CAS 153259-65-5|Cilomilast

Introduction：Basic information about CAS 153259-65-5|Cilomilast, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Cilomilast BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles1
6. Synonyms

Common Name	Cilomilast
CAS Number	153259-65-5	Molecular Weight	343.417
Density	1.2±0.1 g/cm3	Boiling Point	549.1±50.0 °C at 760 mmHg
Molecular Formula	C₂₀H₂₅NO₄	Melting Point	157ºC
MSDS	ChineseUSA	Flash Point	285.9±30.1 °C

Names

Name	4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid
Synonym	More Synonyms

Cilomilast BiologicalActivity

Description	Cilomilast(SB 207499; Ariflo) is a potent PDE4 inhibitor with IC50 of about 110 nM, has anti-inflammatory activity and low central nervous system activity.IC50 value: 110 nMTarget: PDE 4Cilomilast (SB-207499) inhibits HPDE4 and LPDE4 catalytic activity with equal potency (Ki ≈100 nM). SB-207499 and rolipram are equipotent against LPDE4, but Cilomilast (Ariflo, SB-207499) is 100-fold less potent against HPDE4. This profile suggests that Cilomilast (Ariflo, SB-207499) retain the anti-inflammatory activity of rolipram yet have a decreased tendency to produce side effects.
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>Phosphodiesterase (PDE)Research Areas >>Inflammation/Immunology
References	[1]. MARY S. BARNETTE et al. SB 207499 (Ariflo), a Potent and Selective Second-Generation Phosphodiesterase 4 Inhibitor: In Vitro Anti-inflammatory Actions JPET 284:420 -426, 1998 [2]. Munisso MC, Kang JH, Tsurufuji M, Yamaoka T.Cilomilast enhances osteoblast differentiation of mesenchymal stem cells and bone formation induced by bone morphogenetic protein 2.Biochimie. 2012 Jun 15. [3]. Sadrai Z, Stevenson W, Okanobo A, Chen Y, Dohlman TH, Hua J, Amparo F, Chauhan SK, Dana R.PDE4 inhibition suppresses IL-17-associated immunity in dry eye disease.Invest Ophthalmol Vis Sci. 2012 Jun 14;53(7):3584-91. Print 2012 Jun. [4]. Pace E, Ferraro M, Uasuf CG, Giarratano A, La Grutta S, Liotta G, Johnson M, Gjomarkaj M.Cilomilast counteracts the effects of cigarette smoke in airway epithelial cells.Cell Immunol. 2011;268(1):47-53. Epub 2011 Feb 20. [5]. Barton AK, Niedorf F, Gruber AD, Kietzmann M, Ohnesorge B.Pharmacological studies of bronchial constriction inhibited by parasympatholytics and cilomilast using equine precision-cut lung slices.Berl Munch Tierarztl Wochenschr. 2010 May-Jun;123(5-6):229-35

Description

Cilomilast(SB 207499; Ariflo) is a potent PDE4 inhibitor with IC50 of about 110 nM, has anti-inflammatory activity and low central nervous system activity.IC50 value: 110 nMTarget: PDE 4Cilomilast (SB-207499) inhibits HPDE4 and LPDE4 catalytic activity with equal potency (Ki ≈100 nM). SB-207499 and rolipram are equipotent against LPDE4, but Cilomilast (Ariflo, SB-207499) is 100-fold less potent against HPDE4. This profile suggests that Cilomilast (Ariflo, SB-207499) retain the anti-inflammatory activity of rolipram yet have a decreased tendency to produce side effects.

Related Catalog

Signaling Pathways >>Metabolic Enzyme/Protease >>Phosphodiesterase (PDE)Research Areas >>Inflammation/Immunology

References

[1]. MARY S. BARNETTE et al. SB 207499 (Ariflo), a Potent and Selective Second-Generation Phosphodiesterase 4 Inhibitor: In Vitro Anti-inflammatory Actions JPET 284:420 -426, 1998

[2]. Munisso MC, Kang JH, Tsurufuji M, Yamaoka T.Cilomilast enhances osteoblast differentiation of mesenchymal stem cells and bone formation induced by bone morphogenetic protein 2.Biochimie. 2012 Jun 15.

[3]. Sadrai Z, Stevenson W, Okanobo A, Chen Y, Dohlman TH, Hua J, Amparo F, Chauhan SK, Dana R.PDE4 inhibition suppresses IL-17-associated immunity in dry eye disease.Invest Ophthalmol Vis Sci. 2012 Jun 14;53(7):3584-91. Print 2012 Jun.

[4]. Pace E, Ferraro M, Uasuf CG, Giarratano A, La Grutta S, Liotta G, Johnson M, Gjomarkaj M.Cilomilast counteracts the effects of cigarette smoke in airway epithelial cells.Cell Immunol. 2011;268(1):47-53. Epub 2011 Feb 20.

[5]. Barton AK, Niedorf F, Gruber AD, Kietzmann M, Ohnesorge B.Pharmacological studies of bronchial constriction inhibited by parasympatholytics and cilomilast using equine precision-cut lung slices.Berl Munch Tierarztl Wochenschr. 2010 May-Jun;123(5-6):229-35

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	549.1±50.0 °C at 760 mmHg
Melting Point	157ºC
Molecular Formula	C₂₀H₂₅NO₄
Molecular Weight	343.417
Flash Point	285.9±30.1 °C
Exact Mass	343.178345
PSA	79.55000
LogP	3.30
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.568
InChIKey	CFBUZOUXXHZCFB-UHFFFAOYSA-N
SMILES	COc1ccc(C2(C#N)CCC(C(=O)O)CC2)cc1OC1CCCC1
Storage condition	?20°C
Water Solubility	DMSO: soluble15mg/mL, clear

Safety Information

RIDADR	NONH for all modes of transport

Articles1

Blockade of PDE4B limits lung vascular permeability and lung inflammation in LPS-induced acute lung injury.

Biochem. Biophys. Res. Commun. 450(4) , 1560-7, (2014)

Acute lung injury (ALI), acute respiratory distress syndrome (ARDS), is actually involved in an ongoing and uncontrolled inflammatory response in lung tissues. Although extensive studies suggested tha...

Synonyms

cis-4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-4-cyanocyclohexane-1-carboxylic acid

Cyclohexanecarboxylic acid, 4-cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-, cis-

1xlx

Cyclohexanecarboxylic acid, 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, cis-

cis-4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexanecarboxylic acid

cis-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid

S1455_Selleck

Ariflo

Cyclohexanecarboxylic acid, 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-

c-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-r-1-cyclohexane carboxylic acid

1xom

cilomilast

4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid

SB-207499

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