Identification

Name
Mitomycin
Accession Number
DB00305  (APRD00284)
Type
Small Molecule
Groups
Approved
Description

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. [PubChem]

Structure
Thumb
Synonyms
  • 7-Amino-9alpha-methoxymitosane
  • Ametycine
  • Mitamycin
  • Mitocin-C
  • Mitomycin
  • Mitomycin C
  • MMC
External IDs
NSC-26980
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mitomycin for InjectionPowder, for solution20 mgIntravenous; IntravesicalTeva1997-10-22Not applicableCanada
Mitomycin for InjectionPowder, for solution5 mgIntravenous; IntravesicalTeva1997-10-222017-02-10Canada
Mitomycin for Injection USPPowder, for solution5 mgIntravenous; IntravesicalHospira, Inc.1998-07-15Not applicableCanada
Mitomycin for Injection USPPowder, for solution20 mgIntravenous; IntravesicalAccord Healthcare LimitedNot applicableNot applicableCanada
Mitomycin for Injection USPPowder, for solution20 mgIntravenous; IntravesicalHospira, Inc.1998-03-12Not applicableCanada
MitosolKitMobius Therapeutics LLC2012-02-08Not applicableUs
Mutamycin Inj 20mg/vialPowder, for solution20 mgIntravenous; IntravesicalBristol Myers Squibb1984-12-312006-05-29Canada
Mutamycin Inj 5mg/vialPowder, for solution0.5 mgIntravenous; IntravesicalBristol Myers Squibb1977-12-312006-05-29Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MitomycinInjection, powder, lyophilized, for solution40 mg/10mLIntravenousAccord Healthcare Limited2013-05-03Not applicableUs
MitomycinInjection, powder, lyophilized, for solution40 mg/80mLIntravenousAccord Healthcare Limited2011-03-11Not applicableUs
MitomycinInjection, powder, lyophilized, for solution20 mg/10mLIntravenousAccord Healthcare Limited2013-05-03Not applicableUs
MitomycinInjection, powder, lyophilized, for solution5 mg/10mLIntravenousAccord Healthcare Limited2009-06-18Not applicableUs
MitomycinInjection, powder, lyophilized, for solution5 mg/10mLIntravenousAccord Healthcare Limited2013-05-03Not applicableUs
MitomycinInjection, powder, lyophilized, for solution20 mg/40mLIntravenousAccord Healthcare Limited2009-06-10Not applicableUs
MutamycinInjection, powder, lyophilized, for solution5 mg/10mLIntravenousAccord Bio Pharma Inc.2016-10-03Not applicableUs
MutamycinInjection, powder, lyophilized, for solution40 mg/80mLIntravenousAccord Bio Pharma Inc.2016-10-03Not applicableUs
MutamycinInjection, powder, lyophilized, for solution20 mg/40mLIntravenousAccord Bio Pharma Inc.2016-10-03Not applicableUs
International/Other Brands
Mitozytrex / Mutamycin
Categories
UNII
50SG953SK6
CAS number
50-07-7
Weight
Average: 334.3272
Monoisotopic: 334.127719706
Chemical Formula
C15H18N4O5
InChI Key
NWIBSHFKIJFRCO-WUDYKRTCSA-N
InChI
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
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
SMILES
CO[[email protected]]12[[email protected]]3N[[email protected]]3CN1C1=C([[email protected]]2COC(N)=O)C(=O)C(N)=C(C)C1=O

Pharmacology

Indication

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.

Structured Indications
Pharmacodynamics

Mitomycin is one of the older chemotherapy drugs, which has been around and in use for decades. It is an antibiotic which has been shown to have antitumor activity. Mitomycin selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of mitomycin-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. Mitomycin has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2.

Mechanism of action

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.

TargetActionsOrganism
ADNA
antagonist
cross-linking/alkylation
Human
Absorption

Erratic.

Volume of distribution
Not Available
Protein binding
Not Available
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

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 23 mg/kg; Oral, rat: LD50 = 30 mg/kg. Symptoms of overdose include nausea and vomiting.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Mitomycin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Mitomycin.Experimental
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Mitomycin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Mitomycin.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Mitomycin.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Mitomycin.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Mitomycin.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Mitomycin.Approved
Clostridium tetani toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Clostridium tetani toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Mitomycin.Approved
ClozapineThe risk or severity of adverse effects can be increased when Mitomycin is combined with Clozapine.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Mitomycin.Approved
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Mitomycin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Mitomycin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Mitomycin.Experimental
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Mitomycin.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Mitomycin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Mitomycin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Mitomycin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Mitomycin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Mitomycin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Mitomycin.Approved, Investigational
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Mitomycin.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Mitomycin.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Mitomycin.Approved
FingolimodMitomycin may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
G17DTThe therapeutic efficacy of G17DT can be decreased when used in combination with Mitomycin.Investigational
GI-5005The therapeutic efficacy of GI-5005 can be decreased when used in combination with Mitomycin.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Mitomycin.Experimental
Hepatitis A VaccineThe therapeutic efficacy of Hepatitis A Vaccine can be decreased when used in combination with Mitomycin.Approved
Hepatitis B Vaccine (Recombinant)The therapeutic efficacy of Hepatitis B Vaccine (Recombinant) can be decreased when used in combination with Mitomycin.Approved, Withdrawn
INGN 201The therapeutic efficacy of INGN 201 can be decreased when used in combination with Mitomycin.Investigational
INGN 225The therapeutic efficacy of INGN 225 can be decreased when used in combination with Mitomycin.Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Mitomycin.Experimental
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Mitomycin.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Mitomycin is combined with Leflunomide.Approved, Investigational
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Mitomycin.Investigational, Withdrawn
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Mitomycin.Experimental
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Mitomycin.Approved
NatalizumabThe risk or severity of adverse effects can be increased when Mitomycin is combined with Natalizumab.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Mitomycin.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Mitomycin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Mitomycin.Approved, Vet Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Mitomycin.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Mitomycin.Experimental
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Mitomycin.Approved, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Mitomycin.Experimental
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Mitomycin.Approved
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Mitomycin is combined with Rabies virus inactivated antigen, A.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Mitomycin.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Mitomycin.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Mitomycin.Approved, Investigational
RindopepimutThe therapeutic efficacy of Rindopepimut can be decreased when used in combination with Mitomycin.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Mitomycin.Approved
Rotavirus VaccineThe therapeutic efficacy of Rotavirus Vaccine can be decreased when used in combination with Mitomycin.Approved
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Mitomycin.Approved
Salmonella typhi ty21a live antigenThe therapeutic efficacy of Salmonella typhi ty21a live antigen can be decreased when used in combination with Mitomycin.Approved
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Mitomycin.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Mitomycin.Approved
SRP 299The therapeutic efficacy of SRP 299 can be decreased when used in combination with Mitomycin.Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Mitomycin.Approved, Investigational
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with Mitomycin.Investigational
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with Mitomycin.Investigational
TofacitinibMitomycin may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Mitomycin.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Mitomycin.Approved, Investigational
Varicella Zoster Vaccine (Live/Attenuated)The therapeutic efficacy of Zoster vaccine can be decreased when used in combination with Mitomycin.Approved
VinblastineThe risk or severity of adverse effects can be increased when Vinblastine is combined with Mitomycin.Approved
VincamineThe risk or severity of adverse effects can be increased when Vincamine is combined with Mitomycin.Experimental
VincristineThe serum concentration of Vincristine can be increased when it is combined with Mitomycin.Approved, Investigational
VincristineThe risk or severity of adverse effects can be increased when Vincristine is combined with Mitomycin.Approved, Investigational
VindesineThe risk or severity of adverse effects can be increased when Vindesine is combined with Mitomycin.Approved, Investigational
VinflunineThe risk or severity of adverse effects can be increased when Vinflunine is combined with Mitomycin.Approved
VinorelbineThe risk or severity of adverse effects can be increased when Vinorelbine is combined with Mitomycin.Approved, Investigational
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with Mitomycin.Approved
Food Interactions
Not Available

References

Synthesis Reference

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

US5523411
General References
Not Available
External Links
Human Metabolome Database
HMDB14450
KEGG Drug
D00208
KEGG Compound
C06681
PubChem Compound
5746
PubChem Substance
46508353
ChemSpider
5544
BindingDB
50428658
ChEBI
27504
ChEMBL
CHEMBL105
Therapeutic Targets Database
DAP001402
PharmGKB
PA450524
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mitomycin
ATC Codes
L01DC03 — Mitomycin
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (82.3 KB)
MSDS
Download (77.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentSuperficial Bladder Cancer / Transitional Cell Carcinoma of Bladder1
1Active Not RecruitingTreatmentLiver Cancer1
1Active Not RecruitingTreatmentLocally Advanced Cancer in the Anal Region1
1CompletedTreatmentHepatocellular,Carcinoma / Liver Cancer / Localized Unresectable Liver Cancer1
1CompletedTreatmentLeukemias1
1CompletedTreatmentNon-muscle Invasive Bladder Cancer (NMIBC)1
1CompletedTreatmentSolid Neoplasms1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentUrinary Bladder Neoplasms1
1RecruitingTreatmentDiseases of Oesophagus Stomach and Duodenum1
1Unknown StatusNot AvailableMyopia1
1Unknown StatusTreatmentRefractory Glaucoma1
1, 2CompletedTreatmentGlaucoma / Trabeculectomy1
1, 2CompletedTreatmentNeoplasms Metastasis / Neoplasms, Gastrointestinal1
1, 2RecruitingTreatmentAdvanced Hepatocellular Carcinoma / Recurrence Hepatocellular Carcinoma1
1, 2Unknown StatusPreventionBladder Cancers1
2Active Not RecruitingTreatmentCarcinoma of the Appendix / Primary Peritoneal Cavity Cancer1
2Active Not RecruitingTreatmentGastrointestinal Cancers1
2CompletedTreatmentAdenocarcinoma of Colon / Adenocarcinoma of Rectum / Metastatic Disease1
2CompletedTreatmentAdhesions of Nasal Cavity / Nasal Adhesions / Nasal Synechiae / Tissue Adhesions1
2CompletedTreatmentAnal Carcinoma1
2CompletedTreatmentBiliary Tract Cancer1
2CompletedTreatmentBladder Cancers1
2CompletedTreatmentBladder Cancers / Neoplasms / Urinary Bladder Diseases / Urologic Diseases1
2CompletedTreatmentCancer of Stomach / Esophageal Cancers / Esophagus Cancer / Malignant Neoplasm of Stomach1
2CompletedTreatmentLiver Cancer1
2CompletedTreatmentLiver Cancer / Metastatic Cancers1
2CompletedTreatmentMalignant Neoplasm of Pancreas2
2CompletedTreatmentMetastatic Cancers / Sarcomas1
2CompletedTreatmentPterygium1
2CompletedTreatmentSuperficial Bladder Cancer1
2Not Yet RecruitingTreatmentCancer, Appendiceal / Colorectal Cancers1
2RecruitingTreatmentAnus Neoplasms1
2RecruitingTreatmentBladder Cancers2
2RecruitingTreatmentEsophagogastric Junction / Gastric Adenocarcinoma1
2RecruitingTreatmentGlaucoma / Glaucoma, Neovascular / Glaucoma, Primary Open Angle (POAG) / Nonuveitic secondary glaucoma1
2RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2RecruitingTreatmentPrimary Sclerosing Cholangitis (PSC)1
2RecruitingTreatmentSquamous Cell Carcinoma of the Head and Neck (SCCHN) / Squamous Cell Carcinoma, Head And Neck1
2RecruitingTreatmentUrothelial Carcinoma of the Bladder1
2TerminatedTreatmentCarcinoma of Anal Canal1
2TerminatedTreatmentColorectal Cancers1
2TerminatedTreatmentHepatocellular,Carcinoma1
2TerminatedTreatmentMalignant Neoplasm of Pancreas1
2TerminatedTreatmentMetastatic Cancers1
2TerminatedTreatmentSarcomas2
2Unknown StatusTreatmentCancer, Breast / Metastasis1
2Unknown StatusTreatmentCarcinoma of the Appendix / Colorectal Cancers / Primary Peritoneal Cavity Cancer1
2Unknown StatusTreatmentColorectal Cancers / Metastatic Cancers / Primary Peritoneal Cavity Cancer1
2Unknown StatusTreatmentLiver Metastasis1
2Unknown StatusTreatmentLung Cancers1
2Unknown StatusTreatmentMesothelioma, Malignant2
2WithdrawnDiagnosticMalignant Neoplasm of Pancreas1
2WithdrawnTreatmentHepatocellular,Carcinoma / Lung Metastasis1
2, 3CompletedTreatmentGlaucoma3
2, 3RecruitingPreventionCorneal Opacity1
2, 3TerminatedTreatmentAnal Carcinoma1
3Active Not RecruitingTreatmentBladder Cancers1
3Active Not RecruitingTreatmentHepatocellular,Carcinoma / Non-Resectable Hepatocellular Carcinoma1
3CompletedTreatmentAnal Carcinoma2
3CompletedTreatmentBladder Cancers2
3CompletedTreatmentCancer, Breast1
3CompletedTreatmentCarcinoma of Unknown Primary / Head and Neck Carcinoma1
3CompletedTreatmentCervical Cancers1
3CompletedTreatmentColorectal Cancers / Metastatic Cancers1
3CompletedTreatmentGlaucoma / Trabeculectomy1
3CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
3CompletedTreatmentLung Cancers1
3CompletedTreatmentMalignant Neoplasm of Stomach1
3CompletedTreatmentMesothelioma, Malignant1
3Enrolling by InvitationTreatmentAnus Diseases / Anus Neoplasms / Carcinoma NOS / Neoplasms / Neoplasms, Squamous Cell / Squamous Cell Carcinoma (SCC)1
3RecruitingBasic ScienceUrinary Bladder Neoplasms1
3RecruitingTreatmentAnal Carcinoma1
3RecruitingTreatmentBladder Cancers1
3RecruitingTreatmentChronic Rhinosinusitis / Postoperative Nasal Synerchia1
3RecruitingTreatmentNon Muscle Invasive Bladder Cancer1
3RecruitingTreatmentSuperficial Bladder Cancer1
3TerminatedTreatmentBladder Cancers2
3TerminatedTreatmentCarcinoma in Situ / Mycobacterium / Neoplasm Recurrence, Local / Neoplasm, Bladder / Transitional Cell, Carcinoma1
3Unknown StatusTreatmentBladder Cancers1
3Unknown StatusTreatmentColorectal Cancers1
3Unknown StatusTreatmentGlaucoma1
3Unknown StatusTreatmentHepatocellular,Carcinoma1
3Unknown StatusTreatmentLung Cancers3
3Unknown StatusTreatmentMalignant Neoplasm of Pancreas1
3WithdrawnTreatmentHepatocellular,Carcinoma1
4CompletedPreventionGlaucoma1
4CompletedTreatmentConjunctival Intraepithelial Neoplasia / Corneal Intraepithelial Neoplasia1
4CompletedTreatmentDisorders, Refractive1
4CompletedTreatmentGlaucoma1
4CompletedTreatmentOpen Angle Glaucoma (OAG)1
4Not Yet RecruitingPreventionPterygium1
4RecruitingPreventionPresbyopia2
4Unknown StatusTreatmentGlaucoma1
Not AvailableActive Not RecruitingNot AvailableFunction of Mitomycin C in Cornea1
Not AvailableCompletedTreatmentCorneal Diseases1
Not AvailableNot Yet RecruitingTreatmentObstructive Airway Disease1
Not AvailableRecruitingTreatmentGlaucoma1
Not AvailableUnknown StatusNot AvailableHepatocellular,Carcinoma1
Not AvailableUnknown StatusPreventionOpen-angle Glaucoma (OAG)1
Not AvailableUnknown StatusTreatmentBleb1
Not AvailableUnknown StatusTreatmentCaustic Esophageal Stricture / Esophageal Strictures / Peptic Esophageal Stricture / Post-Surgical Esophageal Stricture1

Pharmacoeconomics

Manufacturers
  • Accord healthcare inc
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Supergen inc
  • Bristol laboratories inc div bristol myers co
  • Bristol myers co
Packagers
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous20 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous40 mg/10mL
Powder, for solutionIntravenous; Intravesical20 mg
Powder, for solutionIntravenous; Intravesical5 mg
Kit
Injection, powder, lyophilized, for solutionIntravenous20 mg/40mL
Injection, powder, lyophilized, for solutionIntravenous40 mg/80mL
Injection, powder, lyophilized, for solutionIntravenous5 mg/10mL
Powder, for solutionIntravenous; Intravesical0.5 mg
Prices
Unit descriptionCostUnit
Mutamycin 40 mg vial878.48USD vial
Mutamycin 20 mg vial434.8USD vial
Mitomycin 40 mg vial300.0USD vial
Mitomycin 20 mg vial142.55USD vial
Mutamycin 5 mg vial128.75USD vial
Mitomycin 5 mg vial52.43USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8186511No2006-07-192026-07-19Us
US9205075No2006-07-192026-07-19Us
US7806265No2009-02-012029-02-01Us
US9649428No2009-05-212029-05-21Us
US9539241No2008-01-022028-01-02Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>360 °CPhysProp
boiling point (°C)534 °CPhysProp
water solubilitySoluble (8430 mg/L)Not Available
logP-0.40HANSCH,C ET AL. (1995)
pKa10.9HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility10.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.27 m3·mol-1ChemAxon
Polarizability32.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9154
Blood Brain Barrier-0.9659
Caco-2 permeable-0.6572
P-glycoprotein substrateSubstrate0.7861
P-glycoprotein inhibitor INon-inhibitor0.7231
P-glycoprotein inhibitor IINon-inhibitor0.5469
Renal organic cation transporterNon-inhibitor0.8032
CYP450 2C9 substrateNon-substrate0.8997
CYP450 2D6 substrateNon-substrate0.8332
CYP450 3A4 substrateSubstrate0.6879
CYP450 1A2 substrateNon-inhibitor0.5813
CYP450 2C9 inhibitorNon-inhibitor0.7642
CYP450 2D6 inhibitorNon-inhibitor0.7464
CYP450 2C19 inhibitorNon-inhibitor0.6115
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5204
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.9263
BiodegradationNot ready biodegradable1.0
Rat acute toxicity4.0153 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9788
hERG inhibition (predictor II)Non-inhibitor0.7214
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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
Indoles / Quinones / Pyrrolizines / Piperazines / Vinylogous amides / Pyrrolines / Pyrrolidines / Azacyclic compounds / Aziridines / Carboximidic acids and derivatives
show 7 more
Substituents
Mitomycin / Indole / Quinone / Pyrrolizine / 1,4-diazinane / Piperazine / Pyrrolidine / Vinylogous amide / Pyrroline / Ketone
show 19 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
mitomycin (CHEBI:27504) / Quinones (C06681)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
Cross-linking/alkylation
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. [PubMed: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. [PubMed: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. [PubMed:744262]
  4. Verweij J, Pinedo HM: Mitomycin C: mechanism of action, usefulness and limitations. Anticancer Drugs. 1990 Oct;1(1):5-13. [PubMed:2131038]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name
POR
Uniprot ID
P16435
Uniprot Name
NADPH--cytochrome P450 reductase
Molecular Weight
76689.12 Da
References
  1. Bligh HF, Bartoszek A, Robson CN, Hickson ID, Kasper CB, Beggs JD, Wolf CR: Activation of mitomycin C by NADPH:cytochrome P-450 reductase. Cancer Res. 1990 Dec 15;50(24):7789-92. [PubMed:2123741]
  2. Vromans RM, van de Straat R, Groeneveld M, Vermeulen NP: One-electron reduction of mitomycin c by rat liver: role of cytochrome P-450 and NADPH-cytochrome P-450 reductase. Xenobiotica. 1990 Sep;20(9):967-78. [PubMed:2122607]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18