Mitomycin A

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Names

[ Name ]:
Mitomycin A

[Synonym ]:
[(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
mitomycin-A
Mitomycin A
(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

Chemical & Physical Properties

[ Density]:
1.5g/cm3

[ Boiling Point ]:
587.4ºC at 760 mmHg

[ Melting Point ]:
159-161ºC (dec)

[ Molecular Formula ]:
C₁₆H₁₉N₃O₆

[ Molecular Weight ]:
349.34

[ Flash Point ]:
309.1ºC

[ Exact Mass ]:
349.12700

[ PSA ]:
130.10000

[ LogP ]:
0.00350

[ Vapour Pressure ]:
8.83E-14mmHg at 25°C

[ Index of Refraction ]:
1.638

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CN1050000

CAS REGISTRY NUMBER :: 4055-39-4

LAST UPDATED :: 199706

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C16-H19-N3-O6

MOLECULAR WEIGHT :: 349.38

WISWESSER LINE NOTATION :: T D3 B556 BN EM JV MVTTT&J GO1 H1OVZ KO1 L1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2100 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Phage inhibition capacity

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 3 ug/L

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 20,767,1977

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(8aS)-8a-bromoalbomitomycin A
Mitomycin C
diazomethane
Azirino[2',3'_3,4]pyrrolo[1,2-.α.]indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-6-hydroxy-8-(hydroxymethyl)-8a-methoxy-5-methyl-, 8-carbamate
Methanol
1a-acetyl-7-demethoxy-6,7-dihydro-7,7-(ethylenedioxy)-6-(phenylselenyl)mitomycin A
Sodium Methylate

DownStream

7-(2-hydroxyethoxy)mitosane
Porfiromycin
8-(Aminocarbonyloxymethyl)-1,1a,2,8b-tetrahydro-6-methoxy-1,5-dimethylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
mc 77
7-N-Phenyl-mitomycin C
6-(2-Phenoxyethoxy-6-deaminomitomycin C)
6-Cyclopropylmethoxy-6-deaminomitomycin C
ac1l3usn
Azirino[2',3'_3,4]pyrrolo[1,2-.α.]indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-6-hydroxy-8-(hydroxymethyl)-8a-methoxy-5-methyl-, 8-carbamate
Azirino[2,3:3,4]pyrrolo[1,2-a]indole-4,7-dione, 8-[[ (aminocarbonyl)oxy]methyl]-1,1a,2,8,8a, 8b-hexahydro-8a-methoxy-5-methyl-6-[(2-methyl-2-propenyl)amino]-, (1aR-(1a.alpha.,8.beta.,8a.alpha.,8b.alph