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Chlortetracycline

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Chlortetracycline
Clinical data
Trade namesAureomycin
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
By mouth,IV,topical
ATC code
Pharmacokinetic data
Bioavailability30%
Protein binding50 to 55%
MetabolismGastrointestinal tract,hepatic (75%)
MetabolitesIsochlortetracycline
Eliminationhalf-life5.6 to 9 hours
Excretion60%renal and >10%biliary
Identifiers
  • (4S,4aS,5aS,6S,12aR)-7-Chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide[1]
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E numberE702(antibiotics)Edit this at Wikidata
CompTox Dashboard(EPA)
ECHA InfoCard100.000.310Edit this at Wikidata
Chemical and physical data
FormulaC22H23ClN2O8
Molar mass478.88 g·mol−1
3D model (JSmol)
Specific rotation[α]D25−275°·cm3·dm−1·g−1 (methane)
Melting point168 to 169 °C (334 to 336 °F)
Solubility in water0.5–0.6 mg/mL (20 °C)
  • CN(C)[C@@H]2C(\O)=C(\C(N)=O)C(=O)[C@@]3(O)C(/O)=C4/C(=O)c1c(O)ccc(Cl)c1[C@@](C)(O)[C@H]4C[C@@H]23
  • InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1 checkY
  • Key:CYDMQBQPVICBEU-XRNKAMNCSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Chlortetracycline (trade nameAureomycin,Lederle Laboratories) is atetracyclineantibiotic, the firsttetracycline to be identified. It was discovered in 1945 at Lederle Laboratories under the supervision ofYellapragada Subbarow andBenjamin Minge Duggar. They were helped byLouis T. Wright,[2] a surgeon who conducted this medication's first human experiments. Duggar identified the antibiotic as the product of anactinomycete he cultured from the soil ofSanborn Field at theUniversity of Missouri.[3] The organism was namedStreptomyces aureofaciens and the isolated drug, Aureomycin, because of their golden color.[1]

It is on theWorld Health Organization's List of Essential Medicines.[4]

Medical uses

[edit]

A combination cream withtriamcinolone acetonide is available for the treatment of infectedallergic dermatitis in humans.[5]

Inveterinary medicine, chlortetracycline is commonly used to treatconjunctivitis incats,[6] dogs and horses. It is also used to treat infected wounds in cattle, sheep and pigs, andrespiratory tract infections in calves, pigs and chickens.[5]

Contraindications

[edit]

Chlortetracycline for systemic use is contraindicated in animals with severehepatic orrenal impairment. Topical chlortetracycline must not be used on the udder of animals whose milk is intended for human consumption.[5]

Adverse effects

[edit]

Like other tetracyclines, chlortetracyclin can inhibit bone and tooth mineralization in growing and unborn animals, and color their teeth yellow or brown. It can also impair liver and kidney function. Allergic reactions are rare.[5]

Interactions

[edit]

Chlortetracycline may increase the anticoagulant activities ofacenocoumarol. The risk or severity of adverse effects can be increased when chlortetracycline is combined withacitretin,adapalene, oralitretinoin. Aluminum phosphate and aluminum hydroxide can cause decreases in the absorption of chlortetracycline resulting in a reduced serum concentration and potentially a decrease in efficacy. The therapeutic efficacy ofmecillinam (amdinocillin),amoxicillin, andampicillin can be decreased when used in combination with chlortetracycline. Chlortetracycline may increase the neuromuscular blocking activities ofatracurium besilate.[7]

Pharmacology

[edit]

Mechanism of action

[edit]
Further information:Tetracycline antibiotics § Mechanism of action

References

[edit]
  1. ^ab"chlortetracycline | C22H23ClN2O8 - PubChem".Pubchem.ncbi.nlm.nih.gov. Retrieved2017-03-13.
  2. ^Posner, Gerald. PHARMA : Greed, Lies, and the Poisoning of America. S.L., Avid Reader Pr, 2021, pp. 47–57.
  3. ^Jukes TH (1985). "Some historical notes on chlortetracycline".Reviews of Infectious Diseases.7 (5):702–7.doi:10.1093/clinids/7.5.702.PMID 3903946.
  4. ^World Health Organization (2021).World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization.hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  5. ^abcdAustria-Codex (in German). Vienna: Österreichischer Apothekerverlag. 2018.
  6. ^Merck Veterinary Manual. Retrieved2017-03-13.{{cite book}}:|work= ignored (help)
  7. ^"Chlortetracycline - DrugBank".Drugbank.ca. Retrieved2017-03-13.
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