Doxycycline hyclate

Doxycycline

Clinical data
Pronunciation	/ˌdɒksiˈsaɪklin/ DOX-i-SYE-kleen
Trade names	Doryx, Doxyhexal, Doxylin among others
AHFS/Drugs.com	Monograph
MedlinePlus	a682063
License data	US FDA: Doxycycline
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	By mouth, IV
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	90%
Metabolism	Liver
Biological half-life	15–25 hours
Excretion	Urine (40%)
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	11256
DrugBank	DB00254 Y
ChemSpider	10482106 Y
UNII	334895S862
KEGG	D00307 N
ChEBI	CHEBI:60648 Y
ChEMBL	CHEMBL1433 N
ECHA InfoCard	100.008.429
Chemical and physical data
Formula	C22H24N2O8
Molar mass	444.43 g/mol
3D model (JSmol)	Interactive image
SMILES O.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
NY (what is this?)

Doxycycline is an antibiotic that is used in the treatment of a number of types of infections caused by bacteria and protozoa. It is useful for bacterial pneumonia, acne, chlamydia infections, early Lyme disease, cholera and syphilis. It is also useful for the treatment of malaria when used with quinine and for the prevention of malaria. Doxycycline can be used either by mouth or intravenously.

Common side effects include diarrhea, nausea, vomiting, a red rash, and an increased risk of a sunburn. If used during pregnancy or in young children may result in permanent problems with the teeth including changes in their color. Its use during breastfeeding is probably safe. Doxycycline is a broad-spectrum antibiotic of the tetracycline class. Like other agents of this class it kills bacteria and protozoa by inhibiting protein production.

Doxycycline was patented in 1957 and came into commercial use in 1967. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Doxycycline is available as a generic medicine and is generally inexpensive. The wholesale cost in the developing world is between 0.01 and 0.04 USD per pill. In the United States 10 days of treatment is about 14 USD, however some in 2014 were selling it for more than 3.00 to 10.00 USD per pill.

In addition to the general indications for all members of the tetracycline antibiotics group, doxycycline is frequently used to treat Lyme disease, chronic prostatitis, sinusitis, pelvic inflammatory disease,acne, rosacea, and rickettsial infections.