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Basic Information

Molecular Structure:
CAS No.:	50-07-7
Name:	Mitomycin C
Article Data:	28

Formula:	C₁₅H₁₈N₄O₅
Molecular Weight:	334.332
Synonyms:	Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione,6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-,(1aS,8S,8aR,8bS)-;Mitomycin C (6CI,7CI);Ametycine;MMC;MitoExtra;Mitomycin;Mitonco;Mitoplus;Mytomycin Kyowa S;NSC26980;Mito-C;A0049 1,4-Dihydroxy-2-tetraprenylbenzene derivative;
EINECS:	200-008-6
Density:	1.564 g/cm³
Melting Point:	360 °C
Boiling Point:	581.78 °C at 760 mmHg
Flash Point:	305.65 °C
Solubility:	soluble in water
Appearance:	dark blue grey crystalline powder
Hazard Symbols:	T,Xn,T+
Risk Codes:	25-40-22-45-26/27/28
Safety:	36/37-45-28A-28-53-22
Transport Information:	UN 3462 6.1/PG 2
PSA:	146.89000
LogP:	0.01610

Synthetic route

: 110934-24-2
albomitomycin A

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With ammonia at 25℃; for 0.5h;	99%
Multi-step reaction with 2 steps 1: 1) H2, 2) air / 1) 10percent Pd on carbon / 1) acetonitrile, 1 atm, 25 deg C, 2 h, 2) 25 deg C, 2 h 2: 75 percent / 6 M methanol. NH3 / 5 h / 25 °C View Scheme

: 2-((2-(piperidin-1-yl)ethyl)disulfanyl)ethyl(1aS,8S,8aR,8bS)-6-amino-8-((carbamoyloxy)methyl)-8a-methoxy-5-methyl-4,7-dioxo-1a,4,7,8,8a,8b-hexahydroazirino [2’,3’:3,4]pyrrolo[1,2-a]indole-1(2H)-carboxylate

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With l-cysteine hydrochloride In ethanol; water at 37℃; for 2h;	92%

: 122644-74-0, 122675-60-9, 134679-23-5
1a-acetyl-7-demethoxy-6,7-dihydro-7,7-(ethylenedioxy)-6-(phenylselenyl)mitomycin A

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With ammonia; dimedone In methanol Ambient temperature;	81%

: 128583-70-0
7-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-9a-methoxymitosane

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With ammonium hydroxide In methanol for 0.5h; Ambient temperature;	80%

: 91917-64-5
isomitomycin A

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With ammonia at 25℃; for 5h;	75%

: 88948-91-8
7-<<(dimethylamino)methylene>amino>-N10-<(dimethylamino)methylene>-9a-methoxymitosane

: 91-00-9
Benzhydrylamine

A: 50-07-7
mitomycin C

B: 88949-01-3
7-<<(dimethylamino)methylene>amino>-9a-methoxymitosane

C: 110971-78-3
7-<(diphenylmethyl)amino>-9a-methoxymitosane

Conditions

Conditions	Yield
In methanol at 54℃; for 4h;	A 20% B 41% C 8%

...Expand

: 126900-78-5
2-(2-Pyridinyldithio)benzylmitomycin C-1a-carboxylate

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With diothiothreitol In methanol; water at 30℃; pH 7.2; other (2-pyridinyldithio)benzyl MMC-1a-carboxylates;

: 88949-01-3
7-<<(dimethylamino)methylene>amino>-9a-methoxymitosane

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With phsphate buffer In water at 45℃; Rate constant; Mechanism; pH 6.5, other pH, other buffer, other temperature;

: 92056-69-4
leucomitomycin C

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With oxygen In ethanol

: C15H18N4O6

: 50-07-7
mitomycin C

Conditions

Conditions	Yield
With methanol; water at 20℃; Irradiation;

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Chemistry

Product Name: Mitomycin C
Synonyms: (1aS,8S,8aR,8bS)-6-Amino-8a-methoxy-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 carbamate ; [(1aS,8S,8aR,8bS)-6-Amino-8a-methoxy-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]methylcarbamat ; [1aS-(1aa,8b,8aa,8ba)]-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 ; Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-[(hydroxyiminomethoxy)methyl]-8a-methoxy-5-methyl-, (1aS,8S,8aR,8bS)- ;azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1aS,8S,8aR,8bS)- ;carbamate de [(1aS,8S,8aR,8bS)-6-amino-8a-méthoxy-5-méthyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroaziréno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]méthyle ;MitoExtra ;Mito-medac ;Mitomycin C derivative ;Mitomycin derivative
Product Categories: Antibiotics;Antibiotic Explorer;Intermediates & Fine Chemicals;Pharmaceuticals;Antibiotics G-MAntibiotics;AntibioticsStem Cell Expansion;AziridinesStem Cell Biology;DissociationAntibiotics;Interferes with DNA SynthesisMore...Close...;Antibiotics A to;Antibiotics by Application;AntibioticsAntibiotics;Antineoplastic and Immunosuppressive AntibioticsAntibiotics;Cell Culture;Chemical Structure Class;Culture;Mechanism of Action;Reagents and Supplements;Stem Cell Isolation;AziridinesAntibiotics;Core Bioreagents;Interferes with DNA Synthesis;Research Essentials
Molecular Structure:
Molecular Formula : C₁₅H₁₈N₄O₅
Molecular Weight: 334.33
CAS NO: 50-07-7
EINECS : 200-008-6
Merck : 13,6236
Index of Refraction: 1.68
Surface Tension: 77.2 dyne/cm
Density: 1.56 g/cm³
Flash Point: 305.6 °C
Enthalpy of Vaporization: 86.99 kJ/mol
Boiling Point: 581.8 °C at 760 mmHg
Vapour Pressure: 1.59E-13 mmHg at 25°C
Melting point : 360 ºC
Water solubility : soluble
Storage temp. 2-8°C
Solubility H2O: 4 mL/vial Stock solutions should be filter sterilized and stored at 2-8 °C in the dark., clear to slightly hazy, blue to purple
Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
Blue-Violet Crystals

Uses

Mitomycin C (CAS NO.50-07-7) is an antitumor antibiotic.

Production

Raw materials :Dichloromethane-->streptomyces avermifilis
Mitomycin C (CAS NO.50-07-7) is obtained by the separation and purification of inoculum of the soil actinomycete strain .

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	7500ug/kg (7.5mg/kg)		Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat	LDLo	intravenous	2500ug/kg (2.5mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Cancer Research. Vol. 20, Pg. 1354, 1960.
dog	LD50	intravenous	720ug/kg (0.72mg/kg)		Drugs in Japan Vol. -, Pg. 1129, 1990.
man	TDLo	unreported	1350ug/kg/21W (1.35mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" BLOOD: NORMOCYTIC ANEMIA	Archives of Internal Medicine. Vol. 143, Pg. 803, 1983.
monkey	LDLo	intravenous	1mg/kg (1mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: HEMORRHAGE GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Cancer Research. Vol. 20, Pg. 1354, 1960.
mouse	LD50	intraperitoneal	4mg/kg (4mg/kg)		Journal of Antibiotics, Series A. Vol. 13, Pg. 27, 1960.
mouse	LD50	intravenous	4mg/kg (4mg/kg)		Journal of Antibiotics, Series A. Vol. 13, Pg. 27, 1960.
mouse	LD50	oral	23mg/kg (23mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Cancer Research. Vol. 20, Pg. 1354, 1960.
mouse	LD50	subcutaneous	7300ug/kg (7.3mg/kg)		Japanese Journal of Cancer Research. Vol. 80, Pg. 670, 1989.
mouse	LD50	unreported	12mg/kg (12mg/kg)		Cancer Research. Vol. 46, Pg. 2703, 1986.
mouse	LDLo	intratracheal	4mg/kg (4mg/kg)		Toxicology Letters. Vol. 30, Pg. 63, 1986.
quail	LD50	oral	> 100mg/kg (100mg/kg)		Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rabbit	LD50	intravenous	3400ug/kg (3.4mg/kg)		Drugs in Japan Vol. -, Pg. 1129, 1990.
rat	LD50	intraperitoneal	2mg/kg (2mg/kg)		Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat	LD50	intravenous	3mg/kg (3mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.
rat	LD50	oral	30mg/kg (30mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Cancer Research. Vol. 20, Pg. 1354, 1960.
rat	LD50	subcutaneous	3250ug/kg (3.25mg/kg)		Drugs in Japan Vol. 6, Pg. 798, 1982.
women	TDLo	intravenous	1800ug/kg (1.8mg/kg)	LUNGS, THORAX, OR RESPIRATION: FIBROSING ALVEOLITIS LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Lancet. Vol. 2, Pg. 1037, 1980.
women	TDLo	unreported	2100ug/kg/40W (2.1mg/kg)	BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA BLOOD: OTHER CHANGES	Archives of Internal Medicine. Vol. 143, Pg. 1617, 1983.

Safety Profile

Hazard Codes T,T+,Xn
Risk Statements 25-40-22-45-26/27/28
R25 :Toxic if swallowed.
R40:Limited evidence of a carcinogenic effect.
R22:Harmful if swallowed.
R45:May cause cancer.
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.
Safety Statements 36/37-45-28-53-22
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S28:After contact with skin, wash immediately with plenty of soap-suds.
S53:Avoid exposure - obtain special instructions before use.
S22:Do not breathe dust.
RIDADR UN 3462 6.1/PG 2
WGK Germany 3
RTECS CN0700000
F 8-10
HazardClass 6.1(a)
PackingGroup II

Specification

1.General Description :Blue-violet crystals. Used as an anti-tumor antibiotic complex.
2.Air & Water Reactions :Water soluble.
3.Reactivity Profile: Mitomycin C is sensitive to prolonged exposure to light. Mitomycin C may be sensitive to prolonged exposure to air. Mitomycin C is incompatible with strong oxidizing agents, strong acids and strong bases. Calcium salts may cause decomposition.
4.Health Hazard: Toxic doses as low as 750 mg/kg have been reported in humans. The major toxic effect is myelosuppression, characterized by marked leukopenia and thrombocytopenia; this may be delayed and cumulative. Interstitial pneumonia and glomerular damage resulting in kidney failure are unusual but well documented complications. Lung conditions -- administration of mitomycin has been recognized as causing pneumonitis, alveolitis and pulmonary fibrosis. Kidney conditions -- administration of Mitomycin Can cause kidney damage. Kidney toxicity was observed in 1-5 percent of patients. Depressed immune conditions.
5.Fire Hazard :Flash point data for Mitomycin C are not available; however, Mitomycin C is probably combustible.