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Chemistry

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Also known as: Mitomycin, 50-07-7, Ametycine, Mutamycin, Mitomycin-c, Mitocin-c

Molecular Formula

C₁₅H₁₈N₄O₅

Molecular Weight

334.33 g/mol

InChI Key

NWIBSHFKIJFRCO-WUDYKRTCSA-N

FDA UNII

50SG953SK6

An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.

Mitomycin is an Alkylating Drug. The mechanism of action of mitomycin is as an Alkylating Activity.

1 2D Structure

Mitomycin

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

NWIBSHFKIJFRCO-WUDYKRTCSA-N

2.1.4 Canonical SMILES

CC1=C(C(=O)C2=C(C1=O)N3CC4C(C3(C2COC(=O)N)OC)N4)N

2.1.5 Isomeric 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

2.2 Other Identifiers

2.2.1 UNII

50SG953SK6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ametycine

2. Mitocin C

3. Mitocin-c

4. Mitocinc

5. Mitomycin

6. Mitomycin-c

7. Mutamycin

8. Nsc 26980

9. Nsc-26980

10. Nsc26980

2.3.2 Depositor-Supplied Synonyms

1. Mitomycin

2. 50-07-7

3. Ametycine

4. Mutamycin

5. Mitomycin-c

6. Mitocin-c

7. Mytozytrex

8. Ametycin

9. Mitomycinum

10. Mytomycin

11. Mitozytrex

12. Mitamycin

13. Mitosol

14. Mmc

15. Nsc-26980

16. Muamycin

17. 7-amino-9alpha-methoxymitosane

18. C15h18n4o5

19. Nsc 26980

20. Mitomycyna C

21. Nci-c04706

22. Mito-c

23. Nsc26980

24. Mit-c

25. Mitomycinum C

26. Mitocin C

27. Chebi:27504

28. Rcra Waste Number U010

29. Ugn-101

30. Ugn-102

31. 50sg953sk6

32. Mitomycyna C [polish]

33. 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methylazirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione Carbamate (ester)

34. Dsstox_cid_898

35. Dsstox_rid_75853

36. Dsstox_gsid_20898

37. Mitomycin (tn)

38. [(1as,8s,8ar,8bs)-6-amino-8a-methoxy-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

39. [(4s,6s,7r,8s)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methyl Carbamate

40. Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1as,8s,8ar,8bs)-

41. Cas-50-07-7

42. Muamycin (tn)

43. ((1as,8s,8ar,8bs)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl Carbamate

44. [1as-(1a?,8?,8a?,8b?)]-6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione

45. Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1as,8s,8ar,8bs)-

46. Ccris 414

47. Hsdb 3239

48. Mitomycin (usp/inn)

49. Mls002702984

50. (amino-methoxy-methyl-dioxo-[?]yl)methyl Carbamate

51. Einecs 200-008-6

52. Rcra Waste No. U010

53. 7-amino-9.alpha.-methoxymitosane

54. Mitonco

55. Mitoplus

56. Mitoextra

57. Unii-50sg953sk6

58. Ai3-26199

59. Mitomycin [usan:usp:inn:ban]

60. Ncgc00095258-01

61. [(1as,8s,8ar,8bs)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2'',3'':3,4]pyrrolo[1,2-a]indol-8-yl]methyl Carbamate

62. [(1as,8s,8ar,8bs)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl Carbamate

63. Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-, Carbamate (ester)

64. Jelmyto (tn)

65. Mfcd00078109

66. Jelmyto

67. Mitomycin C- Bio-x

68. Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1as-(1aalpha,8beta,8aalpha,8balpha))-

69. Mitomycin C From Streptomyces Caespitosus

70. Mitomycin [inn]

71. Mitomycin C (jp17)

72. Mitomycin [hsdb]

73. Mitomycin [usan]

74. Mitomycin [vandf]

75. Mitomycin C [mi]

76. Chembl105

77. Mitomycin [mart.]

78. Mitomycin C [jan]

79. Mitomycin [usp-rs]

80. Mitomycin [who-dd]

81. Mitomycin C [iarc]

82. Schembl3760

83. Cbiol_001927

84. Bspbio_001267

85. Kbiogr_000607

86. Kbioss_000607

87. Mitomycin C (4% In Nacl)

88. Mls001332654

89. Mitozytrex (tn) (supergene)

90. 50-07-7 (non-salt)

91. Ametycin Pound Notmitomycin C

92. Gtpl7089

93. Mitomycin [orange Book]

94. Dtxsid2020898

95. Mitomycin [ep Monograph]

96. Kbio2_000607

97. Kbio2_003175

98. Kbio2_005743

99. Kbio3_001073

100. Kbio3_001074

101. Ex-a501

102. Mitomycin [usp Monograph]

103. Bcpp000410

104. Bio1_000213

105. Bio1_000702

106. Bio1_001191

107. Bio2_000464

108. Bio2_000944

109. Hms1362o09

110. Hms1792o09

111. Hms1990o09

112. Hms2089f16

113. Hms3403o09

114. Amy10316

115. Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1as-(1a.alpha.,8.beta.,8a.alpha.,8b.alpha.))-

116. Tox21_111493

117. Ac-918

118. Bdbm50428658

119. Gr-311

120. S8146

121. Zinc30726187

122. Akos015895703

123. Tox21_111493_1

124. Bcp9000285

125. Ccg-208564

126. Cs-0564

127. Db00305

128. Ks-5148

129. Idi1_002219

130. Smp1_000307

131. Mitomycin 100 Microg/ml In Acetonitrile

132. Ncgc00163468-02

133. Ncgc00163468-03

134. Ncgc00163468-05

135. Ncgc00163468-06

136. 1404-00-8

137. Bm164668

138. Hy-13316

139. Smr000058401

140. Bcp0726000181

141. M2320

142. C06681

143. D00208

144. D91590

145. Ab00918689-03

146. Ab00918689-04

147. 078m109

148. Mitomycin C, Antibiotic For Culture Media Use Only

149. Q-201410

150. Brd-k59670716-001-02-6

151. Brd-k59670716-001-06-7

152. Q19856779

153. Wln: T D3 B556 Bn Em Jv Mvttt&j Go1 H1ovz Kz L1

154. Mitomycin C From Streptomyces Caespitosus, >=970 Mug/mg (usp Xxiv)

155. Mitomycin C From Streptomyces Caespitosus, Powder, Bioreagent, Suitable For Cell Culture

156. Mitomycin C From Streptomyces Caespitosus, Powder, Contains Nacl As Solubilizer

157. Azirino[2',4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a- Methoxy-5-methyl-, Carbamate (ester)

158. Azirino[2',4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b- Hexahydro-8a-methoxy-5-methyl-, [1ar-(1a.alpha.,8.beta.,8a.alpha.,8b.alpha.)]-

159. Mitomycin C From Streptomyces Caespitosus, >=98% (hplc), Potency: >=970 Mug Per Mg (usp Xxiv), Gamma-irradiated, Suitable For Cell Culture

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₈N₄O₅
Molecular Weight	334.33 g/mol
XLogP3	-0.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	334.12771969 g/mol
Monoisotopic Mass	334.12771969 g/mol
Topological Polar Surface Area	147 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	757
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Mitomycin
PubMed Health	Mitomycin
Drug Classes	Antibiotic, Antineoplastic Agent
Drug Label	Mitomycin (also known as mitomycin and/or mitomycin-C) is an antibiotic isolated from the broth of Streptomyces caespitosus which has been shown to have antitumor activity. The compound is heat stable, has a high melting point, and is freely soluble...
Active Ingredient	Mitomycin
Dosage Form	Injectable
Route	Injection
Strength	5mg/vial; 20mg/vial; 40mg/vial
Market Status	Prescription
Company	Bedford; Accord Hlthcare; Hikma Maple

2 of 4
Drug Name	Mitosol
Active Ingredient	Mitomycin
Dosage Form	For solution
Route	Topical
Strength	0.2mg/vial
Market Status	Prescription
Company	Mobius Therap

3 of 4
Drug Name	Mitomycin
PubMed Health	Mitomycin
Drug Classes	Antibiotic, Antineoplastic Agent
Drug Label	Mitomycin (also known as mitomycin and/or mitomycin-C) is an antibiotic isolated from the broth of Streptomyces caespitosus which has been shown to have antitumor activity. The compound is heat stable, has a high melting point, and is freely soluble...
Active Ingredient	Mitomycin
Dosage Form	Injectable
Route	Injection
Strength	5mg/vial; 20mg/vial; 40mg/vial
Market Status	Prescription
Company	Bedford; Accord Hlthcare; Hikma Maple

4 of 4
Drug Name	Mitosol
Active Ingredient	Mitomycin
Dosage Form	For solution
Route	Topical
Strength	0.2mg/vial
Market Status	Prescription
Company	Mobius Therap

4.2 Therapeutic Uses

Antibiotics, Antineoplastic; Nucleic Acid Synthesis Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Mitomycin is useful for the palliative treatment of gastric adenocarcinoma, in conjunction with fluorouracil and doxorubicin. It has produced temporary beneficial effects in carcinomas of the cervix, colon, rectum, pancreas, breast, bladder, head and neck, and lung, and in melanoma. It has also shown activity against lymphomas and leukemia, particularly chronic granulocytic leukemia, but not in myeloma.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1247

Thirty patients with advanced colorectal adenocarcinoma were treated by chemotherapy with an alternating regimen consisting of 5-fluorouracil mitomycin C and 5-fluorouracil dacarbazine at 3 wk intervals. ... The toxicity of this regimen was essentially digestive with 30% of grade 3 or 4 nausea and vomiting. In spite of the reported active and synergistic action of drug association in colorectal carcinoma, this treatment schedule is not better than 5-fluorouracil alone. Gastrointestinal toxicity was incr.

PMID:2496369 Herait P et al; Oncology 46 (2): 88-90 (1989)

Forty-two patients with metastatic breast cancer refractory to first line therapies were treated with combination chemotherapy with mitomycin-C and vinblastine. ... The toxicity was acceptable with 20 episodes of moderate myelosuppression (58.8%) and 2 cases with congestive heart failure that responded to medical treatment.

PMID:2497417 Navarro M et al; Oncology 46 (3): 137-42 (1989)

For more Therapeutic Uses (Complete) data for MITOMYCIN C (19 total), please visit the HSDB record page.

4.3 Drug Warning

Mitomycin is contraindicated in patients with pre-existing myelosupression & anemia.

Knoben, J.E. and P.O. Anderson (eds.) Handbook of Clinical Drug Data. 6th ed. Bethesda, MD: Drug Intelligence Publications, Inc. 1988., p. 417

Because normal defense mechanisms may be suppressed by mitomycin therapy, the patient's antibody response to the vaccine may be decreased. The interval between discontinuation of medications that cause immunosuppression and restoration of the patient's ability to respond to the vaccine depends on the intensity and type of immunosuppression-causing medication used, the underlying disease, and other factors; estimates vary from 3 months to 1 year.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2088

cBecause normal defense mechanisms may be suppressed by mitomycin therapy, concurrent use with a live virus vaccine may potentiate the replication of the vaccine virus, may increase the side/adverse effects of the vaccine virus, and/or may decrease the patient's antibody response to the vaccine; immunization of these patients should be undertaken only with extreme caution after careful review of the patient's hematologic status and only with the knowledge and consent of the physician managing the cytarabine therapy. The interval between discontinuation of medication that cause immunosuppression and restoration of the patient's ability to respond to the vaccine depends on the intensity and type of immunosuppression-causing medications used, the underlying disease, and other factors; estimates vary from 3 months to 1 year. Patients with leukemia in remission should not receive live virus vaccine until at least 3 months after their last chemotherapy. In addition, immunization with oral polio-virus vaccine should be postponed in persons in close contact with the patient, especially family members.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2088

Gonadal suppression, resulting in amenorrhea or azoospermia, may occur in patients taking antineoplastic therapy, especially with the alkylating agents. In general, these effects appear to be related to dose and length of therapy and may be irreversible. Prediction of the degree of testicular or ovarian function impairment is complicated by the common use of combinations of several antineoplastics, which makes it difficult to assess the effects of individual agents.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2087

For more Drug Warnings (Complete) data for MITOMYCIN C (6 total), please visit the HSDB record page.

4.4 Drug 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. Mitomycin is also indicated as a pyelocalyceal solution for the treatment of adults with low-grade upper tract urothelial cancer (LG-UTUC).

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

Alkylating Agents

Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases. (See all compounds classified as Alkylating Agents.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

Cross-Linking Reagents

Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other. (See all compounds classified as Cross-Linking Reagents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

MITOMYCIN

5.3.2 FDA UNII

50SG953SK6

5.3.3 Pharmacological Classes

Alkylating Drug [EPC]; Alkylating Activity [MoA]

5.4 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01D - Cytotoxic antibiotics and related substances

L01DC - Other cytotoxic antibiotics

L01DC03 - Mitomycin

5.5 Absorption, Distribution and Excretion

Absorption

Erratic.

Route of Elimination

Approximately 10% of a dose of mitomycin is excreted unchanged in the urine.

FOLLOWING IV INJECTION OF 2 MG/KG BODY WT ... WISTAR RATS, 18% WAS RECOVERED UNCHANGED IN URINE WITHIN 24 HR AT ... 8 MG/KG ... 35% WAS RECOVERED IN URINE, BUT NONE IN FECES OR TISSUES.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 174 (1976)

THIRTY MIN AFTER IV INJECTION OF 8 MG/KG BODY WT TO MICE TRACES REMAINED IN BLOOD. IN GUINEA PIGS DRUG WAS CONCN IN KIDNEYS & NOT IN LIVER, SPLEEN OR BRAIN & WAS EXCRETED IN URINE.

Mitomycin is absorbed inconsistently from the gastrointestinal tract, and it is therefore administered intravenously. It disappears rapidly from the blood after injection. Peak concentrations in plasma are 0.4 ug/ml after doses of 20 mg/m sq ... The drug is widely distributed throughout the body but is not detected in the brain.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1247

In animals, highest mitomycin concentrations are found in the kidneys, followed by muscles, eyes, lung, intestines, and stomach. The drug is not detectable in the liver, spleen, or brain which rapidly inactivate mitomycin. Higher concentrations of the drug are generally present in cancer tissues than in normal tissues.

McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 537

For more Absorption, Distribution and Excretion (Complete) data for MITOMYCIN C (9 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Primarily hepatic, some in various other tissues.

SUGGESTED ALKYLATING METABOLITES OF CARCINOGENS: MITOMYCIN C: REDUCTION PRODUCTS. /FROM TABLE/

Searle, C. E. (ed.). Chemical Carcinogens. ACS Monograph 173. Washington, DC: American Chemical Society, 1976., p. 95

Inactivation occurs by metabolism, but the products have not been identified. It is metabolized primarily in the liver, and less than 10% of the active drug is excreted in the urine or the bile.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1247

The drug is eliminated primarily by hepatic metabolism with about 20% hepatic extraction and 10-30% recovery of intact drug in the urine. Clearance is 0.3-0.4 l/hr/kg.

IATA. Dangerous Goods Regulations. 30th ed. Montreal, Canada: International Air Transport Association. Dangerous Goods Board, January 1, 1989., p. 416

Mitomycin disappears rapidly from the blood after intravenous injection. It is widely distributed but does not appear to cross the blood-brain barrier. Mitomycin is metabolized mainly in the liver; up to 10% of a dose is excreted unchanged in the urine.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 221

MITOMYCIN C WAS PREFERENTIALLY ACTIVATED & METABOLIZED BY SONICATED CELL PREPARATIONS. BIOACTIVATION OF MITOMYCIN TO ALKYLATING AGENT BY EMT6 & SARCOMA 180 CELL SONICATES REQUIRED HYPOXIC CONDITIONS & NADPH-GENERATING SYSTEM.

PMID:7388797 KENNEDY KA ET AL; CANCER RES 40 (7): 2356 (1980)

5.7 Biological Half-Life

8-48 min

After doses of 20 mg/m sq ... Mitomycin is cleared from plasma with a half-time of approximately 1 hour.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1247

/Mitomycin/ has an alpha half-life of 5-10 min after IV injection and beta half-life of 46 min.

Knoben, J.E. and P.O. Anderson (eds.) Handbook of Clinical Drug Data. 6th ed. Bethesda, MD: Drug Intelligence Publications, Inc. 1988., p. 416

5.8 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.

... REACTS WITH BACTERIAL DNA BUT NOT WITH ISOLATED DNA, UNLESS ... REDUCING SYSTEM IS ADDED. CROSS LINKING EFFICIENCY ... INCR IN ISOLATED BACTERIAL DNA CONTAINING INCR AMT OF CYTOSINE & GUANOSINE.

ITS REDUCED FORM CONTAINS INDOLE GROUP EMBODYING ALLYLIC CARBAMATE RESIDUE. ANTIBIOTIC IS CYTOTOXIC & CARCINOGENIC BUT IS INACTIVE AS CYTOTOXIC AGENT UNLESS REDUCED ... IT ACTS AS DIFUNCTIONAL AGENT IN CROSS LINKING DNA.

Searle, C. E. (ed.). Chemical Carcinogens. ACS Monograph 173. Washington, DC: American Chemical Society, 1976., p. 96

The drug inhibits DNA synthesis and cross-links DNA at the N6 position of adenine and at the O6 and N2 positions of guanine. In addition, single-strand breakage of DNA is caused by reduced mitomycin; this can be prevented by free radical scavengers. Its action is most prominent during the late G1 and early S phases of the cell cycle.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1247

In high concentrations ... /mitomycin/ may ... inhibit RNA and protein synthesis.

McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 537

For more Mechanism of Action (Complete) data for MITOMYCIN C (11 total), please visit the HSDB record page.

API SUPPLIERS

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