General Information of Drug (ID: DMH0ZJE)

Drug Name
Mitomycin
Synonyms
Mitomycin C; mitomycin C; 1950/7/7; Mutamycin; Ametycine; Mitocin-C; Ametycin; Mitomycin-C; Mytozytrex; Mitomycinum; Mytomycin; Mitozytrex; Mitomycinum C; Mitocin C; Mitomycins; Mitamycin; MMC; Mitosol; Mitomycyna C; 7-Amino-9alpha-methoxymitosane; NSC-26980; Mitomycyna C [Polish]; Mito-C; Mit-C; Mitomycin (TN); Mitomycinum [INN-Latin]; Mitomycine [INN-French]; Mitomicina [INN-Spanish]; NCI-C04706; RCRA waste number U010; NSC26980; NSC 26980; Mitomycine; CCRIS 414; UNII-50SG953SK6; HSDB 3239; C15H18N4O5; EINECS 200-008-6; Mitomycin C,; Ametycin; Mitomicina; Muamycin; Mitomycin C from Streptomyces caespitosus; Mitomycin C (JP15); Mitomycin C, Streptomyces caespitosus; Muamycin (TN); Mitomycin (USP/INN); Mitomycin [USAN:INN:BAN]; Mitomycin C, Streptomyces caespitosus, Carrier-Free
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Approved [1], [2]
Gastrointestinal cancer 2C11 Approved [1], [2]
Solid tumour/cancer 2A00-2F9Z Approved [2]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 334.33
Topological Polar Surface Area (xlogp) -0.4
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Absorption
The drug is unstablely absorbed [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 8 - 48 minutes [4]
Metabolism
The drug is metabolized via the hepatic [3]
Chemical Identifiers
Formula
C15H18N4O5
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
Canonical SMILES
CC1=C(C(=O)C2=C(C1=O)N3C[C@H]4[C@@H]([C@@]3([C@@H]2COC(=O)N)OC)N4)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
InChIKey
NWIBSHFKIJFRCO-WUDYKRTCSA-N
Cross-matching ID
PubChem CID
5746
ChEBI ID
CHEBI:27504
CAS Number
50-07-7
DrugBank ID
DB00305
TTD ID
D0Y0GH
VARIDT ID
DR01212
ACDINA ID
D01255

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human Deoxyribonucleic acid (hDNA) TTUTN1I NOUNIPROTAC Binder [5], [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Mitomycin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Roflumilast DMPGHY8 Moderate Additive immunosuppressive effects by the combination of Mitomycin and Roflumilast. Asthma [CA23] [24]
Ofloxacin DM0VQN3 Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Ofloxacin. Bacterial infection [1A00-1C4Z] [25]
Ciprofloxacin XR DM2NLS9 Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Ciprofloxacin XR. Bacterial infection [1A00-1C4Z] [25]
Trovafloxacin DM6AN32 Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Trovafloxacin. Bacterial infection [1A00-1C4Z] [25]
Sparfloxacin DMB4HCT Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Sparfloxacin. Bacterial infection [1A00-1C4Z] [25]
Gemifloxacin DMHT34O Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Gemifloxacin. Bacterial infection [1A00-1C4Z] [25]
Norfloxacin DMIZ6W2 Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Norfloxacin. Bacterial infection [1A00-1C4Z] [25]
ABT-492 DMJFD2I Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by ABT-492. Bacterial infection [1A00-1C4Z] [25]
Levofloxacin DMS60RB Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Levofloxacin. Bacterial infection [1A00-1C4Z] [25]
Lomefloxacin DMVRH9C Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Lomefloxacin. Bacterial infection [1A00-1C4Z] [25]
Grepafloxacin DMGLX0T Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Grepafloxacin. Bronchitis [CA20] [25]
Teriflunomide DMQ2FKJ Major Additive immunosuppressive effects by the combination of Mitomycin and Teriflunomide. Hyper-lipoproteinaemia [5C80] [26]
Denosumab DMNI0KO Moderate Additive myelosuppressive effects by the combination of Mitomycin and Denosumab. Low bone mass disorder [FB83] [27]
Thalidomide DM70BU5 Major Additive thrombogenic effects by the combination of Mitomycin and Thalidomide. Multiple myeloma [2A83] [28]
Tecfidera DM2OVDT Moderate Additive immunosuppressive effects by the combination of Mitomycin and Tecfidera. Multiple sclerosis [8A40] [29]
Siponimod DM2R86O Major Additive immunosuppressive effects by the combination of Mitomycin and Siponimod. Multiple sclerosis [8A40] [30]
Fingolimod DM5JVAN Major Additive immunosuppressive effects by the combination of Mitomycin and Fingolimod. Multiple sclerosis [8A40] [31]
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Mitomycin and Ocrelizumab. Multiple sclerosis [8A40] [32]
Ozanimod DMT6AM2 Major Additive immunosuppressive effects by the combination of Mitomycin and Ozanimod. Multiple sclerosis [8A40] [24]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive immunosuppressive effects by the combination of Mitomycin and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [33]
Gatifloxacin DMSL679 Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Gatifloxacin. Respiratory infection [CA07-CA4Z] [25]
Canakinumab DM8HLO5 Moderate Additive immunosuppressive effects by the combination of Mitomycin and Canakinumab. Rheumatoid arthritis [FA20] [34]
Rilonacept DMGLUQS Moderate Additive immunosuppressive effects by the combination of Mitomycin and Rilonacept. Rheumatoid arthritis [FA20] [34]
Golimumab DMHZV7X Major Additive immunosuppressive effects by the combination of Mitomycin and Golimumab. Rheumatoid arthritis [FA20] [35]
Leflunomide DMR8ONJ Major Additive immunosuppressive effects by the combination of Mitomycin and Leflunomide. Rheumatoid arthritis [FA20] [26]
Anthrax vaccine DM9GSWY Moderate Antagonize the effect of Mitomycin when combined with Anthrax vaccine. Sepsis [1G40-1G41] [36]
Fostamatinib DM6AUHV Moderate Decreased clearance of Mitomycin due to the transporter inhibition by Fostamatinib. Thrombocytopenia [3B64] [37]
Azathioprine DMMZSXQ Moderate Additive immunosuppressive effects by the combination of Mitomycin and Azathioprine. Transplant rejection [NE84] [30]
Cinoxacin DM4EWNS Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Cinoxacin. Urinary tract infection [GC08] [25]
Nalidixic acid DMRM0JV Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Nalidixic acid. Urinary tract infection [GC08] [25]
Enoxacin DMYTE6L Minor Decreased absorption of Mitomycin due to intestinal mucosa variation caused by Enoxacin. Urinary tract infection [GC08] [25]
Ganciclovir DM1MBYQ Moderate Increased risk of nephrotoxicity by the combination of Mitomycin and Ganciclovir. Virus infection [1A24-1D9Z] [30]
Valganciclovir DMS2IUH Moderate Increased risk of nephrotoxicity by the combination of Mitomycin and Valganciclovir. Virus infection [1A24-1D9Z] [30]
⏷ Show the Full List of 33 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Hypromellose E00634 Not Available Coating agent
Polyethylene glycol 4000 E00654 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Water E00035 962 Solvent
Hydroxyethyl-beta-cyclodextrin E00631 Not Available Other agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Mitomycin 40mg/vial powder 40mg/vial Powder Pyelocalyceal
Mitomycin 0.2mg/vial For solution 0.2mg/vial For Solution Topical
Mitomycin 5mg/vial injectable 5mg/vial Injectable Injection
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7089).
2 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
3 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Assessment of cell viability, lipid peroxidation and quantification of DNA fragmentation after the treatment of anticancerous drug mitomycin C and ... Exp Toxicol Pathol. 2010 Sep;62(5):503-8.
6 Structural studies of atom-specific anticancer drugs acting on DNA. Pharmacol Ther. 1999 Sep;83(3):181-215.
7 In vivo expansion of MDR1-transduced cells accompanied by a post-transplantation chemotherapy regimen with mitomycin C and methotrexate. J Gene Med. 2010 Jul;12(7):596-603.
8 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
9 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
10 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
11 Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
12 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
13 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
14 Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50.
15 Cisplatin and DNA repair in cancer chemotherapy.Trends Biochem Sci.1995 Oct;20(10):435-9.
16 Structures of oxaliplatin-oligonucleotide adducts from DNA.J Mass Spectrom.2012 Oct;47(10):1282-93.
17 31P NMR spectra of ethidium, quinacrine, and daunomycin complexes with poly(adenylic acid).poly(uridylic acid) RNA duplex and calf thymus DNA. Biochemistry. 1989 Apr 4;28(7):2804-12.
18 Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35.
19 O6-methylguanine-DNA methyltransferase activity and sensitivity to cyclophosphamide and cisplatin in human lung tumor xenografts. Int J Cancer. 1998 Sep 11;77(6):919-22.
20 Inhibition of carboplatin-induced DNA interstrand cross-link repair by gemcitabine in patients receiving these drugs for platinum-resistant ovarian cancer.Clin Cancer Res.2010 Oct 1;16(19):4899-905.
21 DNA intrastrand cross-link at the 5'-GA-3' sequence formed by busulfan and its role in the cytotoxic effect. Cancer Sci. 2004 May;95(5):454-8.
22 Brca2/Xrcc2 dependent HR, but not NHEJ, is required for protection against O(6)-methylguanine triggered apoptosis, DSBs and chromosomal aberrations... DNA Repair (Amst). 2009 Jan 1;8(1):72-86.
23 Predicting the myelotoxicity of chemotherapy: the use of pretreatment O6-methylguanine-DNA methyltransferase determination in peripheral blood mono... Melanoma Res. 2011 Dec;21(6):502-8.
24 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
25 Johnson EJ, MacGowan AP, Potter MN, et al "Reduced absorption of oral ciprofloxacin after chemotherapy for haematological malignancy." J Antimicrob Chemother 25 (1990): 837-42. [PMID: 2373666]
26 Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
27 Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA.
28 Bennett CL, Nebeker JR, Samore MH, et al "The Research on Adverse Drug Events and Reports (RADAR) project." JAMA 293 (2005): 2131-40. [PMID: 15870417]
29 Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
30 Cerner Multum, Inc. "Australian Product Information.".
31 Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
32 Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
33 Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
34 Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
35 Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
36 CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058]
37 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.