D0194 | Menadione

Molecular Formula C11H8O2
Molecular Weight 172.18
State solid
Absorption Variable and ranges from 10% to 80%
Description an analog of 1,4-naphthoquinone; has vitamin K activity (sometimes called vitamin K3)


B02BA02 Menadione

[B02BA] Vitamin K



[B] Blood and blood forming organs

Toxicity Dose Time Species Model Method Action Positive criterion Reference
UNCOUPLING increase 47
NONPROTONOPHORIC UNCOUPLERS rat liver mitochondria RST assay( Respiratory Screening Technology)-measurement of oxygen consumption in isolated mitochondria using a phosphorescent oxygen-sensitive probe A65N-1 increase 204
GLUCOSE GALACTOSE IC50 RATIO 18.0 ± 7.2, 14.7 ± 7.9 ,1.2, 19.5 ± 8.3, 14.0 ± 8.7, 1.4 4hr H9c2 cells high-glucose–galactose cell viability assay with JC-1 mitochondrial membrane potential and ATP-depletion assays (CellTiter-Glo reagent ). glucose/galactose IC50 ratio (JC-1 IC50 in glucose, JC-1 IC50 in galactose, JC-1 glu/gla, ATP IC50 in glucose, ATP IC50 in galactose, ATP glu/gla ) 50
MITOCHONDRIAL MOTILITY 10 μM Time lapse fluorescence microscopy decrease 218
ROS PRODUCTION 20 µM 24hr U2OS mt-roGFP and mitoSOX increase 313
MITOCHONDRIAL DNA METABOLIC PROCESS 6.0 μM 1 hours human pFastBac Meassurement of DNA polymerase gamma activity affect IC50 9

Target Dose Time Species Model Method Action Positive criterion Reference
DNA polymerase gamma 6.0 μM 1 hours human pFastBac Meassurement of DNA polymerase gamma activity not specified IC50 9

Pictogram Signal Statements Precautionary Statement Codes

Aggregated GHS information provided by 70 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (92.86%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (87.14%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (95.71%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure

Respiratory tract irritation]

H341 (12.86%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

H361 (12.86%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H400 (21.43%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute 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, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, 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 intraperitoneal 15mg/kg (15mg/kg) National Technical Information Service. Vol. AD691-490,

  • 001M681 03AAE1E9-B215-45AF-976C-91E61894A467 1,4-Dihydro-2-methylnaphthalene-1,4-dione
    1,4-Naphthalenedione, 2-methyl- 1,4-Naphthalenedione, 2-methyl-, radical ion(1-) 1,4-Naphthoquinone, 2-methyl-
    2-METHYL-1,4-NAPHTHALENEDIONE 2-Methyl-1,4-naftochinon 2-Methyl-1,4-naftochinon [Czech]
    2-Methyl-1,4-naphthalendione 2-Methyl-1,4-naphthalenedione 2-Methyl-1,4-naphthochinon
    2-Methyl-1,4-naphthochinon [German] 2-Methyl-1,4-naphthodione 2-Methyl-1,4-naphthoquinone
    2-Methyl-1,4-naphthoquinone 2-Methyl-1,4-naphthoquinone, 98% 2-Methyl-[1,4]-naphthoquinone
    2-Methylnaphthoquinone 2-methyl-1,4 naphthoquinone 2-methyl-1,4-dihydronaphthalene-1,4-dione
    2-methyl-1,4-naphthoquinone, 5 2-methyl-1,4-napthoquinone 2-methylnaphthalene-1,4-dione
    3-Methyl-1,4-naphthoquinone 3-methyl-1,4-naphthalenedione 34524-96-4
    58-27-5 72060-21-0 723JX6CXY5
    A831816 AB2000387 ACMC-1BCKI
    AI3-14700 AKOS004910447 AKOS025244105
    ANW-32906 ARONIS24154 Aquakay
    Aquinone BBL027351 BB_NC-02319
    BG0249 BIDD:ER0556 BPBio1_000592
    BRD-K78126613-001-16-0 BSPBio_000538 Bio1_000471
    Bio1_000960 Bio1_001449 C-24481
    C05377 C11H8O2 CAS-58-27-5
    CC-30201 CCG-35354 CCRIS 6672
    CHEBI:28869 CHEMBL590 CS-2374
    CTK5A8103 Certified Reference Material D02335
    DB00170 DSSTox_CID_1715 DSSTox_GSID_21715
    DSSTox_RID_76289 DTXSID4021715 DivK1c_000080
    DivK1c_006287 EINECS 200-372-6 FCH1114831
    FS-2556 FT-0612893 H500
    HMS1569K20 HMS1921P06 HMS2092F12
    HMS2096K20 HMS2232A09 HMS2234J16
    HMS3371M08 HMS3373A12 HMS3655P03
    HMS500D22 HSDB 3354 HY-B0332
    Hemodal IDI1_000080 InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H
    Juva-K K-Thrombyl K-Vitan
    KBio1_000080 KBio1_001231 KBio2_001708
    KBio2_002527 KBio2_004276 KBio2_005095
    KBio2_006844 KBio2_007663 KBio3_003005
    KBioGR_000984 KBioGR_002527 KBioSS_001708
    KBioSS_002535 KS-00000C40 KSC608C0H
    Kaergona Kanone Kappaxan (VAN)
    Kappaxin Kappaxin (TN) Karcon
    Kareon Kativ-G Kayklot
    Kaykot Kaynone Kayquinone
    Kipca Kipca, oil soluble Kipca-Oil Soluble
    Klottone Koaxin Kolklot
    LS-95653 LS-95654 M0373
    MCULE-2487773379 MFCD00001681 MFCD00001681 (97+%)
    MNQ Memodol Menadion
    Menadione (K3), analytical standard Menadione (USP) Menadione (Vitamin K3)
    Menadione [USAN:BAN] Menadione [USP:BAN] Menadione semiquinone
    Menadione, 9 Menadione, 98% Menadione, European Pharmacopoeia (EP) Reference Standard
    Menadione, Pharmaceutical Secondary Standard Menadione, United States Pharmacopeia (USP) Reference Standard Menadione, crystalline
    Menadione, meets USP testing specifications Menadione,(S) Menadionum
    Menaphthene Menaphthon Menaphthone
    Menaphthone Menaphtone Menaquinone 0
    Menaquinone O Mendione Methyl-1,4-naphthalenedione
    Methyl-1,4-naphthoquinone Methylnaphthoquinone Mitenon
    Mitenone NAPHTHOQUINONE, METHYL- NCGC00016258-01
    NCGC00016258-02 NCGC00016258-03 NCGC00016258-04
    NCGC00016258-06 NCGC00016258-07 NCGC00016258-08
    NCGC00094978-01 NCGC00094978-02 NCGC00255225-01
    NCI60_003945 NCIMech_000105 NINDS_000080
    NSC 4170 NSC-4170 NSC-758200
    NSC4170 NSC758200 Opera_ID_1802
    Panosine Pharmakon1600-01502254 Prestwick0_000459
    Prestwick1_000459 Prestwick2_000459 Prestwick3_000459
    Prestwick_313 Prokayvit PubChem14596
    Q-201350 Q192471 QTL1_000056
    RTR-037165 SB17255 SBB012369
    SBI-0051776.P002 SC-16348 SC-61015
    SCHEMBL25970 SMR000059102 SMR000653532
    SPBio_001267 SPBio_002477 SPECTRUM1502254
    SR-01000712386 SR-01000712386-2 SR-01000712386-5
    SR-01000712386-6 ST066885 STL377874
    STR01143 SW219798-1 SY018303
    SpecPlus_000191 Spectrum2_001194 Spectrum4_000722
    Spectrum5_001764 Spectrum_001228 Synkay
    TR-037165 TRA0064327 Thyloquinone
    Tox21_110334 Tox21_110334_1 Tox21_301367
    UNII-723JX6CXY5 Usaf ek-5185 VITAMIN K3
    VK3 Vicasol Vitamin K 3
    Vitamin K0 Vitamin K2(0) Vitamin K3
    Vitamin K3 Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalene WLN: L66 BV EVJ C1
    Z-3172 ZINC1677 ZX-AS004517
    ZX-AT006056 cMAP_000077 cid_4055
    menadione s1949

    DrugBank Name Menadione
    DrugBank DB00170
    CAS Number 12001-79-5, 130-37-0, 21715-15-1, 34524-96-4, 57414-02-5, 58-27-5, 72060-21-0
    PubChem Compound 4055
    KEGG Compound ID C05377
    KEGG Drug D02335
    PubChem.Substance 46505447
    ChEBI 28869
    PharmGKB PA450358
    ChemSpider 3915
    BindingDB 24778.0
    TTD DNC001501
    Wikipedia Menadione
    HET VK3
    DPD 4913

    1. Koczor et al 2009