67

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 509092-16-4 (free base)   509088-69-1 (HCl)    

Synonym: KRP203; KRP-203; KRP 203; KRP-203 HCl; KRP-203 hydrochloride; MOCRAVIMOD HYDROCHLORIDE

IUPAC/Chemical Name: 2-amino-2-(4-((3-(benzyloxy)phenyl)thio)-2-chlorophenethyl)propane-1,3-diol hydrochloride

InChi Key: MYIFLDFUXIHOCJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H26ClNO3S.ClH/c25-23-14-22(10-9-19(23)11-12-24(26,16-27)17-28)30-21-8-4-7-20(13-21)29-15-18-5-2-1-3-6-18;/h1-10,13-14,27-28H,11-12,15-17,26H2;1H

SMILES Code: OCC(CCC1=CC=C(SC2=CC=CC(OCC3=CC=CC=C3)=C2)C=C1Cl)(N)CO.[H]Cl

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, not in water

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 480.45 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: Pérez-Jeldres T, Tyler CJ, Boyer JD, Karuppuchamy T, Yarur A, Giles DA, Yeasmin S, Lundborg L, Sandborn WJ, Patel DR, Rivera-Nieves J. Targeting Cytokine Signaling and Lymphocyte Traffic via Small Molecules in Inflammatory Bowel Disease: JAK Inhibitors and S1PR Agonists. Front Pharmacol. 2019 Mar 13;10:212. doi: 10.3389/fphar.2019.00212. eCollection 2019. Review. PubMed PMID: 30930775; PubMed Central PMCID: PMC6425155.

2: Danese S, Furfaro F, Vetrano S. Targeting S1P in Inflammatory Bowel Disease: New Avenues for Modulating Intestinal Leukocyte Migration. J Crohns Colitis. 2018 Aug 22;12(suppl_2):S678-S686. doi: 10.1093/ecco-jcc/jjx107. PubMed PMID: 28961752.

3: Gonzalez-Cabrera PJ, Brown S, Studer SM, Rosen H. S1P signaling: new therapies and opportunities. F1000Prime Rep. 2014 Dec 1;6:109. doi: 10.12703/P6-109. eCollection 2014. Review. PubMed PMID: 25580263; PubMed Central PMCID: PMC4251414.

4: Takasugi N, Sasaki T, Ebinuma I, Osawa S, Isshiki H, Takeo K, Tomita T, Iwatsubo T. FTY720/fingolimod, a sphingosine analogue, reduces amyloid-β production in neurons. PLoS One. 2013 May 7;8(5):e64050. doi: 10.1371/journal.pone.0064050. Print 2013. PubMed PMID: 23667698; PubMed Central PMCID: PMC3646787.

5: Potì F, Gualtieri F, Sacchi S, Weißen-Plenz G, Varga G, Brodde M, Weber C, Simoni M, Nofer JR. KRP-203, sphingosine 1-phosphate receptor type 1 agonist, ameliorates atherosclerosis in LDL-R-/- mice. Arterioscler Thromb Vasc Biol. 2013 Jul;33(7):1505-12. doi: 10.1161/ATVBAHA.113.301347. Epub 2013 May 2. PubMed PMID: 23640484.

6: Khattar M, Deng R, Kahan BD, Schroder PM, Phan T, Rutzky LP, Stepkowski SM. Novel sphingosine-1-phosphate receptor modulator KRP203 combined with locally delivered regulatory T cells induces permanent acceptance of pancreatic islet allografts. Transplantation. 2013 Apr 15;95(7):919-27. doi: 10.1097/TP.0b013e3182842396. PubMed PMID: 23545505; PubMed Central PMCID: PMC3616331.

7: Hamada M, Adachi K, Hikawa H, Yokoyama Y. Synthesis of a key intermediate for the preparation of FTY720 analogs. Chem Pharm Bull (Tokyo). 2012;60(11):1395-8. PubMed PMID: 23124563.

8: Wenderfer SE, Stepkowski SM, Braun MC. Increased survival and reduced renal injury in MRL/lpr mice treated with a novel sphingosine-1-phosphate receptor agonist. Kidney Int. 2008 Nov;74(10):1319-26. doi: 10.1038/ki.2008.396. Epub 2008 Sep 3. PubMed PMID: 18769369; PubMed Central PMCID: PMC3520442.

9: Takabe K, Paugh SW, Milstien S, Spiegel S. "Inside-out" signaling of sphingosine-1-phosphate: therapeutic targets. Pharmacol Rev. 2008 Jun;60(2):181-95. doi: 10.1124/pr.107.07113. Epub 2008 Jun 13. Review. PubMed PMID: 18552276; PubMed Central PMCID: PMC2695666.

10: Huwiler A, Pfeilschifter J. New players on the center stage: sphingosine 1-phosphate and its receptors as drug targets. Biochem Pharmacol. 2008 May 15;75(10):1893-900. doi: 10.1016/j.bcp.2007.12.018. Epub 2008 Jan 5. Review. PubMed PMID: 18321471.

11: Song J, Matsuda C, Kai Y, Nishida T, Nakajima K, Mizushima T, Kinoshita M, Yasue T, Sawa Y, Ito T. A novel sphingosine 1-phosphate receptor agonist, 2-amino-2-propanediol hydrochloride (KRP-203), regulates chronic colitis in interleukin-10 gene-deficient mice. J Pharmacol Exp Ther. 2008 Jan;324(1):276-83. Epub 2007 Sep 26. PubMed PMID: 17898319.

12: Ogawa R, Takahashi M, Hirose S, Morimoto H, Ise H, Murakami T, Yasue T, Kuriyama K, Hongo M, Kobayashi E, Ikeda U. A novel sphingosine-1-phosphate receptor agonist KRP-203 attenuates rat autoimmune myocarditis. Biochem Biophys Res Commun. 2007 Sep 28;361(3):621-8. Epub 2007 Jul 23. PubMed PMID: 17673173.

13: Fujishiro J, Kudou S, Iwai S, Takahashi M, Hakamata Y, Kinoshita M, Iwanami S, Izawa S, Yasue T, Hashizume K, Murakami T, Kobayashi E. Use of sphingosine-1-phosphate 1 receptor agonist, KRP-203, in combination with a subtherapeutic dose of cyclosporine A for rat renal transplantation. Transplantation. 2006 Sep 27;82(6):804-12. PubMed PMID: 17006328.

14: Fujishiro J, Suzuki C, Kudou S, Yasue T, Hakamata Y, Takahashi M, Murakami T, Hashizume K, Kobayashi E. Change from cyclosporine to combination therapy of mycophenolic acid with the new sphingosine-1-phosphate receptor agonist, KRP-203, prevents host nephrotoxicity and transplant vasculopathy in rats. J Heart Lung Transplant. 2006 Jul;25(7):825-33. Epub 2006 Jun 5. PubMed PMID: 16818126.

15: Kaneko T, Murakami T, Kawana H, Takahashi M, Yasue T, Kobayashi E. Sphingosine-1-phosphate receptor agonists suppress concanavalin A-induced hepatic injury in mice. Biochem Biophys Res Commun. 2006 Jun 23;345(1):85-92. Epub 2006 Apr 25. PubMed PMID: 16674913.

16: Suzuki C, Takahashi M, Morimoto H, Izawa A, Ise H, Fujishiro J, Murakami T, Ishiyama J, Nakada A, Nakayama J, Shimada K, Ikeda U, Kobayashi E. Efficacy of mycophenolic acid combined with KRP-203, a novel immunomodulator, in a rat heart transplantation model. J Heart Lung Transplant. 2006 Mar;25(3):302-9. Epub 2006 Jan 18. PubMed PMID: 16507424.

17: Takahashi M, Shimizu H, Murakami T, Enosawa S, Suzuki C, Takeno Y, Hakamata Y, Kudou S, Izawa S, Yasue T, Kobayashi E. A novel immunomodulator KRP-203 combined with cyclosporine prolonged graft survival and abrogated transplant vasculopathy in rat heart allografts. Transplant Proc. 2005 Jan-Feb;37(1):143-5. PubMed PMID: 15808575.

18: Shimizu H, Takahashi M, Kaneko T, Murakami T, Hakamata Y, Kudou S, Kishi T, Fukuchi K, Iwanami S, Kuriyama K, Yasue T, Enosawa S, Matsumoto K, Takeyoshi I, Morishita Y, Kobayashi E. KRP-203, a novel synthetic immunosuppressant, prolongs graft survival and attenuates chronic rejection in rat skin and heart allografts. Circulation. 2005 Jan 18;111(2):222-9. Epub 2005 Jan 10. PubMed PMID: 15642767.