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

MedKoo CAT#: 529608

CAS#: 10356-76-0

Description: FdCyd is a DNA methyltransferase (DNMT) inhibitor potentially for the treatment of solid tumours.


Price and Availability

Size
Price

1g
USD 260
Size
Price

2g
USD 470
Size
Price

5g
USD 820

FdCyd, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529608
Name: FdCyd
CAS#: 10356-76-0
Chemical Formula: C9H12FN3O4
Exact Mass: 245.0812
Molecular Weight: 245.21
Elemental Analysis: C, 44.08; H, 4.93; F, 7.75; N, 17.14; O, 26.10


Synonym: NSC-48006; Ro-5-1090; FdCyd; NSC48006; Ro51090; NSC 48006; Ro 5 1090

IUPAC/Chemical Name: 4-amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

InChi Key: IDYKCXHJJGMAEV-RRKCRQDMSA-N

InChi Code: InChI=1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1

SMILES Code: OC[C@@H]1[C@H](C[C@H](N2C(N=C(C(F)=C2)N)=O)O1)O


Technical Data

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).

Harmonized System Code:
293490


References

1: Holleran JL, Eiseman JL, Parise RA, Kummar S, Beumer JH. LC-MS/MS assay for the quantitation of FdCyd and its metabolites FdUrd and FU in human plasma. J Pharm Biomed Anal. 2016 Sep 10;129:359-66. doi: 10.1016/j.jpba.2016.07.027. PubMed PMID: 27454087; PubMed Central PMCID: PMC5003709.

2: Beumer JH, Parise RA, Newman EM, Doroshow JH, Synold TW, Lenz HJ, Egorin MJ. Concentrations of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine (FdCyd) and its cytotoxic metabolites in plasma of patients treated with FdCyd and tetrahydrouridine (THU). Cancer Chemother Pharmacol. 2008 Jul;62(2):363-8. PubMed PMID: 17899082.

3: Newman EM, Morgan RJ, Kummar S, Beumer JH, Blanchard MS, Ruel C, El-Khoueiry AB, Carroll MI, Hou JM, Li C, Lenz HJ, Eiseman JL, Doroshow JH. A phase I, pharmacokinetic, and pharmacodynamic evaluation of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine, administered with tetrahydrouridine. Cancer Chemother Pharmacol. 2015 Mar;75(3):537-46. doi: 10.1007/s00280-014-2674-7. PubMed PMID: 25567350; PubMed Central PMCID: PMC4344391.

4: Holleran JL, Beumer JH, McCormick DL, Johnson WD, Newman EM, Doroshow JH, Kummar S, Covey JM, Davis M, Eiseman JL. Oral and intravenous pharmacokinetics of 5-fluoro-2'-deoxycytidine and THU in cynomolgus monkeys and humans. Cancer Chemother Pharmacol. 2015 Oct;76(4):803-11. doi: 10.1007/s00280-015-2857-x. PubMed PMID: 26321472; PubMed Central PMCID: PMC4573928.

5: Guo D, Myrdal PB, Karlage KL, O'Connell SP, Wissinger TJ, Tabibi SE, Yalkowsky SH. Stability of 5-fluoro-2'-deoxycytidine and tetrahydrouridine in combination. AAPS PharmSciTech. 2010 Mar;11(1):247-52. doi: 10.1208/s12249-010-9383-2. PubMed PMID: 20151336; PubMed Central PMCID: PMC2850501.

6: Beumer JH, Eiseman JL, Parise RA, Joseph E, Holleran JL, Covey JM, Egorin MJ. Pharmacokinetics, metabolism, and oral bioavailability of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine in mice. Clin Cancer Res. 2006 Dec 15;12(24):7483-91. PubMed PMID: 17138702.

7: Morfouace M, Nimmervoll B, Boulos N, Patel YT, Shelat A, Freeman BB 3rd, Robinson GW, Wright K, Gajjar A, Stewart CF, Gilbertson RJ, Roussel MF. Preclinical studies of 5-fluoro-2'-deoxycytidine and tetrahydrouridine in pediatric brain tumors. J Neurooncol. 2016 Jan;126(2):225-34. doi: 10.1007/s11060-015-1965-0. PubMed PMID: 26518542; PubMed Central PMCID: PMC4718940.

8: Pan Y, Daito T, Sasaki Y, Chung YH, Xing X, Pondugula S, Swamidass SJ, Wang T, Kim AH, Yano H. Inhibition of DNA Methyltransferases Blocks Mutant Huntingtin-Induced Neurotoxicity. Sci Rep. 2016 Aug 12;6:31022. doi: 10.1038/srep31022. PubMed PMID: 27516062; PubMed Central PMCID: PMC4981892.

9: Mekras JA, Boothman DA, Perez LM, Greer S. Use of 5-fluorodeoxycytidine and tetrahydrouridine to exploit high levels of deoxycytidylate deaminase in tumors to achieve DNA- and target-directed therapies. Cancer Res. 1984 Jun;44(6):2551-60. PubMed PMID: 6539164.

10: Boothman DA, Briggle TV, Greer S. Protective, tumor-selective dual pathway activation of 5-fluoro-2'-deoxycytidine provided by tetrahydrouridine in mice bearing mammary adenocarcinoma-755. Cancer Res. 1987 May 1;47(9):2344-53. PubMed PMID: 2436761.

11: Kaysen J, Spriggs D, Kufe D. Incorporation of 5-fluorodeoxycytidine and metabolites into nucleic acids of human MCF-7 breast carcinoma cells. Cancer Res. 1986 Sep;46(9):4534-8. PubMed PMID: 2425957.

12: Boothman DA, Briggle TV, Greer S. Tumor-selective metabolism of 5-fluoro-2'-deoxycytidine coadministered with tetrahydrouridine compared to 5-fluorouracil in mice bearing Lewis lung carcinoma. Cancer Res. 1987 May 1;47(9):2354-62. PubMed PMID: 2952263.

13: Li LS, Morales JC, Veigl M, Sedwick D, Greer S, Meyers M, Wagner M, Fishel R, Boothman DA. DNA mismatch repair (MMR)-dependent 5-fluorouracil cytotoxicity and the potential for new therapeutic targets. Br J Pharmacol. 2009 Oct;158(3):679-92. doi: 10.1111/j.1476-5381.2009.00423.x. Review. PubMed PMID: 19775280; PubMed Central PMCID: PMC2765589.

14: Vandamme B, Liebaers I, Hens L, Bernheim JL, Roobol C. The role of fluorinated pyrimidine analogues in the induction of the in vitro expression of the fragile X chromosome. Hum Genet. 1988 Aug;79(4):341-6. PubMed PMID: 2970425.

15: Newman EM, Santi DV. Metabolism and mechanism of action of 5-fluorodeoxycytidine. Proc Natl Acad Sci U S A. 1982 Nov;79(21):6419-23. PubMed PMID: 6959127; PubMed Central PMCID: PMC347137.

16: Iigo M, Yamaizumi Z, Nishimura S, Hoshi A. Elevation of plasma levels of fluorinated pyrimidines by guanosine 5'-monophosphate. Cancer Chemother Pharmacol. 1987;20(1):1-4. PubMed PMID: 3040286.

17: Briggle TV, Boothman DA, Pfaffenberger CD, Greer S. Analysis of 5-fluoro-2'-deoxycytidine and 5-trifluoromethyl-2'-deoxycytidine and their related antimetabolites by high-performance liquid chromatography. J Chromatogr. 1986 Sep 5;381(2):343-55. PubMed PMID: 2944908.

18: Osterman DG, DePillis GD, Wu JC, Matsuda A, Santi DV. 5-Fluorocytosine in DNA is a mechanism-based inhibitor of HhaI methylase. Biochemistry. 1988 Jul 12;27(14):5204-10. PubMed PMID: 3167042.

19: Janion C. On the ability of Salmonella typhimurium cells to form deoxycytidine nucleotides. Mol Gen Genet. 1977 Jun 8;153(2):179-83. PubMed PMID: 329115.

20: De Clercq E, Bères J, Bentrude WG. Potent activity of 5-fluoro-2'-deoxyuridine and related compounds against thymidine kinase-deficient (TK-) herpes simplex virus: targeted at thymidylate synthase. Mol Pharmacol. 1987 Aug;32(1):286-92. PubMed PMID: 3039343.