AR3

CYTARABINE

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is present as a standalone ligand in 2 entries

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Chemical Component Summary
Name	CYTARABINE
Synonyms	1-BETA-D-ARABINOFURANOSYLCYTOSINE; ARA-C
Identifiers	4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Formula	C₉ H₁₃ N₃ O₅
Molecular Weight	243.217
Type	NON-POLYMER
Isomeric SMILES	C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
InChI	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

Chemical Details
Formal Charge	0
Atom Count	30
Chiral Atom Count	4
Bond Count	31
Aromatic Bond Count	6

Drug Info: DrugBank

DrugBank ID	DB00987
Name	Cytarabine
Groups	approved investigational
Description	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. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)
Synonyms	Cytarabinum Cytarabine Cytosine arabinoside Cytosine-1-beta-D-arabinofuranoside 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone Cytarabine liposome 1-beta-D-Arabinofuranosylcytosine cytosine-β-D-arabinofuranoside Cytarabine hydrochloride Citarabina
Brand Names	Cytarabine Inj 100mg/ml Cytarabine Injection Cytarabine Injection, Mylan Std. Cytarabine - Pws 1gn/vial Vyxeos Depocyte Cytosar Cytarabine-pws 100mg/vial DepoCyt Cytarabine - Pws 500mg/vial Cytarabine - Pws 2gm/vial Cytarabine PMS-cytarabine Vyxeos Liposomal Cytarabine Injection BP Aj-cytarabine
Indication	For the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia. Cytarabine is indicated in combination with [daunorubicin] for the treatment of newly-diagnosed therapy-related acute myeloid leukemia (t-AML) or AML with myelodysplasia-related changes (AML-MRC) in adults and pediatric patients 1 year and older.[L32843]
Categories	Agents Causing Muscle Toxicity Anti-Infective Agents Antimetabolites Antineoplastic Agents Antineoplastic and Immunomodulating Agents Arabinonucleosides Cardiotoxic antineoplastic agents Cytidine Deaminase Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Substrates Immunologic Factors Immunosuppressive Agents Myelosuppressive Agents Narrow Therapeutic Index Drugs Noxae Nucleic Acid Synthesis Inhibitors Nucleic Acids, Nucleotides, and Nucleosides Nucleoside Metabolic Inhibitor Nucleosides OCT1 substrates Pyrimidine Analogues Pyrimidine Nucleosides Pyrimidines Toxic Actions
ATC-Code	L01BC01 L01XY01
CAS number	147-94-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
DNA polymerase beta	MSKRKAPQETLNGGITDMLTELANFEKNVSQAIHKYNAYRKAASVIAKYP...	unknown	inhibitor
DNA	-	unknown	cross-linking/alkylation
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Deoxycytidine kinase	MATPPKRSCPSFSASSEGTRIKKISIEGNIAAGKSTFVNILKQLCEDWEV...	unknown	substrate
5'-nucleotidase	MCPRAARAPATLLLALGAVLWPAAGAWELTILHTNDVHSRLEQTSEDSSK...	unknown	substrate
Deoxycytidylate deaminase	MSEVSCKKRDDYLEWPEYFMAVAFLSAQRSKDPNSQVGACIVNSENKIVG...	unknown	substrate
Cytidine deaminase	MAQKRPACTLKPECVQQLLVCSQEAKKSAYCPYSHFPVGAALLTQEGRIF...	unknown	substrate
Solute carrier family 22 member 4	MRDYDEVIAFLGEWGPFQRLIFFLLSASIIPNGFNGMSVVFLAGTPEHRC...	unknown	substrate
Multidrug resistance-associated protein 7	MERLLAQLCGSSAAWPLPLWEGDTTGHCFTQLVLSALPHALLAVLSACYL...	unknown	substrate
Equilibrative nucleoside transporter 1	MTTSHQPQDRYKAVWLIFFMLGLGTLLPWNFFMTATQYFTNRLDMSQNVS...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682