Metacycline

{{Short description|Chemical compound}}

{{Distinguish|Meticillin|Meclocycline}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 400298582

| 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

| image = Metacycline.svg

| tradename =

| Drugs.com = {{drugs.com|international|metacycline}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 914-00-1

| ATC_prefix = J01

| ATC_suffix = AA05

| PubChem = 54675785

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10468596

| NIAID_ChemDB = 001301

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = IR235I7C5P

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 249837

| C=22 | H=22 | N=2 | O=8

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MHIGBKBJSQVXNH-IWVLMIASSA-N

}}

Metacycline or methacycline is a tetracycline antibiotic. It is used as a precursor in the industrial synthesis of doxycycline hyclate.{{cn|date=March 2023}}

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.{{Cite journal |vauthors=Shukla SJ, Sakamuru S, Huang R, Moeller TA, Shinn P, Vanleer D, Auld DS, Austin CP, Xia M |year=2011 |title=Identification of clinically used drugs that activate pregnane X receptors |url=http://dmd.aspetjournals.org/content/dmd/39/1/151.full.pdf?with-ds=yes |journal=Drug Metab. Dispos. |volume=39 |issue=1 |pages=151–9 |doi=10.1124/dmd.110.035105 |pmc=3014269 |pmid=20966043}}