ContaminantDB: Mitomycin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:32 UTC

Update Date

2026-05-14 16:25:18 UTC

Accession Number

CHEM002165

Identification

Common Name

Mitomycin

Class

Small Molecule

Description

Mitomycin 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.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Alkylating Agent
Amide
Amine
Antibiotic, Antineoplastic
Cross-Linking Reagent
Drug
Ester
Ether
Metabolite
Nucleic Acid Synthesis Inhibitor
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7-Amino-9alpha-methoxymitosane	ChEBI
Ametycine	ChEBI
Mitocin-C	ChEBI
MMC	ChEBI
Mutamycin	ChEBI
Mitomycin C	Kegg
Muamycin	Kegg
7-Amino-9a-methoxymitosane	Generator
7-Amino-9α-methoxymitosane	Generator
Mitamycin	HMDB
Mitocin C	HMDB
Mitomycin-C	HMDB
MitocinC	HMDB
Mitomycin	ChEBI

Chemical Formula

C₁₅H₁₈N₄O₅

Average Molecular Mass

334.327 g/mol

Monoisotopic Mass

334.128 g/mol

CAS Registry Number

50-07-7

IUPAC Name

[(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

Traditional Name

mitomycin c

SMILES

CO[C@]12[C@H]3N[C@H]3CN1C1=C([C@H]2COC(N)=O)C(=O)C(N)=C(C)C1=O

InChI Identifier

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

InChI Key

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolequinones

Direct Parent

Mitomycins

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

mitomycin (CHEBI:27504 )
Quinones (C06681 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	>360°C
Boiling Point	534°C
Solubility	Soluble (8430 mg/L)

Predicted Properties

Property	Value	Source
Water Solubility	10.1 g/L	ALOGPS
logP	-0.55	ALOGPS
logP	-3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	-0.3	ChemAxon
pKa (Strongest Basic)	6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	146.89 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.27 m³·mol⁻¹	ChemAxon
Polarizability	32.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-9032000000-addf881f05b59bd45e65	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-0950000000-a3b5f2c191b66d80a863	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0090000000-894659e6d592c7512847	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-e936bf9eaf319819a3cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-1039000000-d46d2d90cca8822c99bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0603-2094000000-94a0851dbf07fb7b2ede	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9010000000-93ec12977feffeac422b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9012000000-22f59cef40bc61653f39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-0e9aba8bfa2e95134f7e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9010000000-fdd39ddcbff28d118e30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0093000000-0f143a27a21adb246823	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0036-3091000000-9147b389119a364d0a6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-4093000000-4df228a8d47a45ccd618	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dm-0090000000-378c12a5c718b619eafc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0092000000-1f40ea88019c1692b82c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-1095000000-4c654596a0b5503fe79d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Intravesical, erratic, intravenous.

Mechanism of Toxicity

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.

Metabolism

Primarily 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 Values

LD50: 23 mg/kg (Oral, Mouse) (1) LD50: 30 mg/kg (Oral, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (2)

Uses/Sources

For 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 Level

Not Available

Health Effects

Mitomycin 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.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00305

HMDB ID

HMDB0014450

FooDB ID