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Substance Name: Mitomycin [USAN:USP:INN:BAN]
RN: 50-07-7
UNII: 50SG953SK6
InChIKey: NWIBSHFKIJFRCO-WUDYKRTCSA-N

Note

  • An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.

Molecular Formula

  • C15-H18-N4-O5

Molecular Weight

  • 334.33
 

Classification Codes

Classification Codes

  • Alkylating Agents
  • Antibiotics, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Cross-Linking Reagents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Indicators and Reagents
  • Mutation Data
  • Natural Product
  • Noxae
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
  • TSCA Flag S (Substance is Identified in a Final Significant New Use Rule)
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2B
  • Reportable Quantity (RQ) = 10 lb
  • Threshold Planning Quantity (TPQ) = 500/10000 lb

Names and Synonyms

Name of Substance

  • Mitomycin C
  • Mitomycin [USAN:USP:INN:BAN]

MeSH Heading

  • Mitomycin

Synonyms

  • 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)
  • 7-Amino-9alpha-methoxymitosane
  • AI3-26199
  • Ametycin
  • Ametycine
  • 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)
  • CCRIS 414
  • EINECS 200-008-6
  • HSDB 3239
  • Mitocin C
  • Mitocin-C
  • Mitomycin
  • Mitomycin C
  • Mitomycin-C
  • Mitomycinum
  • Mitomycinum C
  • Mitomycyna C
  • Mitomycyna C [Polish]
  • Mitosol
  • Mitozytrex
  • MMC
  • Mutamycin
  • Mytomycin
  • Mytozytrex
  • NCI-C04706
  • NSC 26980
  • NSC-26980
  • RCRA waste number U010
  • UNII-50SG953SK6

Systematic Names

  • 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)-
  • Mitomycin
  • Mitomycin-C

Superlist Names

  • 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))-
  • Mitomycin C
  • RCRA waste no. U010

Registry Numbers

CAS Registry Number

  • 50-07-7

FDA UNII

  • 50SG953SK6

Other Registry Numbers

  • 144085-53-0
  • 74349-48-7
  • 7481-68-7

System Generated Number

  • 0000050077

Structure Descriptors

InChI

1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1

InChIKey

NWIBSHFKIJFRCO-WUDYKRTCSA-N

Smiles

N12C=3C(C(C)=C(C(C3[C@H]([C@@]2([C@H]2[C@H](C1)N2)OC)COC(N)=O)=O)N)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 7500ug/kg (7.5mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LDLo intravenous 2500ug/kg (2.5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Cancer Research. Vol. 20, Pg. 1354, 1960.
dog LD50 intravenous 720ug/kg (0.72mg/kg)   Drugs in Japan Vol. -, Pg. 1129, 1990.
man TDLo unreported 1350ug/kg/21W (1.35mg/kg) BLOOD: NORMOCYTIC ANEMIA

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Archives of Internal Medicine. Vol. 143, Pg. 803, 1983.
monkey LDLo intravenous 1mg/kg (1mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: HEMORRHAGE
Cancer Research. Vol. 20, Pg. 1354, 1960.
mouse LD50 intraperitoneal 4mg/kg (4mg/kg)   Journal of Antibiotics, Series A. Vol. 13, Pg. 27, 1960.
mouse LD50 intravenous 4mg/kg (4mg/kg)   Journal of Antibiotics, Series A. Vol. 13, Pg. 27, 1960.
mouse LD50 oral 23mg/kg (23mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Cancer Research. Vol. 20, Pg. 1354, 1960.
mouse LD50 subcutaneous 7300ug/kg (7.3mg/kg)   Japanese Journal of Cancer Research. Vol. 80, Pg. 670, 1989.
mouse LD50 unreported 12mg/kg (12mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
mouse LDLo intratracheal 4mg/kg (4mg/kg)   Toxicology Letters. Vol. 30, Pg. 63, 1986.
quail LD50 oral > 100mg/kg (100mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rabbit LD50 intravenous 3400ug/kg (3.4mg/kg)   Drugs in Japan Vol. -, Pg. 1129, 1990.
rat LD50 intraperitoneal 2mg/kg (2mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat LD50 intravenous 3mg/kg (3mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.
rat LD50 oral 30mg/kg (30mg/kg)   Cancer Research. Vol. 20, Pg. 1354, 1960.
rat LD50 oral 30mg/kg (30mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Cancer Research. Vol. 20, Pg. 1354, 1960.
rat LD50 subcutaneous 3250ug/kg (3.25mg/kg)   Drugs in Japan Vol. 6, Pg. 798, 1982.
women TDLo intravenous 1800ug/kg (1.8mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: FIBROSING ALVEOLITIS
Lancet. Vol. 2, Pg. 1037, 1980.
women TDLo unreported 2100ug/kg/40W (2.1mg/kg) BLOOD: OTHER CHANGES

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA
Archives of Internal Medicine. Vol. 143, Pg. 1617, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point >360 deg C   EXP
Boiling Point 534 deg C   EXP
pKa Dissociation Constant 10.85 (none)   EXP
log P (octanol-water) -0.4 (none)   EXP
Water Solubility 8430 mg/L 25 EST
Vapor Pressure 6.78E-10 mm Hg 25 EST
Henry's Law Constant 1.14E-24 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.19E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.