Oxytetracycline

Oxytetracycline
Clinical data
Trade namesTerramycin
Pregnancy
category
  • AU: D
Routes of
administration		By mouth, topical (eye drop)
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life6–8 hours
ExcretionKidney
Identifiers
  • (4S,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-3,5,6,10,11,12a-hexahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
E numberE703 (antibiotics) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.001.103 Edit this at Wikidata
Chemical and physical data
FormulaC22H24N2O9
Molar mass460.439 g·mol−1
3D model (JSmol)
Melting point181 to 182 °C (358 to 360 °F)
  • CN(C)[C@@H]3C(\O)=C(\C(N)=O)C(=O)[C@@]4(O)C(/O)=C2/C(=O)c1c(cccc1O)[C@@](C)(O)[C@H]2[C@H](O)[C@@H]34
  • InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1 checkY
  • Key:IWVCMVBTMGNXQD-PXOLEDIWSA-N checkY
  (verify)

Oxytetracycline is a broad-spectrum tetracycline antibiotic, the second of the group to be discovered.

Oxytetracycline works by interfering with the ability of bacteria to produce essential proteins. Without these proteins, the bacteria cannot grow, multiply and increase in numbers. Oxytetracycline therefore stops the spread of the infection, and the remaining bacteria are killed by the immune system or eventually die.

Oxytetracycline is active against a wide variety of bacteria. However, some strains of bacteria have developed resistance to this antibiotic, which has reduced its effectiveness for treating some types of infections.

Oxytetracycline is used to treat infections caused by Chlamydia, such as psittacosis, trachoma, and urethritis, and infections caused by Mycoplasma organisms, such as pneumonia.

Oxytetracycline is used to treat acne, due to its activity against the bacteria on the skin that influence the development of acne (Cutibacterium acnes). It is used to treat flare-ups of chronic bronchitis, due to its activity against Haemophilus influenzae. Oxytetracycline may be used to treat other rarer infections, such as those caused by a group of microorganisms called rickettsiae (e.g., Rocky Mountain spotted fever). To make sure the bacteria causing an infection are susceptible to it, a tissue sample is usually taken; for example, a swab from the infected area or a urine or blood sample.[citation needed]

Oxytetracycline was patented in 1949 and came into commercial use in 1950.[1] It is on the World Health Organization's List of Essential Medicines as an alternative to tetracycline.[2]

  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 9783527607495.
  2. ^ 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.