5628. Lymecycline

Nomenclature

CAS number: 992-21-2
N6-[[[[(4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl]carbonyl]amino]methyl]-l-lysine; tetracyclinemethylene lysine; N-lysinomethyltetracycline; Tetralisal (Galderma); Tetralysal (Galderma).
C29H38N4O10; mol wt 602.63.
C 57.80%, H 6.36%, N 9.30%, O 26.55%.

Description and references

Semi-synthetic antibiotic related to tetracycline, q.v. Prepn: R. K. Blackwood, K. J. Brunings, US 3042716 (1962 to Pfizer); F. Lauria, W. Logemann, DE 1134071 (1962 to Carlo Erba), C.A. 58, 492 (1963); E. Tubaro, E. Raffaldoni, Boll. Chim. Farm. 100, 9 (1961). Clinical pharmacokinetics: A. Schreiner, A. Digranes, Chemotherapy (Basel) 31, 261 (1985). Comparison with doxycycline of phototoxic potential: M. Bjellerup, B. Ljunggren, Br. J. Dermatol. 130, 356 (1994). Clinical trial in acne: L. Bossuyt et al., Eur. J. Dermatol. 13, 130 (2003); of combination with adapalene: W. J. Cunliffe et al., J. Am. Acad. Dermatol. 49, S218 (2003).

Chemical structure

Derivative

Sodium salt.
C29H37N4NaO10; mol wt 624.61.
C 55.76%, H 5.97%, N 8.97%, Na 3.68%, O 25.62%.

Properties

uv max (CH3OH): 376 nm.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); Tetracyclines