Title: Dactinomycin
CAS Registry Number: 50-76-0
CAS Name: Actinomycin D
Additional Names: actinomycin-[thr-val-pro-sar-meval]; meractinomycin; actinomycin AIV; actinomycin IV; actinomycin C1; actinomycin I1; actinomycin X1
Manufacturers' Codes: NSC-3053
Trademarks: Cosmegen (Merck & Co.)
Molecular Formula: C62H86N12O16
Molecular Weight: 1255.42
Percent Composition: C 59.32%, H 6.90%, N 13.39%, O 20.39%
Literature References: Antibiotic substance belonging to the actinomycin complex, produced by several Streptomyces spp. Historical background of actinomycins and chemistry, toxicology, pharmacology of actinomycin D: Ann. N.Y. Acad. Sci. 89, 285-485 (1960). Isoln from broth cultures of S. parvulus: Manaker et al., Antibiot. Ann. 1954/55, 853. Structure: Bullock, Johnson, J. Chem. Soc. 1957, 3280. Synthesis: Brockmann, Manegold, Naturwissenschaften 51, 383 (1964); Brockmann, Lackner, ibid. 384, 435 (1964); Brockmann et al., DE 1172680 (1964 to Bayer); eidem, Ber. 101, 1312 (1968); Meienhofer, J. Am. Chem. Soc. 92, 3771 (1970); T. Tanaka et al., Bull. Chem. Soc. Jpn. 53, 1352 (1980); K. Nakajima et al., Pept. Chem. 19, 143-148 (1981). Conformation from NMR: Conti, DeSantis, Nature 227, 1239 (1970); Lackner, Ber. 104, 3653 (1971). Toxicity data: F. S. Philips et al., Ann. N.Y. Acad. Sci. 89, 348 (1960). Review and evaluation of studies of carcinogenic action in laboratory animals: IARC Monographs 12, 29-41 (1976).
Derivative Type: Trihydrate
Properties: Bright red, rhomboid prisms from abs alc, dec 241.5-243°. [a]D28 -315° (c = 0.25 in methanol). Abs max (methanol): 244, 441 nm (A1%1cm 281, 206). Dil solns are very sensitive to light. Sol in alc, propylene glycol, water + glycol mixtures. LD50 orally in mice, rats: 13.0, 7.2 mg/kg (Philips).
Optical Rotation: [a]D28 -315° (c = 0.25 in methanol)
Absorption maximum: Abs max (methanol): 244, 441 nm (A1%1cm 281, 206)
Toxicity data: LD50 orally in mice, rats: 13.0, 7.2 mg/kg (Philips)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antibiotics and Analogs; Actinomycins. |