Incyclinide

{{Infobox drug

| drug_name =

| IUPAC_name = (4aS,5aR,12aS)-3,10,12,12a-Tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacen-2-carboxamide

| image = Incyclinide skeletal.svg

| alt =

| caption =

| pronounce =

| tradename = Metastat (proposed)

| Drugs.com =

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| legal_AU =

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| legal_NZ =

| legal_UK =

| legal_US =

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| legal_status = Abandoned?

| routes_of_administration =

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| CAS_number = 15866-90-7

| ATCvet =

| ATC_prefix = none

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| PubChem = 54678924

| DrugBank =

| ChemSpiderID = 28530521

| UNII = 21G64WZQ4I

| ChEMBL = 2104970

| KEGG = D04519

| C=19 | H=17 | N=1 | O=7

| 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

| StdInChI=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

| StdInChIKey = 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.{{Cite journal |display-authors=6 |vauthors=Sharma RK, Yang T, Oliveira AC, Lobaton GO, Aquino V, Kim S, Richards EM, Pepine CJ, Sumners C, Raizada MK |date=March 2019 |title=Microglial Cells Impact Gut Microbiota and Gut Pathology in Angiotensin II-Induced Hypertension |journal=Circulation Research |volume=124 |issue=5 |pages=727–736 |doi=10.1161/CIRCRESAHA.118.313882 |pmc=6395495 |pmid=30612527}}

Mechanism of action

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

References

{{reflist|refs=

{{Cite journal |vauthors=Spreitzer H |date=2 July 2007 |title=Neue Wirkstoffe - Incyclinid |journal=Österreichische Apothekerzeitung |language=German |issue=14/2007 |pages=655}}

{{Cite journal |vauthors=Viera MH, Perez OA, Berman B |year=2007 |title=Incyclinide |url=http://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=1083308&p_IsPs=N |journal=Drugs of the Future |volume=32 |issue=3 |pages=209–214 |doi=10.1358/dof.2007.032.03.1083308|url-access=subscription }}

[https://www.reuters.com/article/companyNewsAndPR/idUSWEN127920070926 Reuters: CollaGenex says incyclinide ineffective for rosacea]

ClinicalTrials.gov: [https://clinicaltrials.gov/ct2/results?term=Incyclinide&Search=Search Incyclinide]

}}

Category:Tetracycline antibiotics