Cytarabine hydrochloride
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MedKoo CAT#: 100200

CAS#: 69-74-9 (HCl)

Description: Cytarabine, also known as MK-8242 and SCH-900242, is an antimetabolite analogue of cytidine with a modified sugar moiety (arabinose instead of ribose). Cytarabine is converted to the triphosphate form within the cell and then competes with cytidine for incorporation into DNA. Because the arabinose sugar sterically hinders the rotation of the molecule within DNA, DNA replication ceases, specifically during the S phase of the cell cycle. This agent also inhibits DNA polymerase, resulting in a decrease in DNA replication and repair.

Chemical Structure

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Cytarabine hydrochloride
CAS# 69-74-9 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100200
Name: Cytarabine hydrochloride
CAS#: 69-74-9 (HCl)
Chemical Formula: C9H14ClN3O5
Exact Mass: 0.00
Molecular Weight: 279.680
Elemental Analysis: C, 38.65; H, 5.05; Cl, 12.68; N, 15.02; O, 28.60

Price and Availability

Size Price Availability Quantity
2g USD 150 Ready to ship
5g USD 300 Ready to ship
10g USD 500 2 weeks
25g USD 950 2 Weeks
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Related CAS #: 69-74-9 (HCl)   147-94-4 (free)    

Synonym: MK-8242; MK 8242; MK8242; SCH-900242; SCH900242; SCH 900242; aracytidine; cytarabine hydrochloride.

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

InChi Key: KCURWTAZOZXKSJ-JBMRGDGGSA-N

InChi Code: InChI=1S/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/m1./s1

SMILES Code: O=C1N=C(N)C=CN1[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O.[H]Cl

Appearance: white 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

More Info:  Related CAS# 69-74-9 (Cytarabine hydrochloride); 147-94-4 (Cytarabine free base)

Biological target: Cytarabine hydrochloride is a nucleoside analog that inhibits DNA synthesis with an IC50 of 16 nM.
In vitro activity: In vitro, normal granulocyte-macrophage colony-forming unit (CFU-GM) cells as well as CFU-GM cells obtained from patients with chronic myeloid leukemia (CML) were incubated either with gemcitabine (dFdC) or cytarabine (Ara-C) alone or with adequate concentrations of a combination of these drugs. The in vitro experiments showed that dFdC used together with Ara-C acted additively on normal as well as CML CFU-GM cells. Furthermore, the drugs used jointly inhibited the growth of colonies formed by CML CFU-GM cells to a significantly higher degree than normal CFU-GM and the differences were statistically significant in the case of the combination of highest concentrations. Reference: Haematologica. 2000 Jun;85(6):588-94. https://pubmed.ncbi.nlm.nih.gov/10870114/
In vivo activity: In vivo, mice bearing L1210 or P388 leukemia were treated with dFdC and Ara-C. The drugs were administered alone and in combination according to the following schedules: Ara-C and dFdC at the same time, dFdC before Ara-C, and Ara-C before dFdC. The efficacy of the therapy against leukemia (defined as the increase in lifespan, ILS) was assessed as the percentage of the median survival time (MST) of the treated group (T) in relationship to that of the control group (C): ILS=[(MST(C)/MST(T)) -1]x100. The in vivo experiment revealed that in both leukemias tested, combined therapy with dFdC given before Ara-C and dFdC given at the same time with Ara-C were more effective than monotherapy with either dFdC or Ara-C. The other treatment schedule (Ara-C before dFdC) did not significantly prolong the survival time of the treated mice bearing L1210 or P388 leukemia as compared with the treatment with dFdC alone. Reference: Haematologica. 2000 Jun;85(6):588-94. https://pubmed.ncbi.nlm.nih.gov/10870114/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 55.0 196.65
PBS (pH 7.2) 10.0 35.76

Preparing Stock Solutions

The following data is based on the product molecular weight 279.68 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
Formulation protocol: 1. Lech-Maranda E, Korycka A, Robak T. The interaction of gemcitabine and cytarabine on murine leukemias L1210 or P388 and on human normal and leukemic cell growth in vitro. Haematologica. 2000 Jun;85(6):588-94. PMID: 10870114.
In vitro protocol: 1. Lech-Maranda E, Korycka A, Robak T. The interaction of gemcitabine and cytarabine on murine leukemias L1210 or P388 and on human normal and leukemic cell growth in vitro. Haematologica. 2000 Jun;85(6):588-94. PMID: 10870114.
In vivo protocol: 1. Lech-Maranda E, Korycka A, Robak T. The interaction of gemcitabine and cytarabine on murine leukemias L1210 or P388 and on human normal and leukemic cell growth in vitro. Haematologica. 2000 Jun;85(6):588-94. PMID: 10870114.

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 1: Raut LS. Novel formulation of cytarabine and daunorubicin: A new hope in AML treatment. South Asian J Cancer. 2015 Jan-Mar;4(1):38-40. doi: 10.4103/2278-330X.149950. Review. PubMed PMID: 25839020; PubMed Central PMCID: PMC4382783.

2: Reese ND, Schiller GJ. High-dose cytarabine (HD araC) in the treatment of leukemias: a review. Curr Hematol Malig Rep. 2013 Jun;8(2):141-8. doi: 10.1007/s11899-013-0156-3. Review. PubMed PMID: 23666364.

3: Löwenberg B. Sense and nonsense of high-dose cytarabine for acute myeloid leukemia. Blood. 2013 Jan 3;121(1):26-8. doi: 10.1182/blood-2012-07-444851. Review. PubMed PMID: 23287624.

4: Low M, Lee D, Coutsouvelis J, Patil S, Opat S, Walker P, Schwarer A, Salem H, Avery S, Spencer A, Wei A. High-dose cytarabine (24 g/m2) in combination with idarubicin (HiDAC-3) results in high first-cycle response with limited gastrointestinal toxicity in adult acute myeloid leukaemia. Intern Med J. 2013 Mar;43(3):294-7. doi: 10.1111/j.1445-5994.2012.02868.x. Review. PubMed PMID: 22757980.

5: Wei G, Ni W, Chiao JW, Cai Z, Huang H, Liu D. A meta-analysis of CAG (cytarabine, aclarubicin, G-CSF) regimen for the treatment of 1029 patients with acute myeloid leukemia and myelodysplastic syndrome. J Hematol Oncol. 2011 Nov 14;4:46. doi: 10.1186/1756-8722-4-46. Review. PubMed PMID: 22082134; PubMed Central PMCID: PMC3230125.

6: Chhikara BS, Parang K. Development of cytarabine prodrugs and delivery systems for leukemia treatment. Expert Opin Drug Deliv. 2010 Dec;7(12):1399-414. doi: 10.1517/17425247.2010.527330. Epub 2010 Oct 22. Review. PubMed PMID: 20964588.

7: Seif AE, Reilly AF, Rheingold SR. Intrathecal liposomal cytarabine in relapsed or refractory infant and pediatric leukemias: the Children's Hospital of Philadelphia experience and review of the literature. J Pediatr Hematol Oncol. 2010 Nov;32(8):e349-52. doi: 10.1097/MPH.0b013e3181ec0c25. Review. PubMed PMID: 20962675.

8: Romaguera JE, Fayad LE, Feng L, Hartig K, Weaver P, Rodriguez MA, Hagemeister FB, Pro B, McLaughlin P, Younes A, Samaniego F, Goy A, Cabanillas F, Kantarjian H, Kwak L, Wang M. Ten-year follow-up after intense chemoimmunotherapy with Rituximab-HyperCVAD alternating with Rituximab-high dose methotrexate/cytarabine (R-MA) and without stem cell transplantation in patients with untreated aggressive mantle cell lymphoma. Br J Haematol. 2010 Jul;150(2):200-8. doi: 10.1111/j.1365-2141.2010.08228.x. Epub 2010 May 26. Review. Erratum in: Br J Haematol.n 2010 Oct;151(1):111. PubMed PMID: 20528872.

9: Lamba JK. Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. Review. PubMed PMID: 19842938; PubMed Central PMCID: PMC2828057.

10: Fathi AT, Karp JE. New agents in acute myeloid leukemia: beyond cytarabine and anthracyclines. Curr Oncol Rep. 2009 Sep;11(5):346-52. Review. PubMed PMID: 19679009; PubMed Central PMCID: PMC3066101.