8252. Rolitetracycline
Nomenclature
CAS number: 751-97-3
[4S-(4α,4aα,5aα,6β,12aα)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-2-naphthacenecarboxamide; N-(pyrrolidinomethyl)tetracycline; N-(1-pyrrolidinylmethyl)tetracycline; Reverin (HMR); Syntetrin (BMS); Tetraverin (Polfa); Transcycline (HMR). C27H33N3O8; mol wt 527.57.
C 61.47%, H 6.30%, N 7.96%, O 24.26%.
Description and references
Semi-synthetic antibiotic prepd from tetracycline: Siedel et al., Muench. Med. Wochenschr. 100, 661 (1958); Lindner et al., ZA 5703169. Alternate procedure and structure: Gottstein et al., J. Am. Chem. Soc. 81, 1198 (1959); Cheney et al., US 3104240 (1963 to Bristol-Myers). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).
Properties
Fine, pale yellow needles, dec 162-165°. Amphoteric. More sol than tetracycline and tetracycline hydrochloride. Soly in water at 25°: 1.25 g/ml. Freely sol in alc. Sol in dil acids and alkalies.Derivative
Nitrate sesquihydrate.Nomenclature
CAS number: 26657-13-6
Bristacin (BMS); Pyrrocycline-N (Banyu). C27H33N3O8.HNO3.1 1/2 H2O; mol wt 599.59.
C 54.09%, H 5.88%, N 9.34%, O 30.69%.
Properties
LD50 i.v. in rats: 91 mg/kg (Goldenthal).Derivative
Compd with chloramphenicol succinate.Nomenclature
CAS number: 4154-10-3
Cafrolicycline; gradocycline; levocycline; senociclin; Clorociclin (Panthox & Burck); Crovicina (Viti); Metilcaf (Ital Suisse); Proterciclina (Proter); Reicaf (San Carlo); Tecaf (Farmochim. Ital.); Tetrafenicol (Medici Domus). C27H33N3O8.C15H16Cl2N2O8; mol wt 950.77.
C 53.06%, H 5.19%, N 7.37%, O 26.92%, Cl 7.46%.
Description and references
Prepn: BE 636234; Scevola, US 3218335 (1963, 1965 both to Lab. Pro-Ter).
Properties
Bright yellow powder, dec 140-144°. Bitter taste. Very sol in water. Practically insol in ether, ligroin, hexane.Therapeutic Category
Antibacterial.
Keywords
Antibacterial (Antibiotics); Tetracyclines