Metacycline

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

Not to be confused with Meticillin, Minocycline, or Meclocycline.
Metacycline
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
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
PubChem CID
ChemSpider
UNII
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.011.834
Chemical and physical data
FormulaC22H22N2O8
Molar mass442.424 g·mol−1
3D model (JSmol)
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 Y
  • Key:MHIGBKBJSQVXNH-IWVLMIASSA-N Y
 NY (what is this?)  (verify)

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.[1]

References
  1. Shukla SJ, Sakamuru S, Huang R, Moeller TA, Shinn P, Vanleer D, Auld DS, Austin CP, Xia M (2011). "Identification of clinically used drugs that activate pregnane X receptors" (PDF). Drug Metab. Dispos. 39 (1): 151–9. doi:10.1124/dmd.110.035105. PMC 3014269. PMID 20966043.



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