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MedKoo Cat#: 329506 | Name: Mocravimod

Description:

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

Mocravimod, also known as KRP-203, is a sphingosine 1-phosphate receptor type 1 agonist, ameliorates atherosclerosis in LDL-R-/- mice. KRP-203 attenuates rat autoimmune myocarditis. KRP-203 combined with cyclosporine prolonged graft survival and abrogated transplant vasculopathy in rat heart allografts.

Chemical Structure

Mocravimod
CAS#509092-16-4

Theoretical Analysis

MedKoo Cat#: 329506

Name: Mocravimod

CAS#: 509092-16-4

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 #
No Data
Synonym
Mocravimod; KRP-203; KRP203; KRP 203 free base.
IUPAC/Chemical Name
2-Amino-2-(2-(2-chloro-4-(3-benzyloxyphenylthio)phenyl)ethyl)-1,3-propanediol
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
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

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. PubMed PMID: 23640484. 2: 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. PubMed PMID: 17673173. 3: 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. PubMed PMID: 17898319. 4: 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. PubMed PMID: 16818126. 5: 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. 6: 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. PubMed PMID: 16507424. 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. PubMed PMID: 15808575. 8: 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. PubMed PMID: 15642767. 9: 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. PubMed PMID: 18769369; PubMed Central PMCID: PMC3520442. 10: 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. PubMed PMID: 16674913. 11: 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. 12: 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. Review. PubMed PMID: 25580263; PubMed Central PMCID: PMC4251414. 13: 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. PubMed PMID: 23667698; PubMed Central PMCID: PMC3646787. 14: 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. 15: 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. Review. PubMed PMID: 18552276; PubMed Central PMCID: PMC2695666. 16: 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. Review. PubMed PMID: 18321471.