Metolazone

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  • Identifiers

    CAS number
    17560-51-9

    Molecular formula
    C16H16ClN3O3S

    SMILES
    CC1NC2=CC(=C(C=C2C(=O)N1C3=CC=CC=C3C)S(=O)(=O)N)Cl

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 79.86%
    Bitter 21.94%
    Cooked 20.38%
    Savory 19.46%
    Roasted 16.31%
    Grape 15.79%
    Meaty 15.44%
    Burnt 15.21%
    Cooling 13.86%
    Milky 13.08%

     

    Flavor
    Bitter 92.88%
    Odorless 32.62%
    Bland 19.87%
    Nitrile 19.64%
    Very strong 18.35%
    Cedarleaf 18.33%
    Sweet-like 18.31%
    Indole 18.08%
    Taco 18.01%
    Bread crust 17.91%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    4.1

    pKa est.
    7.82 (neutral)

    Molecular weight
    365.8 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    596°C

    Melting point expt.

    • 256 °C
    • 253-259 °C

    Flash point

    • 283.91 ˚C est.

    Solubility expt.

    • 60.3 mg/L (at 25 °C)
    • INSOL IN WATER & ALCOHOL
    • 4.07e-02 g/L

  • Synonyms

    • metolazone
    • 17560-51-9
    • Zaroxolyn
    • Mykrox
    • Diulo
    • Oldren
    • Metenix
    • Metalozone
    • Microx
    • Metolazona
    • Metolazonum
    • metozalone
    • Xuret
    • 7-Chloro-2-methyl-4-oxo-3-(o-tolyl)-1,2,3,4-tetrahydroquinazoline-6-sulfonamide
    • Metolazonum [INN-Latin]
    • Metolazona [INN-Spanish]
    • 6-Quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-
    • SR 720-22
    • SR-720-22
    • Metazoline
    • Normelan
    • 7-Chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinesulfonamide
    • Metolazone (Zaroxolyn)
    • 7-Chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-o-tolyl-6-quinazolinesulfonamide
    • HSDB 3367
    • 2-Methyl-3-o-tolyl-6-sulfamyl-7-chloro-1,2,3,4-tetrahydro-4-quinazolinone
    • UNII-TZ7V40X7VX
    • EINECS 241-539-3
    • TZ7V40X7VX
    • NSC-759581
    • 7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2-dihydroquinazoline-6-sulfonamide
    • BRN 0965506
    • DTXSID6045167
    • Metolazone, (+)-
    • Metolazone, (-)-
    • CHEBI:64354
    • 7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide
    • MFCD00069304
    • NM7V2Y3G0U
    • 6-Quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-o-tolyl-
    • DTXCID4025167
    • 5-25-09-00212 (Beilstein Handbook Reference)
    • 6-Quinazolinesulfonamide, 1,2,3,4-tetrahydro-7-chloro-2-methyl-4-oxo-3-o-tolyl-
    • NN9U607695
    • NSC 759581
    • Metolazone [USAN:USP:INN:BAN:JAN]
    • NCGC00093985-07
    • Metalazone
    • Metolazonum (INN-Latin)
    • Metolazona (INN-Spanish)
    • METOLAZONE (MART.)
    • METOLAZONE [MART.]
    • METOLAZONE (USP-RS)
    • METOLAZONE [USP-RS]
    • 56436-32-9
    • METOLAZONE (EP IMPURITY)
    • METOLAZONE [EP IMPURITY]
    • METOLAZONE (EP MONOGRAPH)
    • METOLAZONE [EP MONOGRAPH]
    • METOLAZONE (USP MONOGRAPH)
    • METOLAZONE [USP MONOGRAPH]
    • Metolazone (USAN:USP:INN:BAN:JAN)
    • Zaroxolyn (TN)
    • 56436-31-8
    • 6-Quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-, (+)-
    • 6-Quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-, (-)-
    • SMR001230730
    • SR-05000001765
    • Metolazon
    • Metolazone (JAN/USP/INN)
    • Metolazone; (2RS)-7-Chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide
    • Prestwick_333
    • CAS-17560-51-9
    • Metolazone (Standard)
    • Spectrum_000456
    • METOLAZONE [MI]
    • METOLAZONE [INN]
    • METOLAZONE [JAN]
    • Prestwick0_000112
    • Prestwick1_000112
    • Prestwick2_000112
    • Prestwick3_000112
    • Spectrum2_001741
    • Spectrum4_000229
    • Spectrum5_001237
    • METOLAZONE [HSDB]
    • METOLAZONE [USAN]
    • METOLAZONE [VANDF]
    • CHEMBL878
    • UNII-NM7V2Y3G0U
    • METOLAZONE [WHO-DD]
    • SCHEMBL40558
    • BSPBio_000124
    • BSPBio_002422
    • KBioGR_000897
    • KBioSS_000936
    • MLS002153316
    • MLS002154200
    • DivK1c_000275
    • SPECTRUM2300325
    • SPBio_001842
    • SPBio_002063
    • BPBio1_000138
    • GTPL4838
    • METOLAZONE [ORANGE BOOK]
    • UNII-NN9U607695
    • BDBM25899
    • HMS500N17
    • HY-B0209R
    • KBio1_000275
    • KBio2_000936
    • KBio2_003504
    • KBio2_006072
    • C03BA08
    • NINDS_000275
    • BCPP000166
    • HMS1568G06
    • HMS1922L16
    • HMS2093P14
    • HMS2095G06
    • HMS2230J15
    • HMS3261J22
    • HMS3373C11
    • HMS3655M09
    • HMS3712G06
    • HMS3744I19
    • Pharmakon1600-02300325
    • BCP21574

  • Applications

    Metolazone (CAS 17560-51-9) is a thiazide-like diuretic primarily used as an active pharmaceutical ingredient for the treatment of hypertension and edema; in pharmaceutical manufacturing it functions as the API and can serve as a building block for the synthesis of related diuretic agents; in research and development settings it is often employed as an intermediate or reference compound for organic synthesis toward thiazide analogs; in analytical laboratories it supports method development, calibration, and quality control; its use is subject to local pharmaceutical regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.64
    methanol 7.96
    isopropanol 1.11
    water 0.04
    ethyl acetate 2.75
    n-propanol 1.8
    acetone 9.98
    n-butanol 1.07
    acetonitrile 4.47
    DMF 111.47
    toluene 0.08
    isobutanol 0.78
    1,4-dioxane 4.52
    methyl acetate 3.88
    THF 12.89
    2-butanone 8.97
    n-pentanol 0.61
    sec-butanol 0.81
    n-hexane 0.0
    ethylene glycol 3.61
    NMP 63.19
    cyclohexane 0.01
    DMSO 40.39
    n-butyl acetate 2.23
    n-octanol 0.3
    chloroform 1.48
    n-propyl acetate 2.24
    acetic acid 8.98
    dichloromethane 1.83
    cyclohexanone 8.26
    propylene glycol 5.6
    isopropyl acetate 1.44
    DMAc 93.46
    2-ethoxyethanol 11.89
    isopentanol 0.79
    n-heptane 0.01
    ethyl formate 4.77
    1,2-dichloroethane 1.27
    n-hexanol 0.4
    2-methoxyethanol 39.82
    isobutyl acetate 1.08
    tetrachloromethane 0.08
    n-pentyl acetate 1.89
    transcutol 11.51
    n-heptanol 0.52
    ethylbenzene 0.06
    MIBK 1.74
    2-propoxyethanol 12.75
    tert-butanol 0.7
    MTBE 0.3
    2-butoxyethanol 6.19
    propionic acid 4.14
    o-xylene 0.08
    formic acid 14.46
    diethyl ether 0.44
    m-xylene 0.08
    p-xylene 0.14
    chlorobenzene 0.45
    dimethyl carbonate 5.42
    n-octane 0.01
    formamide 27.65
    cyclopentanone 21.48
    2-pentanone 4.16
    anisole 0.84
    cyclopentyl methyl ether 0.86
    gamma-butyrolactone 25.09
    1-methoxy-2-propanol 20.82
    pyridine 5.12
    3-pentanone 2.54
    furfural 27.73
    n-dodecane 0.01
    diethylene glycol 17.41
    diisopropyl ether 0.08
    tert-amyl alcohol 0.58
    acetylacetone 9.39
    n-hexadecane 0.01
    acetophenone 2.62
    methyl propionate 4.5
    isopentyl acetate 1.92
    trichloroethylene 4.61
    n-nonanol 0.36
    cyclohexanol 0.42
    benzyl alcohol 1.9
    2-ethylhexanol 0.31
    isooctanol 0.48
    dipropyl ether 0.5
    1,2-dichlorobenzene 0.64
    ethyl lactate 4.71
    propylene carbonate 9.02
    n-methylformamide 30.97
    2-pentanol 0.35
    n-pentane 0.01
    1-propoxy-2-propanol 6.81
    1-methoxy-2-propyl acetate 6.65
    2-(2-methoxypropoxy) propanol 6.74
    mesitylene 0.06
    ε-caprolactone 7.54
    p-cymene 0.17
    epichlorohydrin 16.77
    1,1,1-trichloroethane 0.56
    2-aminoethanol 5.96
    morpholine-4-carbaldehyde 50.73
    sulfolane 35.22
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 1.97
    n-hexyl acetate 1.37
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 7.16
    sec-butyl acetate 1.04
    tert-butyl acetate 1.39
    decalin 0.01
    glycerin 19.91
    diglyme 15.83
    acrylic acid 6.62
    isopropyl myristate 0.61
    n-butyric acid 4.68
    acetyl acetate 2.49
    di(2-ethylhexyl) phthalate 2.04
    ethyl propionate 2.03
    nitromethane 36.87
    1,2-diethoxyethane 2.27
    benzonitrile 2.38
    trioctyl phosphate 1.05
    1-bromopropane 0.27
    gamma-valerolactone 53.34
    n-decanol 0.27
    triethyl phosphate 1.65
    4-methyl-2-pentanol 0.26
    propionitrile 2.53
    vinylene carbonate 9.16
    1,1,2-trichlorotrifluoroethane 23.64
    DMS 3.06
    cumene 0.06
    2-octanol 0.26
    2-hexanone 2.29
    octyl acetate 0.93
    limonene 0.19
    1,2-dimethoxyethane 15.7
    ethyl orthosilicate 1.23
    tributyl phosphate 1.25
    diacetone alcohol 5.66
    N,N-dimethylaniline 0.66
    acrylonitrile 7.0
    aniline 0.76
    1,3-propanediol 8.29
    bromobenzene 0.27
    dibromomethane 0.58
    1,1,2,2-tetrachloroethane 3.05
    2-methyl-cyclohexyl acetate 1.96
    tetrabutyl urea 2.54
    diisobutyl methanol 0.25
    2-phenylethanol 1.98
    styrene 0.1
    dioctyl adipate 1.95
    dimethyl sulfate 13.25
    ethyl butyrate 2.23
    methyl lactate 11.67
    butyl lactate 3.85
    diethyl carbonate 1.96
    propanediol butyl ether 4.54
    triethyl orthoformate 1.93
    p-tert-butyltoluene 0.14
    methyl 4-tert-butylbenzoate 4.57
    morpholine 8.88
    tert-butylamine 0.15
    n-dodecanol 0.19
    dimethoxymethane 22.23
    ethylene carbonate 6.05
    cyrene 15.18
    2-ethoxyethyl acetate 5.27
    2-ethylhexyl acetate 1.35
    1,2,4-trichlorobenzene 1.19
    4-methylpyridine 2.69
    dibutyl ether 0.32
    2,6-dimethyl-4-heptanol 0.25
    DEF 7.93
    dimethyl isosorbide 14.51
    tetrachloroethylene 1.42
    eugenol 6.86
    triacetin 4.55
    span 80 4.27
    1,4-butanediol 2.36
    1,1-dichloroethane 0.66
    2-methyl-1-pentanol 0.57
    methyl formate 19.65
    2-methyl-1-butanol 0.73
    n-decane 0.01
    butyronitrile 2.0
    3,7-dimethyl-1-octanol 0.32
    1-chlorooctane 0.08
    1-chlorotetradecane 0.04
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 1.23
    tetrahydropyran 0.99
    tert-amyl methyl ether 0.35
    2,5,8-trioxanonane 11.82
    1-hexene 0.04
    2-isopropoxyethanol 4.4
    2,2,2-trifluoroethanol 4.8
    methyl butyrate 3.51

    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