Incyclinide

Systematic (IUPAC) name

(4aS,5aR,12aS)-3,10,12,12a-Tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacen-2-carboxamide
Clinical data
Trade names	Metastat (proposed)
Legal status	Abandoned?
Identifiers
CAS Number	15866-90-7
ATC code	None
PubChem	CID 54678924
ChemSpider	28530521
UNII	21G64WZQ4I
KEGG	D04519
ChEMBL	CHEMBL2104970
Chemical data
Formula	C₁₉H₁₇NO₇
Molar mass	371.35 g·mol⁻¹
SMILES c1cc2c(c(c1)O)C(=O)C3=C([C@]4([C@@H](C[C@@H]3C2)CC(=C(C4=O)C(=O)N)O)O)O
InChI InChI=1S/C19H17NO7/c20-18(26)14-11(22)6-9-5-8-4-7-2-1-3-10(21)12(7)15(23)13(8)16(24)19(9,27)17(14)25/h1-3,8-9,21-22,24,27H,4-6H2,(H2,20,26)/t8-,9-,19-/m0/s1 Key:ZXFCRFYULUUSDW-OWXODZSWSA-N

Incyclinide (proposed trade name Metastat) is a chemically modified tetracycline antibiotic that was investigated in clinical trials for the treatment of rosacea,^[1] various tumours, allergic and inflammatory diseases and a number of other conditions. The drug has no antibiotic properties.^[2]^[3]^[4]

Mechanism of action

Like other tetracyclines, incyclinide inhibits matrix metalloproteinases.^[2]

References

↑ Reuters: CollaGenex says incyclinide ineffective for rosacea
1 2 Viera, MH, Perez, OA, Berman, B. "Incyclinide". Drugs of the Future 32 (3): 209–214.
↑ H. Spreitzer (2 July 2007). "Neue Wirkstoffe - Incyclinid". Österreichische Apothekerzeitung (in German) (14/2007): 655.
↑ ClinicalTrials.gov: Incyclinide

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