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MedKoo Cat#: 414271 | Name: KRP-203 free base

Description:

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

KRP-203 free base 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

KRP-203 free base
KRP-203 free base
CAS#509092-16-4 (free base)

Theoretical Analysis

MedKoo Cat#: 414271

Name: KRP-203 free base

CAS#: 509092-16-4 (free base)

Chemical Formula: C24H26ClNO3S

Exact Mass: 443.1322

Molecular Weight: 443.99

Elemental Analysis: C, 64.93; H, 5.90; Cl, 7.98; N, 3.15; O, 10.81; S, 7.22

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.
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Related CAS #
509092-16-4 (free base) 509088-69-1 (HCl)
Synonym
KRP-203 free base; KRP203 free base; KRP 203 free base
IUPAC/Chemical Name
1,3-Propanediol, 2-amino-2-(2-(2-chloro-4-((3-(phenylmethoxy)phenyl)thio)phenyl)ethyl)-
InChi Key
IINUNQPYJGJCJI-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H26ClNO3S/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
SMILES Code
OCC(CCC1=CC=C(SC2=CC=CC(OCC3=CC=CC=C3)=C2)C=C1Cl)(N)CO
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 443.99 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
1: 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. PMID: 23640484. 2: 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. doi: 10.1161/01.CIR.0000152101.41037.AB. Epub 2005 Jan 10. PMID: 15642767. 3: Argollo M, Furfaro F, Gilardi D, Roda G, Allocca M, Peyrin-Biroulet L, Danese S. Modulation of sphingosine-1-phosphate in ulcerative colitis. Expert Opin Biol Ther. 2020 Apr;20(4):413-420. doi: 10.1080/14712598.2020.1732919. Epub 2020 Feb 25. PMID: 32093531. 4: 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. doi: 10.1097/01.tp.0000232687.78242.cd. PMID: 17006328. 5: 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. doi: 10.1016/j.healun.2005.09.021. Epub 2006 Jan 18. PMID: 16507424. 6: 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. PMID: 30930775; PMCID: PMC6425155. 7: 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. doi: 10.1016/j.transproceed.2004.12.107. PMID: 15808575. 8: 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. doi: 10.1016/j.bbrc.2007.07.061. Epub 2007 Jul 23. PMID: 17673173. 9: 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. doi: 10.1124/jpet.106.119172. Epub 2007 Sep 26. PMID: 17898319. 10: 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. doi: 10.1016/j.healun.2006.03.014. Epub 2006 Jun 5. PMID: 16818126.

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