Mitomycin A

HCID 19972CAS 4055-39-4

Substructure search Find similar structures

Basic information

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
Molecular formula: C16H19N3O6
Average molar mass: 349.34 g/mol
Monoisotopic mass: 349.12738533

Names & identifiers

Preferred 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

Names & synonyms

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

Show more names

RefChem:159093DTXCID201747920Mitomycin EP Impurity BMitomycinA((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)-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 CarbamateUNII-87TMG6FJHV[(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

Database identifiers

CAS: 4055-39-4
PubChem CID: 19972
DTXSID: DTXSID201318131
ChEMBL: CHEMBL298359
ChEBI: CHEBI:85412
UNII: 87TMG6FJHV
Nikkaji: J62.411J

Properties

Computed structural properties

XLogP: 0.3
Topological polar surface area: 130 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 8
Rotatable bonds: 5
Heavy atoms: 25
Formal charge: 0
Complexity: 772

Experimental & physicochemical properties

Color/FormRED-VIOLET CRYSTALS FROM ACETONE + CARBON TETRACHLORIDE

Solubility · 2 items

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

Safety & regulation

Hazard information

Hazards SummaryEmergency treatment: Mitomycin C; [HSDB] See Mitomycin C.

Safety & protection

Disposal Methods · 1 item

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.

Chemistry & industry

Uses & manufacturing

Uses · 2 items

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/