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Chlortetracycline

Chlortetracycline (trade name Aureomycin, Lederle Laboratories) is a tetracycline antibiotic, the first tetracycline to be identified. It was discovered in 1945 at Lederle Laboratories under the supervision of scientist Yellapragada Subbarow, Benjamin Minge Duggar. They were helped by Louis T. Wright,[2] a surgeon who conducted this medications first human experiments. Duggar identified the antibiotic as the product of an actinomycete he cultured from a soil sample collected from Sanborn Field at the University of Missouri.[3] The organism was named Streptomyces aureofaciens and the isolated drug, Aureomycin, because of their golden color.[1]

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
Elimination half-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
  • 57-62-5 Y
PubChem CID
  • 54675777
DrugBank
  • DB09093 Y
ChemSpider
  • 10469370 Y
UNII
  • WCK1KIQ23Q
KEGG
  • D07689 Y
ChEMBL
  • ChEMBL456066 N
E numberE702 (antibiotics)
CompTox Dashboard (EPA)
  • DTXSID9022811
ECHA InfoCard100.000.310
Chemical and physical data
FormulaC22H23ClN2O8
Molar mass478.882 g·mol−1
3D model (JSmol)
  • Interactive image
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 Y
  • Key:CYDMQBQPVICBEU-XRNKAMNCSA-N Y
 NY (what is this?)  (verify)

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

Medical uses edit

A combination cream with triamcinolone acetonide is available for the treatment of infected allergic dermatitis in humans.[5]

In veterinary medicine, chlortetracycline is commonly used to treat conjunctivitis in cats,[6] dogs and horses. It is also used to treat infected wounds in cattle, sheep and pigs, and respiratory tract infections in calves, pigs and chickens.[5]

Contraindications edit

Chlortetracycline for systemic use is contraindicated in animals with severe hepatic or renal 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 of acenocoumarol. The risk or severity of adverse effects can be increased when chlortetracycline is combined with acitretin, adapalene, or alitretinoin. 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 of mecillinam (amdinocillin), amoxicillin, and ampicillin can be decreased when used in combination with chlortetracycline. Chlortetracycline may increase the neuromuscular blocking activities of atracurium besilate.[7]

Pharmacology edit

Mechanism of action edit

References edit

  1. ^ a b "chlortetracycline | C22H23ClN2O8 - PubChem". Pubchem.ncbi.nlm.nih.gov. Retrieved 2017-03-13.
  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. ^ a b c d Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. 2018.
  6. ^ Merck Veterinary Manual. Retrieved 2017-03-13. {{cite book}}: |website= ignored (help)
  7. ^ "Chlortetracycline - DrugBank". Drugbank.ca. Retrieved 2017-03-13.

chlortetracycline, trade, name, aureomycin, lederle, laboratories, tetracycline, antibiotic, first, tetracycline, identified, discovered, 1945, lederle, laboratories, under, supervision, scientist, yellapragada, subbarow, benjamin, minge, duggar, they, were, h. Chlortetracycline trade name Aureomycin Lederle Laboratories is a tetracycline antibiotic the first tetracycline to be identified It was discovered in 1945 at Lederle Laboratories under the supervision of scientist Yellapragada Subbarow Benjamin Minge Duggar They were helped by Louis T Wright 2 a surgeon who conducted this medications first human experiments Duggar identified the antibiotic as the product of an actinomycete he cultured from a soil sample collected from Sanborn Field at the University of Missouri 3 The organism was named Streptomyces aureofaciens and the isolated drug Aureomycin because of their golden color 1 ChlortetracyclineClinical dataTrade namesAureomycinAHFS Drugs comMicromedex Detailed Consumer InformationRoutes ofadministrationBy mouth IV topicalATC codeA01AB21 WHO D06AA02 WHO J01AA03 WHO S01AA02 WHO QG51AA08 WHO QJ51AA03 WHO Pharmacokinetic dataBioavailability30 Protein binding50 to 55 MetabolismGastrointestinal tract hepatic 75 MetabolitesIsochlortetracyclineElimination half life5 6 to 9 hoursExcretion60 renal and gt 10 biliaryIdentifiersIUPAC name 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 Number57 62 5 YPubChem CID54675777DrugBankDB09093 YChemSpider10469370 YUNIIWCK1KIQ23QKEGGD07689 YChEMBLChEMBL456066 NE numberE702 antibiotics CompTox Dashboard EPA DTXSID9022811ECHA InfoCard100 000 310Chemical and physical dataFormulaC 22H 23Cl N 2O 8Molar mass478 882 g mol 13D model JSmol Interactive imageSpecific rotation a 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 SMILES 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 23InChI 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 YKey CYDMQBQPVICBEU XRNKAMNCSA N Y N Y what is this verify It is on the World Health Organization s List of Essential Medicines 4 Contents 1 Medical uses 2 Contraindications 3 Adverse effects 4 Interactions 5 Pharmacology 5 1 Mechanism of action 6 ReferencesMedical uses editA combination cream with triamcinolone acetonide is available for the treatment of infected allergic dermatitis in humans 5 In veterinary medicine chlortetracycline is commonly used to treat conjunctivitis in cats 6 dogs and horses It is also used to treat infected wounds in cattle sheep and pigs and respiratory tract infections in calves pigs and chickens 5 Contraindications editChlortetracycline for systemic use is contraindicated in animals with severe hepatic or renal impairment Topical chlortetracycline must not be used on the udder of animals whose milk is intended for human consumption 5 Adverse effects editLike 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 editChlortetracycline may increase the anticoagulant activities of acenocoumarol The risk or severity of adverse effects can be increased when chlortetracycline is combined with acitretin adapalene or alitretinoin 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 of mecillinam amdinocillin amoxicillin and ampicillin can be decreased when used in combination with chlortetracycline Chlortetracycline may increase the neuromuscular blocking activities of atracurium besilate 7 Pharmacology editMechanism of action edit Further information Tetracycline antibiotics Mechanism of actionReferences edit a b chlortetracycline C22H23ClN2O8 PubChem Pubchem ncbi nlm nih gov Retrieved 2017 03 13 Posner Gerald PHARMA Greed Lies and the Poisoning of America S L Avid Reader Pr 2021 pp 47 57 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 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 a b c d Austria Codex in German Vienna Osterreichischer Apothekerverlag 2018 Merck Veterinary Manual Retrieved 2017 03 13 a href Template Cite book html title Template Cite book cite book a website ignored help Chlortetracycline DrugBank Drugbank ca Retrieved 2017 03 13 Retrieved from https en wikipedia org w index php title Chlortetracycline amp oldid 1205419426, wikipedia, wiki, book, books, library,

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