Sulfamethoxazole

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  • Identifiers

    CAS number
    723-46-6

    Molecular formula
    C10H11N3O3S

    SMILES
    CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 67.6%
    Meaty 32.35%
    Cooked 32.05%
    Roasted 30.92%
    Savory 27.25%
    Sulfurous 20.57%
    Burnt 19.99%
    Grape 19.23%
    Bitter 17.53%
    Fruity 16.1%

     

    Flavor
    Bitter 78.19%
    Odorless 31.62%
    Mild 21.69%
    Nitrile 21.03%
    Bread crust 20.53%
    Taco 20.46%
    Roasted peanuts 20.4%
    Bland 20.12%
    Very strong 19.54%
    Scallion 19.45%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    6.5 (neutral)

    Molecular weight
    253.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    753°C

    Melting point expt.

    • 333 °F (NTP, 1992)
    • 167 °C
    • MP: 209-210 °C; crystals from alcohol /N4-Acetylsulfamethoxazole/
    • MP: 171 °C

    Flash point

    • 237.52 ˚C est.

    Solubility expt.

    • >38 [ug/mL] (The mean of the results at pH 7.4)
    • less than 1 mg/mL at 68 °F (NTP, 1992)
    • 610 mg/L (at 37 °C)
    • PRACTICALLY INSOL IN WATER, ETHER & CHLOROFORM; 1 G IN 50 ML ALCOHOL & ABOUT 4 ML ACETONE; DISSOLVES IN HCL HYDROGEN CHLORIDE OR SODIUM HYDROXIDE SOLN THROUGH SALT FORMATION
    • Insoluble in ethyl ether
    • In water, 610 mg/L at 37 °C
    • The solubility interactions of trimethoprim and sulfamethoxazole in binary solvents were studied using hexane (n-hexane)-ethyl acetate, ethyl acetate-methyl alcohol (methanol), and methyl alcohol-water as the solve mixtures. When solubilities were obtained for individual components, trimethoprim exhibited solvation in ethyl acetate-methyl alcohol mixtures, while sulfamethoxazole showed weaker solute-solvent interactions in the solvent series. At its peak, the solubility of sulfamethoxazole was about 8 times higher than that of trimethoprim when the drugs were combined. Sulfamethoxazole lowered trimethoprim solubility by 13-74%. Similarly, trimethoprim suppressed sulfamethoxazole solubility by 10-94%. In water, although mutual solubility was reduced, the solubility ratio of trimethoprim to sulfamethoxazole was 1:4 on the mol fraction scale.
    • 4.59e-01 g/L

  • Synonyms

    • sulfamethoxazole
    • 723-46-6
    • Gantanol
    • Sulphamethoxazole
    • Sulfisomezole
    • Sulfamethoxazol
    • 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide
    • Metoxal
    • Sulfamethylisoxazole
    • Simsinomin
    • Radonil
    • Sinomin
    • Sulphamethoxazol
    • Sulpha-methoxizole
    • Sulfamethalazole
    • Azo-gantanol
    • Sulphamethylisoxazole
    • Bactrim
    • Urobak
    • Sulfamethoxizole
    • 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide
    • Gantanol-DS
    • Ro 4-2130
    • 3-Sulfanilamido-5-methylisoxazole
    • Sulfametoxazol
    • Gamazole
    • Sulfamethoxazolum
    • Solfametossazolo
    • 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
    • Sulphisomezole
    • 5-Methyl-3-sulfanilamidoisoxazole
    • MS 53
    • 3-Sulphanilamido-5-methylisoxazole
    • 5-Methyl-3-sulphanil-amidoisoxazole
    • Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)-
    • 3-(p-Aminophenylsulfonamido)-5-methylisoxazole
    • 5-Methyl-3-sulfanylamidoisoxazole
    • N'-(5-Methyl-3-isoxazolyl)sulfanilamide
    • N1-(5-Methyl-3-isoxazolyl)sulfanilamide
    • N'-(5-Methylisoxazol-3-yl)sulphanilamide
    • 3-(para-Aminophenylsulphonamido)-5-methylisoxazole
    • SMX
    • A047
    • CCRIS 567
    • Sulfametoxazol [INN-Spanish]
    • Sulfamethoxazolum [INN-Latin]
    • Sulfanilamide, N1-(5-methyl-3-isoxazolyl)-
    • CHEBI:9332
    • HSDB 3186
    • N(sup 1)-(5-Methyl-3-isoxazolyl)sulphanilamide
    • STX-608
    • EINECS 211-963-3
    • Sulfanilamide, N'-(5-methyl-3-isoxazolyl)-
    • UNII-JE42381TNV
    • MFCD00010546
    • NSC 147832
    • NSC-147832
    • Ro-4-2130
    • N(sup 1)-(5-Methyl-3-isoxazolyl)sulfanilamide
    • 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
    • BRN 0226453
    • JE42381TNV
    • N'-(5-Methyl-3-isoxazole)sulfanilamide
    • DTXSID8026064
    • Ro 6-2580/11
    • 4-Amino-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide
    • NSC147832
    • Sulfanilamide, N(1)-(5-methyl-3-isoxazolyl)-
    • CHEMBL443
    • MLS000069732
    • DTXCID006064
    • 4-AMINO-N-(5-METHYL-3-ISOXAZOYL)BENZENESULFONAMIDE
    • N(sup1)-(5-Methyl-3-isoxazolyl)sulfanilamide
    • 5-Methyl-3-sulfonylamidoisoxazole
    • 3-(p-Aminobenzenesulfonamido)-5-methylisoxazole
    • Ro-42130
    • 4-Amino-N-(5-methyl-3-isoxazolyl)-benzenesulfonamide
    • COTRIM COMPONENT SULFAMETHOXAZOLE
    • SEPTRA COMPONENT SULFAMETHOXAZOLE
    • BACTRIM COMPONENT SULFAMETHOXAZOLE
    • NCGC00016533-05
    • NCGC00186654-01
    • UROPLUS COMPONENT SULFAMETHOXAZOLE
    • CAS-723-46-6
    • SMR000058223
    • SULFATRIM COMPONENT SULFAMETHOXAZOLE
    • SULMEPRIM COMPONENT SULFAMETHOXAZOLE
    • Co-trimethoxazole component sulfamethoxazole
    • BACTRIM DS COMPONENT SULFAMETHOXAZOLE
    • Sulfamethoxazole [USAN:USP:INN:BAN:JAN]
    • AZO GANTANOL COMPONENT SULFAMETHOXAZOLE
    • COTRIM D.S. COMPONENT SULFAMETHOXAZOLE
    • SULFAMETHOPRIM COMPONENT SULFAMETHOXAZOLE
    • Sulfamethoxazole 100 microg/mL in Acetonitrile
    • Solfametossazolo [DCIT]
    • 3-METHYL-1-(4-SULFOAMIDOPHENYL)-5-PYRA&
    • BACTRIM PEDIATRIC COMPONENT SULFAMETHOXAZOLE
    • Sulfametoxazol (INN-Spanish)
    • Sulfamethoxazolum (INN-Latin)
    • SULFAMETHOXAZOLE (IARC)
    • SULFAMETHOXAZOLE [IARC]
    • SULFAMETHOXAZOLE (MART.)
    • SULFAMETHOXAZOLE [MART.]
    • SULFAMETHOXAZOLE (USP-RS)
    • SULFAMETHOXAZOLE [USP-RS]
    • SULFAMETHOXAZOLE (EP MONOGRAPH)
    • SULFAMETHOXAZOLE [EP MONOGRAPH]
    • SULFAMETHOXAZOLE (USP MONOGRAPH)
    • SULFAMETHOXAZOLE [USP MONOGRAPH]
    • 144930-01-8
    • Sulfamethoxazole (USAN:USP:INN:BAN:JAN)
    • SR-01000000217
    • sulfametoxazolo
    • ulfamethoxazole
    • Sulfamethoxazole; 4-Amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide
    • 08D
    • Prestwick_453
    • ALBB-002089
    • Septran (Salt/Mix)
    • Septrin (Salt/Mix)
    • Eusaprim (Salt/Mix)
    • RP-2145
    • Spectrum_000994
    • Sulfamethoxazole(USAN)
    • N1-(5-Methylisoxazol-3-yl)sulfanilamide
    • starbld0000281
    • Opera_ID_882
    • Maybridge1_007190

  • Applications

    Sulfamethoxazole (CAS 723-46-6) is primarily used as an active pharmaceutical ingredient in antibiotics, typically formulated in combination with trimethoprim in prescription products. It is also used in veterinary medicine as a component of antibacterial treatments for animals. In the chemical industry, sulfamethoxazole serves as a precursor for the synthesis of other sulfonamide compounds and as an analytical reference standard for quantitative methods targeting sulfonamides. It is encountered in research and development contexts related to sulfonamide chemistry. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.62
    methanol 10.64
    isopropanol 2.86
    water 0.42
    ethyl acetate 10.79
    n-propanol 2.95
    acetone 49.1
    n-butanol 2.09
    acetonitrile 56.09
    DMF 491.82
    toluene 0.22
    isobutanol 1.45
    1,4-dioxane 80.62
    methyl acetate 39.05
    THF 108.12
    2-butanone 45.42
    n-pentanol 1.61
    sec-butanol 2.85
    n-hexane 0.01
    ethylene glycol 11.92
    NMP 392.22
    cyclohexane 0.04
    DMSO 246.31
    n-butyl acetate 10.01
    n-octanol 1.18
    chloroform 0.68
    n-propyl acetate 12.15
    acetic acid 40.08
    dichloromethane 1.54
    cyclohexanone 47.2
    propylene glycol 21.55
    isopropyl acetate 6.26
    DMAc 494.98
    2-ethoxyethanol 40.77
    isopentanol 2.2
    n-heptane 0.04
    ethyl formate 23.3
    1,2-dichloroethane 1.77
    n-hexanol 1.63
    2-methoxyethanol 112.67
    isobutyl acetate 5.6
    tetrachloromethane 0.08
    n-pentyl acetate 4.37
    transcutol 72.23
    n-heptanol 1.45
    ethylbenzene 0.22
    MIBK 5.96
    2-propoxyethanol 32.12
    tert-butanol 4.02
    MTBE 2.54
    2-butoxyethanol 14.63
    propionic acid 18.27
    o-xylene 0.32
    formic acid 46.7
    diethyl ether 1.53
    m-xylene 0.19
    p-xylene 0.66
    chlorobenzene 1.15
    dimethyl carbonate 23.31
    n-octane 0.02
    formamide 181.47
    cyclopentanone 134.22
    2-pentanone 10.71
    anisole 7.4
    cyclopentyl methyl ether 4.65
    gamma-butyrolactone 177.65
    1-methoxy-2-propanol 52.63
    pyridine 27.15
    3-pentanone 9.15
    furfural 151.02
    n-dodecane 0.04
    diethylene glycol 46.42
    diisopropyl ether 0.33
    tert-amyl alcohol 3.77
    acetylacetone 47.99
    n-hexadecane 0.05
    acetophenone 17.82
    methyl propionate 16.93
    isopentyl acetate 8.95
    trichloroethylene 4.77
    n-nonanol 1.33
    cyclohexanol 2.12
    benzyl alcohol 7.43
    2-ethylhexanol 1.26
    isooctanol 1.29
    dipropyl ether 1.88
    1,2-dichlorobenzene 1.8
    ethyl lactate 17.88
    propylene carbonate 57.08
    n-methylformamide 137.56
    2-pentanol 0.97
    n-pentane 0.01
    1-propoxy-2-propanol 18.75
    1-methoxy-2-propyl acetate 26.06
    2-(2-methoxypropoxy) propanol 27.81
    mesitylene 0.19
    ε-caprolactone 47.94
    p-cymene 0.59
    epichlorohydrin 77.02
    1,1,1-trichloroethane 0.81
    2-aminoethanol 14.08
    morpholine-4-carbaldehyde 311.84
    sulfolane 198.11
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 20.76
    n-hexyl acetate 4.83
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 27.83
    sec-butyl acetate 5.59
    tert-butyl acetate 8.8
    decalin 0.03
    glycerin 60.94
    diglyme 73.25
    acrylic acid 31.53
    isopropyl myristate 2.61
    n-butyric acid 12.47
    acetyl acetate 13.45
    di(2-ethylhexyl) phthalate 6.71
    ethyl propionate 9.12
    nitromethane 282.55
    1,2-diethoxyethane 11.79
    benzonitrile 13.07
    trioctyl phosphate 3.44
    1-bromopropane 0.23
    gamma-valerolactone 302.41
    n-decanol 1.08
    triethyl phosphate 8.41
    4-methyl-2-pentanol 0.83
    propionitrile 11.8
    vinylene carbonate 50.41
    1,1,2-trichlorotrifluoroethane 69.39
    DMS 16.11
    cumene 0.23
    2-octanol 0.83
    2-hexanone 11.03
    octyl acetate 3.67
    limonene 0.86
    1,2-dimethoxyethane 101.73
    ethyl orthosilicate 6.02
    tributyl phosphate 4.62
    diacetone alcohol 25.74
    N,N-dimethylaniline 4.42
    acrylonitrile 34.94
    aniline 2.34
    1,3-propanediol 20.1
    bromobenzene 0.63
    dibromomethane 0.38
    1,1,2,2-tetrachloroethane 3.58
    2-methyl-cyclohexyl acetate 9.96
    tetrabutyl urea 9.45
    diisobutyl methanol 0.97
    2-phenylethanol 7.55
    styrene 0.39
    dioctyl adipate 8.22
    dimethyl sulfate 68.55
    ethyl butyrate 9.86
    methyl lactate 41.3
    butyl lactate 10.0
    diethyl carbonate 9.7
    propanediol butyl ether 15.53
    triethyl orthoformate 9.15
    p-tert-butyltoluene 0.54
    methyl 4-tert-butylbenzoate 15.33
    morpholine 94.26
    tert-butylamine 0.78
    n-dodecanol 0.83
    dimethoxymethane 71.38
    ethylene carbonate 36.66
    cyrene 59.13
    2-ethoxyethyl acetate 15.2
    2-ethylhexyl acetate 6.47
    1,2,4-trichlorobenzene 4.31
    4-methylpyridine 13.21
    dibutyl ether 1.54
    2,6-dimethyl-4-heptanol 0.97
    DEF 36.05
    dimethyl isosorbide 57.48
    tetrachloroethylene 1.42
    eugenol 18.43
    triacetin 21.21
    span 80 15.06
    1,4-butanediol 7.77
    1,1-dichloroethane 0.61
    2-methyl-1-pentanol 1.82
    methyl formate 105.77
    2-methyl-1-butanol 1.72
    n-decane 0.05
    butyronitrile 7.25
    3,7-dimethyl-1-octanol 1.46
    1-chlorooctane 0.27
    1-chlorotetradecane 0.18
    n-nonane 0.04
    undecane 0.04
    tert-butylcyclohexane 0.02
    cyclooctane 0.01
    cyclopentanol 6.21
    tetrahydropyran 10.63
    tert-amyl methyl ether 2.25
    2,5,8-trioxanonane 56.53
    1-hexene 0.08
    2-isopropoxyethanol 17.81
    2,2,2-trifluoroethanol 23.76
    methyl butyrate 18.03

    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