Oxytetracycline

Oxytetracycline

Clinical data
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	Oral, Ophthalmic
ATC code	D06AA03 (WHO) G01AA07 (WHO) J01AA06 (WHO) S01AA04 (WHO) QG51AA01 (WHO) QJ51AA06 (WHO)
Legal status
Legal status	Prescription only
Pharmacokinetic data
Biological half-life	6-8 hours
Excretion	Renal
Identifiers
IUPAC name (4S,4aR,5S,5aR,6S,12aS) -4-(dimethylamino)-3,5,6,10,11,12a-hexahydroxy -6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene -2-carboxamide
CAS Number	79-57-2 Y
PubChem (CID)	54675779
DrugBank	DB00595 Y
ChemSpider	10482174 Y
UNII	SLF0D9077S Y
KEGG	D00205 Y
ChEBI	CHEBI:27701 Y
ChEMBL	CHEMBL1517 Y
PDB ligand ID	OAQ (PDBe, RCSB PDB)
E number	E703 (Citation needed) (antibiotics)
ECHA InfoCard	100.001.103
Chemical and physical data
Formula	C22H24N2O9
Molar mass	460.434 g/mol
3D model (Jmol)	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@@](C)(O)[C@H]2[C@H](O)[C@@H]34
InChI InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1 Y Key:IWVCMVBTMGNXQD-PXOLEDIWSA-N Y

Oxytetracycline was the second of the broad-spectrum tetracycline group of antibiotics to be discovered.

Oxytetracycline works by interfering with the ability of bacteria to produce essential proteins. Without these proteins, the bacteria cannot grow, multiply and increase in numbers. Oxytetracycline therefore stops the spread of the infection and the remaining bacteria are killed by the immune system or eventually die.

Oxytetracycline is a broad-spectrum antibiotic, active against a wide variety of bacteria. However, some strains of bacteria have developed resistance to this antibiotic, which has reduced its effectiveness for treating some types of infections.

Oxytetracycline is still used to treat infections caused by Chlamydia (e.g. the chest infection psittacosis, the eye infection trachoma, and the genital infection urethritis) and infections caused by Mycoplasma organisms (e.g. pneumonia).

Oxytetracycline is also used to treat acne, due to its activity against the bacteria on the skin that cause acne (Propionibacterium acnes). It is used to treat flare-ups of chronic bronchitis, due to its activity against the bacteria usually responsible, Haemophilus influenzae. Oxytetracycline may also be used to treat other rarer infections, such as those caused by a group of micro-organisms called rickettsiae (e.g. Q fever). To make sure the bacteria causing an infection are susceptible to it, a tissue sample is usually taken, for example a swab from the infected area, or a urine or blood sample.

Oxytetracycline was patented in 1949 and came into commercial use in 1950.

Oxytetracycline, like other tetracyclines, is used to treat many infections, both common and rare (see Tetracycline antibiotics group). Its better absorption profile makes it preferable to tetracycline for moderately severe acne at a dosage of 250–500 mg four times a day for usually six to eight weeks at a time, but alternatives should be sought if no improvement occurs by three months. Avoid milk, iron, zinc or indigestion remedies while taking oxytetracycline. Take before food or on an empty stomach. Always follow your doctors' instructions and instruction leaflet.