R547
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MedKoo CAT#: 202420

CAS#: 741713-40-6 (free base)

Description: R547 is orally bioavailable diaminopyrimidine cyclin-dependent kinase inhibitor (CDKI) with potential antineoplastic activity. CDKI R547 selectively binds to and inhibits CDKs, especially CDK1/cyclin B, CDK2/cyclin E, and CDK4/cyclin D1. The inhibition of CDKs results in cell cycle arrest, inhibition of tumor cell proliferation, and induction of apoptosis. Through CDK inhibition, this agent also reduces phosphorylation of the retinoblastoma (Rb) protein, thus preventing activation of transcription factor E2F and so further suppressing tumor cell proliferation. CDKs are ATP-dependent serine/threonine kinases that are important regulators of cell cycle progression and are frequently overexpressed in tumor cells.


Chemical Structure

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R547
CAS# 741713-40-6 (free base)

Theoretical Analysis

MedKoo Cat#: 202420
Name: R547
CAS#: 741713-40-6 (free base)
Chemical Formula: C18H21F2N5O4S
Exact Mass: 441.12823
Molecular Weight: 441.45
Elemental Analysis: C, 48.97; H, 4.79; F, 8.61; N, 15.86; O, 14.50; S, 7.26

Price and Availability

Size Price Availability Quantity
5.0mg USD 225.0 2 weeks
25.0mg USD 695.0 2 weeks
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Related CAS #: 869369-26-6 (mesylate)   741713-40-6 (free base)  

Synonym: R547; R 547; R-547; Ro4584820; Ro-4584820; Ro 4584820.

IUPAC/Chemical Name: (4-amino-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

InChi Key: JRNJNYBQQYBCLE-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H21F2N5O4S/c1-29-13-4-3-12(19)15(20)14(13)16(26)11-9-22-18(24-17(11)21)23-10-5-7-25(8-6-10)30(2,27)28/h3-4,9-10H,5-8H2,1-2H3,(H3,21,22,23,24)

SMILES Code: O=C(C1=CN=C(NC2CCN(S(=O)(C)=O)CC2)N=C1N)C3=C(OC)C=CC(F)=C3F

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

Preparing Stock Solutions

The following data is based on the product molecular weight 441.45 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

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1: Sawant RR, Jhaveri AM, Koshkaryev A, Zhu L, Qureshi F, Torchilin VP. Targeted transferrin-modified polymeric micelles: enhanced efficacy in vitro and in vivo in ovarian carcinoma. Mol Pharm. 2014 Feb 3;11(2):375-81. doi: 10.1021/mp300633f. Epub 2013 Dec 19. PubMed PMID: 24325630.

2: Martin F, Thomson TM, Sewer A, Drubin DA, Mathis C, Weisensee D, Pratt D, Hoeng J, Peitsch MC. Assessment of network perturbation amplitudes by applying high-throughput data to causal biological networks. BMC Syst Biol. 2012 May 31;6:54. doi: 10.1186/1752-0509-6-54. PubMed PMID: 22651900; PubMed Central PMCID: PMC3433335.

3: Sangwan M, McCurdy SR, Livne-Bar I, Ahmad M, Wrana JL, Chen D, Bremner R. Established and new mouse models reveal E2f1 and Cdk2 dependency of retinoblastoma, and expose effective strategies to block tumor initiation. Oncogene. 2012 Nov 29;31(48):5019-28. doi: 10.1038/onc.2011.654. Epub 2012 Jan 30. PubMed PMID: 22286767.

4: Cohen-Solal KA, Merrigan KT, Chan JL, Goydos JS, Chen W, Foran DJ, Liu F, Lasfar A, Reiss M. Constitutive Smad linker phosphorylation in melanoma: a mechanism of resistance to transforming growth factor-β-mediated growth inhibition. Pigment Cell Melanoma Res. 2011 Jun;24(3):512-24. doi: 10.1111/j.1755-148X.2011.00858.x. Epub 2011 Apr 28. PubMed PMID: 21477078; PubMed Central PMCID: PMC3108265.

5: DePinto W, Chu XJ, Yin X, Smith M, Packman K, Goelzer P, Lovey A, Chen Y, Qian H, Hamid R, Xiang Q, Tovar C, Blain R, Nevins T, Higgins B, Luistro L, Kolinsky K, Felix B, Hussain S, Heimbrook D. In vitro and in vivo activity of R547: a potent and selective cyclin-dependent kinase inhibitor currently in phase I clinical trials. Mol Cancer Ther. 2006 Nov;5(11):2644-58. PubMed PMID: 17121911.

6: Chu XJ, DePinto W, Bartkovitz D, So SS, Vu BT, Packman K, Lukacs C, Ding Q, Jiang N, Wang K, Goelzer P, Yin X, Smith MA, Higgins BX, Chen Y, Xiang Q, Moliterni J, Kaplan G, Graves B, Lovey A, Fotouhi N. Discovery of [4-Amino-2-(1-methanesulfonylpiperidin-4-ylamino)pyrimidin-5-yl](2,3-difluoro-6- methoxyphenyl)methanone (R547), a potent and selective cyclin-dependent kinase inhibitor with significant in vivo antitumor activity. J Med Chem. 2006 Nov 2;49(22):6549-60. PubMed PMID: 17064073.

R547

5.0mg / USD 225.0


Additional Information