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Doxycycline

From Wikipedia
doxycycline
type of chemical entity
Subclass oftetracycline polyketide Edit
Get useMedication Edit
Stereoisomer of4-epidoxycycline, 6-epidoxycycline, 4-epi-6-epidoxycycline Edit
Tautomer ofdoxycycline tautomer Edit
Chemical formulaC₂₂H₂₄N₂O₈ Edit
Canonical SMILESCC1C2=CC=CC(=C2C(=O)C3=C(C4(C(C(C13)O)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O Edit
Isomeric SMILESC[C@H]1C2=CC=CC(=C2C(=O)C3=C([C@]4([C@@H]([C@H]([C@H]13)O)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O Edit
World Health Organisation international non-proprietary namedoxycycline Edit
Found insyd taxonStreptomyces hygroscopicus Edit
Significant drug interactionrac-warfarin, tretinoin, acitretin, isotretinoin, carbamazepin Edit
Pregnancy categoryAustralian pregnancy category D, US pregnancy category D Edit
LiverTox likelihood scoreLiverTox toxicity likelihood category B Edit
ManufacturerPfizer Edit
WHO Aware Classificationaccess Edit

Doxycycline be a broad-spectrum antibiotic of de tetracycline class dem use insyd de treatment of infections wey be caused by bacteria den certain parasites.[1] Dem dey use to treat bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, den syphilis.[1] Dem sanso dey use am to prevent malaria.[2][3] Dem fi take doxycycline by mouth anaa intravenously.[1]

Common side effects dey include diarrhea, nausea, vomiting, abdominal pain, den an increased risk of sunburn.[1] Ein use during pregnancy no be recommended.[1] Like oda agents of de tetracycline class, e either dey slow anaa dey kill bacteria by inhibiting protein production.[1][4] E dey kill Plasmodium—microorganisms wey be associated plus malaria—by targeting a plastid organelle, de apicoplast.[5][6]

Dem sanso dey use doxycycline as prophylaxis against sexually transmitted infections, particularly insyd men wey dey have sex plus men.[7] E be used for post-exposure prophylaxis (PEP) to reduce de incidence of sexually transmitted bacterial infections (STIs), wey be supported by guidelines from de US Centers for Disease Control and Prevention (CDC)[8] den de Australasian Society for HIV Medicine.[9][10]

According to NHS guidance, de use of Doxy-PEP be associated plus reductions in risk of chlamydia by 70–89%, syphilis by 73–87%, den gonorrhoea by 51–57%.[11]

Na dem patent doxycycline insyd 1957 wey e cam into commercial use insyd 1967.[12][13] E dey on de World Health Organization's List of Essential Medicines.[14] Doxycycline be available as a generic medicine.[1][15] Insyd 2023, na e be de 77th most commonly prescribed medication insyd de United States, plus more dan 8 million prescriptions.[16][17]

References

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  1. 1 2 3 4 5 6 7 "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. ↑ Nelson ML, Levy SB (December 2011). "The history of the tetracyclines". Annals of the New York Academy of Sciences. 1241 (1): 17–32. Bibcode:2011NYASA1241...17N. doi:10.1111/j.1749-6632.2011.06354.x. PMID 22191524. S2CID 34647314.
  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. ↑ "Preventing STIs with Doxy PEP". U.S. Centers for Disease Control and Prevention (CDC). 5 December 2024. Retrieved 26 December 2024.
  8. ↑ "Guidelines for the Use of Doxycycline Post-Exposure Prophylaxis for Bacterial STI Prevention". U.S. Centers for Disease Control and Prevention (CDC). 29 September 2023. Archived from the original on 10 March 2024. Retrieved 10 March 2024.
  9. ↑ "2023 Consensus Statement on doxycycline prophylaxis (Doxy-PEP) for the prevention of syphilis, chlamydia and gonorrhoea among gay, bisexual, and other men who have sex with men in Australia". Australasian Society for HIV Medicine. Archived from the original on 10 March 2024. Retrieved 10 March 2024.
  10. ↑ Highleyman L (5 March 2024). "Sexually transmitted infections in San Francisco have fallen since doxyPEP roll-out". Aidsmap. Archived from the original on 10 March 2024. Retrieved 10 March 2024.
  11. ↑ "Doxy-PEP". Central and North West London NHS Foundation Trust (in English). Retrieved 4 August 2025.
  12. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 978-3-527-60749-5.
  13. ↑ 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.
  14. ↑ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  15. ↑ Hamilton RJ (2011). Tarascon pharmacopoeia (12th ed.). Sudbury, MA: Jones & Bartlett Learning. p. 79. ISBN 978-1-4496-0067-9.
  16. ↑ "Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025.
  17. ↑ "Doxycycline Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
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Dem retrieve am from "https://gpe.wikipedia.org/w/index.php?title=Doxycycline&oldid=82958"