Drug

D0083 | Mitomycin

Molecular Formula C15H18N4O5
Molecular Weight 334.33
Structure
State solid
Route of elimination Approximately 10% of a dose of mitomycin is excreted unchanged in the urine.
Half life 8-48 min
Absorption Erratic.

L

L01DC03 Mitomycin


[L01DC] Other cytotoxic antibiotics


[L01D] CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES


[L01] ANTINEOPLASTIC AGENTS


[L] Antineoplastic and immunomodulating agents


Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL > 200 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 4.9 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
SWELLING ND 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) Negative EC20 36

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 4.9 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
Cytochrome c > 200 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 53 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H300 (92.45%): Fatal if swallowed [Danger Acute toxicity, oral]


H351 (92.45%): Suspected of causing cancer [Warning Carcinogenicity]


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, P264, P270, P281, P301+P310, P308+P313, P321, P330, 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
rabbit LD50 intravenous 3400ug/kg (3.4mg/kg) Drugs in Japan Vol. -, Pg. 1129, 1990.
quail LD50 oral > 100mg/kg (100mg/kg) Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
mouse LDLo intratracheal 4mg/kg (4mg/kg) Toxicology Letters. Vol. 30, Pg. 63, 1986.
mouse LD50 unreported 12mg/kg (12mg/kg) Cancer Research. Vol. 46, Pg. 2703, 1986.
rat LD50 intraperitoneal 2mg/kg (2mg/kg) Advances in Teratology. Vol. 3, Pg. 181, 1968.
mouse LD50 intraperitoneal 4mg/kg (4mg/kg) Journal of Antibiotics, Series A. Vol. 13, Pg. 27, 1960.
monkey LDLo intravenous 1mg/kg (1mg/kg) Cancer Research. Vol. 20, Pg. 1354, 1960.
man TDLo unreported 1350ug/kg/21W (1.35mg/kg) Archives of Internal Medicine. Vol. 143, Pg. 803, 1983.
women TDLo unreported 2100ug/kg/40W (2.1mg/kg) Archives of Internal Medicine. Vol. 143, Pg. 1617, 1983.
mouse LD50 subcutaneous 7300ug/kg (7.3mg/kg) Japanese Journal of Cancer Research. Vol. 80, Pg. 670, 1989.
women TDLo intravenous 1800ug/kg (1.8mg/kg) Lancet. Vol. 2, Pg. 1037, 1980.
rat LD50 subcutaneous 3250ug/kg (3.25mg/kg) Drugs in Japan Vol. 6, Pg. 798, 1982.
dog LD50 intravenous 720ug/kg (0.72mg/kg) Drugs in Japan Vol. -, Pg. 1129, 1990.
rat LD50 oral 30mg/kg (30mg/kg) Cancer Research. Vol. 20, Pg. 1354, 1960.
cat LDLo intravenous 2500ug/kg (2.5mg/kg) Cancer Research. Vol. 20, Pg. 1354, 1960.
bird - wild LD50 oral 7500ug/kg (7.5mg/kg) Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
rat LD50 intravenous 3mg/kg (3mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.
mouse LD50 oral 23mg/kg (23mg/kg) Cancer Research. Vol. 20, Pg. 1354, 1960.
mouse LD50 intravenous 4mg/kg (4mg/kg) Journal of Antibiotics, Series A. Vol. 13, Pg. 27, 1960.

  • Metastatic neoplasm

  • Neoplasm malignant

  • Pulmonary oedema (0.65)

  • ((1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate (1ar)-6-amino-8-(((aminoc arbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione (1ar)-6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
    (amino-methoxy-methyl-dioxo-[?]yl)methyl carbamate 078M109 1404-00-8
    50-07-7 50SG953SK6 6-Amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methylazirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione carbamate (ester)
    6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methylazirino[2',3':3, 4]pyrrolo[1,2-a]indole-4,7-dione, carbamate (ester) 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, carbamate (ester) 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl, [1aS-(1aalpha,8beta,8aalpha,8balpha)]-azirino[2',3':3,4]pyrrol o[1,2a]indole-4,7-dione
    6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl, [1aS-(1aalpha,8beta,8aalpha,8balpha)]-azirino[2',3':3,4]pyrrolo[1,2a]indole-4,7-dione 7-Amino-9.alpha.-methoxymitosane 7-Amino-9alpha-methoxymitosane
    AB00918689-03 AB00918689-04 ACN-038344
    AI3-26199 AKOS015895703 AMETYCIN pound notmitomycin C
    Ametycin Ametycine Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-, carbamate (ester)
    Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1aS,8S,8aR,8bS)- Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1aS-(1aalpha,8beta,8aalpha,8balpha))- Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1aS-(1aalpha,8beta,8aalpha,8balpha))- (9CI)
    Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl -, [1aS-(1aalpha,8beta,8aalpha,8balpha)]- Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1aS,8S,8aR,8bS)- Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, [1aS-(1aalpha,8beta,8aalpha,8balpha)]-
    Azirino[2',4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a- methoxy-5-methyl-, carbamate (ester) Azirino[2',4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b- hexahydro-8a-methoxy-5-methyl-, [1aR-(1a.alpha.,8.beta.,8a.alpha.,8b.alpha.)]- BCP0726000181
    BCP9000285 BCPP000410 BDBM50428658
    BRD-K59670716-001-02-6 BRD-K59670716-001-06-7 BSPBio_001267
    Bio1_000213 Bio1_000702 Bio1_001191
    Bio2_000464 Bio2_000944 C-20147
    C06681 C15H18N4O5 CAS-50-07-7
    CBiol_001927 CC-30970 CCG-208564
    CCRIS 414 CHEBI:27504 CHEMBL105
    CS-0564 D00208 DB00305
    DSSTox_CID_898 DSSTox_GSID_20898 DSSTox_RID_75853
    DTXSID2020898 EINECS 200-008-6 EX-A501
    GR-311 GTPL7089 HMS1362O09
    HMS1792O09 HMS1990O09 HMS2089F16
    HMS3403O09 HSDB 3239 HY-13316
    IDI1_002219 KBio2_000607 KBio2_003175
    KBio2_005743 KBio3_001073 KBio3_001074
    KBioGR_000607 KBioSS_000607 KS-5148
    LS-136 LS-173087 M2320
    MFCD00078109 MLS001332654 MLS002702984
    MMC Mit-C Mitamycin
    Mito-C MitoExtra Mitocin C
    Mitocin-C Mitomicina Mitomicina [INN-Spanish]
    Mitomycin Mitomycin (TN) Mitomycin (USP/INN)
    Mitomycin C (JP17) Mitomycin C from Streptomyces caespitosus Mitomycin C from Streptomyces caespitosus, >=970 mug/mg (USP XXIV)
    Mitomycin C from Streptomyces caespitosus, >=98% (HPLC), potency: >=970 mug per mg (USP XXIV), gamma-irradiated, suitable for cell culture Mitomycin C from Streptomyces caespitosus, powder, BioReagent, suitable for cell culture Mitomycin C from Streptomyces caespitosus, powder, contains NaCl as solubilizer
    Mitomycin C, Antibiotic for Culture Media Use Only Mitomycin C, Streptomyces caespitosus Mitomycin C, Streptomyces caespitosus, Carrier-Free
    Mitomycin C, contains 2 mg Mitomycin C and 48 mg NaCl Mitomycin [USAN:INN:BAN] Mitomycin [USAN:USP:INN:BAN]
    Mitomycin-C Mitomycine Mitomycine [INN-French]
    Mitomycins Mitomycinum Mitomycinum C
    Mitomycinum [INN-Latin] Mitomycyna C Mitomycyna C [Polish]
    Mitonco Mitoplus Mitosol
    Mitozytrex Mitozytrex (TN) (Supergene) Muamycin (TN)
    Mutamycin Mytomycin Mytozytrex
    NCGC00095258-01 NCGC00163468-02 NCGC00163468-03
    NCGC00163468-05 NCGC00163468-06 NCI-C04706
    NSC 26980 NSC-26980 NSC26980
    NWIBSHFKIJFRCO-WUDYKRTCSA-N Q-201410 Q19856779
    RCRA waste no. U010 RCRA waste number U010 SC-17000
    SCHEMBL3760 SMP1_000307 SMR000058401
    Tox21_111493 Tox21_111493_1 UNII-50SG953SK6
    UNII-V03E10691T component NWIBSHFKIJFRCO-WUDYKRTCSA-N W-5071 WLN: T D3 B556 BN EM JV MVTTT&J GO1 H1OVZ KZ L1
    ZINC30726187 ZX-AFC000411 [(1aS,8S,8aR,8bS)-6-Amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2'',3'':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate
    [(1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate [(1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate [(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methyl carbamate
    [1aR-(1aalpha,8beta,8aalpha,8balpha)]-6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-alpha]indole-4,7-dione [1aS-(1a?,8?,8a?,8b?)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione [1aS-(1aalpha,8beta,8aalpha,8balpha)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
    mitomycin C s8146

    DrugBank Name Mitomycin
    DrugBank DB00305
    CAS Number 1404-00-8, 50-07-7
    PubChem Compound 5746
    KEGG Compound ID C06681
    KEGG Drug D00208
    PubChem.Substance 46508353
    ChEBI 27504
    PharmGKB PA450524
    ChemSpider 5544
    BindingDB 50428658.0
    TTD DAP001402
    Wikipedia Mitomycin
    DPD 2195

    1. Chan et al. (2005)