[(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

• ChemBase ID: 190
• Molecular Formular: C15H18N4O5
• Molecular Mass: 334.32722
• Monoisotopic Mass: 334.1277197
• SMILES: O([C@@]12N(C[C@@H]3N[C@H]13)C1=C([C@H]2COC(=O)N)C(=O)C(=C(C1=O)C)N)C
• Canonical SMILES: CO[C@@]12[C@H]3N[C@H]3CN2C2=C([C@H]1COC(=O)N)C(=O)C(=C(C2=O)C)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

NAMES AND DATABASE IDS

Names

• IUPAC name: [(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; [(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
• IUPAC Systematic name: {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
• IUPAC Traditional name: mitomycin-C; mitamycin
• Brand Name: Ametycin; Ametycine; Mit-C; Mito-C; Mitocin-C; Mitomycin (TN); Mitomycin C; Mitomycin-C; Mitomycinum; Mitomycinum C; Mitomycyna C [Polish]; Mitozytrex; Muamycin; Mutamycin; Mytomycin; Mytozytrex
• Synonyms: Mitomycin C from Streptomyces caespitosus; [1aS-(1aα,8β,8aα,8bα)-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; Ametycine; Mutamycin; Mitonco; Mitoplus; NSC 26980; Mitocin C; Mitomycin C; 7-Amino-9α -methoxymitosane; Mitamycin; MMC; Mitomycin; Mitomycin C; 丝裂霉素 C 来源于头状链霉菌

Database IDs

• CAS Number: 50-07-7
• EC Number: 200-008-6
• MDL Number: MFCD00078109
• Beilstein Number: 7231816; 3570056
• PubChem SID: 46508353; 160963653; 24896554
• PubChem CID: 5746
• CHEBI ID: 27504
• ATC CODE: L01DC03
• CHEMBL: 105
• Chemspider ID: 5544
• DrugBank ID: DB00305
• KEGG ID: C06681
• Unique Ingredient Identifier: 50SG953SK6
• Wikipedia Title: Mitomycin

CALCULATED PROPERTIES

JChem

• Acid pKa: -0.3018127
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.9682753
• LogD (pH = 7.4): -3.2154355
• Log P: -2.9575114
• Molar Refractivity: 83.2689 cm^3
• Polarizability: 31.659235 Å^3
• Polar Surface Area: 146.89 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.55
• LOG S: -1.52
• Solubility (Water): 1.01e+01 g/l

PROPERTIES

Physical Property

• Solubility: 8.43 g L^-1 in water; Acetone; Methanol; Soluble (8430 mg/L); Water
• Apperance: Blue-Violet Crystals; White or colourless solid
• Melting Point: >300°C; 360°C (low of range)
• Partition Coefficient: -1.6
• Hydrophobicity(logP): -1.6
• Isoelectric Point: 10.9

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• RTECS: CN0700000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 22-40; 25-40
• Safety Statements: 28-36/37-45; 36/37
• GHS Pictograms: GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H300-H351; H302-H351
• GHS Precautionary statements: P264-P281-P301 + P310; P281
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Eye drops Intravenous
• Half Life: 8–48 min
• Metabolism: Hepatic
• Legal Status: POM (UK); Rx (US)
• Pregnancy Category: D (Australia); D (US)

Product Information

• Purity: ≥970 μg/mg (USP XXIV)
• Empirical Formula (Hill Notation): C15H18N4O5

DETAILS

DrugBank - DB00305

• Drug 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]
• 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.
• 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.
• 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
• Biotransformation: Primarily hepatic, some in various other tissues.
• Absorption: Erratic.
• Half Life: 8-48 min
• Elimination: Approximately 10% of a dose of mitomycin is excreted unchanged in the urine.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - M0440

Application
Used as a sequence specific (5′-CpG-3′) DNA crosslinking (alkylation) agent.
Biochem/physiol Actions
Inhibitor of DNA synthesis, nuclear division, and cancer cells. Antibacterial to gram positive, gram negative, acid-fast bacilli.
Other Notes
NaCl free
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 69824

Biochem/physiol Actions
Inhibitor of DNA synthesis, nuclear division, and cancer cells. Antibacterial to gram positive, gram negative, acid-fast bacilli.
Other Notes
Vial contains 2 mg mitomycin C and 48 mg NaCl (increases solubility).

Toronto Research Chemicals - M371900

An antitumor antibiotic. It is used as antineoplastic.

REFERENCES

• Kinoshita, S., et al.: J. Med. Chem., 14, 13 (1971)
• Beijnen, J.H., et al.: Anal. Profiles Drug Subs., 16, 361 (1971)