Incyclinide

Incyclinide
Clinical data
Trade namesMetastat (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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC19H17NO7
Molar mass371.345 g·mol−1
3D model (JSmol)
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 antibiotic properties.[5]

References

  1. ↑ Reuters: CollaGenex says incyclinide ineffective for rosacea
  2. ↑ Spreitzer H (2 July 2007). "Neue Wirkstoffe - Incyclinid". Österreichische Apothekerzeitung (in German) (14/2007): 655.
  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.
  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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