Chlortetracycline

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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E numberE702 (antibiotics) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.000.310 Edit 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 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 and Benjamin Minge Duggar. They were helped by Louis T. Wright,[2] a surgeon who conducted this medication's 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]

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

  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.