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.
Oxythiamine Oxythioquinox Ozagrel (p-Nonylphenoxy)acetic Acid p-(2-Methylpropenyl)phenol Acetate

Oxytetracycline
Oxytetracycline-2D-skeletal.png
Oxytetracycline-3D-balls.png
Systematic (IUPAC) name
(4S,4aR,5S,5aR,6S,12aS) -4-(dimethylamino)-3,5,6,10,11,12a-hexahydroxy -6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene -2-carboxamide
Clinical data
Pregnancy cat. D: (United States)
D: (Australia])
Legal status Prescription only
Routes Oral, Ophthalmic
Pharmacokinetic data
Half-life 6-8 hours
Excretion Renal
Identifiers
CAS number 79-57-2 YesY
ATC code D06AA03 G01AA07 J01AA06 S01AA04 QG51AA01 QJ51AA06
PubChem CID 5353856
DrugBank DB00595
ChemSpider 10482174 YesY
UNII SLF0D9077S YesY
KEGG D00205 YesY
ChEBI CHEBI:27701 YesY
ChEMBL CHEMBL1517 YesY
Chemical data
Formula C22H24N2O9 
Mol. mass 460.434 g/mol
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Oxytetracycline was the second of the broad-spectrum tetracycline group of antibiotics to be discovered.

Oxytetracycline works by interfering with the ability of bacteria to produce essential proteins. Without these proteins, the bacteria cannot grow, multiply and increase in numbers. Oxytetracycline therefore stops the spread of the infection and the remaining bacteria are killed by the immune system or eventually die.

Oxytetracycline is a broad-spectrum antibiotic, active against a wide variety of bacteria. However, some strains of bacteria have developed resistance to this antibiotic, which has reduced its effectiveness for treating some types of infections.

Oxytetracycline is still used to treat infections caused by Chlamydia (e.g. the chest infection psittacosis, the eye infection trachoma, and the genital infection urethritis) and infections caused by Mycoplasma organisms (e.g. pneumonia).

Oxytetracycline is also used to treat acne, due to its activity against the bacteria on the skin that cause acne (Propionibacterium acnes). It is used to treat flare-ups of chronic bronchitis, due to its activity against the bacteria usually responsible, Haemophilus influenzae.

Oxytetracycline may also be used to treat other rarer infections, such as those caused by a group of micro-organisms called rickettsiae (e.g. Q fever). To make sure the bacteria causing an infection are susceptible to it, a tissue sample is usually taken, for example a swab from the infected area, or a urine or blood sample.