Basic information
- CAS
4055-40-7- Standard SMILES
COC1=C(C)C(=O)C2=C(C1=O)[C@H](COC(N)=O)[C@@]1(O)[C@@H]3[C@H](CN21)N3C- InChIKey
UZUUQCBCWDBYCG-DQRAMIIBSA-N- Molecular formula
- C16H19N3O6
- Average molar mass
- 349.34 g/mol
- Monoisotopic mass
- 349.12738533
Overview
Mitomycin B is a member of the family of mitomycins that exhibits antibiotic and antitumour properties. It has a role as an antimicrobial agent and an antineoplastic agent. It is a mitomycin and an ether. It is a conjugate acid of a mitomycin B(1-).
Names & identifiers
- Preferred name
- Mitomycin B
- IUPAC
- [(4S,6S,7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
- English name
- Mitomycin B.
- Molecular formula
- C16H19N3O6
- Molecular weight
- 349.34
Names & synonyms
MITOMYCIN B4055-40-7HSDB 3419VT1IGL3D7V[(4S,6S,7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamateCHEBI:85416DTXSID001318185Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-8a-hydroxy-8-(hydroxymethyl)-6-methoxy-1,5-dimethyl-, 8-carbamateNSC75987((4S,6S,7R,8R)-7-hydroxy-11-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo(7.4.0.02,7.04,6)trideca-1(9),11-dien-8-yl)methyl carbamateRefChem:159094DTXCID301747973
Show more names
Mitomycin B.Mitomycin Impurity 3(Mitomycin EP Impurity C)(Mitomycin B)(1aS)-8α-[[(Aminocarbonyl)oxy]methyl]-1,1aα,2,8,8aα,8bα-hexahydro-1,5-dimethyl-8a-hydroxy-6-methoxyazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dioneAzirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-hydroxy-6-methoxy-1,5-dimethyl-, (1aS,8R,8aR,8bS)-[1aS-(1aalpha,8alpha,8aalpha,8balpha)]-8-[[(Aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-hydroxy-6-methoxy-1,5-dimethyl-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 122 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 787
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Bacterial Toxins
Color/FormVIOLET CRYSTALS FROM ACETONE + CARBON TETRACHLORIDE
SolubilitySOL IN WATER & MANY ORGANIC SOLVENTS; PRACTICALLY INSOL IN XYLENE, CARBON TETRACHLORIDE, CARBON DISULFIDE, PETROLEUM ETHER, LIGROIN, CYCLOHEXANE, BENZENE, TOLUENE, TRICHLOROETHYLENE, NITROBENZENE.
Physical DescriptionViolet solid; [Merck Index]
Other Experimental PropertiesDECOMP AT 182-184 °C
Physicochemical properties
- Boiling point
- 483.53 °C · 483.53°C (rough estimate)
- Density
- 1.2205 · 1.2205 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
- pka
- 11.41 · 11.41±0.70(Predicted)
- FDA UNII
- 1 IGL3D7V · VT1IGL3D7V
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards SummaryEmergency treatment: Mitomycin C; [HSDB] See Mitomycin C.
Safety & protection
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.
Safety data
- Toxicity
- LD50 i.v. in mice: 10 mg/kg (Hata, 1956); also reported as 3 mg/kg (Kinoshita)
- Hazardous Substances Data
- 4055-40-7(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
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/
Applications
UsesAn antitumor antibiotic. It is used as antineoplastic.
UsesAs an antitumor antibiotic, Mitomycin B is used as antineoplastic.
Suppliers14 total
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
深圳市简一生物科技有限公司0755-84826604 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
深圳菲斯生物科技有限公司0755-83725681-603
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
坛墨质检科技股份有限公司19850211281 · [email protected]
BOC Sciences16314854226 · [email protected]
广州佳途科技股份有限公司
Related reactions
1 records
Compound notes
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