Doxycycline

Doxycycline
Clinical data
Pronunciation	/ˌdɒksɪˈsaɪkliːn/; DOKS-ih-SYE-kleen
Trade names	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;

Doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites. It is used to treat bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, and syphilis, and is sometimes used to prevent malaria. Doxycycline may be taken by mouth or intravenously.

Common side effects include diarrhea, nausea, vomiting, abdominal pain, and an increased risk of sunburn. Use during pregnancy is not recommended. Doxycycline can be used in children of all ages, including for Lyme disease and rickettsial infections. Like other agents of the tetracycline class, it slows or kills bacteria by inhibiting protein production. It kills Plasmodium—microorganisms associated with malaria—by targeting a plastid organelle, the apicoplast.

Doxycycline post-exposure prophylaxis (doxyPEP) is also used to prevent sexually transmitted infections, particularly in men who have sex with men, and is supported by CDC guidelines.

Doxycycline was patented in 1957 and came into commercial use in 1967. It is on the World Health Organization's List of Essential Medicines. Doxycycline is available as a generic medicine. In 2023, it was the 77th most commonly prescribed medication in the United States, with more than 8 million prescriptions.