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User:MdWikiBot/Doxycycline

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MdWikiBot/Doxycycline
Clinical data
Pronunciation/ˌdɒksɪˈsaɪkliːn/
DOKS-i-SY-kleen
Trade namesDoryx, Doxyhexal, Doxylin among others
AHFS/Drugs.comSystemic: Monograph
Mouth: Monograph
MedlinePlusa682063
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth, IV[1]
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 faeces, 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
Chemical and physical data
FormulaC22H24N2O8
Molar mass444.44 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 an antibiotic used in the treatment of infections caused by bacteria and certain parasites.[1] It is used to treat bacterial pneumonia, acne, chlamydia infections, early Lyme disease, cholera, typhus, and syphilis.[1] It is also used to prevent malaria and in combination with quinine, to treat malaria.[1] Doxycycline may be taken by mouth or by injection into a vein.[1]

Common side effects include diarrhea, nausea, vomiting, and an increased risk of sunburn.[1] There have been concerns in the first trimester of pregnancy or in young children may result in permanent discoloration of the teeth.[1] Though in children this does not occur with normal doses.[2] Its use during breastfeeding is probably safe.[1] Doxycycline is a broad-spectrum antibiotic, of the tetracycline class.[1] Like other agents of this class, it either slows or kills bacteria by inhibiting protein production.[1][3] It kills malaria by targeting a plastid organelle, the apicoplast.[4][5]

Doxycycline was patented in 1957 and came into commercial use in 1967.[6][7] It is on the World Health Organization's List of Essential Medicines.[8] Doxycycline is available as a generic medicine and is generally inexpensive.[1][9] The wholesale cost in the developing world is between US$0.01 and US$0.04 per pill.[10] In the United States, ten days of treatment has a wholesale costs of about US$3.40 as of 2019.[11] However, in 2014, due to supply issues, it was being sold for as much as US$60–200 for that amount.[1][12] In 2017, it was the 113th most commonly prescribed medication in the United States, with more than six million prescriptions.[13][14]

References

change
  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 "Doxycycline calcium". The American Society of Health-System Pharmacists. Archived from the original on 23 September 2015. Retrieved 18 August 2015.
  2. ↑ Ravindra, D; Huang, G; Hallett, K; Burgner, DP; Gwee, A; Silva, MJ (1 July 2023). "Antibiotic Exposure and Dental Health: A Systematic Review". Pediatrics. 152 (1). doi:10.1542/peds.2023-061350. PMID 37264510.
  3. ↑ 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.
  4. ↑ McFadden GI (March 2014). "Apicoplast". Curr. Biol. 24 (7): R262–3. doi:10.1016/j.cub.2014.01.024. PMID 24698369.
  5. ↑ Schlagenhauf-Lawlor, Patricia (2008). Travelers' Malaria. PMPH-USA. p. 148. ISBN 9781550093360. Archived from the original on 1 August 2020. Retrieved 18 August 2019.
  6. ↑ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 9783527607495. Archived from the original on 1 August 2020. Retrieved 9 September 2017.
  7. ↑ Corey, E.J. (2013). Drug discovery practices, processes, and perspectives. Hoboken, N.J.: John Wiley & Sons. p. 406. ISBN 9781118354469. Archived from the original on 1 August 2020. Retrieved 9 September 2017.
  8. ↑ 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.
  9. ↑ Hamilton, Richard J. (2011). Tarascon pharmacopoeia (12th ed.). Sudbury, MA: Jones & Bartlett Learning. p. 79. ISBN 9781449600679. Archived from the original on 1 August 2020. Retrieved 9 September 2017.
  10. ↑ "Doxycycline". International Medical Products Price Guide. Archived from the original on 30 March 2019. Retrieved 16 January 2018.
  11. ↑ "NADAC as of 2019-09-11 | Data.Medicaid.gov". Centers for Medicare and Medicaid Services. Archived from the original on 30 December 2019. Retrieved 10 September 2019.
  12. ↑ "Officials Question the Rising Costs of Generic Drugs". New York Times. 7 October 2014. Archived from the original on 28 October 2015. Retrieved 22 September 2015.
  13. ↑ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
  14. ↑ "Doxycycline - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 11 April 2020.
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