Fazarabine

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

MedKoo CAT#: 205963

CAS#: 65886-71-7

Description: Fazarabine, also known as Kymarabine, is an orally-active pyrimidine analogue of an aza-substituted cytidine in which the ribose moiety is replaced by an arabinose sugar. Similar in action to cytarabine, fazarabine is phosphorylated by deoxycytidine kinase to a triphosphate form which competes with thymidine for incorporation into DNA; its incorporation into DNA inhibits DNA synthesis, resulting in tumor cell death and tumor necrosis. The presence of deoxycytidine kinase in a tumor is a determinant of tumor sensitivity to this drug.


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Fazarabine is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205963
Name: Fazarabine
CAS#: 65886-71-7
Chemical Formula: C8H12N4O5
Exact Mass: 244.08077
Molecular Weight: 244.20468
Elemental Analysis: C, 39.35; H, 4.95; N, 22.94; O, 32.76


Synonym: CCRIS 93; CCRIS-93; CCRIS93; NSC 281272; NSC-281272; NSC281272; Fazarabine. AraAC; Kymarabine

IUPAC/Chemical Name: 4-amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one

InChi Key: NMUSYJAQQFHJEW-ARQDHWQXSA-N

InChi Code: InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5+,6-/m1/s1

SMILES Code: O=C1N([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C=NC(N)=N1


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, not in water

Shelf Life:
>5 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


Additional Information

  
 
 
 


References

1: Wilhelm M, O'Brien S, Rios MB, Estey E, Keating MJ, Plunkett W, Sorenson M, Kantarjian HM. Phase I study of arabinosyl-5-azacytidine (fazarabine) in adult acute leukemia and chronic myelogenous leukemia in blastic phase. Leuk Lymphoma. 1999 Aug;34(5-6):511-8. PubMed PMID: 10492074.

2: Goldberg RM, Reid JM, Ames MM, Sloan JA, Rubin J, Erlichman C, Kuffel MJ, Fitch TR. Phase I and pharmacological trial of fazarabine (Ara-AC) with granulocyte colony-stimulating factor. Clin Cancer Res. 1997 Dec;3(12 Pt 1):2363-70. PubMed PMID: 9815635.

3: Barchi JJ Jr, Cooney DA, Ahluwalia GS, Gharehbaghi K, Covey JM, Hochman I, Paull KD, Jayaram HN. Studies on the mechanism of action of 1-beta-D-arabinofuranosyl-5-azacytosine (fazarabine) in mammalian lymphoblasts. J Exp Ther Oncol. 1996 May;1(3):191-203. PubMed PMID: 9414404.

4: Manetta A, Blessing JA, Mann WJ, Smith DM. A phase II study of fazarabine (NSC 281272) in patients with advanced squamous cell carcinoma of the cervix. A Gynecologic Oncology Group study. Am J Clin Oncol. 1995 Oct;18(5):439-40. PubMed PMID: 7572764.

5: Manetta A, Blessing JA, Look KY. A phase II study of fazarabine in patients with advanced ovarian cancer. A Gynecologic Oncology Group study. Am J Clin Oncol. 1995 Apr;18(2):156-7. PubMed PMID: 7534978.

6: Williamson SK, Crowley JJ, Livingston RB, Panella TJ, Goodwin JW. Phase II trial and cost analysis of fazarabine in advanced non-small cell carcinoma of the lung: a Southwest Oncology Group study. Invest New Drugs. 1995;13(1):67-71. PubMed PMID: 7499111.

7: Selby GB, Upchurch C, Townsend J, Eyre HJ. A phase II evaluation of fazarabine in high-grade gliomas: a Southwest Oncology Group study. Cancer Chemother Pharmacol. 1994;34(2):179-80. PubMed PMID: 7514963.

8: Bernstein ML, Whitehead VM, Grier H, Dubowy R, Land V, Devine S, Murphy S, Kung F. A phase I trial of fazarabine in refractory pediatric solid tumors. A Pediatric Oncology Group study. Invest New Drugs. 1993 Nov;11(4):309-12. PubMed PMID: 7512539.

9: Heideman RL, McCully C, Balis FM, Poplack DG. Cerebrospinal fluid pharmacokinetics and toxicology of intraventricular and intrathecal arabinosyl-5-azacytosine (fazarabine, NSC 281272) in the nonhuman primate. Invest New Drugs. 1993 May-Aug;11(2-3):135-40. PubMed PMID: 7505267.

10: Ben-Baruch N, Denicoff AM, Goldspiel BR, O'Shaughnessy JA, Cowan KH. Phase II study of fazarabine (NSC 281272) in patients with metastatic colon cancer. Invest New Drugs. 1993 Feb;11(1):71-4. PubMed PMID: 7688714.