1.0 2010-04-08 22:05:11 UTC 2019-11-26 02:56:50 UTC FDB001979 Cytarabine Isolated from the mushroom Xerocomus nigromaculatus of unknown palatability Cytarabine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute myelogenous leukemia and meningeal leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Cytarabine is metabolized intracellularly into its active triphosphate form (cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA repair through an effect on beta-DNA polymerase, and incorporation into DNA. The latter mechanism is probably the most important. Cytotoxicity is highly specific for the S phase of the cell cycle.; Cytarabine, or cytosine arabinoside, is a chemotherapy agent used mainly in the treatment of hematological malignancies such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma. It is also known as ara C.; Cytosine arabinoside is an antimetabolic agent with the chemical name of 1?-arabinofuranosylcytosine. Its mode of action is due to its rapid conversion into cytosine arabinoside triphosphate, which damages DNA when the cell cycle holds in the S phase (synthesis of DNA). Rapidly dividing cells, which require DNA replication for mitosis, are therefore most affected. Cytosine arabinoside also inhibits both DNA and RNA polymerases and nucleotide reductase enzymes needed for DNA synthesis. Cytarabine is found in mushrooms. (beta-d-arabinofuranosyl)cytosine β-arabinosylcytosine β-cytosine arabinoside β-d-arabinosylcytosine 1-β-D-Arabinofaranosylcytosine 1-β-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone 1-β-D-Arabinofuranosylcytosine 1-Arabinofuranosylcytosine 1-b-D-Arabinofuranosylcytosine 1-beta -D-Arabinofaranosylcytosine 1-beta -D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone 1-beta -D-Arabinofuranosylcytosine 1-beta-D-Arabinofaranosylcytosine 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone 1-beta-D-Arabinofuranosyl-cytosine 1-beta-D-arabinofuranosylcytosine 1-beta-D-Arabinofuranosylcytosine, Cytosine Arabinoside 1-beta-D-Arabinosyl-cytosine 1-beta-D-Arabinosylcytosine 1-β-D-arabinofuranosylcytosine 1β-Arabinofuranasylcytosine 1β-D-Arabinofuranosylcytosine 1β-D-Arabinosylcytosine 147-94-4 (FREE BASE) 1beta -Arabinofuranasylcytosine 1beta -D-Arabinofuranosylcytosine 1beta -D-Arabinosylcytosine 1beta-Arabinofuranasylcytosine 1beta-D-Arabinofuranosylcytosine 1beta-D-Arabinosylcytosine 2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosyl 2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosyl- [CAS] 2(1H)-Pyrimidinone, 4-amino-1-β-D-arabinofuranosyl- 2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl- 2(1H)-Pyrimidinone, 4-amino-1β-D-arabinofuranosyl- 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine 4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone 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)-pyrimidinone 4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one 4-amino-1-β-D-arabinofuranosyl-2(1H)-pyrimidinone Alexan Ara-C Arabinocytidine Arabinofuranosylcytosine Arabinosylcytosine Arabitin ARAC Aracytidine Aracytin Aracytine Arafcyt beta -Arabinosylcytosine beta -Cytosine arabinoside beta -D-Arabinosylcytosine Beta-ara c Beta-arabinosylcytosine Beta-cytosine arabinoside Beta-d-arabinosylcytosine Citarabina Cytarabin Cytarabina Cytarabine - Pws 1gn/Vial Cytarabine - Pws 2gm/Vial Cytarabine - Pws 500mg/Vial Cytarabine (JP15/USP/INN) CYTARABINE (SEE ALSO CYTARABINE HYDROCHLORIDE 69-74-9) Cytarabine [usan:inn:ban:jan] Cytarabine liposome injection Cytarabine-Pws 100mg/Vial Cytarabine, BAN, INN, JAN, USAN Cytarabine(usan) Cytarabinoside Cytarabinum Cytonal Cytosar Cytosar-U Cytosine 1-beta-D-arabinofuranoside Cytosine arabinofuranoside Cytosine arabinose Cytosine arabinoside Cytosine arabinoside (van) Cytosine beta-d-arabinofuranoside Cytosine beta-d-arabinoside Cytosine-β-arabinoside Cytosine-β-d-arabinofuranoside Cytosine-1-b-D-arabinofuranoside Cytosine-1-beta-D-arabinofuranoside Cytosine-1-beta-D-arabinofuranoside hydrochloride Cytosine-1-β-D-arabinofuranoside Cytosine-b-D-arabinofuranoside Cytosine-beta -arabinoside Cytosine-beta -D-arabinofuranoside Cytosine-beta-arabinoside Cytosine-beta-d-arabinofuranoside Cytosine-β-D-arabinofuranoside Cytosine, β-d-arabinoside Cytosine, 1-β-D-arabinofuranosyl- Cytosine, 1-β-D-arabinosyl- Cytosine, 1-beta-D-arabinofuranosyl- Cytosine, 1-beta-D-arabinosyl- Cytosine, beta -D-arabinoside Cytosine, beta-d-arabinoside Cytosinearabinoside Depocyt Depocyt (liposomal) Depocyt (TN) Depocyte Erpalfa Intrathecal (injected into the spinal fluid) depocyt Intrathecal cytarabine (also known as ara-c) Iretin NSC 63878 Spongocytidine Tarabine U 19920 Udicil C9H13N3O5 243.2166 243.085520541 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one cytidine 147-94-4 OCC1OC(C(O)C1O)N1C=CC(=N)N=C1O 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) UHDGCWIWMRVCDJ-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. Pyrimidine nucleosides Organic compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleosides Aromatic heteromonocyclic compounds Aminopyrimidines and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidines Imidolactams Organic oxides Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Primary amines Pyrimidones Secondary alcohols Tetrahydrofurans Alcohol Amine Aminopyrimidine Aromatic heteromonocyclic compound Azacycle Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Imidolactam Monosaccharide N-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Primary amine Pyrimidine Pyrimidine nucleoside Pyrimidone Secondary alcohol Tetrahydrofuran a pyrimidine ribonucleoside Solid logp -2.04 ALOGPS logs -1.94 ALOGPS solubility 2.80e+00 g/l ALOGPS melting_point Mp 223-224° logp -2.8 ChemAxon pka_strongest_acidic 12.55 ChemAxon pka_strongest_basic -0.062 ChemAxon iupac 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one ChemAxon average_mass 243.2166 ChemAxon mono_mass 243.085520541 ChemAxon smiles OCC1OC(C(O)C1O)N1C=CC(=N)N=C1O ChemAxon formula C9H13N3O5 ChemAxon 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) ChemAxon inchikey UHDGCWIWMRVCDJ-UHFFFAOYSA-N ChemAxon polar_surface_area 128.61 ChemAxon refractivity 54.54 ChemAxon polarizability 22.74 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 4680 Specdb::NmrOneD 4708 Specdb::NmrOneD 210927 Specdb::NmrOneD 210928 Specdb::NmrOneD 210929 Specdb::NmrOneD 210930 Specdb::NmrOneD 210931 Specdb::NmrOneD 210932 Specdb::NmrOneD 210933 Specdb::NmrOneD 210934 Specdb::NmrOneD 210935 Specdb::NmrOneD 210936 Specdb::NmrOneD 210937 Specdb::NmrOneD 210938 Specdb::NmrOneD 210939 Specdb::NmrOneD 210940 Specdb::NmrOneD 210941 Specdb::NmrOneD 210942 Specdb::NmrOneD 210943 Specdb::NmrOneD 210944 Specdb::NmrOneD 210945 Specdb::NmrOneD 210946 Specdb::MsMs 19949 Specdb::MsMs 19950 Specdb::MsMs 19951 Specdb::MsMs 21500 Specdb::MsMs 21501 Specdb::MsMs 21502 Specdb::MsMs 2231804 Specdb::MsMs 2232366 Specdb::MsMs 2234246 Specdb::MsMs 2234716 Specdb::MsMs 3416273 Specdb::MsMs 3416274 Specdb::MsMs 3416275 Specdb::MsMs 3416276 Specdb::MsMs 3416277 Specdb::MsMs 3416278 Specdb::CMs 98038 Specdb::CMs 123905 Specdb::CMs 848193 Specdb::CMs 848194 Specdb::CMs 848195 Specdb::CMs 848196 Specdb::CMs 848197 Specdb::CMs 848198 Specdb::CMs 848199 Specdb::CMs 848200 Specdb::CMs 848201 Specdb::CMs 848202 Specdb::CMs 848203 Specdb::CMs 848204 Specdb::CMs 848205 Specdb::CMs 848206 Specdb::CMs 848207 Specdb::CMs 848208 Specdb::CMs 848209 Specdb::CMs 848210 Specdb::CMs 848211 Specdb::CMs 848212 Specdb::CMs 848213 Specdb::CMs 848214 Specdb::CMs 848215 HMDB15122 28680 AR3 #<Reference:0x000055ce326120f0> #<Reference:0x000055ce32611f38> #<Reference:0x000055ce32611d80> #<Reference:0x000055ce32611bc8> #<Reference:0x000055ce32611a10> Common mushroom Type 1 specific Agaricus bisporus 5341 Mushrooms Unknown generic Oyster mushroom Type 1 specific Pleurotus ostreatus 5322 Deoxycytidine kinase P27707 DCK