Metacycline

Not to be confused with Meticillin or Meclocycline.

Metacycline

File:Metacycline.svg
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01AA05 (WHO)
Identifiers
IUPAC name (2Z,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
CAS Number	914-00-1 ☒N
PubChem CID	54675785
ChemSpider	10468596 checkY
UNII	IR235I7C5P
ChEMBL	ChEMBL249837 ☒N
NIAID ChemDB	001301
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C22H22N2O8
Molar mass	442.424 g·mol−1
3D model (JSmol)	Interactive image
SMILES NC(=O)C=3C(=O)[C@@]4(O)C(\O)=C2\C(=O)c1c(O)cccc1C(=C)[C@H]2[C@H](O)[C@H]4[C@H](N(C)C)C=3O
InChI InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1 checkY Key:MHIGBKBJSQVXNH-IWVLMIASSA-N checkY
☒NcheckY (what is this?)  (verify)

Metacycline or methacycline is a tetracycline antibiotic. It is used as a precursor in the industrial synthesis of doxycycline hyclate.

It has been found to act as an agonist of the human pregnane X receptor ligand-binding domain and to induce CYP3A4 expression in vitro.