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MedKoo Cat#: 524920 | Name: CX-659S

Description:

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

CX-659S is a novel diaminouracil derivative that has an inhibitory effect on hapten-induced contact hypersensitivity reaction in mice. CX-659S indirectly inhibits the function of Langerhans cells by blocking the MEK1/2-Erk1/2 pathway in keratinocytes.

Chemical Structure

CX-659S
CX-659S
CAS#204980-81-4

Theoretical Analysis

MedKoo Cat#: 524920

Name: CX-659S

CAS#: 204980-81-4

Chemical Formula: C25H28N4O5

Exact Mass: 464.2060

Molecular Weight: 464.51

Elemental Analysis: C, 64.64; H, 6.08; N, 12.06; O, 17.22

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 #
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Synonym
CX-659S; CX 659S; CX659S; UNII-YG2F04AVMQ.
IUPAC/Chemical Name
2H-1-Benzopyran-2-carboxamide, N-(6-amino-1,2,3,4-tetrahydro-3-methyl-2,4-dioxo-1-phenyl-5-pyrimidinyl)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-, (2S)-
InChi Key
NOYZWUQUALADDO-VWLOTQADSA-N
InChi Code
InChI=1S/C25H28N4O5/c1-13-14(2)20-17(15(3)19(13)30)11-12-25(4,34-20)23(32)27-18-21(26)29(16-9-7-6-8-10-16)24(33)28(5)22(18)31/h6-10,30H,11-12,26H2,1-5H3,(H,27,32)/t25-/m0/s1
SMILES Code
Cc1c(c2c(c(c1O)C)CC[C@@](O2)(C)C(=O)Nc3c(n(c(=O)n(c3=O)C)c4ccccc4)N)C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 464.51 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: Tobe M, Tsuboi K, Hasegawa F, Fujiwara N, Inoue Y, Isobe M, Isobe Y. Synthesis and biological evaluation of novel orally available 1-phenyl-6-aminouracils containing dimethyldihydrobenzofuranol structure for the treatment of allergic skin diseases. Bioorg Med Chem Lett. 2016 Feb 15;26(4):1292-5. doi: 10.1016/j.bmcl.2016.01.019. Epub 2016 Jan 8. PubMed PMID: 26786694. 2: Kido M, Takeuchi S, Esaki H, Hayashida S, Furue M. Scratching behavior does not necessarily correlate with epidermal nerve fiber sprouting or inflammatory cell infiltration. J Dermatol Sci. 2010 May;58(2):130-5. doi: 10.1016/j.jdermsci.2010.03.007. Epub 2010 Mar 19. PubMed PMID: 20399618. 3: Ohmori K, Adachi K, Manabe H, Harada D, Ohshima E. [Recent development of new drugs for the treatment of allergic diseases]. Nihon Yakurigaku Zasshi. 2004 May;123(5):335-48. Review. Japanese. PubMed PMID: 15118258. 4: Isobe Y, Tobe M, Inoue Y, Isobe M, Tsuchiya M, Hayashi H. Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents. Bioorg Med Chem. 2003 Nov 17;11(23):4933-40. PubMed PMID: 14604654. 5: Inoue Y, Isobe M, Shiohara T, Hayashi H. Inhibitory activity of CX-659S, a novel diaminouracil derivative, against the rebound phenomenon following withdrawal of corticosteroid therapy for chronic contact hypersensitivity responses. Int Arch Allergy Immunol. 2003 Jun;131(2):143-52. PubMed PMID: 12811023. 6: Uchi H, Koga T, Urabe K, Moroi Y, Furue M. CX-659S, a diaminouracil derivative, indirectly inhibits the function of Langerhans cells by blocking the MEK1/2-Erk1/2 pathway in keratinocytes. J Invest Dermatol. 2003 Jun;120(6):983-9. PubMed PMID: 12787125. 7: Inoue Y, Isobe M, Hayashi H. The combined effect of topical CX-659S, a novel diaminouracil derivative, with topical corticosteroid on the three types of allergic responses in mice or guinea pigs. J Pharmacol Sci. 2003 Jan;91(1):71-8. PubMed PMID: 12686733. 8: Isobe Y, Tobe M, Takahashi O, Goto Y, Inoue Y, Obara F, Tsuchiya M, Hayashi H. Synthesis and activity of a metabolite of (S)-6-amino-5-(6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamido)-3-methyl-1-phe nyl-2,4-(1H,3H)-pyrimidinedione (CX-659S). Chem Pharm Bull (Tokyo). 2002 Oct;50(10):1418-20. PubMed PMID: 12372880. 9: Inoue Y, Isobe M, Shiohara T, Goto Y, Hayashi H. Protective and curative effects of topically applied CX-659S, a novel diaminouracil derivative, on chronic picryl chloride-induced contact hypersensitivity responses. Br J Dermatol. 2002 Oct;147(4):675-82. PubMed PMID: 12366412. 10: Goto Y, Watanabe N, Kogawa N, Tsuchiya M, Takahashi O, Uchi H, Furue M, Hayashi H. CX-659S: a novel diaminouracil derivative that has antioxidative and acute anti-inflammatory activities. Eur J Pharmacol. 2002 Mar 8;438(3):189-96. PubMed PMID: 11909611. 11: Goto Y, Inoue Y, Tsuchiya M, Isobe M, Ueno T, Uchi H, Furue M, Hayashi H. Suppressive effect of topically applied CX-659S, a novel diaminouracil derivative, on the contact hypersensitivity reaction in various animal models. Int Arch Allergy Immunol. 2000 Dec;123(4):341-8. PubMed PMID: 11146392. 12: Tobe M, Isobe Y, Goto Y, Obara F, Tsuchiya M, Matsui J, Hirota K, Hayashi H. Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction. Bioorg Med Chem. 2000 Aug;8(8):2037-47. PubMed PMID: 11003148.