Minocycline

Minocycline, sold under the brand name Minocin among others, is a tetracycline antibiotic medication used to treat a number of bacterial infections such as pneumonia. It is generally (but not always) less preferred than the tetracycline doxycycline. Minocycline is also used for the treatment of acne and rheumatoid arthritis. It is taken by mouth or applied to the skin.

Minocycline

Clinical data
Trade names	Minocin, Amzeeq, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682101
License data	US DailyMed: Minocycline US FDA: Minocycline
Pregnancy category	AU: D
Routes of administration	By mouth, intravenous, topical
ATC code	J01AA08 (WHO) A01AB23 (WHO), D10AF07 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	90–100%
Protein binding	70–75%
Metabolism	Liver
Elimination half-life	14–22 (11–26) hours
Excretion	Mostly fecal, 10–15% renal
Identifiers
IUPAC name (2E,4S,4aR,5aS,12aR)-2-(Amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6- tetrahydro-4H-tetracene-1,3,12-trione
CAS Number	10118-90-8 Y
PubChem CID	54675783
DrugBank	DB01017 N
ChemSpider	16735907 Y
UNII	FYY3R43WGO
KEGG	D05045 Y
ChEBI	CHEBI:50694 N
ChEMBL	ChEMBL1434 Y
CompTox Dashboard (EPA)	DTXSID1045033
ECHA InfoCard	100.226.626
Chemical and physical data
Formula	C23H27N3O7
Molar mass	457.483 g·mol−1
3D model (JSmol)	Interactive image
Specific rotation	${\displaystyle [\alpha ]_{D}^{25}}$ = −166°
Solubility in water	Low
SMILES CN(C)c1ccc(c2c1C[C@H]3C[C@H]4[C@@H](C(=C(C(=O)[C@]4(C(=C3C2=O)O)O)C(=O)N)O)N(C)C)O
InChI InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1 Y Key:DYKFCLLONBREIL-KVUCHLLUSA-N Y
NY (what is this?)  (verify)

Common side effects include nausea, diarrhea, dizziness, allergic reactions, and kidney problems. Serious side effects may include anaphylaxis, a lupus-like syndrome, and easy sunburning. Use in the later part of pregnancy may harm the baby and safety during breastfeeding is unclear. It works by decreasing a bacterium's ability to make protein thus stopping its growth.

Minocycline was patented in 1961 and came into commercial use in 1971. It is available as a generic medication. In 2020, it was the 236th most commonly prescribed medication in the United States, with more than 1 million prescriptions.