Oxytetracycline

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Oxytetracycline

Clinical data
Trade names	Terramycin
Pregnancy category	AU: D
Routes of administration	By mouth, topical (eye drop)
ATC code	D06AA03 (WHO) A01AB25 (WHO), G01AA07 (WHO), J01AA06 (WHO), S01AA04 (WHO), QA01AB25 (WHO), QJ51AA06 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	6–8 hours
Excretion	Kidney
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
KEGG	C06624 Y
ChEBI	CHEBI:27701 Y
ChEMBL	ChEMBL1517 Y
PDB ligand	OAQ (PDBe, RCSB PDB)
E number	E703 (antibiotics)
CompTox Dashboard (EPA)	DTXSID1034260
ECHA InfoCard	100.001.103
Chemical and physical data
Formula	C22H24N2O9
Molar mass	460.439 g·mol−1
3D model (JSmol)	Interactive image
Melting point	181 to 182 °C (358 to 360 °F)
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
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Oxytetracycline is a broad-spectrum tetracycline antibiotic, the second of the group 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 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 used to treat infections caused by Chlamydia, such as psittacosis, trachoma, and urethritis, and infections caused by Mycoplasma organisms, such as pneumonia.

Oxytetracycline is used to treat acne, due to its activity against the bacteria on the skin that influence the development of acne (Cutibacterium acnes). It is used to treat flare-ups of chronic bronchitis, due to its activity against Haemophilus influenzae. Oxytetracycline may be used to treat other rarer infections, such as those caused by a group of microorganisms called rickettsiae (e.g., Rocky Mountain spotted 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.^{[citation needed]}

Oxytetracycline was patented in 1949 and came into commercial use in 1950.^[1] It is on the World Health Organization's List of Essential Medicines as an alternative to tetracycline.^[2]