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.
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
This product is not in stock, which may be available by custom synthesis.
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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
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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 244.20468 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 |
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.
