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Record Information
Version2.0
Creation Date2009-07-21 20:26:32 UTC
Update Date2014-12-24 20:25:51 UTC
Accession NumberT3D2743
Identification
Common NameMitomycin
ClassSmall Molecule
DescriptionMitomycin is only found in individuals that have used or taken this drug. It is 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. Mitomycin is activated in vivo to a bifunctional and trifunctional alkylating agent. Binding to DNA leads to cross-linking and inhibition of DNA synthesis and function. Mitomycin is cell cycle phase-nonspecific.
Compound Type
  • Alkylating Agent
  • Amide
  • Amine
  • Antibiotic, Antineoplastic
  • Cross-Linking Reagent
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Nucleic Acid Synthesis Inhibitor
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
7-Amino-9alpha-methoxymitosane
7-Amino-9α-methoxymitosane
Ametycine
Mitamycin
Mitocin-C
Mitomycin C
Mitosol
Mitozytrex
MMC
Mutamycin
Chemical FormulaC15H18N4O5
Average Molecular Mass334.327 g/mol
Monoisotopic Mass334.128 g/mol
CAS Registry Number50-07-7
IUPAC Name[(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,⁷.0⁴,⁶]trideca-1(9),11-dien-8-yl]methyl carbamate
Traditional Namemitomycin c
SMILES[H][C@]12CN3C4=C(C(=O)C(N)=C(C)C4=O)[C@@]([H])(COC(O)=N)[C@@]3(OC)[C@@]1([H])N2
InChI IdentifierInChI=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
InChI KeyInChIKey=NWIBSHFKIJFRCO-WUDYKRTCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as mitomycins. These are polycyclic compounds with a structure based on an aziridine ring linked to a 7-amino-6-methyl-cyclohexa[b]pyrrolizine-5,8-dione.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolequinones
Direct ParentMitomycins
Alternative Parents
Substituents
  • Mitomycin
  • Indole
  • Quinone
  • Pyrrolizine
  • 1,4-diazinane
  • Piperazine
  • Pyrrolidine
  • Vinylogous amide
  • Pyrroline
  • Ketone
  • Aziridine
  • Carboximidic acid derivative
  • Secondary aliphatic amine
  • Enamine
  • Azacycle
  • Secondary amine
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Imine
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point>360°C
Boiling Point534°C
SolubilitySoluble (8430 mg/L)
LogP-0.4
Predicted Properties
PropertyValueSource
Water Solubility10.1 g/LALOGPS
logP-0.55ALOGPS
logP-3ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)-0.3ChemAxon
pKa (Strongest Basic)6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area146.89 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.27 m³·mol⁻¹ChemAxon
Polarizability32.77 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k96-9032000000-addf881f05b59bd45e65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1039000000-d46d2d90cca8822c99bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-2094000000-94a0851dbf07fb7b2edeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9010000000-93ec12977feffeac422bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9012000000-22f59cef40bc61653f39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-0e9aba8bfa2e95134f7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-fdd39ddcbff28d118e30JSpectraViewer
Toxicity Profile
Route of ExposureIntravesical, erratic, intravenous.
Mechanism of ToxicityMitomycin is activated in vivo to a bifunctional and trifunctional alkylating agent. Binding to DNA leads to cross-linking and inhibition of DNA synthesis and function. Mitomycin is cell cycle phase-nonspecific.
MetabolismPrimarily hepatic, some in various other tissues. Route of Elimination: Approximately 10% of a dose of mitomycin is excreted unchanged in the urine. Half Life: 8-48 min
Toxicity ValuesLD50: 23 mg/kg (Oral, Mouse) (1) LD50: 30 mg/kg (Oral, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (3)
Uses/SourcesFor treatment of malignant neoplasm of lip, oral cavity, pharynx, digestive organs, peritoneum, female breast, and urinary bladder. Also used as an adjunct to ab externo glaucoma surgery.
Minimum Risk LevelNot Available
Health EffectsMitomycin C causes delayed bone marrow toxicity and therefore it is usually administered at 6-weekly intervals. Prolonged use may result in permanent bone-marrow damage. It may also cause lung fibrosis and renal damage.
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00305
HMDB IDHMDB14450
PubChem Compound ID5746
ChEMBL IDCHEMBL105
ChemSpider ID5544
KEGG IDC06681
UniProt IDNot Available
OMIM ID
ChEBI ID27504
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMitomycin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMitomycin
References
Synthesis Reference

Leslie Jimenez, Zheng Wang, “Synthesis of mitomycin and its analogs.” U.S. Patent US5523411, issued June, 1972.

MSDSLink
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Drugs.com [Link]
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Rodighiero G, Marciani Magno S, Dell'Acqua F, Vedaldi D: Studies on the mechanism of action of mitomycin C. Farmaco Sci. 1978 Sep;33(9):651-66. [744262 ]
  4. Verweij J, Pinedo HM: Mitomycin C: mechanism of action, usefulness and limitations. Anticancer Drugs. 1990 Oct;1(1):5-13. [2131038 ]