1870. Carubicin

Nomenclature

CAS number: 50935-04-1
(8S-cis)-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-l-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-5,12-naphthacenedione; (1S,3S)-3-acetyl-1,2,3,4,6,11-hexahydro-3,5,10,12-tetrahydroxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-α-l-lyxo-hexopyranoside; 4-O-demethyldaunorubicin; carminomycin; carminomycin I; karminomycin.
C26H27NO10; mol wt 513.49.
C 60.81%, H 5.30%, N 2.73%, O 31.16%.

Description and references

Anthracycline antitumor antibiotic, related to daunorubicin and doxorubicin, q.q.v. Isoln from Actinomadura carminata: G. F. Gauze et al., Antibiotiki 18, 675 (1973); M. G. Brazhnikova et al., ibid. 678. Antitumor activity: V. A. Shorin et al., ibid. 681. Physico-chemical characteristics, structure: M. G. Brazhnikova et al., J. Antibiot. 27, 254 (1974). Pharmacokinetics, pharmacodynamics, toxicity study: L. E. Goldberg et al., Antibiotiki 19, 57 (1974). Production: M. G. Brazhnikova et al., SU 508076 (1976 to Inst. Antibiot. Res., USSR), C.A. 86, 15215 (1977). Stereochemistry: eidem, J. Antibiot. 29, 469 (1976). Synthesis from daunomycinone: G. Cassinelli et al., ibid. 31, 178 (1978). Molecular pharmacology: V. H. DuVernay et al., Cancer Res. 40, 387 (1980). Analysis in human serum: S. E. Fandrich, K. A. Pittman, J. Chromatogr. 223, 155 (1981). Early clinical studies: L.H. Baker et al., Cancer Treat. Rep. 63, 899 (1979). Embryotoxicity and teratogenicity study: I. Damjanov, A. Celluzzi, Res. Commun. Chem. Pathol. Pharmacol. 28, 497 (1980).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 52794-97-5
NSC-180024.
C26H27NO10.HCl; mol wt 549.95.
C 56.78%, H 5.13%, N 2.55%, O 29.09%, Cl 6.45%.

Properties

Crystals from ethanol/benzene. [α]D20 +289°. uv max (ethanol): 236, 255, 462, 478, 492 (E1%1cm 300), 510, 525 nm. pKa1 8.00; pKa2 10.16. Sol in water, methanol. Practically insol in other organic solvents. LD50 in mice (mg/kg): 7.3 orally; 1.3 i.v.; 3.7 s.c. (Goldberg).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antibiotics and Analogs; Anthracyclines