Drug

D0086 | Nabumetone

Molecular Formula C15H16O2
Molecular Weight 228.29
Structure
State solid
Clearance 6-MNA has an apparent steady-state clearance of 20 - 30 mL/min.[label]
Volume of distribution The Vd of 6-MNA reported after administration of a single dose is 0.1-0.2 L/kg or approximately 5-10 L.[A178903] Vdss reported in official product labeling is approximately 53 L.[label,L6466]
Route of elimination Most drug is eliminated via hepatic metabolism with minimal to no parent drug detectable in the plasma.[label,A178903] 80% of the dose is then excreted by the kidneys and 10% in the feces. It does not appear to undergo enterohepatic recirculation.
Protein binding 6-MNA is over 99% bound to plasma proteins, likely albumin.[label,A178903] The unbound fraction is 0.1-0.2% and remains proportional in the dose range of 1000-2000mg
Half life 6-MNA has a mean half-life of 24 hours with a range of 19-36 hours.[label]
Absorption Nabumetone is well-absorbed from the GI tract and undergoes significant first pass metabolism resulting in approximately 35% being converted to the active metabolite, 6-MNA.[label,A178903] Tmax for 6-MNA varies widely with a mean values of 3 and 11 hours reported in official product monographs, and described as 9-12 hours in published literature [label,L6466,A178903] Administration with food increases Cmax by 33% and increases absorption rate.[label,A178903] If formulated as a suspension the Cmax increases and the Tmax is reduced by 0.8 hours while the all other pharmacokinetic parameters remain unchanged.[A178903]

M

M01AX01 Nabumetone


[M01AX] Other antiinflammatory and antirheumatic agents, non-steroids


[M01A] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS


[M01] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS


[M] Musculoskeletal system


Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 7 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 1 of 7 companies. For more detailed information, please visit ECHA C&L website


Of the 6 notification(s) provided by 6 of 7 companies with hazard statement code(s):


H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (33.33%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (16.67%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H332 (16.67%): Harmful if inhaled [Warning Acute toxicity, inhalation]


H335 (16.67%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H361 (33.33%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H373 (16.67%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]


H400 (16.67%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]


H410 (50%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


H411 (16.67%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) skin and appendages (skin): "dermatitis, other: after systemic exposure" Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
monkey LD50 oral 3200mg/kg (3200mg/kg) gastrointestinal: changes in structure or function of salivary glands Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg) skin and appendages (skin): "dermatitis, other: after systemic exposure" Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
rat LD50 oral 3880mg/kg (3880mg/kg) Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
rat LD50 intraperitoneal 1520mg/kg (1520mg/kg) Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
mouse LD50 intraperitoneal 2380mg/kg (2380mg/kg) Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
women TDLo oral 1260mg/kg/6W- (1260mg/kg) Postgraduate Medical Journal. Vol. 67, Pg. 1021, 1991.
monkey LD50 oral 3200mg/kg (3200mg/kg) Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
mouse LD50 oral 4290mg/kg (4290mg/kg) Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.

  • Arthritis

  • Osteoarthritis

  • Rheumatoid arthritis

  • Abdominal pain (0.12)

  • Weight increased (0.007)

  • Asthenia

  • Dizziness

  • Feeling abnormal

  • 2-Butanone, 4-(6-methoxy-2-naphthalenyl)- 4-(2-Methoxynaphthalen-6-yl)butan-2-one 4-(6-Methoxy-2-naphthalenyl)-2-butanone
    4-(6-Methoxy-2-naphthyl)-2-butanone 4-(6-methoxy-2-naphthyl)butan-2-one 4-(6-methoxynaphthalen-2-yl)butan-2-one
    4-[6-methoxy-2-naphthyl]-2-butanone 42924-53-8 924N538
    AB00052392 AB00052392-13 AB00052392_14
    AB00052392_15 AC-19025 AK-86115
    AKOS009529199 AM20040460 ANW-46490
    API0003472 AX8142896 Arthaxan
    BC966361 BCP12152 BDBM40128
    BIDD:GT0104 BLXXJMDCKKHMKV-UHFFFAOYSA-N BPBio1_000834
    BRD-K65146499-001-04-8 BRD-K65146499-001-14-7 BRL 14777
    BRL-14777 BRL14777 BRN 2103472
    BSPBio_000758 Balmox C-13097
    CAS-42924-53-8 CC-32257 CCG-39507
    CCRIS 8108 CHEBI:7443 CHEMBL1070
    CPD000058835 CS-2669 CTK8B4843
    Consolan D00425 DB00461
    DSSTox_CID_25472 DSSTox_GSID_45472 DSSTox_RID_80901
    DTXSID4045472 DivK1c_000850 Dolsinal
    FT-0629765 Flambate GTPL7245
    HMS1570F20 HMS1922G10 HMS2090D13
    HMS2093I05 HMS2097F20 HMS2230H12
    HMS3259I16 HMS3652M04 HMS3714F20
    HMS502K12 HY-B0559 IDI1_000850
    KBio1_000850 KBio2_001966 KBio2_004534
    KBio2_007102 KBioGR_000687 KBioSS_001966
    KS-1371 LS-46825 LW0TIW155Z
    Listran M727 MFCD00079518
    MLS000069541 MLS001076325 Mebutan
    NC00579 NCGC00016853-01 NCGC00016853-02
    NCGC00016853-03 NCGC00016853-06 NCGC00095063-01
    NCGC00095063-02 NINDS_000850 NSC-758623
    NSC758623 Nabumatone Form II Nabumetona
    Nabumetone (JP17/USP/INN) Nabumetone [USAN:BAN:INN:JAN] Nabumetone [USAN:USP:INN:BAN:JAN]
    Nabumetone, British Pharmacopoeia (BP) Reference Standard Nabumetone, European Pharmacopoeia (EP) Reference Standard Nabumetone, United States Pharmacopeia (USP) Reference Standard
    Nabumetone, analytical standard Nabumetonum Nabumetonum [INN-Latin]
    Nabuser Opera_ID_765 Pharmakon1600-01503650
    Prestwick0_000909 Prestwick1_000909 Prestwick2_000909
    Prestwick3_000909 Prodac Q425207
    Relafen Relafen (TN) Relif
    Relifen Relifex SAM002564225
    SBI-0051869.P002 SC-77045 SCHEMBL2256
    SMR000058835 SPBio_002097 SPBio_002957
    SPECTRUM1503650 SR-01000759138 SR-01000759138-2
    SR-01000759138-3 ST2405403 SW197312-3
    Spectrum2_001969 Spectrum4_000174 Spectrum5_001286
    Spectrum_001486 TC-135235 Tox21_110647
    Tox21_110647_1 UNII-LW0TIW155Z Unimetone
    ZINC20221 cid_4409 nabumeton
    nabumetone s4051

    DrugBank Name Nabumetone
    DrugBank DB00461
    CAS Number 1216770-08-9, 42924-53-8
    PubChem Compound 4409
    KEGG Drug D00425
    PubChem.Substance 46507729
    ChEBI 7443
    PharmGKB PA450572
    ChemSpider 4256
    BindingDB 40128.0
    TTD DAP000735
    Wikipedia Nabumetone
    HET NBO
    DPD 946

    1. Dykens et al. (2007)