Carbamic acid,N,N'-[2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-diyl]bis-,C,C'-diethyl ester

Names

[ Name ]:
Carbamic acid,N,N'-[2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-diyl]bis-,C,C'-diethyl ester

[Synonym ]:
AZQ
2,5-di(aziridin-1-yl)-3,6-bis(carboethoxyamino)-1,4-benzoquinone
3,6-bis<(ethylcarboxy)amino>-2,5-diaziridinyl-1,4-benzoquinone
2,5-diaziridinyl-3,6-bis(carboethoxy-amino)-1,4-benzoquinone
diaziquone
CI-904
Diaziquonum [INN-Latin]
Aziridinylquinone
Aziridinylbenzoquinone

Biological Activity

[Description]:

Diaziquone (Diaziquone) is a water-soluble, synthetic aziridinylbenzoquinone with potential antineoplastic activity[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vivo]

Diaziquone (6.75mg /sq m daily for 5 consecutive days or single-dose 26 mg/sq m) has a broad range of activity of diaziquone against primary nervous system tumors and has enhancement effect combined with either 1,3-bis(2-chloroethyl)-1-nitrosourea or procarbazine in athymic mice[1]. Animal Model: Homozygous nu/nu BALB/c athymic mice[1] Dosage: 6.75mg /sq m or 26 mg/sq m Administration: 6.75mg /sq m daily for 5 consecutive days or single-dose 26 mg/sq m Result: Showed rapid clearance in the plasma of athymic mice with a half-life of approximately 11.5 min. Produced significant growth delays. Produced significant increases in the median growth delay, significant increases in the number of tumor regressions.

Chemical & Physical Properties

[ Density]:
1.45g/cm3

[ Boiling Point ]:
469ºC at 760mmHg

[ Molecular Formula ]:
C₁₆H₂₀N₄O₆

[ Molecular Weight ]:
364.35300

[ Flash Point ]:
237.4ºC

[ Exact Mass ]:
364.13800

[ PSA ]:
116.82000

[ LogP ]:
0.34240

[ Index of Refraction ]:
1.62

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EY8794000

CHEMICAL NAME :: Carbamic acid, (2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadien-1, 4-diyl)bis-, diethyl ester

CAS REGISTRY NUMBER :: 57998-68-2

BEILSTEIN REFERENCE NO. :: 1333277

LAST UPDATED :: 199612

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C16-H20-N4-O6

MOLECULAR WEIGHT :: 364.40

WISWESSER LINE NOTATION :: L6V DV AU DUTJ BMVO2 C- AT3NTJ& EMVO2 F- AT3NTJ

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 :: 11290 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 :: 10300 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1250 ug/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1550 ug/kg/5D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - changes in bone marrow (not otherwise specified) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 2400 ug/kg/33D-I

TOXIC EFFECTS :: Gastrointestinal - other changes Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 6250 ug/kg/5D-I

TOXIC EFFECTS :: Gastrointestinal - other changes Blood - changes in bone marrow (not otherwise specified) Blood - changes in spleen

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Sister chromatid exchange

MUTATION DATA

TYPE OF TEST :: Unscheduled DNA synthesis

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 300 nmol/L

REFERENCE :: PAACA3 Proceedings of the American Association for Cancer Research. (Waverly Press, 428 E. Preston St., Baltimore, MD 21202) V.1- 1954- Volume(issue)/page/year: 24,322,1983

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
40

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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