Compound: cytarabine
SMILES: O=c1nc(N)ccn1[C@@H]2O[C@H](CO)[C@H]([C@@H]2O)O
InChIKey: UHDGCWIWMRVCDJ-CCXZUQQUSA-N
Synonyms: cytarabine, 147-94-4, Ara-C, Cytosine arabinoside, Aracytidine, Cytarabinoside, Arabinocytidine, Spongocytidine, Aracytin, Alexan, Depocyt, Udicil, Cytosar-U, Aracytine, Arabitin, Erpalfa, Cytarabina, Arafcyt, Cytosine beta-D-arabinofuranoside, 1-beta-D-Arabinofuranosylcytosine, DepoCyte, arabinocytosine, Citarabina, Cytarabinum, Cytosar, Arabinofuranosylcytosine, Cytosine-beta-D-arabinofuranoside, Cytosinearabinoside, 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone, Arabinosylcytosine, beta-D-Arabinosylcytosine, Cytarabin, Cytosine arabinofuranoside, Cytosine beta-D-arabinoside, Arabinoside C, 1beta-D-Arabinosylcytosine, Cytosine-1-beta-D-arabinofuranoside, Cytosine arabinose, cytarabine liposome, 1beta-Arabinofuranasylcytosine, Beta-cytosine arabinoside, Cytosine 1-beta-D-arabinofuranoside, 1beta-D-Arabinofuranosylcytosine, 1-beta-D-Arabinofaranosylcytosine, beta-Arabinosylcytosine, Ara-Cytidine, U 19920A, Cytosine-beta-arabinoside, 4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one, U-19,920, 1-Arabinofuranosylcytosine, Cytosine, 1-beta-D-arabinosyl-, 1-beta-D-Arabinosylcytosine, 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone, Cytosine, 1-beta-D-arabinofuranosyl-, 1-beta-arabinofuranosylcytosine, U-19920, DTXSID3022877, CHEBI:28680, 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin, 04079A1RDZ, Arabinofuranosyl Cytidine, NSC-287459, 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one, 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one, 2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-, DTXCID702877, NCI-C04728, VYXEOS COMPONENT CYTARABINE, 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine, AC-1075, NSC287459, Cytarbel, Cytosar U, Tarabine PFS, Ara C, Ara-cell, Arabine, CHX-3311, NSC 63878, 4-amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidin-2-one, beta Ara C, 1-(beta-d-arabinofuranosyl)cytosine, 4-amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydropyrimidin-2-one, cytarabine ocphosphate, Arabinoside, Cytosine, Alexan 100, RefChem:5727, U 19920, 2(1H)-Pyrimidinone, 4-amino-1beta-D-arabinofuranosyl-, L01BC01, WR-28453, 205-705-9, 4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidin-2-one, Starasid, Tarabine, 4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one, Cytarabinum [INN-Latin], Citarabina [INN-Spanish], AraC, MFCD00066487, Cytosine |A-D-Arabinofuranoside, Depocyt (liposomal), C9H13N3O5, CHEMBL803, 2(1H)-Pyrimidinone, 4-amino-1-.beta.-D-arabinofuranosyl-, AR3, CHX 3311, 1-beta-D-arabinofuranosyl-cytosine, CCRIS 913, HSDB 3049, NCGC00093356-03, 2(1H)-Pyrimidinone, 4-amino-1-y-D-arabinofuranosyl- [CAS], Cytonal, NSC 287459, beta-Ara C, AI3-52329, Cytosine arabinoside (VAN), (beta-D-Arabinofuranosyl)cytosine, Cytarabine Impurity, cytarabine liposome injection, Arabinosyl Cytosine, Cytosine, beta-D-arabinoside, 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one, CAS-147-94-4, SMR000449317, Depocyt (TN), EINECS 205-705-9, 1-(arabinofuranosyl)cytosine, Cytartbine, UNII-04079A1RDZ, 1-.beta.-D-Arabinofuranosylcytosine, Cytarabine; 4-amino-1-beta-d-arabinofuranosylpyrimidin-2(1H)-one, SR-01000075773, Cytarabine RS, Cytarabine CRS, 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon [Czech], 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin [Czech], 1-.beta.-D-arabinofuranosyl-cytosine, 4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone, 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon, 1-beta-D-Arabinofuranosylcytosine, Cytosine Arabinoside, Cytarabine [USAN:USP:INN:BAN:JAN], MK 8242, Cytarabine (Standard), beta -arabinosylcytosine, Arabinofuranosylcytosine?, CYTARABINE [MI], CYTARABINE [INN], CYTARABINE [JAN], CYTARABINE [HSDB], CYTARABINE [USAN], beta -cytosine arabinoside, beta -D-arabinosylcytosine, Cytosine-beta -arabinoside, CYTARABINE [VANDF], Epitope ID:768768, CYTARABINE [MART.], SCHEMBL3140, 1beta -D-Arabinosylcytosine, CYTARABINE [USP-RS], CYTARABINE [WHO-DD], CYTARABINE [WHO-IP], BIDD:PXR0139, Lopac0_000316, MLS000758310, MLS001066340, MLS001424023, 1-beta-D-Arabinosyl-Cytosine, BIDD:GT0371, CYTARABINE [EMA EPAR], cytosine-b-D-arabinofuranoside, Cytosine, beta -D-arabinoside, 1beta -Arabinofuranasylcytosine, Cytarabine (JP18/USP/INN), Cytarabine - Bio-X trade mark, GTPL4827, orb1309161, orb3141269, 1-ss-D-Arabinofuranosylcytosine, CYTARABINE [ORANGE BOOK], SCHEMBL22591193, SCHEMBL23152019, 1beta -D-Arabinofuranosylcytosine, CYTARABINE [EP MONOGRAPH], CYTARABINE [USP IMPURITY], 1-(b-D-Arabinofuranosyl)cytosine, Cytosine, 1-beta -D-arabinosyl-, 1-beta -d-arabinofuranosylcytosine, 1-beta-D-arabinofuranosyl cytosine, CYTARABINE [USP MONOGRAPH], Cytosine-beta -D-arabinofuranoside, GLXC-07791, HMS2051K19, HMS2090A18, HMS2230M16, HMS3713N12, 1-beta -D-Arabinofaranosylcytosine, CYTARABINE LIPOSOME [VANDF], CYTARABINUM [WHO-IP LATIN], Tox21_111203, Tox21_301971, BDBM50087289, CCG-51297, EBC-13057, HY-13605R, MSK001344, s1648, AKOS007930145, AKOS015896896, Cytosine, 1-beta -D-arabinofuranosyl-, DB00987, KS-5063, MSK001344-100W, NA05771, NC00070, SDCCGSBI-0050304.P002, Cytarabine Solution in Water, 100ug/mL, NCGC00093356-04, NCGC00093356-05, NCGC00093356-06, NCGC00093356-19, NCGC00142483-02, NCGC00255381-01, BA164339, HY-13605, SRI-10828-19, SRI-10828-20, SRI-10828_24, SY004943, SL-000002, C2035, NS00005949, SW197450-5, C02961, D00168, EN300-118320, 1-BETA-D-ARABINOFURANOSYLCYTOSINE; ARA-C, F222319, Q180983, SR-01000721860, SR-01000075773-3, SR-01000075773-5, SR-01000721860-6, 1-beta -D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone, 2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosyl, 4-Amino-1-(b-D-Arabinofuranosyl)-2(1H)pyrimidinone, 4-Amino-1-|_-D-arabinofuranosyl-2(1H)-pyrimidinone, BRD-K33106058-001-07-7, BRD-K33106058-001-16-8, BRD-K33106058-003-20-6, 2(1H)-Pyrimidinone, 4-amino-1beta -D-arabinofuranosyl-, Cytosine -D-arabinofuranoside;Cytosine Arabinoside;Ara-C, Z1511499171, 2(1H)-Pyrimidinone, 4-amino-1-beta -D-arabinofuranosyl-, Cytarabine, European Pharmacopoeia (EP) Reference Standard, Cytarabine, United States Pharmacopeia (USP) Reference Standard, Cytosine beta-D-arabinofuranoside, crystalline, >=90% (HPLC), Cytosine beta-D-arabinofuranoside, Vetec(TM) reagent grade, 90%, Cytarabine, Pharmaceutical Secondary Standard; Certified Reference Material, Cytosine -D-arabinofuranoside hydrochloride;Cytosine Arabinoside hydrochloride;Ara-C hydrochloride
Theoretical properties:
molecular_formula: C9H13N3O5
molecular_weight: 243.22 g/mol
exact_mass: 243.08552052 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 17
topological_polar_surface_area: 129 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Prisms from 50% ethanol
color: Prisms from 50% ethanol
odor: ODORLESS
melting_point: 414 to 415 °F (NTP, 1992)
solubility: Freely soluble
Descriptions:
pubchem: Cytarabine can cause developmental toxicity according to an independent committee of scientific and health experts.
chebi: A pyrimidine nucleoside in which cytosine is attached to <small>D</small>-arabinofuranose via a β-<em>N</em><small><sup>1</small></sup>-glycosidic bond. Used mainly in the treatment of leukaemia, especially acute non-lymphoblastic leukaemia, cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. It also has antiviral and immunosuppressant properties.
chembl: CYTARABINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Cytarabine, also known as cytosine arabinoside (ara-C), is a chemotherapy medication used to treat acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myelogenous leukemia (CML), and non-Hodgkin's lymphoma. It is given by injection into a vein, under the skin, or into the cerebrospinal fluid. There is a liposomal formulation for which there is tentative evidence of better outcomes in lymphoma involving the meninges.
Common side effects include bone marrow suppression, vomiting, diarrhea, liver problems, rash, ulcer formation in the mouth, and bleeding. Other serious side effects include loss of consciousness, lung disease, and allergic reactions. Use during pregnancy may harm the baby. Cytarabine is in the antimetabolite and nucleoside analog families of medication. It works by blocking the function of DNA polymerase.
Cytarabine was patented in 1960 and approved for medical use in 1969. It is on the World Health Organization's List of Essential Medicines.