Oxytetracycline
Title: Oxytetracycline
CAS Registry Number: 79-57-2
CAS Name: [4S-(4a,4aa,5a,5aa,6b,12aa)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
Additional Names: glomycin; riomitsin; hydroxytetracycline
Molecular Formula: C22H24N2O9
Molecular Weight: 460.43
Percent Composition: C 57.39%, H 5.25%, N 6.08%, O 31.27%
Literature References: Antibiotic substance isolated from the elaboration products of the actinomycete, Streptomyces rimosus, grown on a suitable medium: Finlay et al., Science 111, 85 (1950). Isoln: Regna, Solomons, Ann. N.Y. Acad. Sci. 53, 221 (1950); Regna et al., J. Am. Chem. Soc. 73, 4211 (1951). Production from Streptomyces rimosus: Sobin et al., US 2516080 (1950 to Pfizer). Isoln from S. xanthophaeus: Brockmann, Musso, Naturwissenschaften 41, 451 (1954); Brockmann et al., DE 913687 (1954 to Bayer), C.A. 53, 4662h (1959). Solubility data: Weiss et al., Antibiot. Chemother. 7, 374 (1957). Structure: Hochstein et al., J. Am. Chem. Soc. 74, 3708 (1952). Abs config: Dobrynin et al., Tetrahedron Lett. 1962, 901. Stereochemistry: Schach von Wittenau et al., J. Am. Chem. Soc. 87, 134 (1965). Total synthesis of the dl-form: H. Muxfeldt et al., ibid. 101, 689 (1979).
Properties: Stability: Oxytetracycline crystals show no loss in potency on heating for 4 days at 100°, the hydrochloride crystals show <5% inactivation after 4 mos at 56°. Aq solns of the hydrochloride at pH 1.0 to 2.5 are stable for at least 30 days at 25°. Solns at pH 3.0 to 9.0 show no detectable loss in potency on storage at 5° for at least 30 days. Half-life in hours of aq oxytetracycline solns at 37°: pH 1.0 = 114; pH 2.5 = 134; pH 4.6 = 45; pH 5.5 = 45; pH 7.0 = 26; pH 8.5 = 33; pH 10.0 = 14.
 
Derivative Type: Dihydrate
Trademarks: Alamycin (Norbrook); Imperacin (AstraZeneca); Liquamycin (Pfizer); Terralon (Virbac); Terramycin (Pfizer); Tetradure (Merial)
Properties: Needles from water or methanol, dec 181-182°. [a]D25 -196.6° (0.1N HCl); [a]D25 -2.1° (0.1N NaOH); [a]D25 +26.5° (methanol). uv max (pH 4.5 phosphate buffer 0.1M): 249, 276, 353 nm (E1%1cm 240, 322, 301). Soly in water at 23°: pH 1.2 = 31,400 mg/ml, pH 2.0 = 4600 mg/ml, pH 3.0 = 1400 mg/ml; pH 5.0 = 500 mg/ml, pH 6.0 = 700 mg/ml, pH 7.0 = 1100 mg/ml, pH 9.0 = 38,600 mg/ml. Soly in abs ethanol 12,000 mg/ml, in 95% ethanol 200 mg/ml.
Optical Rotation: [a]D25 -196.6° (0.1N HCl); [a]D25 -2.1° (0.1N NaOH); [a]D25 +26.5° (methanol)
Absorption maximum: uv max (pH 4.5 phosphate buffer 0.1M): 249, 276, 353 nm (E1%1cm 240, 322, 301)
 
Derivative Type: Hydrochloride
CAS Registry Number: 2058-46-0
Trademarks: Berkmycen (APS); Duphacycline (Solvay Duphar); Engemycin (Intervet); Geomycin (Pliva); Oxy-Mycin (AgriPharm); Oxytetrin (Schering-Plough); Posicycline (Alcon); Tetra-Tablinen (Lichtenstein); Toxinal (Pharma-Selz)
Properties: Yellow platelets from water. Very soluble in water (1 g/ml). Concd aq solns at neutral pH hydrolyze on standing and deposit crystals of oxytetracycline. Soly in abs ethanol: 12,000 mg/ml, in 95% ethanol: 33,000 mg/ml.
 
Derivative Type: Disodium salt dihydrate
Molecular Formula: C22H22N2Na2O9.2H2O
Molecular Weight: 540.43
Percent Composition: C 48.89%, H 4.85%, N 5.18%, Na 8.51%, O 32.57%
Properties: Yellow crystals; darkens on standing. Soly in abs alc: 8,000 mg/ml, in methanol: 1500 mg/ml.
 
Use: To treat lethal yellowing in palm trees.
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Tetracyclines.

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