Compounds > mitomycin a
Page last updated: 2024-12-06

mitomycin a

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Description

mitomycin A: RN given refers to (1aS-(1aalpha,8beta,8aalpha,8balpha))-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

mitomycin A : A member of the family of mitomycins that exhibits antibiotic and antitumour properties as well as a high level of toxicity. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID19972
CHEMBL ID298359
CHEBI ID85412
SCHEMBL ID13033872
MeSH IDM0133476

Synonyms (22)

Synonym
4055-39-4
nsc-75986
mitomycin a
azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methyl-, (1ar-(1aalpha,8beta,8aalpha,8balpha))-
nsc 75986
azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-6,8a-dimethoxy-5-methyl-, carbamate (ester)
hsdb 3418
[(1as,8s,8ar,8bs)-6,8a-dimethoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate
CHEMBL298359
chebi:85412 ,
87tmg6fjhv ,
unii-87tmg6fjhv
SCHEMBL13033872
mitomycin a [mi]
mitomycin impurity b [ep impurity]
azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methyl-, (1as,8s,8ar,8bs)-
HYFMSAFINFJTFH-NGSRAFSJSA-N
mitomycina
C21161
Q22252148
DTXSID201318131
AKOS040755422
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
toxinPoisonous substance produced by a biological organism such as a microbe, animal or plant.
antimicrobial agentA substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
alkylating agentHighly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
mitomycinA family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (102)

Assay IDTitleYearJournalArticle
AID1133511Induction of lambda-bacteriophage expression in Escherichia coli assessed as induction of plaques at 0.05 ug/ml relative to control1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID1149655Toxicity in Escherichia coli W1709(lambda) at 0.05 ug/ml1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1149667Toxicity in CDF1 mouse allografted with mouse P388 cells assessed as change in weight at 0.4 mg/kg/day administered qd on day 1 and 5 (Rvb = 3.4 g)1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID110915Degree of leukopenia produced by compound is assessed form Percent change in white cells on days 51981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID1149679Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 1.6 mg/kg/day administered qd on day 1 and 5 measured on day 301977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID432750Toxicity in ip dosed ddY mouse bearing mouse S180 cells2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Aziridine alkaloids as potential therapeutic agents.
AID39559Antitumor activity against subcutaneously B16 melanoma cells in mice expressed as ratio of median survival time for treated group to that of control group at an optimal dose of 0.3 mg/kg1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Preparation and antitumor activity of new mitomycin A analogues.
AID1133515Toxicity in lambda-bacteriophage infected Escherichia coli at 0.8 ug/ml1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID78806in vitro inhibition of tumor cell growth in cultured HCT-8 human tumor cell line2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Synthesis, DNA cross-linking activity, and cytotoxicity of dimeric mitomycins.
AID1133503Antibacterial activity against Staphylococcus aureus Smith P assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID1133499Antibacterial activity against Escherichia coli K-12 assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID88850Antitumor potency on human ovarian 2780 cell lines.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Structure-activity relationships for mitomycin C and mitomycin A analogues.
AID1149661Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as effect on median survival time at 0.2 mg/kg/day administered qd on day 1 and 5 relative to control1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1133504Antibacterial activity against Staphylococcus aureus 209P assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID87724In vitro anticellular activity against HeLa S3 cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Synthesis and antitumor activity of novel 6-alkyl-6-demethylmitomycins.
AID1149675Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 0.2 mg/kg/day administered qd on day 1 and 5 measured on day 51977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID8298in vitro anticancer activity against cultured A549 human tumor(lung) cell line2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Synthesis, DNA cross-linking activity, and cytotoxicity of dimeric mitomycins.
AID214043in vitro anticancer activity against cultured U87MG (glioblastoma) human tumor cell line2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Synthesis, DNA cross-linking activity, and cytotoxicity of dimeric mitomycins.
AID1149672Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 1.6 mg/kg/day administered qd on day 1 and 5 measured on day 51977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1133517Toxicity in lambda-bacteriophage infected Escherichia coli at 0.05 ug/ml1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID23505Partition coefficient (logP)1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Preparation and antitumor activity of new mitomycin A analogues.
AID1149683Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 0.1 mg/kg/day administered qd on day 1 and 5 measured on day 301977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1133506Antibacterial activity against Sarcina lutea assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID153944Minimum effective dose was determined on P388 leukemia cells in mice1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Preparation and antitumor activity of additional mitomycin A analogues.
AID1149671Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 3.2 mg/kg/day administered qd on day 1 and 5 measured on day 51977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1149678Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 3.2 mg/kg/day administered qd on day 1 and 5 measured on day 301977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID23684Calculated partition coefficient for the compound (logP)1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Structure-activity relationships for mitomycin C and mitomycin A analogues.
AID110925Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 1.3 mg/kg on day 51981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID110920Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 0.96 mg/kg on day 71981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID26044log(1/C) was estimated in mice1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Preparation and antitumor activity of additional mitomycin A analogues.
AID1149657Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as effect on median survival time at 3.2 mg/kg/day administered qd on day 1 and 5 relative to control1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID221155in vitro inhibition of tumor cell growth in cultured HepG2 human tumor cell line2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Synthesis, DNA cross-linking activity, and cytotoxicity of dimeric mitomycins.
AID1133507Antibacterial activity against Mycobacterium smegmatis 607 assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID110927Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 1.3 mg/kg on day 31981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID1149681Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 0.4 mg/kg/day administered qd on day 1 and 5 measured on day 301977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID90437Antitumor potency on human colon WIDR cell lines.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Structure-activity relationships for mitomycin C and mitomycin A analogues.
AID90128Antitumor potency on human breast MCF-7 cell lines.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Structure-activity relationships for mitomycin C and mitomycin A analogues.
AID1149669Toxicity in CDF1 mouse allografted with mouse P388 cells assessed as change in weight at 0.1 mg/kg/day administered qd on day 1 and 5 (Rvb = 3.4 g)1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID128822Anti cancer activity was determined as effective dose1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Structure-activity relationships for mitomycins. Application of the distance and charge analysis method.
AID228938Mean IC50 for all seven tumor cell lines was determined2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Synthesis, DNA cross-linking activity, and cytotoxicity of dimeric mitomycins.
AID1133509Induction of lambda-bacteriophage expression in Escherichia coli assessed as induction of plaques at 0.8 ug/ml relative to control1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID1149662Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as effect on median survival time at 0.1 mg/kg/day administered qd on day 1 and 5 relative to control1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1149666Toxicity in CDF1 mouse allografted with mouse P388 cells assessed as change in weight at 0.8 mg/kg/day administered qd on day 1 and 5 (Rvb = 3.4 g)1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID432751Antitumor activity against mouse S180 cells implanted in ip dosed ddY mouse assessed as tumor volume after 7 days2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Aziridine alkaloids as potential therapeutic agents.
AID1133510Induction of lambda-bacteriophage expression in Escherichia coli assessed as induction of plaques at 0.2 ug/ml relative to control1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID101083Inhibitory concentration on parentral (sensitive) L1210 leukemia cells.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Additional nucleotide derivatives of mitosenes. Synthesis and activity against parental and multidrug resistant L1210 leukemia.
AID121921Antitumor activity against P-388 murine leukemia cells in CDF1 female mice after intraperitoneal administration at the specified optimal dose of 3.2 mg/kg1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID1149650Induction of lambda phage lytic activity in Escherichia coli W1709(lambda) assessed as ratio of plaques in treated culture to control at 0.0125 ug/ml preincubated for 90 mins followed by heart infusion broth and glucose addition measured after 120 mins1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1149673Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 0.8 mg/kg/day administered qd on day 1 and 5 measured on day 51977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID134403Anti cancer activity was determined as lethal dose1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Structure-activity relationships for mitomycins. Application of the distance and charge analysis method.
AID1149680Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 0.8 mg/kg/day administered qd on day 1 and 5 measured on day 301977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID119960Optimal dose against sarcoma 180 tumor in ddY mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Synthesis and antitumor activity of novel 6-alkyl-6-demethylmitomycins.
AID23453Partition coefficient (logP)1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Preparation and antitumor activity of additional mitomycin A analogues.
AID110934Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 1.7 mg/kg on day 71981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID1133502Antibacterial activity against Klebsiella pneumoniae assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID87728In vitro anticellular activity tested against HeLa S3 cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Synthesis and antitumor activity of novel mitomycin derivatives containing functional groups at the C-6-methyl position.
AID119966Optimal dose was measured against sarcoma 180 cell in mice1995Journal of medicinal chemistry, Aug-04, Volume: 38, Issue:16
Synthesis and antitumor activity of various 6-demethylmitomycins and 6-demethyl-6-halomitomycins.
AID121386Treated versus control value of tumor volume was measured in ddY mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Synthesis and antitumor activity of novel 6-alkyl-6-demethylmitomycins.
AID1133516Toxicity in lambda-bacteriophage infected Escherichia coli at 0.2 ug/ml1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID110919Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 0.96 mg/kg on day 51981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID1133512Induction of lambda-bacteriophage expression in Escherichia coli assessed as induction of plaques at 0.0125 ug/ml relative to control1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID39421Antitumor activity against subcutaneously B16 melanoma cells in mice at an optimal dose of 0.3 mg/kg expressed as maximal effective dose1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Preparation and antitumor activity of new mitomycin A analogues.
AID1149660Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as effect on median survival time at 0.4 mg/kg/day administered qd on day 1 and 5 relative to control1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID133107Minimum effective dose was measured against P388 leukemia in mice.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Structure-activity relationships for mitomycin C and mitomycin A analogues.
AID235400Therapeutic ratio is expressed as ratio of optimal dose and minimum effective dose1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID120904T/C value was measured as tumor volume in the treated versus control mice.1995Journal of medicinal chemistry, Aug-04, Volume: 38, Issue:16
Synthesis and antitumor activity of various 6-demethylmitomycins and 6-demethyl-6-halomitomycins.
AID109892Half-wave potential produced by the compound at their optimal dose1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID229265Ratio of IC50 for Parental L1210 to that of multidrug resistant L1210.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Additional nucleotide derivatives of mitosenes. Synthesis and activity against parental and multidrug resistant L1210 leukemia.
AID1133505Antibacterial activity against Streptococcus faecalis P1377 assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID115629Minimum effective dose that show activity against P-388 murine leukemia cells in CDF1 female mice, after intraperitoneal administration (optimal dose is 3.2 mg/kg)1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID154478Antitumor activity against intraperitoneally implanted P388 leukemia cells in mice at an optimal dose of 3.2 mg/kg expressed as maximal effective dose1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Preparation and antitumor activity of new mitomycin A analogues.
AID1149668Toxicity in CDF1 mouse allografted with mouse P388 cells assessed as change in weight at 0.2 mg/kg/day administered qd on day 1 and 5 (Rvb = 3.4 g)1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID156010in vitro inhibition of tumor cell growth in cultured PC-3 human tumor cell line2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Synthesis, DNA cross-linking activity, and cytotoxicity of dimeric mitomycins.
AID153165Antitumor activity against intraperitoneally implanted P388 leukemia cells in mice expressed as ratio of median survival time for treated group to that of control group at an optimal dose of 3.2 mg/kg1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Preparation and antitumor activity of new mitomycin A analogues.
AID1149651Induction of lambda phage lytic activity in Escherichia coli W1709(lambda) assessed as ratio of plaques in treated culture to control at 0.003 ug/ml preincubated for 90 mins followed by heart infusion broth and glucose addition measured after 120 mins1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID110926Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 1.3 mg/kg on day 71981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID1133513Induction of lambda-bacteriophage expression in Escherichia coli assessed as induction of plaques at 0.003 ug/ml relative to control1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID40583Maximal effect of the given optimal dose of 0.3 mg/kg against B16 melanoma in mice1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Preparation and antitumor activity of additional mitomycin A analogues.
AID1149658Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as effect on median survival time at 1.6 mg/kg/day administered qd on day 1 and 5 relative to control1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID101082Inhibitory concentration on multidrug-resistant L1210 leukemia cells.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Additional nucleotide derivatives of mitosenes. Synthesis and activity against parental and multidrug resistant L1210 leukemia.
AID1149682Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 0.2 mg/kg/day administered qd on day 1 and 5 measured on day 301977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID95330in vitro anticancer activity against cultured KB(epidermoid) human tumor cell line2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Synthesis, DNA cross-linking activity, and cytotoxicity of dimeric mitomycins.
AID227069Inhibition of HeLa S3 cell growth relative to mitomycin C action (ratio of IC50 values)1995Journal of medicinal chemistry, Aug-04, Volume: 38, Issue:16
Synthesis and antitumor activity of various 6-demethylmitomycins and 6-demethyl-6-halomitomycins.
AID1133500Antibacterial activity against Escherichia coli B A9885 assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID110918Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 0.96 mg/kg on day 31981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID1149676Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 0.1 mg/kg/day administered qd on day 1 and 5 measured on day 51977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID11333350% inhibition of solid tumor growth (Sarcoma 180 cells) in mice1995Journal of medicinal chemistry, Aug-04, Volume: 38, Issue:16
Synthesis and antitumor activity of various 6-demethylmitomycins and 6-demethyl-6-halomitomycins.
AID110932Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 1.7 mg/kg on day 31981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID110933Effect of compound on total white blood cell count in BDG1 male mice, after intraperitoneal administration at a dose of 1.7 mg/kg on day 51981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Development of new mitomycin C and porfiromycin analogues.
AID1133501Antibacterial activity against Bacillus subtilis assessed as zone of inhibition by disk-plate assay1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID1149664Toxicity in CDF1 mouse allografted with mouse P388 cells assessed as change in weight at 3.2 mg/kg/day administered qd on day 1 and 5 (Rvb = 3.4 g)1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1149656Toxicity in Escherichia coli W1709(lambda) at 0.0125 ug/ml1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID112163Effective dose that gave 50 percent inhibition of sarcoma 180 tumor growth in ddY mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Synthesis and antitumor activity of novel 6-alkyl-6-demethylmitomycins.
AID1133518Toxicity in lambda-bacteriophage infected Escherichia coli at 0.0125 ug/ml1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID103358in vitro inhibition of tumor cell growth in cultured MCF-7 human tumor cell line2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Synthesis, DNA cross-linking activity, and cytotoxicity of dimeric mitomycins.
AID40571Minimum effective dose was determined on B16 melanoma cells in mice1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Preparation and antitumor activity of additional mitomycin A analogues.
AID1149674Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as mouse survival at 0.4 mg/kg/day administered qd on day 1 and 5 measured on day 51977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID154425Maximal effect of the given optimal dose of 3.2 mg/kg against P388 leukemia cells in mice1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Preparation and antitumor activity of additional mitomycin A analogues.
AID1149665Toxicity in CDF1 mouse allografted with mouse P388 cells assessed as change in weight at 1.6 mg/kg/day administered qd on day 1 and 5 (Rvb = 3.4 g)1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1149659Antitumor activity against mouse P388 cells allografted in CDF1 mouse assessed as effect on median survival time at 0.8 mg/kg/day administered qd on day 1 and 5 relative to control1977Journal of medicinal chemistry, Jun, Volume: 20, Issue:6
Comparative stereochemistry in the aziridine ring openings of N-methylmitomycin A and 7-methoxy-1,2-(N-methylaziridino)mitosene.
AID1133520Antitumor activity against mouse P388 cells allografted CDF mouse assessed as increase in maximum survival time at 3.2 mg/kg treated on days 1 and 5 following tumor implantation relative to saline treated control1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Mitomycin antibiotics. Synthesis and activity of 1,2-disubstituted mitosenes.
AID153213Antitumor potency on P388 leukemia cells in culture1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Structure-activity relationships for mitomycin C and mitomycin A analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (33.33)18.7374
1990's12 (36.36)18.2507
2000's8 (24.24)29.6817
2010's2 (6.06)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.27

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.27 (24.57)
Research Supply Index3.56 (2.92)
Research Growth Index4.24 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.27)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.94%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other33 (97.06%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetic acid
Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.		1.9610monocarboxylic acidantimicrobial food preservative;
Daphnia magna metabolite;
food acidity regulator;
protic solvent
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		210alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
3-methylcholanthrene
Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.		2.0310ortho- and peri-fused polycyclic arenearyl hydrocarbon receptor agonist;
carcinogenic agent
quinone
benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).		7101,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
mitomycin
Mitomycin: 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 : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		5.32180mitomycinalkylating agent;
antineoplastic agent
cysteamine
Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.		1.9810amine;
thiol		geroprotector;
human metabolite;
mouse metabolite;
radiation protective agent
cytidine monophosphate
Cytidine Monophosphate: Cytidine (dihydrogen phosphate). A cytosine nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. cytidine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.		1.9710cytidine 5'-phosphate;
pyrimidine ribonucleoside 5'-monophosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
methionine
Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.		1.9410aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical
cytarabine
[no description available]		1.9710beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
histidine
Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.		2.0310amino acid zwitterion;
histidine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
aziridine
[no description available]		3.5420azacycloalkane;
aziridines;
saturated organic heteromonocyclic parent		alkylating agent
betamethasone
Betamethasone: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)		2.021011beta-hydroxy steroid;
17alpha-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(1),Delta(4)-steroid;
fluorinated steroid;
glucocorticoid;
primary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone		anti-asthmatic agent;
anti-inflammatory drug;
immunosuppressive agent
porfiromycin
Porfiromycin: Toxic antibiotic of the mitomycin group, obtained from MITOMYCIN and also from Streptomyces ardus and other species. It is proposed as an antineoplastic agent, with some antibiotic properties.		4.3360
ammonium hydroxide
Ammonium Hydroxide: The hydroxy salt of ammonium ion. It is formed when AMMONIA reacts with water molecules in solution.. ammonium hydroxide : A solution of ammonia in water.		210inorganic hydroxy compoundfood acidity regulator
dithiothreitol
1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.		2101,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		1.9610dihydrogen
ethionine
L-ethionine : An S-ethylhomocysteine that has S-configuration at the chiral centre.		1.9410S-ethylhomocysteineantimetabolite;
carcinogenic agent
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		1.9610benzenes;
phenyl acetates
methionine methyl ester
[no description available]		1.9410
imiphos
imiphos: structure		3.1410
n-methylmitomycin a
[no description available]		8.9940
azicemicin a
azicemicin A: structure given in first source; isolated from Amycolatopsis		3.1410
24,25-iminolanosterol
24,25-iminolanosterol: structure given in first source		3.1410
mercaptopurine
Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.		1.9710aryl thiol;
purines;
thiocarbonyl compound		anticoronaviral agent;
antimetabolite;
antineoplastic agent
thioinosine
Thioinosine: Sulfhydryl analog of INOSINE that inhibits nucleoside transport across erythrocyte plasma membranes, and has immunosuppressive properties. It has been used similarly to MERCAPTOPURINE in the treatment of leukemia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p503)		1.9710
mitosene
mitosene: structure given in first source		1.9610
antazirine
antazirine: RN refers to (4Z)-isomer; isolated from Dysidea fragilis; structure in first source		3.1410alpha-amino acid ester
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.0810ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Leukemia
[description not available]		02.6530
Leukemia L 1210
[description not available]		02.3720
Breast Cancer
[description not available]		01.9710
Cancer of Colon
[description not available]		01.9710
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		03.2360
Cancer of Ovary
[description not available]		01.9710
Breast Neoplasms
Tumors or cancer of the human BREAST.		01.9710
Colonic Neoplasms
Tumors or cancer of the COLON.		01.9710
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		01.9710
Malignant Melanoma
[description not available]		02.3720
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.3720
B16 Melanoma
[description not available]		01.9710
Experimental Neoplasms
[description not available]		01.9610
Sarcoma 180
An experimental sarcoma of mice.		02.3920
EHS Tumor
[description not available]		02.3920
Peritoneal Carcinomatosis
[description not available]		02.0610
Complication, Postoperative
[description not available]		02.0610
Ascites, Gelatinous
[description not available]		02.0610
Local Neoplasm Recurrence
[description not available]		02.0610
Peritoneal Neoplasms
Tumors or cancer of the PERITONEUM.		02.0610
Postoperative Complications
Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.		02.0610
Pseudomyxoma Peritonei
A peritoneal adenocarcinoma characterized by build-up of MUCUS in the PERITONEAL CAVITY. Mucus secreting cells may attach to the peritoneal lining and continue to secrete mucus. The majority of cases represent tumor spread from a primary low-grade mucinous neoplasm of the APPENDIX (NCI Thesaurus).		02.0610
Atresia, Choanal
[description not available]		02.0210
Cardiac Diseases
[description not available]		01.9810
Kahler Disease
[description not available]		01.9810
Heart Diseases
Pathological conditions involving the HEART including its structural and functional abnormalities.		01.9810
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		01.9810