Doxycycline

Doxycycline
Clinical data
Pronunciation/ˌdɒksɪˈsaɪkliːn/
DOKS-iss-EYE-kleen
Trade namesDoxy, Doryx, Vibramycin, others
AHFS/Drugs.comMonograph
MedlinePlusa682063
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth, intravenous[1]
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability~100%
Protein binding80–90%
MetabolismNegligible
Elimination half-life10–22 hours
ExcretionMainly feces, 40% urine
Identifiers
  • (4S,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.429 Edit this at Wikidata
Chemical and physical data
FormulaC22H24N2O8
Molar mass444.440 g·mol−1
3D model (JSmol)
  • CN(C)[C@@H]3C(\O)=C(\C(N)=O)C(=O)[C@@]4(O)C(/O)=C2/C(=O)c1c(cccc1O)[C@H](C)[C@H]2[C@H](O)[C@@H]34
  • InChI=1S/C22H24N2O8.H2O/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);1H2/t7-,10+,14+,15-,17-,22-;/m0./s1 checkY
  • Key:XQTWDDCIUJNLTR-CVHRZJFOSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites.[1] It is used to treat bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, and syphilis.[1] It is also used to prevent malaria.[2][3] Doxycycline may be taken by mouth or by injection into a vein.[1]

Common side effects include diarrhea, nausea, vomiting, abdominal pain, and an increased risk of sunburn.[1] Use during pregnancy is not recommended.[1] Like other agents of the tetracycline class, it either slows or kills bacteria by inhibiting protein production.[1][4] It kills malaria by targeting a plastid organelle, the apicoplast.[5][6]

Doxycycline was patented in 1957 and came into commercial use in 1967.[7][8] It is on the World Health Organization's List of Essential Medicines.[9] Doxycycline is available as a generic medicine.[1][10] In 2022, it was the 68th most commonly prescribed medication in the United States, with more than 9 million prescriptions.[11][12]

  1. ^ a b c d e f g h "Doxycycline calcium". The American Society of Health-System Pharmacists. Archived from the original on 23 September 2015. Retrieved 18 August 2015.
  2. ^ "Malaria". Fit for Travel. Public Health Scotland. Chemoprophylaxis. Archived from the original on 4 December 2023. Retrieved 4 December 2023.
  3. ^ "Choosing a Drug to Prevent Malaria". Centers for Disease Control and Prevention. February 2023. Doxycycline. Archived from the original on 13 November 2016. Retrieved 4 December 2023.
  4. ^ Cite error: The named reference pmid22191524 was invoked but never defined (see the help page).
  5. ^ McFadden GI (March 2014). "Apicoplast". Current Biology. 24 (7): R262-3. Bibcode:2014CBio...24.R262M. doi:10.1016/j.cub.2014.01.024. PMID 24698369.
  6. ^ Schlagenhauf-Lawlor P (2008). Travelers' Malaria. PMPH-USA. p. 148. ISBN 978-1-55009-336-0.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 978-3-527-60749-5.
  8. ^ Corey EJ (2013). Drug discovery practices, processes, and perspectives. Hoboken, N.J.: John Wiley & Sons. p. 406. ISBN 978-1-118-35446-9. Archived from the original on 14 January 2023. Retrieved 9 September 2017.
  9. ^ 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.
  10. ^ Hamilton RJ (2011). Tarascon pharmacopoeia (12th ed.). Sudbury, MA: Jones & Bartlett Learning. p. 79. ISBN 978-1-4496-0067-9.
  11. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  12. ^ "Doxycycline Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Archived from the original on 8 July 2020. Retrieved 30 August 2024.