Tetracycline

This article is about the specific antibiotic. For the family of antibiotics, see Tetracycline antibiotics.

Tetracycline
tetracycline 2D skeletal
tetracycline 3D BS
Clinical data
Pronunciation/ˌtɛtrəˈsaɪkliːn/
Trade namesTetracyn
Other namesTE/TET/TC/TCY[1]
AHFS/Drugs.comMonograph
MedlinePlusa682098
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability80%
MetabolismNot metabolized
Elimination half-life8–11 hours, 57–108 hours (kidney impairment)
ExcretionUrine (>60%), feces
Identifiers
  • (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide[2]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.438 Edit this at Wikidata
Chemical and physical data
FormulaC22H24N2O8
Molar mass444.440 g·mol−1
3D model (JSmol)
  • C[C@]1(c2cccc(c2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O
  • InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1 checkY
  • Key:OFVLGDICTFRJMM-WESIUVDSSA-N checkY
  (verify)

Tetracycline, sold under various brand names, is an oral antibiotic in the tetracyclines family of medications, used to treat a number of infections,[3] including acne, cholera, brucellosis, plague, malaria, and syphilis.[3]

Common side effects include vomiting, diarrhea, rash, and loss of appetite.[3] Other side effects include poor tooth development if used by children less than eight years of age, kidney problems, and sunburning easily.[3] Use during pregnancy may harm the baby.[3] It works by inhibiting protein synthesis in bacteria.[3]

Tetracycline was patented in 1953[4] and was approved for prescription use in 1954.[5][6] It is on the World Health Organization's List of Essential Medicines.[7] Tetracycline is available as a generic medication.[3] Tetracycline was originally made from bacteria of the genus Streptomyces.[3]

  1. ^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
  2. ^ "Tetracycline". PubChem. National Center for Biotechnology Information.
  3. ^ a b c d e f g h "Tetracycline". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  4. ^ U.S. patent 2699054A
  5. ^ Cite error: The named reference History was invoked but never defined (see the help page).
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 9783527607495. Archived from the original on 20 December 2016.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.