Mitomycin A
Grundinformationen
- CAS
4055-39-4- Standard-SMILES
COC1=C(C)C(=O)C2=C(C1=O)[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N[C@H]3CN21- InChIKey
HYFMSAFINFJTFH-NGSRAFSJSA-N- Summenformel
- C16H19N3O6
- Durchschnittliche Molmasse
- 349,34 g/mol
- Monoisotopische Masse
- 349,12738533
Überblick
Mitomycin A is a member of the family of mitomycins that exhibits antibiotic and antitumour properties as well as a high level of toxicity. It has a role as an alkylating agent, a toxin, an antimicrobial agent and an antineoplastic agent. It is a mitomycin and an ether. It is a conjugate acid of a mitomycin A(1-).
Namen und Bezeichner
- Bevorzugter Name
- Mitomycin A
- IUPAC
- [(4S,6S,7R,8S)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
- Englischer Name
- Mitomycin A
- Summenformel
- C16H19N3O6
- Molmasse
- 349.34
Namen und Synonyme
Mitomycin A4055-39-4HSDB 3418NSC 7598687TMG6FJHVNSC-75986CHEBI:85412DTXSID201318131Azirino(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)[(4S,6S,7R,8S)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamateNSC75986((4S,6S,7R,8S)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo(7.4.0.02,7.04,6)trideca-1(9),11-dien-8-yl)methyl carbamate
Weitere Namen anzeigen
Mitomycin EP Impurity B (Mitomycin A)Mitomycin Impurity 2(Mitomycin EP Impurity B)(Mitomycin A）[(1aS,8S,8aR,8bS)-6,8a-Dimethoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2,3,4]pyrrolo[1,2-a]indol-8-yl]methyl Carbamate[(1aS,8S,8aR,8bS)-6,8a-Dimethoxy-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(1aS,8S,8aR,8bS)-8-[[(Aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,3
- Polarare Oberfläche (TPSA)
- 130 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 25
- Formalladung
- 0
- Komplexität
- 772
Experimentelle und physikochemische Eigenschaften
Chemical ClassesBiological Agents -> Bacterial Toxins
Color/FormRED-VIOLET CRYSTALS FROM ACETONE + CARBON TETRACHLORIDE
Solubility
Freely soluble in organic solvents
SOL IN WATER, BENZENE, TOLUENE, TRICHLOROETHYLENE, NITROBENZENE & MANY ORG SOLVENTS; PRACTICALLY INSOL IN XYLENE, CARBON TETRACHLORIDE, CARBON DISULFIDE, PETROLEUM ETHER, LIBROIN, CYCLOHEXANE
Physical DescriptionRed-violet solid; [Merck Index]
Other Experimental PropertiesDECOMP AT 159-161 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 159 · 159-1610C (dec)
- Siedepunkt
- 483.53 °C · 483.53°C (rough estimate)
- Dichte
- 1.2205 · 1.2205 (rough estimate)
- Brechungsindex
- 1.65 · 1.6500 (estimate)
- storage temp.
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
Hazards SummaryEmergency treatment: Mitomycin C; [HSDB] See Mitomycin C.
Sicherheit und Schutzausrüstung
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Sicherheitsdaten
- Toxizität
- LD50 i.v. in mice: 2 mg/kg (Hata, 1956; Kinoshita)
- Giftige Stoffe Daten
- 4055-39-4(Hazardous Substances Data)
Chemie und Industrie
Verwendung und Herstellung
Uses
Mitomycins are antitumor antibiotics made by Streptomyces caespitosus (griseovinaceseus); Mitomycin C is used as an antineoplastic drug; [Merck Index] Mitomycins: Used as DNA alkylating/cross-linking agents; [HSDB]
DNA alkylating/cross-linking agent /mitomycins/
Methods of ManufacturingYamamoto, Kenkyusho, Japan pat. 2898 (1956); Kenkyusho, Brit. pat. 830,874 (1960 to Kyowa); Gourevitch et al, U.S. pat. 3,042583 (1962 to Bristol-Myers) /production of the complex/
Anwendungen
VerwendenThe 6-methoxy analog of Mitomycin C. An antitumor antibiotic
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