Cytarabine

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  • Identifiers

    CAS number
    147-94-4

    Molecular formula
    C9H13N3O5

    SMILES
    C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 84.64%
    Bitter 20.17%
    Savory 19.23%
    Sweet 16.26%
    Milky 14.58%
    Cooked 14.26%
    Meaty 14.19%
    Burnt 14.14%
    Popcorn 13.1%
    Cooling 12.67%

     

    Flavor
    Bitter 76.98%
    Odorless 43.15%
    Sweet-like 25.19%
    Bland 24.37%
    Very mild 20.19%
    Mild 19.73%
    Cedarleaf 19.42%
    Alkaline 19.3%
    Very slight 19.28%
    Bread crust 19.14%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.1

    pKa est.
    4.27 (weak acid)

    Molecular weight
    243.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1468°C

    Melting point expt.

    • 414 to 415 °F (NTP, 1992)
    • 186-188
    • 212-213 °C
    • 212 - 213 °C

    Flash point

    • 278.8 ˚C est.

    Solubility expt.

    • >36.5 [ug/mL] (The mean of the results at pH 7.4)
    • Freely soluble
    • 1 G IN ABOUT 5 ML WATER & 500 ML ALC; 1 G IN ABOUT 1000 ML CHLOROFORM & 300 ML METHANOL
    • Soluble in water
    • 4.38e+01 g/L

  • Synonyms

    • cytarabine
    • 147-94-4
    • Ara-C
    • Cytosine arabinoside
    • Aracytidine
    • Arabinocytidine
    • Cytarabinoside
    • Spongocytidine
    • Aracytin
    • Cytosar-U
    • Depocyt
    • Udicil
    • Arabitin
    • Aracytine
    • Cytarabina
    • Tarabine
    • Arafcyt
    • Erpalfa
    • Arabinofuranosylcytosine
    • Cytosine beta-D-arabinofuranoside
    • arabinocytosine
    • Citarabina
    • Cytarabinum
    • DepoCyte
    • 1-beta-D-Arabinofuranosylcytosine
    • Arabinosylcytosine
    • Cytarabin
    • Cytosar
    • Cytosinearabinoside
    • Depocyt (liposomal)
    • beta-D-Arabinosylcytosine
    • Cytosine arabinofuranoside
    • Alexan
    • Cytosine beta-D-arabinoside
    • Cytarabinum [INN-Latin]
    • Arabinoside C
    • 1beta-D-Arabinosylcytosine
    • Citarabina [INN-Spanish]
    • Cytosine-1-beta-D-arabinofuranoside
    • AraC
    • Cytosine arabinose
    • 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone
    • 4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
    • 1beta-Arabinofuranasylcytosine
    • Iretin
    • Cytosine 1-beta-D-arabinofuranoside
    • 1beta-D-Arabinofuranosylcytosine
    • 1-beta-D-Arabinofaranosylcytosine
    • beta-Arabinosylcytosine
    • Ara-Cytidine
    • U 19920A
    • Beta-cytosine arabinoside
    • Cytosine-beta-arabinoside
    • Cytosine-beta-D-arabinofuranoside
    • cytarabine liposome
    • CHX 3311
    • CCRIS 913
    • U-19,920
    • 1-Arabinofuranosylcytosine
    • 4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one
    • Arabinofuranosyl Cytidine
    • Cytosine |A-D-Arabinofuranoside
    • Cytosine, 1-beta-D-arabinosyl-
    • 1-beta-D-Arabinosylcytosine
    • HSDB 3049
    • 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone
    • EINECS 205-705-9
    • 1-(arabinofuranosyl)cytosine
    • MFCD00066487
    • Cyclocide
    • Cytosine, 1-beta-D-arabinofuranosyl-
    • NSC 287459
    • UNII-04079A1RDZ
    • 1-beta-arabinofuranosylcytosine
    • U-19920
    • DTXSID3022877
    • CHEBI:28680
    • AI3-52329
    • (beta-D-Arabinofuranosyl)cytosine
    • 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin
    • 04079A1RDZ
    • 2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-
    • CHEMBL803
    • NSC-287459
    • MK 8242
    • 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon
    • 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
    • C9H13N3O5
    • DTXCID702877
    • 2(1H)-Pyrimidinone, 4-amino-1-.beta.-D-arabinofuranosyl-
    • AR3
    • Cytonal
    • NCI-C04728
    • VYXEOS COMPONENT CYTARABINE
    • 1-beta-D-arabinofuranosyl-cytosine
    • 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine
    • AC-1075
    • beta-Ara C
    • 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
    • Cytarabine [USAN:USP:INN:BAN:JAN]
    • NCGC00093356-03
    • Cytosine beta-D-arabinofuranoside hydrochloride
    • 2(1H)-Pyrimidinone, 4-amino-1-y-D-arabinofuranosyl- [CAS]
    • Cytarbel
    • (Arabinofuranosyl)cytosine
    • Cytarabinum (INN-Latin)
    • Citarabina (INN-Spanish)
    • CYTARABINE (MART.)
    • CYTARABINE [MART.]
    • CYTARABINE (USP-RS)
    • CYTARABINE [USP-RS]
    • Citozar
    • ara-Cytosine
    • Cytosine arabinoside (VAN)
    • Tarabine PFS
    • CYTARABINE (EP MONOGRAPH)
    • CYTARABINE (USP IMPURITY)
    • CYTARABINE [EP MONOGRAPH]
    • CYTARABINE [USP IMPURITY]
    • Cytosine-1-beta-arabinofuranoside
    • CYTARABINE (USP MONOGRAPH)
    • CYTARABINE [USP MONOGRAPH]
    • Ara-cell
    • Cytarabine (USAN:USP:INN:BAN:JAN)
    • cytarabine liposome injection
    • Arabinosyl Cytosine
    • Cytosine, beta-D-arabinoside
    • CAS-147-94-4

  • Applications

    Cytarabine (CAS 147-94-4) is primarily used in the pharmaceutical industry as an active pharmaceutical ingredient in anticancer chemotherapy regimens, acting as a pyrimidine nucleoside analog antimetabolite to disrupt DNA synthesis. In biomedical research, it serves as a nucleoside analog tool to study DNA replication inhibition and cellular effects. It is also supplied to teaching and research laboratories as a nucleoside reagent/standard for analytical and educational purposes. In drug development, cytarabine provides a template for designing and evaluating related nucleoside analogs, with stringent handling and regulatory controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.42
    methanol 6.48
    isopropanol 0.62
    water 133.4
    ethyl acetate 0.12
    n-propanol 0.77
    acetone 0.31
    n-butanol 0.71
    acetonitrile 0.4
    DMF 116.92
    toluene 0.1
    isobutanol 0.39
    1,4-dioxane 0.92
    methyl acetate 0.18
    THF 2.24
    2-butanone 0.35
    n-pentanol 0.31
    sec-butanol 0.49
    n-hexane 0.03
    ethylene glycol 6.93
    NMP 153.39
    cyclohexane 0.11
    DMSO 207.63
    n-butyl acetate 0.27
    n-octanol 0.2
    chloroform 0.09
    n-propyl acetate 0.15
    acetic acid 23.84
    dichloromethane 0.12
    cyclohexanone 2.41
    propylene glycol 10.66
    isopropyl acetate 0.11
    DMAc 63.56
    2-ethoxyethanol 6.42
    isopentanol 0.52
    n-heptane 0.1
    ethyl formate 0.74
    1,2-dichloroethane 0.14
    n-hexanol 0.54
    2-methoxyethanol 24.24
    isobutyl acetate 0.08
    tetrachloromethane 0.09
    n-pentyl acetate 0.2
    transcutol 4.84
    n-heptanol 0.49
    ethylbenzene 0.06
    MIBK 0.27
    2-propoxyethanol 4.87
    tert-butanol 0.73
    MTBE 0.11
    2-butoxyethanol 2.9
    propionic acid 2.26
    o-xylene 0.18
    formic acid 431.25
    diethyl ether 0.13
    m-xylene 0.13
    p-xylene 0.11
    chlorobenzene 0.05
    dimethyl carbonate 0.99
    n-octane 0.04
    formamide 265.22
    cyclopentanone 3.07
    2-pentanone 0.28
    anisole 0.17
    cyclopentyl methyl ether 0.8
    gamma-butyrolactone 5.71
    1-methoxy-2-propanol 9.99
    pyridine 1.19
    3-pentanone 0.31
    furfural 13.04
    n-dodecane 0.02
    diethylene glycol 16.46
    diisopropyl ether 0.06
    tert-amyl alcohol 0.64
    acetylacetone 0.58
    n-hexadecane 0.02
    acetophenone 0.54
    methyl propionate 0.45
    isopentyl acetate 0.3
    trichloroethylene 0.28
    n-nonanol 0.23
    cyclohexanol 1.14
    benzyl alcohol 0.64
    2-ethylhexanol 0.34
    isooctanol 0.34
    dipropyl ether 0.34
    1,2-dichlorobenzene 0.1
    ethyl lactate 1.59
    propylene carbonate 2.39
    n-methylformamide 33.23
    2-pentanol 0.31
    n-pentane 0.04
    1-propoxy-2-propanol 2.67
    1-methoxy-2-propyl acetate 1.05
    2-(2-methoxypropoxy) propanol 2.91
    mesitylene 0.12
    ε-caprolactone 2.44
    p-cymene 0.17
    epichlorohydrin 1.58
    1,1,1-trichloroethane 0.06
    2-aminoethanol 9.72
    morpholine-4-carbaldehyde 45.46
    sulfolane 44.18
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 0.71
    n-hexyl acetate 0.21
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 3.4
    sec-butyl acetate 0.09
    tert-butyl acetate 0.24
    decalin 0.03
    glycerin 60.94
    diglyme 6.61
    acrylic acid 6.49
    isopropyl myristate 0.11
    n-butyric acid 1.92
    acetyl acetate 0.19
    di(2-ethylhexyl) phthalate 0.4
    ethyl propionate 0.18
    nitromethane 16.32
    1,2-diethoxyethane 0.3
    benzonitrile 0.43
    trioctyl phosphate 0.33
    1-bromopropane 0.07
    gamma-valerolactone 15.7
    n-decanol 0.18
    triethyl phosphate 0.61
    4-methyl-2-pentanol 0.22
    propionitrile 0.29
    vinylene carbonate 2.41
    1,1,2-trichlorotrifluoroethane 20.26
    DMS 0.35
    cumene 0.07
    2-octanol 0.21
    2-hexanone 0.2
    octyl acetate 0.18
    limonene 0.25
    1,2-dimethoxyethane 3.87
    ethyl orthosilicate 0.5
    tributyl phosphate 0.34
    diacetone alcohol 2.3
    N,N-dimethylaniline 0.37
    acrylonitrile 0.83
    aniline 0.48
    1,3-propanediol 9.74
    bromobenzene 0.04
    dibromomethane 0.08
    1,1,2,2-tetrachloroethane 0.31
    2-methyl-cyclohexyl acetate 0.47
    tetrabutyl urea 0.85
    diisobutyl methanol 0.24
    2-phenylethanol 0.75
    styrene 0.05
    dioctyl adipate 0.28
    dimethyl sulfate 7.33
    ethyl butyrate 0.35
    methyl lactate 6.3
    butyl lactate 1.05
    diethyl carbonate 0.29
    propanediol butyl ether 3.18
    triethyl orthoformate 0.54
    p-tert-butyltoluene 0.16
    methyl 4-tert-butylbenzoate 1.23
    morpholine 2.98
    tert-butylamine 0.24
    n-dodecanol 0.13
    dimethoxymethane 4.53
    ethylene carbonate 1.36
    cyrene 10.51
    2-ethoxyethyl acetate 0.36
    2-ethylhexyl acetate 0.23
    1,2,4-trichlorobenzene 0.17
    4-methylpyridine 0.75
    dibutyl ether 0.12
    2,6-dimethyl-4-heptanol 0.24
    DEF 3.23
    dimethyl isosorbide 5.23
    tetrachloroethylene 0.37
    eugenol 1.87
    triacetin 0.63
    span 80 2.21
    1,4-butanediol 3.18
    1,1-dichloroethane 0.04
    2-methyl-1-pentanol 0.26
    methyl formate 10.54
    2-methyl-1-butanol 0.49
    n-decane 0.03
    butyronitrile 0.28
    3,7-dimethyl-1-octanol 0.19
    1-chlorooctane 0.06
    1-chlorotetradecane 0.03
    n-nonane 0.03
    undecane 0.02
    tert-butylcyclohexane 0.01
    cyclooctane 0.05
    cyclopentanol 1.6
    tetrahydropyran 0.54
    tert-amyl methyl ether 0.2
    2,5,8-trioxanonane 5.4
    1-hexene 0.05
    2-isopropoxyethanol 1.77
    2,2,2-trifluoroethanol 21.13
    methyl butyrate 0.39

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction