Incyclinide

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,^[1] various tumours, allergic and inflammatory diseases and a number of other conditions.^[2]^[3]

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.^[4]

Mechanism of action

Like other tetracyclines, incyclinide inhibits matrix metalloproteinases. In contrast to traditional tetracyclines, it lacks strong antibiotic properties.^[5]

References

↑ Reuters: CollaGenex says incyclinide ineffective for rosacea
↑ Spreitzer H (2 July 2007). "Neue Wirkstoffe - Incyclinid". Österreichische Apothekerzeitung (in German) (14/2007): 655.
↑ ClinicalTrials.gov: Incyclinide
↑ Sharma RK, Yang T, Oliveira AC, Lobaton GO, Aquino V, Kim S, et al. (March 2019). "Microglial Cells Impact Gut Microbiota and Gut Pathology in Angiotensin II-Induced Hypertension". Circulation Research. 124 (5): 727–736. doi:10.1161/CIRCRESAHA.118.313882. PMC 6395495. PMID 30612527.
↑ Viera MH, Perez OA, Berman B (2007). "Incyclinide". Drugs of the Future. 32 (3): 209–214. doi:10.1358/dof.2007.032.03.1083308.

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[Reuters-1] Reuters: CollaGenex says incyclinide ineffective for rosacea

[Spreitzer-2] Spreitzer H (2 July 2007). "Neue Wirkstoffe - Incyclinid". Österreichische Apothekerzeitung (in German) (14/2007): 655.

[clinicaltrials-3] ClinicalTrials.gov: Incyclinide

[4] Sharma RK, Yang T, Oliveira AC, Lobaton GO, Aquino V, Kim S, et al. (March 2019). "Microglial Cells Impact Gut Microbiota and Gut Pathology in Angiotensin II-Induced Hypertension". Circulation Research. 124 (5): 727–736. doi:10.1161/CIRCRESAHA.118.313882. PMC 6395495. PMID 30612527.

[DrugsFuture-5] Viera MH, Perez OA, Berman B (2007). "Incyclinide". Drugs of the Future. 32 (3): 209–214. doi:10.1358/dof.2007.032.03.1083308.

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Mechanism of action

References