Cytarabine
A synthetic pyrimidine nucleoside analogue used primarily in the treatment of acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), and other hematological malignancies. Cytarabine is intracellularly phosphorylated to its active triphosphate metabolite (ara-CTP), which inhibits DNA polymerase and interferes with DNA synthesis through incorporation into DNA. Its cytotoxic activity is predominantly restricted to the S phase of the cell cycle
CAS Number: 147-94-4
Molecular Mass: 243.22 g/mol
Formula: C9H13N3O5
Smiles: Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
Synonymes:
Cytarabine, 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, Cytosine beta-D-arabinofuranoside hydrochloride, 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
Bioactivity: Antineoplastic antimetabolite; DNA polymerase inhibitor (cytidine nucleoside analogue)
Solubility in Different Solvents
| Solvent | Temperature [K] | Crystal form | Solubility [mg/mL] | Reference |
|---|---|---|---|---|
| Ethanol | 293.15 | - | 1.17 | [68] |
| Ethanol | 298.15 | - | 1.2 | [68] |
| Ethanol | 303.15 | - | 1.485 | [68] |
| Ethanol | 308.15 | - | 2.09 | [68] |
| Ethanol | 313.15 | - | 3.02 | [68] |
| Ethanol | 318.15 | - | 5.113 | [68] |
| Ethanol | 323.15 | - | 9.856 | [68] |
| Ethanol | 328.15 | - | 18.06 | [68] |
| Ethanol | 333.15 | - | 38.89 | [68] |
| Ethylene Glycol | 293.15 | - | 1.53 | [68] |
| Ethylene Glycol | 298.15 | - | 2.96 | [68] |
| Ethylene Glycol | 303.15 | - | 7.165 | [68] |
| Ethylene Glycol | 308.15 | - | 14.87 | [68] |
| Ethylene Glycol | 313.15 | - | 28.05 | [68] |
| Ethylene Glycol | 318.15 | - | 43.02 | [68] |
| Ethylene Glycol | 323.15 | - | 61.64 | [68] |
| Ethylene Glycol | 328.15 | - | 89.4 | [68] |
| Ethylene Glycol | 333.15 | - | 137.4 | [68] |
| Methanol | 293.15 | - | 4.57 | [68] |
| Methanol | 298.15 | - | 6.693 | [68] |
| Methanol | 303.15 | - | 7.485 | [68] |
| Methanol | 308.15 | - | 9.51 | [68] |
| Methanol | 313.15 | - | 10.63 | [68] |
| Methanol | 318.15 | - | 12.3 | [68] |
| Methanol | 323.15 | - | 13.9 | [68] |
| Methanol | 328.15 | - | 15.74 | [68] |
| Methanol | 333.15 | - | 18.4 | [68] |
| Water | 293.15 | - | 109.8 | [68] |
| Water | 298.15 | - | 135.4 | [68] |
| Water | 303.15 | - | 188.0 | [68] |
| Water | 308.15 | - | 246.3 | [68] |
| Water | 313.15 | - | 289.4 | [68] |
| Water | 318.15 | - | 342.4 | [68] |
| Water | 323.15 | - | 413.7 | [68] |
| Water | 328.15 | - | 505.3 | [68] |
| Water | 333.15 | - | 587.5 | [68] |
Molecule 3D descriptors
| Descriptor | Value |
|---|---|
| PMI1 | 608.5778 |
| PMI2 | 1731.6466 |
| PMI3 | 1984.8484 |
| NPR1 | 0.3066 |
| NPR2 | 0.8724 |
| RadiusOfGyration | 2.9818 |
| InertialShapeFactor | 0.0014 |
| Eccentricity | 0.9518 |
| Asphericity | 0.3442 |
| SpherocityIndex | 0.2745 |
| PBF | 0.8272 |