Esonarimod | CAS#101973-77-7 | antirheumatic drug

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

MedKoo CAT#: 558198

CAS#: 101973-77-7

Description: Esonarimod is an antirheumatic drug, suppressing lymphocyte activating factor activity or biosynthesis.

Chemical Structure

Esonarimod

CAS# 101973-77-7

Instruction

Theoretical Analysis

MedKoo Cat#: 558198
Name: Esonarimod
CAS#: 101973-77-7
Chemical Formula: C14H16O4S
Exact Mass: 280.08
Molecular Weight: 280.340
Elemental Analysis: C, 59.98; H, 5.75; O, 22.83; S, 11.44

Price and Availability

Size	Price	Availability
25mg	USD 250	2 Weeks
50mg	USD 450	2 Weeks
100mg	USD 750	2 Weeks
200mg	USD 1250	2 Weeks
500mg	USD 2650	2 Weeks
1g	USD 3850	2 Weeks
2g	USD 6450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Esonarimod; KE-298; KE298; KE 298;

IUPAC/Chemical Name: Benzenebutanoic acid, alpha-((acetylthio)methyl)-4-methyl-gamma-oxo-

InChi Key: YRSSFEUQNAXQMX-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H16O4S/c1-9-3-5-11(6-4-9)13(16)7-12(14(17)18)8-19-10(2)15/h3-6,12H,7-8H2,1-2H3,(H,17,18)

SMILES Code: O=C(O)C(CSC(C)=O)CC(C1=CC=C(C)C=C1)=O

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 280.34 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:
In vitro protocol:
In vivo protocol:

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1: Noguchi T, Onodera A, Tomisawa K, Yamashita M, Takeshita K, Yokomori S. Synthesis and antirheumatic activity of the metabolites of esonarimod. Bioorg Med Chem. 2002 Aug;10(8):2713-21. PubMed PMID: 12057660.

2: Ohmi N, Yoshida H, Endo H, Hasegawa M, Akimoto M, Higuchi S. S-oxidation of S-methyl-esonarimod by flavin-containing monooxygenases in human liver microsomes. Xenobiotica. 2003 Dec;33(12):1221-31. PubMed PMID: 14742144.

3: Yamaguchi J, Ohmichi M, Hasegawa M, Yoshida H, Ogawa N, Higuchi S. Identification of rat urinary and biliary metabolites of esonarimod, a novel antirheumatic drug, using liquid chromatography/electrospray ionization tandem mass spectrometry with postcolumn addition of 2-(2-methoxyethoxy)ethanol, a signal-enhancing modifier. Drug Metab Dispos. 2001 Jun;29(6):806-12. PubMed PMID: 11353748.

4: Hasegawa M, Omi N, Endo H, Yoshida H, Higuchi S. Formation of a disulfide protein conjugate of the SH-group-containing metabolite (M-I) of esonarimod (KE-298) and its elimination in rats. J Pharm Pharmacol. 2002 Apr;54(4):493-8. PubMed PMID: 11999126.

5: Noguchi T, Onodera A, Tomisawa K, Yokomori S. A practical procedure for the synthesis of esonarimod, (R,S)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid, an antirheumatic agent (part 1). Chem Pharm Bull (Tokyo). 2002 Oct;50(10):1407-12. PubMed PMID: 12372877.

6: Noguchi T, Hasegawa M, Tomisawa K, Mitsukuchi M. Synthesis and structure-activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents. Bioorg Med Chem. 2003 Nov 3;11(22):4729-42. PubMed PMID: 14556788.

7: Zhang J, Cerny MA, Lawson M, Mosadeghi R, Cashman JR. Functional activity of the mouse flavin-containing monooxygenase forms 1, 3, and 5. J Biochem Mol Toxicol. 2007;21(4):206-15. PubMed PMID: 17721934.

8: Nagai H, Takaoka Y, Mori H, Kawada K. Effect of KE-298 on experimental arthritis in mice. Pharmacology. 1996 Sep;53(3):190-6. PubMed PMID: 8931104.

9: Hashimoto M, Kobayashi K, Yamagata N, Katsura T, Sugihara S, Iwabuchi H, Kasama T, Kasahara K, Takahashi T, Takeshita K, et al. Suppression of pulmonary granulomatous inflammation by immunomodulating agents. Agents Actions. 1992 Sep;37(1-2):99-106. PubMed PMID: 1456185.

10: Yoshida H, Kohno Y, Endo H, Ohmi N, Fukushima K, Suwa T, Hayashi M. Stereoselective disposition and chiral inversion of KE-298, a new antirheumatic drug, in rats. Chirality. 1997;9(1):22-8. PubMed PMID: 9094199.

11: Yasuda Y, Inoue T, Takeshita K. Pharmacological profile of KE-758, the main metabolite of the antirheumatic agent KE-298. Drugs Exp Clin Res. 1996;22(1):1-8. PubMed PMID: 8839631.

12: Endo H, Yoshida H, Hasegawa M, Ohmi N, Horiuchi N, Hamada Y, Higuchi S. Stereoselectivity and species difference in plasma protein binding of KE-298 and its metabolites. Biol Pharm Bull. 2001 Jul;24(7):800-5. PubMed PMID: 11456121.

13: Honda S, Migita K, Hirai Y, Origuchi T, Yamasaki S, Kamachi M, Shibatomi K, Fukuda T, Kita M, Hida A, Ida H, Aoyagi T, Kawakami A, Kawabe Y, Oizumi K, Eguchi K. Expression of membrane-type 1 matrix metalloproteinase in rheumatoid synovial cells. Clin Exp Immunol. 2001 Oct;126(1):131-6. PubMed PMID: 11678909; PubMed Central PMCID: PMC1906171.

14: Sakane T, Suzuki N, Hirose Y, Miura K, Wakisaka S, Nagafuchi H, Ichino M, Tomita T, Hashimoto H, Ochi T, Mihara S. Mechanisms of KE298, 2-acetylthiomethyl-3-(4-methylbenzoyl) propionic acid, to suppress abnormal synovial cell functions in patients with rheumatoid arthritis. J Rheumatol. 1997 Nov;24(11):2213-20. PubMed PMID: 9375886.

15: Sugimoto M, Inoue T, Takeshita K, Nakamura H, Yodoi J. Effects of a new anti-rheumatic drug KE-298 and its active metabolite: KE-758 on secretion of thioredoxin and on the level of intracellular glutathione in human monocytes and T cells. Mol Immunol. 2002 Feb;38(10):793-9. PubMed PMID: 11841839.

16: Inoue T, Yamashita M, Higaki M. The new antirheumatic drug KE-298 suppresses monocyte chemoattractant protein (MCP)-1 and RANTES production in rats with adjuvant-induced arthritis and in IL-1beta-stimulated synoviocytes of patients with rheumatoid arthritis. Rheumatol Int. 2001 May;20(4):149-53. PubMed PMID: 11411959.

17: Takahashi S, Inoue T, Higaki M, Mizushima Y. Suppressive effects of the new antirheumatic drug KE-298 on TNF alpha-induced production of matrix metalloproteinases but not of tissue inhibitor-1 of metalloproteinases in human rheumatoid synoviocytes. Drugs Exp Clin Res. 1998;24(2):67-71. PubMed PMID: 9675546.

18: Inoue T, Hamada Y, Takeshita K, Fukushima K, Higaki M. KE-298 and its active metabolite KE-758 suppress nitric oxide production by murine macrophage cells and peritoneal cells from rats with adjuvant induced arthritis. J Rheumatol. 2001 Jun;28(6):1229-37. PubMed PMID: 11409114.

19: Sugimoto M, Inoue T, Yamashita M, Takeshita K, Nakaike S. KE-758, an active metabolite of the new anti-rheumatic drug KE-298, suppresses production of tumor necrosis factor-alpha and interleukin-1 beta in THP-1, a human monocyte cell line. Drugs Exp Clin Res. 2002;28(5):197-205. PubMed PMID: 12635495.

20: Inoue T, Takeshita K, Fukushima K. Effects of KE-758; an active metabolite of the new anti-rheumatic drug KE-298, D-penicillamine, bucillamine and auranofin on the proliferation of murine lymphocytes, and the production of nitric oxide by murine macrophages. Int Immunopharmacol. 2001 May;1(5):833-42. PubMed PMID: 11379039.

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