Cytarabine free base| CAS#147-94-4 | pyrimidine nucleoside analog

MedKoo Cat#: 592264 | Name: Cytarabine free base

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Description:

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

Cytarabine is a pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties.

Chemical Structure

Cytarabine free base

CAS#147-94-4 (free)

Theoretical Analysis

MedKoo Cat#: 592264

Name: Cytarabine free base

CAS#: 147-94-4 (free)

Chemical Formula: C9H13N3O5

Exact Mass: 243.0855

Molecular Weight: 243.22

Elemental Analysis: C, 44.45; H, 5.39; N, 17.28; O, 32.89

Price and Availability

Size	Price	Availability
500mg	USD 90.00	Ready to ship
1g	USD 150.00	Ready to ship
2g	USD 225.00	Ready to ship
5g	USD 450.00	Ready to ship
10g	USD 750.00	Ready to ship
20g	USD 1,250.00	Ready to ship

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Related CAS #

69-74-9 (HCl) 147-94-4 (free)

Synonym

Cytarabine, AC-1075; CHX 3311, MK 8242; NCI-C04728; NSC 287459; Cytosine arabinose; Arabitin; Aracytidine; Cytarabine free base

IUPAC/Chemical Name

2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-

InChi Key

UHDGCWIWMRVCDJ-CCXZUQQUSA-N

InChi Code

InChI=1S/C9H13N3O5/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)/t4-,6-,7+,8-/m1/s1

SMILES Code

O=C1N=C(N)C=CN1[C@H]2[C@H]([C@@H]([C@@H](CO)O2)O)O

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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# C21R01B22

QC Data

View QC data: current batch, Lot# C21R01B22

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Cytarabine 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/

	Solvent	mg/mL	mM
Solubility
	Water	40.1	164.91
	DMSO	19.4	79.85
	DMF	0.1	0.41
	PBS (pH 7.2)	2.0	8.22

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 243.22 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

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:

In vivo protocol:

1: Luo H, Nishi K, Ishikura S, Swain A, Morishige N, Yazaki R, Ohshima T, Shirasawa S, Tsunoda T. Growth Suppression of Human Colorectal Cancer Cells with Mutated KRAS by 3-Deaza-cytarabine in 3D Floating Culture. Anticancer Res. 2018 Jul;38(7):4247-4256. doi: 10.21873/anticanres.12721. PubMed PMID: 29970558. 2: Flasinski M, Scheibke K, Zimmermann M, Creutzig U, Reinhardt K, Verwer F, de Haas V, van der Velden VHJ, von Neuhoff C, Zwaan CM, Reinhardt D, Klusmann JH. Low-dose cytarabine to prevent myeloid leukemia in children with Down syndrome: TMD Prevention 2007 study. Blood Adv. 2018 Jul 10;2(13):1532-1540. doi: 10.1182/bloodadvances.2018018945. PubMed PMID: 29959152. 3: Dotson JL, Jamil MO. Successful treatment of cytarabine-related neurotoxicity with corticosteroids, a case series. Int J Hematol. 2018 Jun 26. doi: 10.1007/s12185-018-2485-4. [Epub ahead of print] PubMed PMID: 29946854. 4: Chen EC, Fathi AT, Brunner AM. Reformulating acute myeloid leukemia: liposomal cytarabine and daunorubicin (CPX-351) as an emerging therapy for secondary AML. Onco Targets Ther. 2018 Jun 12;11:3425-3434. doi: 10.2147/OTT.S141212. eCollection 2018. Review. PubMed PMID: 29928134; PubMed Central PMCID: PMC6003284. 5: Wang Z, Fang X, Huang H, Hong H, Li X, Guo C, Fu X, Zhang M, Lam ST, Li S, Li F, Peng C, Tian Y, Lin T. Recombinant human thrombopoietin (rh-TPO) for the prevention of severe thrombocytopenia induced by high-dose cytarabine: a prospective, randomized, self-controlled study. Leuk Lymphoma. 2018 Jun 18:1-8. doi: 10.1080/10428194.2018.1459605. [Epub ahead of print] PubMed PMID: 29909708. 6: Hochberg J, Zahler S, Geyer MB, Chen N, Krajewski J, Harrison L, Militano O, Ozkaynak MF, Cheerva AC, Talano J, Moore TB, Gillio AP, Walters MC, Baxter-Lowe LA, Hamby C, Cairo MS. The safety and efficacy of clofarabine in combination with high-dose cytarabine and total body irradiation myeloablative conditioning and allogeneic stem cell transplantation in children, adolescents, and young adults (CAYA) with poor-risk acute leukemia. Bone Marrow Transplant. 2018 Jun 13. doi: 10.1038/s41409-018-0247-9. [Epub ahead of print] PubMed PMID: 29899571. 7: Bertoli S, Tavitian S, Berard E, Gadaud N, Luquet I, Huynh A, Sarry A, Huguet F, Récher C. Outcome of relapsed or refractory acute myeloid leukemia treated with intensive salvage chemotherapy in real life in comparison to intermediate dose cytarabine in phase 3 studies. Leuk Lymphoma. 2018 Jun 12:1-4. doi: 10.1080/10428194.2018.1464156. [Epub ahead of print] PubMed PMID: 29893611. 8: Aznab M, Khazaie M. Intermediate dose cytarabine in treatment myeloid sarcoma of the bilateral breast after allogeneic stem cell transplantation: A case report and literature review. J Cancer Res Ther. 2018 Apr-Jun;14(3):703-705. doi: 10.4103/0973-1482.174174. PubMed PMID: 29893346. 9: Tomizawa D, Tanaka S, Hasegawa D, Iwamoto S, Hiramatsu H, Kiyokawa N, Miyachi H, Horibe K, Saito AM, Taga T, Adachi S. Evaluation of high-dose cytarabine in induction therapy for children with de novo acute myeloid leukemia: a study protocol of the Japan Children's Cancer Group Multi-Center Seamless Phase II-III Randomized Trial (JPLSG AML-12). Jpn J Clin Oncol. 2018 Jun 1;48(6):587-593. doi: 10.1093/jjco/hyy061. PubMed PMID: 29889285. 10: Ottmann OG, Müller-Tidow C, Krämer A, Schlenk RF, Lübbert M, Bug G, Krug U, Bochtler T, Voss F, Taube T, Liu D, Garin-Chesa P, Döhner H. Phase I dose-escalation trial investigating volasertib as monotherapy or in combination with cytarabine in patients with relapsed/refractory acute myeloid leukaemia. Br J Haematol. 2018 Jun 8. doi: 10.1111/bjh.15204. [Epub ahead of print] PubMed PMID: 29882583. 11: Chen K, Chen Y, Chen Z, Shi Y, He Z, Ding B, Wang C, Yu L. miR-134 increases the antitumor effects of cytarabine by targeting Mnks in acute myeloid leukemia cells. Onco Targets Ther. 2018 May 25;11:3141-3147. doi: 10.2147/OTT.S143465. eCollection 2018. PubMed PMID: 29872325; PubMed Central PMCID: PMC5975600. 12: de Souza Silva PM, de Sousa RV, Simão AA, Cesar PHS, Trento MVC, Marcussi S. Protective effect of β-D-glucan and glutamine on the genomic instability induced by Cytarabine/Ara-C in BALB/c mice. Int J Biol Macromol. 2018 May 28;117:559-564. doi: 10.1016/j.ijbiomac.2018.05.206. [Epub ahead of print] PubMed PMID: 29852229. 13: Treggiari E, Arrol LP. Clinical response to a lomustine/cytarabine-based chemotherapy protocol in a case of canine large granular lymphocyte T-cell lymphoma with spinal involvement. Open Vet J. 2018;8(2):154-159. doi: 10.4314/ovj.v8i2.7. Epub 2018 May 8. PubMed PMID: 29805960; PubMed Central PMCID: PMC5961131. 14: Ravandi F, Ritchie EK, Sayar H, Lancet JE, Craig MD, Vey N, Strickland SA, Schiller GJ, Jabbour E, Pigneux A, Horst HA, Récher C, Klimek VM, Cortes JE, Carella AM, Egyed M, Krug U, Fox JA, Craig AR, Ward R, Smith JA, Acton G, Kantarjian HM, Stuart RK. Phase 3 results for vosaroxin/cytarabine in the subset of patients ≥60 years old with refractory/early relapsed acute myeloid leukemia. Haematologica. 2018 May 24. pii: haematol.2018.191361. doi: 10.3324/haematol.2018.191361. [Epub ahead of print] PubMed PMID: 29794146. 15: Liu B, Narurkar R, Hanmantgad M, Zafar W, Song Y, Liu D. Venetoclax and low-dose cytarabine induced complete remission in a patient with high-risk acute myeloid leukemia: a case report. Front Med. 2018 May 21. doi: 10.1007/s11684-018-0635-y. [Epub ahead of print] PubMed PMID: 29785506. 16: van Eijkelenburg NKA, Rasche M, Ghazaly E, Dworzak MN, Klingebiel T, Rossig C, Leverger G, Stary J, de Bont ESJM, Chitu DA, Bertrand Y, Brethon B, Strahm B, van der Sluis IM, Kaspers GJL, Reinhardt D, Zwaan CM. Clofarabine, high-dose cytarabine and liposomal daunorubicin in pediatric relapsed/refractory acute myeloid leukemia: a phase IB study. Haematologica. 2018 May 17. pii: haematol.2017.187153. doi: 10.3324/haematol.2017.187153. [Epub ahead of print] PubMed PMID: 29773602. 17: Raj R, Raj PM, Ram A. Nanosized ethanol based malleable liposomes of cytarabine to accentuate transdermal delivery: formulation optimization, in vitro skin permeation and in vivo bioavailability. Artif Cells Nanomed Biotechnol. 2018 May 17:1-13. doi: 10.1080/21691401.2018.1473414. [Epub ahead of print] PubMed PMID: 29771146. 18: Pastina B, Early PJ, Bergman RL, Nettifee J, Maller A, Bray KY, Waldron RJ, Castel AM, Munana KR, Papich MG, Messenger KM. The pharmacokinetics of cytarabine administered subcutaneously, combined with prednisone, in dogs with meningoencephalomyelitis of unknown etiology. J Vet Pharmacol Ther. 2018 May 15. doi: 10.1111/jvp.12667. [Epub ahead of print] PubMed PMID: 29761906. 19: Albanesi M, Carluccio P, Nico A, Giliberti L, Di Bona D, Caiaffa MF, Specchia G, Macchia L. A desensitization protocol for delayed allergy to cytarabine: analysis of two cases. Postepy Dermatol Alergol. 2018 Apr;35(2):222-224. doi: 10.5114/ada.2018.75249. Epub 2018 Apr 24. PubMed PMID: 29760627; PubMed Central PMCID: PMC5949556. 20: Gruffaz M, Zhou S, Vasan K, Rushing T, Michael QL, Lu C, Jung JU, Gao SJ. Repurposing Cytarabine for Treating Primary Effusion Lymphoma by Targeting Kaposi's Sarcoma-Associated Herpesvirus Latent and Lytic Replications. MBio. 2018 May 8;9(3). pii: e00756-18. doi: 10.1128/mBio.00756-18. PubMed PMID: 29739902; PubMed Central PMCID: PMC5941074.