Cilomilast (SB-207499) is a potent PDE4 inhibitor with an IC50 of 110 nM, anti-inflammatory activity and weak central nervous system activity. Phase 3.

 

Brand: BCM

 

Target: PDE

 

Signaling Pathways: Metabolism

 

In Vitro: Cilomilast produces a concentration-dependent increase in cAMP content in U937 cells. Cilomilast produces a concentration-dependent increase in cAMP content in U937 cells. In isolated human monocytes, Cilomilast and (R)-rolipram are equipotent at suppressing LPS-induced TNF-α formation with -log (IC50) of 7.0 and 7.2, respectively. Both Cilomilast and (R)-rolipram produces a modest prevention of fMLP-induced degranulation of human neutrophils. Cilomilast and (R)-rolipram are equipotent at suppressing neutrophil activation with -log (IC50) of 7.1 and 6.4, respectively. Cilomilast significantly decreases the expression of TNF-α in the cornea and IL-1α, IL-1β, and TNF-α in the conjunctivaas compared to vehicle control. Cilomilast treatment markedly decreases the presence of CD11b+ antigen-presenting cells in the central and peripheral cornea, and leads to decreased conjunctival expression of cytokines IL-6, IL-23, and IL-17. Moreover, Cilomilast decreases the expression of IL-17 and IL-23 in the draining lymph nodes. Cilomilast reduces TLR4 expression, IL-8 release and neutrophil chemotactic activity as well as it increased IP-10 release and lymphocyte chemotactic activity.

 

Melting Point: 157°C

 

Boiling Point: 549.1±50.0 °C(Predicted)

 

pKa: 4.45±0.25(Predicted)

 

Solubility: Soluble in DMSO; Soluble in Ethanol. Insoluble in Water.

 

Isomeric SMILES: COC1=C(C=C(C=C1)C2(CCC(CC2)C(=O)O)C#N)OC3CCCC3  

 

InChIKey: CFBUZOUXXHZCFB-UHFFFAOYSA-N  

 

InChI: InChI=1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)

 

Attribute
[Chem Name]	4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid
[Synonym]	Cilomilast; SB-207499
[CAS No.]	153259-65-5
[EINECS]	200-258-5
[MDL No.]	MFCD00924373
[Formula]	C20H25NO4
[Molecular]	343.42
[Form]	White to beige powder
[Storage]	Stored at -20°C

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