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MedKoo Cat#: 205963 | Name: Fazarabine

Description:

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

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.

Chemical Structure

Fazarabine
Fazarabine
CAS#65886-71-7

Theoretical Analysis

MedKoo Cat#: 205963

Name: Fazarabine

CAS#: 65886-71-7

Chemical Formula: C8H12N4O5

Exact Mass: 244.0808

Molecular Weight: 244.20

Elemental Analysis: C, 39.35; H, 4.95; N, 22.94; O, 32.76

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 #
No Data
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
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Preparing Stock Solutions

The following data is based on the product molecular weight 244.20 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: 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.