Tolazamide

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  • Identifiers

    CAS number
    1156-19-0

    Molecular formula
    C14H21N3O3S

    SMILES
    CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CCCCCC2

    Safety labels

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 64.07%
    Cooked 25.45%
    Savory 24.89%
    Roasted 20.21%
    Meaty 19.61%
    Cooling 16.99%
    Popcorn 16.9%
    Pungent 16.89%
    Bitter 16.8%
    Fishy 14.96%

     

    Flavor
    Bitter 79.3%
    Odorless 30.7%
    Bland 22.37%
    Nitrile 20.75%
    Cedarleaf 19.16%
    Taco 19.13%
    Very strong 18.91%
    Lovage 18.76%
    Indole 18.72%
    Bread crust 18.64%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    6.59 (neutral)

    Molecular weight
    311.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    610°C

    Melting point expt.

    • 322 to 336 °F (with decomposition) (NTP, 1992)
    • 170-173 °C
    • 170 - 173 °C

    Flash point

    • 217.94 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 77 °F (NTP, 1992)
    • 65.4 mg/L (at 30 °C)
    • VERY SLIGHTLY SOL IN WATER; FREELY SOL IN CHLOROFORM; SOL IN ACETONE; SIGHTLY SOL IN ALCOHOL
    • In water, 65.4 mg/l @ 30 °C
    • 3.08e-01 g/L

  • Synonyms

    • tolazamide
    • 1156-19-0
    • Tolinase
    • Norglycin
    • Tolanase
    • Tolazolamide
    • Diabewas
    • Tolazamida
    • Tolazamidum
    • 1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylurea
    • N-(p-Toluenesulfonyl)-N'-hexamethyleniminourea
    • NSC-70762
    • 1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea
    • NCI-C03327
    • U-17835
    • 4-(p-Tolylsulfonyl)-1,1-hexamethylenesemicarbazide
    • CCRIS 591
    • U 17835
    • Tolazamidum [INN-Latin]
    • Benzenesulfonamide, N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methyl-
    • Tolazamida [INN-Spanish]
    • 1-(azepan-1-yl)-3-(4-methylphenyl)sulfonylurea
    • EINECS 214-588-3
    • Urea, 1-(hexahydroazepin-1-yl)-3-p-tolylsulfonyl-
    • BRN 1323565
    • HSDB 3192
    • Urea, 1-(hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)-
    • UNII-9LT1BRO48Q
    • 9LT1BRO48Q
    • NSC 70762
    • CHEBI:9613
    • DTXSID3021358
    • AI3-50826
    • Benzenesulfonamide, N-(((hexahydro-1H-azepin-1-yl)amino)carbonyl)-4-methyl-
    • NSC70762
    • N-(azepan-1-ylcarbamoyl)-4-methylbenzenesulfonamide
    • N-(((Hexahydro-1H-azepin-1-yl)-amino)carbonyl)-4-methylbenzenesulfonamide
    • MLS000028534
    • DTXCID401358
    • N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
    • 5-20-04-00062 (Beilstein Handbook Reference)
    • Benzenesulfonamide, N-(((hexahydro-1H-azepin-1-yl)-amino)carbonyl)-4-methyl-
    • Tolazamide [USAN:USP:INN:BAN:JAN]
    • 1-(Hexahydro-1H-azepin-1-yl)-3-(p-toluenesulfonyl)urea
    • NCGC00016009-10
    • SMR000058290
    • CAS-1156-19-0
    • Tolazamidum (INN-Latin)
    • Tolazamida (INN-Spanish)
    • N-(((hexahydro-1H-azepin-1-yl)amino)carbonyl)-4-methylbenzenesulfonamide
    • TOLAZAMIDE (MART.)
    • TOLAZAMIDE [MART.]
    • TOLAZAMIDE (USP-RS)
    • TOLAZAMIDE [USP-RS]
    • 1-(((((4-Methylphenyl)sulfonyl)amino)carbonyl)amino)azepane
    • 1-(4-Methylphenylsulfonyl)-3-(hexahydro-1H-azepin-1-yl)urea
    • TOLAZAMIDE (USP MONOGRAPH)
    • TOLAZAMIDE [USP MONOGRAPH]
    • N-[[(Hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide
    • Tolazamide (USAN:USP:INN:BAN:JAN)
    • Tolinase (TN)
    • TOLBUTAMIDE IMPURITY C (EP IMPURITY)
    • TOLBUTAMIDE IMPURITY C [EP IMPURITY]
    • SR-01000003105
    • 1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
    • Tolazamid
    • 1-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]azepane
    • Ronase
    • N-{[(hexahydro-1H-azepin-1-yl)-amino]carbonyl}-4-methylbenzenesulfonamide
    • Prestwick_865
    • Tolazamide (Standard)
    • Spectrum_001269
    • TOLAZAMIDE [MI]
    • TOLAZAMIDE [INN]
    • TOLAZAMIDE [JAN]
    • Opera_ID_1740
    • Prestwick0_000554
    • Prestwick1_000554
    • Prestwick2_000554
    • Prestwick3_000554
    • Spectrum2_001449
    • Spectrum3_001473
    • Spectrum4_000240
    • Spectrum5_001204
    • Lopac-T-2408
    • TOLAZAMIDE [HSDB]
    • TOLAZAMIDE [USAN]
    • TOLAZAMIDE [VANDF]
    • CHEMBL817
    • T 2408
    • 3-azepan-1-yl-1-(4-methylphenyl)sulfonyl-urea
    • NCIOpen2_008361
    • TOLAZAMIDE [WHO-DD]
    • CBiol_001918
    • Lopac0_001195
    • Oprea1_061180
    • SCHEMBL34417
    • BSPBio_000627
    • BSPBio_001505
    • BSPBio_003025
    • KBioGR_000225
    • KBioGR_000939
    • KBioSS_000225
    • KBioSS_001749
    • Tolazamide (JAN/USP/INN)
    • 1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea
    • MLS001076161
    • DivK1c_000212
    • SPECTRUM1501201
    • SPBio_001317
    • SPBio_002548
    • BPBio1_000691
    • GTPL6847
    • NCI-CO3327
    • WLN: T7NTJ AMVMSWR D1
    • TOLAZAMIDE [ORANGE BOOK]
    • BCBcMAP01_000061
    • HMS500K14
    • HY-B0920R
    • KBio1_000212
    • KBio2_000225
    • KBio2_001749
    • KBio2_002793
    • KBio2_004317
    • KBio2_005361
    • KBio2_006885
    • KBio3_000449
    • KBio3_000450

  • Applications

    Tolazamide (CAS 1156-19-0) is a sulfonylurea compound primarily employed as an active pharmaceutical ingredient for oral antidiabetic therapy; practical applications include its use as an API in tablet formulations and large-scale manufacturing, involvement in formulation development and process optimization, development of analytical methods and quality-control testing (including impurity profiling), supported pharmacological research and SAR studies within the sulfonylurea class, and its role as a reference standard for analytical laboratories, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 14.03
    methanol 26.27
    isopropanol 5.54
    water 0.21
    ethyl acetate 13.41
    n-propanol 9.89
    acetone 50.94
    n-butanol 6.86
    acetonitrile 22.37
    DMF 465.3
    toluene 3.49
    isobutanol 5.13
    1,4-dioxane 28.87
    methyl acetate 24.82
    THF 140.19
    2-butanone 41.09
    n-pentanol 5.28
    sec-butanol 5.22
    n-hexane 0.11
    ethylene glycol 15.32
    NMP 575.71
    cyclohexane 0.33
    DMSO 417.52
    n-butyl acetate 16.94
    n-octanol 1.1
    chloroform 118.81
    n-propyl acetate 13.97
    acetic acid 62.75
    dichloromethane 118.31
    cyclohexanone 75.24
    propylene glycol 27.45
    isopropyl acetate 9.85
    DMAc 437.62
    2-ethoxyethanol 34.48
    isopentanol 6.05
    n-heptane 0.16
    ethyl formate 21.74
    1,2-dichloroethane 66.37
    n-hexanol 5.22
    2-methoxyethanol 91.79
    isobutyl acetate 8.28
    tetrachloromethane 4.78
    n-pentyl acetate 7.18
    transcutol 79.58
    n-heptanol 2.66
    ethylbenzene 1.88
    MIBK 11.4
    2-propoxyethanol 39.89
    tert-butanol 6.17
    MTBE 2.97
    2-butoxyethanol 18.3
    propionic acid 29.77
    o-xylene 2.79
    formic acid 69.71
    diethyl ether 2.67
    m-xylene 2.46
    p-xylene 3.6
    chlorobenzene 17.65
    dimethyl carbonate 32.94
    n-octane 0.06
    formamide 152.37
    cyclopentanone 214.4
    2-pentanone 19.7
    anisole 10.44
    cyclopentyl methyl ether 15.22
    gamma-butyrolactone 241.79
    1-methoxy-2-propanol 53.77
    pyridine 67.72
    3-pentanone 16.99
    furfural 206.34
    n-dodecane 0.06
    diethylene glycol 48.36
    diisopropyl ether 0.88
    tert-amyl alcohol 5.77
    acetylacetone 57.67
    n-hexadecane 0.07
    acetophenone 25.86
    methyl propionate 25.57
    isopentyl acetate 15.8
    trichloroethylene 208.09
    n-nonanol 1.32
    cyclohexanol 6.99
    benzyl alcohol 18.11
    2-ethylhexanol 3.15
    isooctanol 2.31
    dipropyl ether 3.18
    1,2-dichlorobenzene 21.18
    ethyl lactate 21.21
    propylene carbonate 92.25
    n-methylformamide 143.48
    2-pentanol 2.91
    n-pentane 0.11
    1-propoxy-2-propanol 23.33
    1-methoxy-2-propyl acetate 37.54
    2-(2-methoxypropoxy) propanol 26.65
    mesitylene 1.59
    ε-caprolactone 60.62
    p-cymene 2.38
    epichlorohydrin 221.35
    1,1,1-trichloroethane 29.02
    2-aminoethanol 25.41
    morpholine-4-carbaldehyde 225.45
    sulfolane 449.22
    2,2,4-trimethylpentane 0.12
    2-methyltetrahydrofuran 34.89
    n-hexyl acetate 5.93
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 28.63
    sec-butyl acetate 8.23
    tert-butyl acetate 13.46
    decalin 0.26
    glycerin 63.28
    diglyme 58.6
    acrylic acid 51.58
    isopropyl myristate 2.83
    n-butyric acid 29.73
    acetyl acetate 18.95
    di(2-ethylhexyl) phthalate 9.83
    ethyl propionate 11.87
    nitromethane 180.71
    1,2-diethoxyethane 9.91
    benzonitrile 25.22
    trioctyl phosphate 4.95
    1-bromopropane 8.74
    gamma-valerolactone 250.69
    n-decanol 1.07
    triethyl phosphate 11.97
    4-methyl-2-pentanol 2.33
    propionitrile 15.28
    vinylene carbonate 81.98
    1,1,2-trichlorotrifluoroethane 213.7
    DMS 21.88
    cumene 1.57
    2-octanol 1.14
    2-hexanone 14.0
    octyl acetate 4.28
    limonene 3.1
    1,2-dimethoxyethane 46.2
    ethyl orthosilicate 8.83
    tributyl phosphate 7.05
    diacetone alcohol 34.13
    N,N-dimethylaniline 8.83
    acrylonitrile 42.25
    aniline 14.41
    1,3-propanediol 27.67
    bromobenzene 15.34
    dibromomethane 43.73
    1,1,2,2-tetrachloroethane 147.97
    2-methyl-cyclohexyl acetate 15.92
    tetrabutyl urea 12.29
    diisobutyl methanol 2.05
    2-phenylethanol 17.77
    styrene 3.03
    dioctyl adipate 9.78
    dimethyl sulfate 112.71
    ethyl butyrate 12.54
    methyl lactate 52.18
    butyl lactate 15.51
    diethyl carbonate 11.54
    propanediol butyl ether 17.27
    triethyl orthoformate 10.36
    p-tert-butyltoluene 2.12
    methyl 4-tert-butylbenzoate 23.48
    morpholine 52.04
    tert-butylamine 2.08
    n-dodecanol 0.83
    dimethoxymethane 64.62
    ethylene carbonate 52.59
    cyrene 68.52
    2-ethoxyethyl acetate 17.73
    2-ethylhexyl acetate 11.77
    1,2,4-trichlorobenzene 36.47
    4-methylpyridine 40.88
    dibutyl ether 1.21
    2,6-dimethyl-4-heptanol 2.05
    DEF 45.2
    dimethyl isosorbide 80.0
    tetrachloroethylene 64.39
    eugenol 28.52
    triacetin 21.31
    span 80 19.88
    1,4-butanediol 11.3
    1,1-dichloroethane 32.25
    2-methyl-1-pentanol 5.05
    methyl formate 91.76
    2-methyl-1-butanol 5.47
    n-decane 0.08
    butyronitrile 11.36
    3,7-dimethyl-1-octanol 1.86
    1-chlorooctane 0.55
    1-chlorotetradecane 0.32
    n-nonane 0.06
    undecane 0.07
    tert-butylcyclohexane 0.17
    cyclooctane 0.1
    cyclopentanol 20.35
    tetrahydropyran 16.2
    tert-amyl methyl ether 3.4
    2,5,8-trioxanonane 45.77
    1-hexene 0.73
    2-isopropoxyethanol 17.01
    2,2,2-trifluoroethanol 41.74
    methyl butyrate 20.37

    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