Rivaroxaban

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  • Identifiers

    CAS number
    366789-02-8

    Molecular formula
    C19H18ClN3O5S

    SMILES
    C1COCC(=O)N1C2=CC=C(C=C2)N3C[C@@H](OC3=O)CNC(=O)C4=CC=C(S4)Cl

    Safety labels

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 61.5%
    Meaty 37.11%
    Roasted 34.16%
    Savory 33.49%
    Cooked 31.78%
    Nutty 25.66%
    Popcorn 22.85%
    Burnt 20.84%
    Milky 17.19%
    Bitter 16.08%

     

    Flavor
    Bitter 83.63%
    Odorless 31.47%
    Bland 22.15%
    Roasted 21.84%
    Sweet-like 20.4%
    Bread crust 19.23%
    Scallion 19.19%
    Taco 19.14%
    Cereal 19.08%
    Cedarleaf 19.01%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    4.92 (weak acid)

    Molecular weight
    435.9 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    172°C

    Flash point

    • 266.35 ˚C est.

    Solubility expt.

    • Slightly soluble in organic solvents (e.g. acetone, polyethylene glycol 400) and is pratically insoluble in water and aqueous media

  • Synonyms

    • Rivaroxaban
    • 366789-02-8
    • Xarelto
    • BAY 59-7939
    • (S)-5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide
    • BAY59-7939
    • UNII-9NDF7JZ4M3
    • 9NDF7JZ4M3
    • CHEBI:68579
    • HSDB 8149
    • 5-Chloro-N-({(5s)-2-Oxo-3-[4-(3-Oxomorpholin-4-Yl)phenyl]-1,3-Oxazolidin-5-Yl}methyl)thiophene-2-Carboxamide
    • BAY-59-7939
    • JNJ39039039
    • JNJ-39039039
    • 5-chloro-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide
    • DTXSID3057723
    • RIVAROXABAN (MART.)
    • RIVAROXABAN [MART.]
    • RIVAROXABAN (USP-RS)
    • RIVAROXABAN [USP-RS]
    • 2-Thiophenecarboxamide, 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-
    • 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide
    • 5-CHLORO-N-[[(S)-3-(4-(3-OXOMORPHOLIN-4-YL)PHENYL)-2-OXO-1,3-OXAZOLIDIN-5-YL]METHYL]-THIOPHENE-2-CARBOXAMIDE
    • RIVAROXABAN (EP MONOGRAPH)
    • RIVAROXABAN [EP MONOGRAPH]
    • Rivaroxaban (Xarelto)
    • 5-Chloro-N-(((5S)-2-oxo-3-(4-(3-oxomorpholin-4-yl)phenyl)-1,3-oxazolidin-5-yl)methyl)thiophene-2-carboxamide
    • 5-CHLORO-N-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-2-THIOPHENECARBOXAMIDE
    • Xarelto (TN)
    • Rivaroxaban [INN]
    • DTXCID4031512
    • rivaroxabanum
    • (S)-Rivaroxaban
    • 2-Thiophenecarboxamide, 5-chloro-N-(((5S)-2-oxo-3-(4-(3-oxo-4-morpholinyl)phenyl)-5-oxazolidinyl)methyl)-
    • 5-Chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-2-thiophenecarboxamide;BAY 59-7939
    • RIV
    • Rivaroxaban [USAN:INN:BAN:JAN]
    • MFCD11974010
    • Rivaroxaban (Standard)
    • RIVAROXABAN [MI]
    • RIVAROXABAN [JAN]
    • RIVAROXABAN [USAN]
    • RIVAROXABAN [VANDF]
    • SCHEMBL3914
    • RIVAROXABAN [WHO-DD]
    • MLS006010027
    • Rivaroxaban (JAN/USAN/INN)
    • RIVAROXABAN [EMA EPAR]
    • BDBM7840
    • CHEMBL198362
    • GTPL6388
    • Rivaroxaban - Bio-X trade mark
    • B01AF01
    • BAY 59-7939 (Rivaroxaban)
    • EX-A206
    • RIVAROXABAN [ORANGE BOOK]
    • 2w26
    • KGFYHTZWPPHNLQ-AWEZNQCLSA-N
    • Rivaroxaban,Xarelto,BAY 59-7939
    • HY-50903R
    • AKOS005145918
    • CCG-212899
    • CS-0555
    • DB06228
    • FR27742
    • NCGC00262945-10
    • NCGC00379033-04
    • BR164355
    • HY-50903
    • SMR002529611
    • 1ST158364
    • D07086
    • AB01563270_01
    • EN300-6733490
    • US8822458, 44
    • US8822458, 97
    • Q420262
    • SR-01000944189
    • SR-01000944189-1
    • BRD-K37130656-001-01-2
    • BRD-K37130656-001-03-8
    • Z1741977097
    • (S)-5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)-oxazolidin-5-yl)methyl)thiophene-2-carboxamide
    • 1429742-50-6
    • 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide
    • 5-chloro-n-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl) phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide
    • 5-Chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophenecarboxamide
    • 5-Chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophencarboxamide
    • 5-chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophene-carboxamide
    • 5-chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide
    • 5-chloro-N-({(5s)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl} methyl)thiophene-2-carboxamide
    • 5-Chloro-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl}thiophene-2-carboxamide

  • Applications

    Rivaroxaban (CAS 366789-02-8) is primarily used as an active pharmaceutical ingredient (API) in prescription direct oral anticoagulant medications. In pharmaceutical manufacturing, it is synthesized and formulated into tablet products and explored in formulation development and regulatory-scale processes. In analytical chemistry and quality control, methods for quantification and impurity profiling of rivaroxaban are developed and validated. It is also handled in contract development and manufacturing (CDMO) settings for scale-up, process optimization, and regulatory submissions, and is managed within pharmaceutical supply chains regarding procurement, stability testing, and regulatory compliance.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.21
    methanol 0.48
    isopropanol 0.12
    water 0.02
    ethyl acetate 0.33
    n-propanol 0.12
    acetone 0.79
    n-butanol 0.09
    acetonitrile 1.12
    DMF 53.13
    toluene 0.1
    isobutanol 0.1
    1,4-dioxane 0.81
    methyl acetate 0.5
    THF 1.87
    2-butanone 0.62
    n-pentanol 0.13
    sec-butanol 0.1
    n-hexane 0.0
    ethylene glycol 0.53
    NMP 20.32
    cyclohexane 0.0
    DMSO 9.77
    n-butyl acetate 0.44
    n-octanol 0.41
    chloroform 2.62
    n-propyl acetate 0.44
    acetic acid 2.97
    dichloromethane 2.13
    cyclohexanone 2.37
    propylene glycol 0.47
    isopropyl acetate 0.31
    DMAc 68.76
    2-ethoxyethanol 2.39
    isopentanol 0.15
    n-heptane 0.0
    ethyl formate 0.88
    1,2-dichloroethane 0.7
    n-hexanol 0.1
    2-methoxyethanol 4.19
    isobutyl acetate 0.4
    tetrachloromethane 0.12
    n-pentyl acetate 1.05
    transcutol 6.27
    n-heptanol 0.35
    ethylbenzene 0.06
    MIBK 0.49
    2-propoxyethanol 2.79
    tert-butanol 0.16
    MTBE 0.11
    2-butoxyethanol 3.45
    propionic acid 0.75
    o-xylene 0.09
    formic acid 3.96
    diethyl ether 0.06
    m-xylene 0.08
    p-xylene 0.16
    chlorobenzene 0.33
    dimethyl carbonate 1.78
    n-octane 0.0
    formamide 5.91
    cyclopentanone 3.79
    2-pentanone 0.44
    anisole 0.42
    cyclopentyl methyl ether 0.28
    gamma-butyrolactone 4.44
    1-methoxy-2-propanol 2.69
    pyridine 2.07
    3-pentanone 0.34
    furfural 8.97
    n-dodecane 0.01
    diethylene glycol 3.38
    diisopropyl ether 0.02
    tert-amyl alcohol 0.22
    acetylacetone 1.75
    n-hexadecane 0.01
    acetophenone 1.38
    methyl propionate 0.71
    isopentyl acetate 0.65
    trichloroethylene 3.93
    n-nonanol 0.5
    cyclohexanol 0.17
    benzyl alcohol 1.17
    2-ethylhexanol 0.13
    isooctanol 0.35
    dipropyl ether 0.13
    1,2-dichlorobenzene 0.54
    ethyl lactate 1.48
    propylene carbonate 2.33
    n-methylformamide 6.21
    2-pentanol 0.06
    n-pentane 0.0
    1-propoxy-2-propanol 1.78
    1-methoxy-2-propyl acetate 1.62
    2-(2-methoxypropoxy) propanol 4.85
    mesitylene 0.05
    ε-caprolactone 2.15
    p-cymene 0.1
    epichlorohydrin 3.99
    1,1,1-trichloroethane 0.48
    2-aminoethanol 0.7
    morpholine-4-carbaldehyde 17.52
    sulfolane 10.36
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.4
    n-hexyl acetate 1.18
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 4.8
    sec-butyl acetate 0.28
    tert-butyl acetate 0.42
    decalin 0.0
    glycerin 2.73
    diglyme 9.84
    acrylic acid 1.77
    isopropyl myristate 0.46
    n-butyric acid 0.85
    acetyl acetate 0.59
    di(2-ethylhexyl) phthalate 1.49
    ethyl propionate 0.41
    nitromethane 8.03
    1,2-diethoxyethane 0.89
    benzonitrile 1.77
    trioctyl phosphate 0.76
    1-bromopropane 0.11
    gamma-valerolactone 12.52
    n-decanol 0.34
    triethyl phosphate 0.72
    4-methyl-2-pentanol 0.08
    propionitrile 0.63
    vinylene carbonate 3.34
    1,1,2-trichlorotrifluoroethane 12.76
    DMS 1.51
    cumene 0.06
    2-octanol 0.25
    2-hexanone 0.59
    octyl acetate 0.77
    limonene 0.1
    1,2-dimethoxyethane 4.13
    ethyl orthosilicate 0.57
    tributyl phosphate 0.89
    diacetone alcohol 1.7
    N,N-dimethylaniline 0.51
    acrylonitrile 2.23
    aniline 0.47
    1,3-propanediol 0.88
    bromobenzene 0.26
    dibromomethane 0.63
    1,1,2,2-tetrachloroethane 2.83
    2-methyl-cyclohexyl acetate 0.83
    tetrabutyl urea 2.37
    diisobutyl methanol 0.09
    2-phenylethanol 1.04
    styrene 0.09
    dioctyl adipate 1.33
    dimethyl sulfate 5.24
    ethyl butyrate 0.49
    methyl lactate 2.77
    butyl lactate 2.23
    diethyl carbonate 0.5
    propanediol butyl ether 3.2
    triethyl orthoformate 0.72
    p-tert-butyltoluene 0.09
    methyl 4-tert-butylbenzoate 3.03
    morpholine 1.48
    tert-butylamine 0.05
    n-dodecanol 0.23
    dimethoxymethane 4.5
    ethylene carbonate 1.91
    cyrene 6.76
    2-ethoxyethyl acetate 2.19
    2-ethylhexyl acetate 0.46
    1,2,4-trichlorobenzene 1.1
    4-methylpyridine 1.65
    dibutyl ether 0.28
    2,6-dimethyl-4-heptanol 0.09
    DEF 2.44
    dimethyl isosorbide 6.85
    tetrachloroethylene 1.39
    eugenol 4.81
    triacetin 2.88
    span 80 2.85
    1,4-butanediol 0.65
    1,1-dichloroethane 0.4
    2-methyl-1-pentanol 0.2
    methyl formate 3.72
    2-methyl-1-butanol 0.13
    n-decane 0.01
    butyronitrile 0.5
    3,7-dimethyl-1-octanol 0.32
    1-chlorooctane 0.12
    1-chlorotetradecane 0.05
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.3
    tetrahydropyran 0.23
    tert-amyl methyl ether 0.13
    2,5,8-trioxanonane 7.54
    1-hexene 0.01
    2-isopropoxyethanol 1.37
    2,2,2-trifluoroethanol 2.65
    methyl butyrate 0.74

    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