Tetracycline

Tetracycline
Clinical data
Pronunciation	/ˌtɛtrəˈsaɪkliːn/
Other names	TE/TET/TC/TCY
AHFS/Drugs.com	Monograph
MedlinePlus	a682098
License data	US FDA: Tetracycline;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
ATC code	A01AB13 (WHO) D06AA04 (WHO) J01AA07 (WHO) S01AA09 (WHO) S02AA08 (WHO) S03AA02 (WHO) QG01AA90 (WHO) QG51AA02 (WHO) QJ51AA07 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	80%
Metabolism	Not metabolized
Elimination half-life	8–11 hours, 57–108 hours (kidney impairment)
Excretion	Urine (>60%), feces
Identifiers
	IUPAC name (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;
CAS Number	60-54-8 ; 64-75-5 (hydrochloride);
PubChem CID	54675776;
DrugBank	DB00759 ;
ChemSpider	10257122 ;
UNII	F8VB5M810T;
KEGG	D00201 ;
ChEBI	CHEBI:27902 ;
ChEMBL	ChEMBL1440 ;
PDB ligand	TAC (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID7023645 ;
ECHA InfoCard	100.000.438
Chemical and physical data
Formula	C22H24N2O8
Molar mass	444.440 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]1(c2cccc(c2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O;
	InChI InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1 ; Key:OFVLGDICTFRJMM-WESIUVDSSA-N ;
	(verify)

Tetracycline, sold under various brand names, is an oral antibiotic in the tetracyclines family of medications, used to treat a number of infections, including acne, cholera, brucellosis, plague, malaria, and syphilis.

Common side effects include vomiting, diarrhea, rash, and loss of appetite. Other side effects include poor tooth development if used by children less than eight years of age, kidney problems, and sunburning easily. Use during pregnancy may harm the baby. It works by inhibiting protein synthesis in bacteria.

Tetracycline was patented in 1953 and was approved for prescription use in 1954. It is on the World Health Organization's List of Essential Medicines. Tetracycline is available as a generic medication. Tetracycline was originally made from bacteria of the genus Streptomyces.

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