Chemistry:Incyclinide

Short description: Chemical compound

Incyclinide

Clinical data
Trade names	Metastat (proposed)
ATC code	none
Legal status
Legal status	Abandoned?
Identifiers
IUPAC name (4aS,5aR,12aS)-3,10,12,12a-Tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacen-2-carboxamide
CAS Number	15866-90-7
PubChem CID	54678924
ChemSpider	28530521
UNII	21G64WZQ4I
KEGG	D04519
ChEMBL	ChEMBL2104970
Chemical and physical data
Formula	C19H17NO7
Molar mass	371.345 g·mol−1
3D model (JSmol)	Interactive image
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, various tumours, allergic and inflammatory diseases and a number of other conditions.

Data from animal studies suggest that centrally infused incyclinide attenuates microglial mediated neuroinflammation in the paraventricular nucleus of the hypothalamus and sympathetic activation in angiotensin II-induced hypertension. This was also associated with unique changes in gut microbial communities and profound attenuation of gut pathology in animal models of hypertension.

Mechanism of action

Like other tetracyclines, incyclinide inhibits matrix metalloproteinases. In contrast to traditional tetracyclines, it lacks antibiotic properties.