User:Mr. Ibrahem/Chlortetracycline

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Mr. Ibrahem/Chlortetracycline
chlortetracycline 2D skeletal
chlortetracycline 3D BS
Clinical data
Trade namesAureomycin
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		By mouth, IV, topical
Drug classTetracycline[1]
Pharmacokinetic data
Bioavailability30%
Protein binding50 to 55%
MetabolismGastrointestinal tract, liver (75%)
MetabolitesIsochlortetracycline
Elimination half-life5.6 to 9 hours
Excretion60% kidney 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[2]
Chemical and physical data
FormulaC22H23ClN2O8
Molar mass478.882 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, sold under the brand name Aureomycin among others, is an antibiotic used to treat conjunctivitis, including trachoma.[3] It is generally used as an eye drop.[5] It may also be used for Rickettsiae.[4]

Side effects may include tooth staining, sun sensitivity, nausea, and diarrhea.[4] Other side effects may include kidney and liver problems.[4] Use is not recommended during pregnancy or breastfeeding.[4] It is a tetracycline and works by interfering with protein production.[1]

Chlortetracycline was discovered in 1945 by Benjamin Minge Duggar and came into medical use in 1948.[6][7] The eye drop was approved in the United States in 1950; though is no longer commercially available.[5] It is on the World Health Organization's List of Essential Medicines as an alternative to tetracycline.[8] It is also used in veterinary medicine.[9]

References[edit]

  1. ^ a b Sneader, Walter (23 June 2005). Drug Discovery: A History. John Wiley & Sons. p. 304. ISBN 978-0-471-89979-2. Archived from the original on 13 September 2023. Retrieved 10 September 2023.
  2. ^ "chlortetracycline | C22H23ClN2O8 - PubChem". Pubchem.ncbi.nlm.nih.gov. Archived from the original on 2016-12-21. Retrieved 2017-03-13.
  3. ^ a b "eEML - Electronic Essential Medicines List". list.essentialmeds.org. Archived from the original on 29 May 2023. Retrieved 10 September 2023.
  4. ^ a b c d e Scholar, Eric (2007). "Chlortetracycline". xPharm: The Comprehensive Pharmacology Reference: 1–5. doi:10.1016/B978-008055232-3.61451-5.
  5. ^ a b "Chlortetracycline: Indications, Side Effects, Warnings". Drugs.com. Archived from the original on 12 August 2022. Retrieved 10 September 2023.
  6. ^ Ravina, Enrique (18 April 2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. p. 279. ISBN 978-3-527-32669-3. Archived from the original on 13 September 2023. Retrieved 10 September 2023.
  7. ^ Riviere, Jim E.; Papich, Mark G. (17 March 2009). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. p. 902. ISBN 978-0-8138-2061-3. Archived from the original on 13 September 2023. Retrieved 10 September 2023.
  8. ^ 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.
  9. ^ "Click to open content tools § 558.128 Chlortetracycline". Archived from the original on 20 March 2022. Retrieved 10 September 2023.
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