Drug Details

General Information of the Drug (ID: DR7876)
Name
Cytarabine
Synonyms
Alexan; AraC; Arabinocytidine; Arabinofuranosylcytosine; Arabinosylcytosine; Arabitin; Aracytidine; Aracytin; Aracytine; Arafcyt; Citarabina; Cytarabin; Cytarabina; Cytarabinoside; Cytarabinum; Cytarbel; Cytonal; Cytosar; Cytosinearabinoside; DepoCyte; Depocyt; Erpalfa; Iretin; Spongocytidine; Tarabine; Udicil; Arabinosyl Cytosine; Cytarabine liposome injection; Cytosine arabinofuranoside; Cytosine arabinose; Cytosine arabinoside; AR3; BTB15125; CHX 3311; U 19920A; Ara-C; Ara-Cytidine; Beta-Ara C; Beta-Arabinosylcytosine; Beta-cytosine arabinoside; Citarabina [INN-Spanish]; Cytarabinum [INN-Latin]; Cytosar-U; Cytosine arabinoside (VAN); Depocyt (TN); Depocyt (liposomal); Intrathecal (injected into the spinal fluid) DepoCyt; U-19920; Beta-D-Arabinosylcytosine; Cytosar-U (TN); Cytosine beta-D-arabinofuranoside; Cytosine beta-D-arabinofuranoside hydrochloride; Cytosine beta-D-arabinoside; Cytosine-beta-arabinoside; Intrathecal cytarabine (also known as ara-C); U-19,920; CYTARABINE (SEE ALSO CYTARABINE HYDROCHLORIDE 69-74-9); Cytarabine (JP15/USP/INN); Cytarabine [USAN:INN:BAN:JAN]; Cytosine 1-beta-D-arabinofuranoside; Cytosine, beta-D-arabinoside; Cytosine-beta-D-arabinofuranoside; Cytosine-1-beta-D-arabinofuranoside; Ara-C, Cytosine Arabinoside, Cytosar-U, Cytarabine; (beta-D-Arabinofuranosyl)cytosine; 1-.beta.-D-arabinofuranosyl-cytosine; 1-Arabinofuranosylcytosine; 1-beta-D-Arabinofaranosylcytosine; 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone; 1-beta-D-Arabinofuranosylcytosine; 1-beta-D-Arabinofuranosylcytosine, Cytosine Arabinoside; 1-beta-D-Arabinosylcytosine; 1beta-Arabinofuranasylcytosine; 1beta-D-Arabinofuranosylcytosine; 1beta-D-Arabinosylcytosine; 2(1H)-Pyrimidinone, 4-amino-1-D-arabinofuranosyl-[CAS]; 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin; 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin [Czech]; 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine; 4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone; 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon; 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon [Czech]; 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone; 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one; 4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one
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Molecular Type
Small molecule
Disease Mantle cell lymphoma [ICD-11: 2A85] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C9H13N3O5
PubChem CID
6253
Canonical SMILES
C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
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
InChIKey
UHDGCWIWMRVCDJ-CCXZUQQUSA-N
CAS Number
CAS 147-94-4
ChEBI ID
CHEBI:28680
GDSC
Cytarabine
TTD Drug ID
D07XSN
DrugBank ID
DB00987
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Aclarubicin      Streptomyces galilaeus     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Increasing the dose of aclarubicin in CAG regimen seemed to be useful and relatively safe in relapsed and refractory AML.
          Curcumin      Hellenia speciosa     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
                    In-vitro Model Bone marrow samples from newly diagnosed AML patients Acute myeloid leukemia Homo sapiens
                    Experimental
                    Result(s)		 Curcumin down regulates MDR genes. Curcumin can be used as MDR modulator as well as chemosensitizer in combination with cytarabine to reduce the cytotoxicity profile as IC50 value decreases when treated in combination.
          Emodin      Oplopanax elatus     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression BID  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK2  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation mTOR  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation S6K1  Molecule Info 
Pathway MAP
                    In-vitro Model HL-60 CVCL_0002 Adult acute myeloid leukemia Homo sapiens
ARAC-8C CVCL_GZ09 T acute lymphoblastic leukemia Homo sapiens
Jurkat CVCL_0065 T acute lymphoblastic leukemia Homo sapiens
MOLT-4 CVCL_0013 Adult T acute lymphoblastic leukemia Homo sapiens
CA46 CVCL_1101 Burkitt lymphoma Homo sapiens
                    In-vivo Model Around 1.5*107 HL-60/H3 cells were subcutaneously injected into the right flank of BALB/C-nude mice.
                    Experimental
                    Result(s)		 Emodin significantly enhanced chemosensitivity of AML cells to Ara-C, inhibited leukemic cell growth, and improved survival in the mouse xenograft model of AML. Dual targeting of Akt and ERK signaling pathways might contribute to the anti-leukemia effects on AML cells in vitro and in vivo.
          Ginsenoside compound K      Panax ginseng     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Up-regulation Ratio of dCKappa to CDA
                    In-vitro Model HL-60 CVCL_0002 Adult acute myeloid leukemia Homo sapiens
THP-1 CVCL_0006 Childhood acute monocytic leukemia Homo sapiens
U-937 CVCL_0007 Adult acute monocytic leukemia Homo sapiens
NCI-H358 CVCL_1559 Lung adenocarcinoma Homo sapiens
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
C2C12 CVCL_0188 Healthy Mus musculus
HAECT-1 CVCL_VU17 Healthy Homo sapiens
RAW 264.7 CVCL_0493 Mouse leukemia Mus musculus
MOLM-13 CVCL_2119 Adult acute myeloid leukemia Homo sapiens
                    Experimental
                    Result(s)		 Ara-C combined with CK could achieve the efficacy of higher concentration of ara-C. CK promoted ara-C-induced cell membrane damage and mitochondrial dysfunction and increased ara-C-induced DNA damage.
    β. A List of Natural Product(s) Able to Reverse the Resistance of This Drug
          Triptolide      Tripterygium hypoglaucum     Click to Show/Hide the Molecular Data of This NP
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CASP9  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation CHK1  Molecule Info 
Pathway MAP
Up-regulation Expression H2AFX  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation RAD53  Molecule Info 
Pathway MAP
                    In-vitro Model NALM-6 CVCL_0092 Adult B acute lymphoblastic leukemia Homo sapiens
                    In-vivo Model To generate a mouse model of araC-resistant ALL, NALM-6/R cells (5 * 105) were subcutaneously injected into the angular veins of sublethally irradiated adult NSI (NOD/SCID IL2rg-/-) mice (20-30 g body weight, 2-3 months of age).
                    Experimental
                    Result(s)		 Low dose triptolide reverses chemoresistance in adult acute lymphoblastic leukemia cells via reactive oxygen species generation and DNA damage response disruption.
Target and Pathway
Target(s) Herpes simplex virus DNA polymerase UL30 (HSV UL30)  Molecule Info  [7]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4827).
Reference 2 Increasing the dose of aclarubicin in low-dose cytarabine and aclarubicin in combination with granulocyte colony-stimulating factor (CAG regimen) can safely and effectively treat relapsed or refractory acute myeloid leukemia. Int J Hematol. 2014;99(5):603-8.
Reference 3 Synergism of Curcumin and Cytarabine in the Down Regulation of Multi-Drug Resistance Genes in Acute Myeloid Leukemia. Anticancer Agents Med Chem. 2016;16(1):128-35.
Reference 4 Emodin and Its Combination with Cytarabine Induce Apoptosis in Resistant Acute Myeloid Leukemia Cells in Vitro and in Vivo. Cell Physiol Biochem. 2018;48(5):2061-2073.
Reference 5 The effects of cytarabine combined with ginsenoside compound K synergistically induce DNA damage in acute myeloid leukemia cells. Biomed Pharmacother. 2020 Dec;132:110812.
Reference 6 Low dose triptolide reverses chemoresistance in adult acute lymphoblastic leukemia cells via reactive oxygen species generation and DNA damage response disruption. Oncotarget. 2016 Dec 20;7(51):85515-85528.
Reference 7 Chromatin-associated proteins HMGB1/2 and PDIA3 trigger cellular response to chemotherapy-induced DNA damage. Mol Cancer Ther. 2009 Apr;8(4):864-72.
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