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 solution20 mgIntravenous; IntravesicalHospira, Inc.1998-03-12Not applicableCanada
Mitomycin for Injection USPPowder, for solution20 mgIntravenous; IntravesicalAccord Healthcare LimitedNot applicableNot applicableCanada
Mitomycin for Injection USPPowder, for solution5 mgIntravenous; IntravesicalHospira, Inc.1998-07-15Not 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 solution20 mg/40mLIntravenousAccord Healthcare Limited2009-06-10Not applicableUs
MitomycinInjection, powder, lyophilized, for solution5 mg/10mLIntravenousAccord Healthcare Limited2013-05-03Not applicableUs
MitomycinInjection, powder, lyophilized, for solution5 mg/10mLIntravenousAccord Healthcare Limited2009-06-18Not applicableUs
MitomycinInjection, powder, lyophilized, for solution20 mg/10mLIntravenousAccord Healthcare Limited2013-05-03Not applicableUs
MitomycinInjection, powder, lyophilized, for solution40 mg/80mLIntravenousAccord Healthcare Limited2011-03-11Not applicableUs
MitomycinInjection, powder, lyophilized, for solution40 mg/10mLIntravenousAccord Healthcare Limited2013-05-03Not applicableUs
MutamycinInjection, powder, lyophilized, for solution40 mg/80mLIntravenousAccord Bio Pharma Inc.2016-10-03Not applicableUs
MutamycinInjection, powder, lyophilized, for solution5 mg/10mLIntravenousAccord 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
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Mitomycin.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Mitomycin.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Mitomycin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Mitomycin.Experimental
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Mitomycin.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Mitomycin.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Mitomycin.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Mitomycin.Approved, Investigational
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Mitomycin.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Mitomycin.Approved
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Mitomycin.Approved
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Mitomycin.Approved, Investigational
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Mitomycin.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Mitomycin.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Mitomycin.Approved, Investigational
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Mitomycin.Investigational
BelinostatThe serum concentration of Belinostat can be increased when it is combined with Mitomycin.Approved, Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Mitomycin.Approved, Vet Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Mitomycin.Approved, Investigational
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Mitomycin.Withdrawn
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
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Mitomycin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Mitomycin.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Mitomycin.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Mitomycin.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Mitomycin.Approved
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Mitomycin.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Mitomycin.Approved
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Mitomycin.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Mitomycin.Withdrawn
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Mitomycin.Approved, Vet Approved
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Mitomycin.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Mitomycin.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Mitomycin.Approved
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Mitomycin.Approved
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Mitomycin.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Mitomycin.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Mitomycin.Approved, Investigational
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Mitomycin.Approved
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Mitomycin.Approved, Nutraceutical
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
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Mitomycin.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Mitomycin.Approved
Conjugated estrogensThe serum concentration of Conjugated estrogens can be increased when it is combined with Mitomycin.Approved
CopanlisibThe serum concentration of Copanlisib 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
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Mitomycin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Mitomycin.Approved, Investigational
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Mitomycin.Approved, Investigational, Vet Approved
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
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Mitomycin.Approved
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Mitomycin.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Mitomycin.Approved
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Mitomycin.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Mitomycin.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined 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
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Mitomycin.Approved, Investigational, Vet Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Mitomycin.Approved, Illicit, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Mitomycin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Mitomycin.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Mitomycin.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Mitomycin.Illicit
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Mitomycin.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Mitomycin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Mitomycin.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Mitomycin.Approved, Investigational, Vet Approved
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
ElbasvirThe serum concentration of Elbasvir can be increased when it is combined with Mitomycin.Approved
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Mitomycin.Approved, Investigational
EnasidenibThe serum concentration of Enasidenib can be increased when it is combined with Mitomycin.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Mitomycin.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Mitomycin.Approved, Investigational
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Mitomycin.Approved, Vet Approved
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Mitomycin.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Mitomycin.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Mitomycin.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Mitomycin.Approved
EtoposideThe serum concentration of Etoposide 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
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Mitomycin.Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Mitomycin.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Mitomycin.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Mitomycin.Approved
FingolimodMitomycin may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Mitomycin.Approved
G17DTThe therapeutic efficacy of G17DT can be decreased when used in combination with Mitomycin.Investigational
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Mitomycin.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Mitomycin.Approved
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
GlecaprevirThe serum concentration of Glecaprevir can be increased when it is combined with Mitomycin.Approved
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Mitomycin.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Mitomycin.Withdrawn
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Mitomycin.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Mitomycin.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Mitomycin.Approved
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Mitomycin.Approved
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Mitomycin.Approved
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Mitomycin.Approved
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Mitomycin.Approved
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Mitomycin.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Mitomycin.Approved, Investigational
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
Inotuzumab ozogamicinThe serum concentration of Inotuzumab ozogamicin can be increased when it is combined with Mitomycin.Approved
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Mitomycin.Approved, Investigational
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Mitomycin.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Mitomycin.Approved
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Mitomycin.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Mitomycin.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Mitomycin.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Mitomycin.Experimental
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Mitomycin.Approved, Investigational
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
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Mitomycin.Approved
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Mitomycin.Approved
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Mitomycin.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Mitomycin.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Mitomycin.Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Mitomycin.Approved
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Mitomycin.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Mitomycin.Approved
MannitolThe serum concentration of Mannitol can be increased when it is combined with Mitomycin.Approved, Investigational
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Mitomycin.Withdrawn
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Mitomycin.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Mitomycin.Approved, Vet Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Mitomycin.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Mitomycin.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Mitomycin.Approved, Illicit
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Mitomycin.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Mitomycin.Approved, Investigational
MorphineThe serum concentration of Morphine can be increased when it is combined with Mitomycin.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Mitomycin.Approved, Investigational
NadololThe serum concentration of Nadolol can be increased when it is combined with Mitomycin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Mitomycin.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Mitomycin.Approved, Vet Approved
NatalizumabThe risk or severity of adverse effects can be increased when Mitomycin is combined with Natalizumab.Approved, Investigational
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Mitomycin.Approved
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Mitomycin.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Mitomycin.Approved
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Mitomycin.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Mitomycin.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Mitomycin.Approved
OdanacatibThe serum concentration of Odanacatib can be increased when it is combined with Mitomycin.Investigational
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Mitomycin.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Mitomycin.Experimental
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Mitomycin.Approved
OsimertinibThe serum concentration of Osimertinib can be increased when it is combined with Mitomycin.Approved
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
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Mitomycin.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Mitomycin.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Mitomycin.Experimental
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Mitomycin.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Mitomycin.Approved, Vet Approved
PibrentasvirThe serum concentration of Pibrentasvir can be increased when it is combined with Mitomycin.Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Mitomycin.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Mitomycin.Approved
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Mitomycin.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Mitomycin.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Mitomycin.Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Mitomycin.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Mitomycin.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Mitomycin.Approved, Vet Approved
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Mitomycin.Approved, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it 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
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Mitomycin.Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Mitomycin.Approved
QuinineThe serum concentration of Quinine 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
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Mitomycin.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Mitomycin.Approved, Investigational
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Mitomycin.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Mitomycin.Approved
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
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Mitomycin.Approved, Investigational
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Mitomycin.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Mitomycin.Approved
RoflumilastRoflumilast may increase the immunosuppressive activities of Mitomycin.Approved
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Mitomycin.Approved, Investigational
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
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Mitomycin.Approved, Vet Approved
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Mitomycin.Approved, Investigational
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Mitomycin.Approved
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Mitomycin.Approved
SimeprevirThe serum concentration of Simeprevir 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
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Mitomycin.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Mitomycin.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Mitomycin.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Mitomycin.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Mitomycin.Experimental
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
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Mitomycin.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Mitomycin.Experimental
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with Mitomycin.Investigational
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Mitomycin.Approved
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Mitomycin.Withdrawn
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Mitomycin.Approved
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with Mitomycin.Investigational
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Mitomycin.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Mitomycin.Approved
TofacitinibMitomycin may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Mitomycin.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Mitomycin.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Mitomycin.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Mitomycin.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Mitomycin.Approved
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Mitomycin.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Mitomycin.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Mitomycin.Approved
VelpatasvirThe serum concentration of Velpatasvir can be increased when it is combined with Mitomycin.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Mitomycin.Approved
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Mitomycin.Approved
VerapamilThe serum concentration of Verapamil can be increased when it is combined 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
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
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Mitomycin.Approved
VoxilaprevirThe serum concentration of Voxilaprevir can be increased when it is combined with Mitomycin.Approved
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with Mitomycin.Approved
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Mitomycin.Approved
Zoster vaccineThe therapeutic efficacy of Zoster 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
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
2Not Yet RecruitingTreatmentGlaucoma / Glaucoma, Neovascular / Glaucoma, Primary Open Angle (POAG) / Nonuveitic secondary glaucoma1
2RecruitingTreatmentAnus Neoplasms1
2RecruitingTreatmentBladder Cancers2
2RecruitingTreatmentEsophagogastric Junction / Gastric Adenocarcinoma1
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 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/40mL
Injection, powder, lyophilized, for solutionIntravenous20 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous40 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous40 mg/80mL
Injection, powder, lyophilized, for solutionIntravenous5 mg/10mL
Powder, for solutionIntravenous; Intravesical20 mg
Powder, for solutionIntravenous; Intravesical5 mg
Kit
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

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 October 21, 2017 19:21