Doxycycline

Doxycycline
Clinical data
Pronunciation	/ˌdɒksɪˈsaɪkliːn/; DOKS-iss-EYE-kleen
Trade names	Doxy, Doryx, Vibramycin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682063
License data	US DailyMed: Doxycycline;
Pregnancy; category	AU: D; ;
Routes of; administration	By mouth, intravenous
ATC code	J01AA02 (WHO) A01AB22 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	~100%
Protein binding	80–90%
Metabolism	Negligible
Elimination half-life	10–22 hours
Excretion	Mainly feces, 40% urine
Identifiers
	IUPAC name (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	564-25-0 ;
PubChem CID	Doxycycline;
DrugBank	DB00254 ;
ChemSpider	10482106 ;
UNII	334895S862;
KEGG	D07876 ;
ChEBI	CHEBI:60648 ;
ChEMBL	ChEMBL1433 ;
CompTox Dashboard (EPA)	DTXSID0037653 ;
ECHA InfoCard	100.008.429
Chemical and physical data
Formula	C22H24N2O8
Molar mass	444.440 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:XQTWDDCIUJNLTR-CVHRZJFOSA-N ;
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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 2021, it was the 82nd most commonly prescribed medication in the United States, with more than 8 million prescriptions.^[11]^[12]

^ ^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.
^ "Malaria". Fit for Travel. Public Health Scotland. Chemoprophylaxis. Archived from the original on 4 December 2023. Retrieved 4 December 2023.
^ "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.
^ Cite error: The named reference pmid22191524 was invoked but never defined (see the help page).
^ 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.
^ Schlagenhauf-Lawlor P (2008). Travelers' Malaria. PMPH-USA. p. 148. ISBN 978-1-55009-336-0.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 978-3-527-60749-5.
^ 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.
^ 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.
^ Hamilton RJ (2011). Tarascon pharmacopoeia (12th ed.). Sudbury, MA: Jones & Bartlett Learning. p. 79. ISBN 978-1-4496-0067-9.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Doxycycline - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 14 January 2024.

[AHFS2015-1] ^ ^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.

[Fit_for_Travel-2] "Malaria". Fit for Travel. Public Health Scotland. Chemoprophylaxis. Archived from the original on 4 December 2023. Retrieved 4 December 2023.

[Centers_for_Disease_Control_and_Prevention-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.

[pmid22191524-4] Cite error: The named reference pmid22191524 was invoked but never defined (see the help page).

[pmid24698369-5] 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.

[Schlagenhauf-Lawlor-2008-6] Schlagenhauf-Lawlor P (2008). Travelers' Malaria. PMPH-USA. p. 148. ISBN 978-1-55009-336-0.

[Fischer-2006-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 978-3-527-60749-5.

[Corey-2013-8] 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.

[WHO21st-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.

[Hamilton-2011-10] Hamilton RJ (2011). Tarascon pharmacopoeia (12th ed.). Sudbury, MA: Jones & Bartlett Learning. p. 79. ISBN 978-1-4496-0067-9.

[ClinCalc-300-2021-11] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[ClinCalc-Usage-2020-12] "Doxycycline - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 14 January 2024.

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Clinical data


Pronunciation	/ˌdɒksɪˈsaɪkliːn/ DOKS-iss-EYE-kleen
Trade names	Doxy, Doryx, Vibramycin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682063
License data	US DailyMed: Doxycycline
Pregnancy category	AU: D
Routes of administration	By mouth, intravenous^[1]
ATC code	J01AA02 (WHO) A01AB22 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	~100%
Protein binding	80–90%
Metabolism	Negligible
Elimination half-life	10–22 hours
Excretion	Mainly feces, 40% urine
Identifiers
IUPAC name (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	564-25-0^Y
PubChem CID	Doxycycline
DrugBank	DB00254^Y
ChemSpider	10482106^Y
UNII	334895S862
KEGG	D07876^N
ChEBI	CHEBI:60648^Y
ChEMBL	ChEMBL1433^N
CompTox Dashboard (EPA)	DTXSID0037653
ECHA InfoCard	100.008.429
Chemical and physical data
Formula	C₂₂H₂₄N₂O₈
Molar mass	444.440 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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^Y Key:XQTWDDCIUJNLTR-CVHRZJFOSA-N^Y
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