Tetracyn

Tetracycline

Clinical data
Pronunciation	/ˌtɛtrəˈsaɪkliːn/
Trade names	Sumycin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682098
License data	US FDA: Tetracycline
Pregnancy category	AU: D US: D (Evidence of risk)
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	75%
Metabolism	Not metabolized
Biological half-life	8–11 hours, 57–108 hours (kidney impairment)
Excretion	Urine (>60%), feces
Identifiers
CAS Number	60-54-8 Y 64-75-5 (hydrochloride)
PubChem CID	643969
DrugBank	DB00759 Y
ChemSpider	10257122 Y
UNII	F8VB5M810T
KEGG	D00201 Y
ChEBI	CHEBI:27902 Y
ChEMBL	CHEMBL1440 Y
ECHA InfoCard	100.000.438
Chemical and physical data
Formula	C22H24N2O8
Molar mass	444.435 g/mol
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 Y Key:OFVLGDICTFRJMM-WESIUVDSSA-N Y

Tetracycline, sold under the brand name Sumycin among others, is an antibiotic used to treat a number of infections. This includes acne, cholera, brucellosis, plague, malaria, and syphilis. It is taken by mouth.

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. Tetracycline is in the tetracyclines family of medications. It works by blocking the ability of bacteria to make proteins.

Tetracycline was patented in 1953 and came into commercial use in 1978. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Tetracycline is available as a generic medication. The wholesale cost in the developing world is about 0.35 to 1.78 USD for a course of treatment. In the United States a course of treatment typically costs less than 25 USD. Tetracycline was originally made from bacteria of the Streptomyces type.

It is first-line therapy for Rocky Mountain spotted fever (Rickettsia), Lyme disease (B. burgdorferi), Q fever (Coxiella), psittacosis, lymphogranuloma venereum (Chlamydia), and Mycoplasma pneumoniae and to eradicate nasal carriage of meningococci. Tetracycline tablets were used in the plague outbreak in India in 1994.