1824. Carboquone

Nomenclature

CAS number: 24279-91-2
2-[2-[(Aminocarbonyl)oxy]-1-methoxyethyl]-3,6-bis(1-aziridinyl)-5-methyl-2,5-cyclohexadiene-1,4-dione; 2,5-bis(1-aziridinyl)-3-(2-hydroxy-1-methoxyethyl)-6-methyl-p-benzoquinone carbamate (ester); 2,5-bis(1-aziridinyl)-3-(2-carbamoyloxy-1-methoxyethyl)-6-methyl-1,4-benzoquinone; carbazilquinone; Esquinon (Sankyo).
C15H19N3O5; mol wt 321.33.
C 56.07%, H 5.96%, N 13.08%, O 24.90%.

Description and references

Prepn and antitumor activity: Nakao et al., Chem. Pharm. Bull. 20, 1968 (1972); T. Nakamura et al., DE 1905224; H. Nakao et al., US 3631026 (1969, 1971 both to Sankyo). Effect on tumors in mice: Arakawa et al., Gann 61, 535 (1970). Acute toxicity: H. Masuda, Y. Suzuki, Oyo Yakuri 8, 501 (1974), C.A. 81, 163349g (1974).

Chemical structure

Properties

Red to reddish-brown crystals, mp 202° (dec). Slightly sol in chloroform, acetone, abs alcohol. Practically insol in water. LD50 in male mice, male rats (mg/kg): 6.09, 3.88 i.v.; 3.84, 3.16 i.p.; 30.8, 28.0 orally (Masuda, Suzuki).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents; Aziridines