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Cilomilast

CAS No.:
153259-65-5
Catalog Number:
AG00AOPF
Molecular Formula:
C20H25NO4
Molecular Weight:
343.4168
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$91
- +
5mg
≥98%
1 week
United States
$204
- +
10mg
≥98%
1 week
United States
$335
- +
Product Description
Catalog Number:
AG00AOPF
Chemical Name:
Cilomilast
CAS Number:
153259-65-5
Molecular Formula:
C20H25NO4
Molecular Weight:
343.4168
MDL Number:
MFCD00924373
IUPAC Name:
4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid
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)
InChI Key:
CFBUZOUXXHZCFB-UHFFFAOYSA-N
SMILES:
N#C[C@@]1(CC[C@H](CC1)C(=O)O)c1ccc(c(c1)OC1CCCC1)OC
UNII:
8ATB1C1R6X
Properties
Complexity:
511  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
343.178g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
343.423g/mol
Monoisotopic Mass:
343.178g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
79.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.4  
Literature
Title Journal
Cilomilast enhances osteoblast differentiation of mesenchymal stem cells and bone formation induced by bone morphogenetic protein 2. Biochimie 20121101
Design, synthesis, and pharmacological evaluation of N-acylhydrazones and novel conformationally constrained compounds as selective and potent orally active phosphodiesterase-4 inhibitors. Journal of medicinal chemistry 20120913
3D QSAR pharmacophore, CoMFA and CoMSIA based design and docking studies on phenyl alkyl ketones as inhibitors of phosphodiesterase 4. Medicinal chemistry (Shariqah (United Arab Emirates)) 20120901
PDE4 inhibition suppresses IL-17-associated immunity in dry eye disease. Investigative ophthalmology & visual science 20120601
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Anti-asthmatic effect of ASP3258, a novel phosphodiesterase 4 inhibitor. International immunopharmacology 20120101
Anti-neutrophilic inflammatory activity of ASP3258, a novel phosphodiesterase type 4 inhibitor. International immunopharmacology 20120101
Hesperetin, a Selective Phosphodiesterase 4 Inhibitor, Effectively Suppresses Ovalbumin-Induced Airway Hyperresponsiveness without Influencing Xylazine/Ketamine-Induced Anesthesia. Evidence-based complementary and alternative medicine : eCAM 20120101
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ASP3258, an orally active potent phosphodiesterase 4 inhibitor with low emetic activity. International immunopharmacology 20110601
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GSK256066, an exceptionally high-affinity and selective inhibitor of phosphodiesterase 4 suitable for administration by inhalation: in vitro, kinetic, and in vivo characterization. The Journal of pharmacology and experimental therapeutics 20110401
In vivo characterization of GSK256066, a high-affinity inhaled phosphodiesterase 4 inhibitor. The Journal of pharmacology and experimental therapeutics 20110401
S-Petasin, the Main Sesquiterpene of Petasites formosanus, Inhibits Phosphodiesterase Activity and Suppresses Ovalbumin-Induced Airway Hyperresponsiveness. Evidence-based complementary and alternative medicine : eCAM 20110101
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Inhibition of granulocyte migration by tiotropium bromide. Respiratory research 20110101
Cilomilast counteracts the effects of cigarette smoke in airway epithelial cells. Cellular immunology 20110101
Biochanin a, a phytoestrogenic isoflavone with selective inhibition of phosphodiesterase 4, suppresses ovalbumin-induced airway hyperresponsiveness. Evidence-based complementary and alternative medicine : eCAM 20110101
New therapeutic options in the management of COPD - focus on roflumilast. International journal of chronic obstructive pulmonary disease 20110101
β2-Agonist induced cAMP is decreased in asthmatic airway smooth muscle due to increased PDE4D. PloS one 20110101
Health status in the TORCH study of COPD: treatment efficacy and other determinants of change. Respiratory research 20110101
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Roflumilast attenuates allergen-induced inflammation in mild asthmatic subjects. Respiratory research 20110101
Hesperetin-7,3'-O-dimethylether selectively inhibits phosphodiesterase 4 and effectively suppresses ovalbumin-induced airway hyperresponsiveness with a high therapeutic ratio. Journal of biomedical science 20110101
Roflumilast, a Novel Phosphodiesterase 4 Inhibitor, for COPD Patients with a History of Exacerbations. Clinical medicine insights. Circulatory, respiratory and pulmonary medicine 20110101
Relationship between phosphodiesterase type 4 inhibition and anti-inflammatory activity of CI-1044 in rat airways. Fundamental & clinical pharmacology 20100201
Effects of phosphodiesterase 4 inhibition on bleomycin-induced pulmonary fibrosis in mice. BMC pulmonary medicine 20100101
Pharmacological studies of bronchial constriction inhibited by parasympatholytics and cilomilast using equine precision-cut lung slices. Berliner und Munchener tierarztliche Wochenschrift 20100101
Influencing the decline of lung function in COPD: use of pharmacotherapy. International journal of chronic obstructive pulmonary disease 20100101
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Effects of the new benzimidazole derivative TAS-203, an orally active phosphodiesterase 4 inhibitor, on airway inflammation in rats and emetic responses in ferrets. Arzneimittel-Forschung 20100101
The identification of a novel phosphodiesterase 4 inhibitor, 1-ethyl-5-{5-[(4-methyl-1-piperazinyl)methyl]-1,3,4-oxadiazol-2-yl}-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (EPPA-1), with improved therapeutic index using pica feeding in rats as a measure of emetogenicity. The Journal of pharmacology and experimental therapeutics 20090901
Granulocyte-macrophage colony-stimulating factor expression in induced sputum and bronchial mucosa in asthma and COPD. Thorax 20090801
A phosphodiesterase inhibitor, cilomilast, enhances cAMP activity to restore conditioned odor preference memory after serotonergic depletion in the neonate rat. Neurobiology of learning and memory 20090701
Does PDE4 inhibition improve alveolarisation in hyperoxia-exposed immature rodents? The European respiratory journal 20090501
Inhibition of phosphodiesterase 4 enhances lung alveolarisation in neonatal mice exposed to hyperoxia. The European respiratory journal 20090401
Pharmacology of a novel, orally active PDE4 inhibitor. Pharmacology 20090101
A multi-target antisense approach against PDE4 and PDE7 reduces smoke-induced lung inflammation in mice. Respiratory research 20090101
Exacerbation rate, health status and mortality in COPD--a review of potential interventions. International journal of chronic obstructive pulmonary disease 20090101
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Chronic obstructive pulmonary disease: towards pharmacogenetics. Genome medicine 20090101
ABCD of the phosphodiesterase family: interaction and differential activity in COPD. International journal of chronic obstructive pulmonary disease 20081201
PDE4 inhibitors: current status. British journal of pharmacology 20081001
Can the anti-inflammatory potential of PDE4 inhibitors be realized: guarded optimism or wishful thinking? British journal of pharmacology 20081001
Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease. Journal of medicinal chemistry 20080925
Curative effects of phosphodiesterase 4 inhibitors cilomilast, roflumilast, and rolipram in dermatitis mouse model. Journal of dermatological science 20080901
Airways inflammation and treatment during acute exacerbations of COPD. International journal of chronic obstructive pulmonary disease 20080601
Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2[4-(4,4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl)-1H-benzimidazoles. European journal of medicinal chemistry 20080501
PDE4 inhibitor, roflumilast protects cardiomyocytes against NO-induced apoptosis via activation of PKA and Epac dual pathways. Cellular signalling 20080501
Human PDE4A8, a novel brain-expressed PDE4 cAMP-specific phosphodiesterase that has undergone rapid evolutionary change. The Biochemical journal 20080415
Inhibition by salmeterol and cilomilast of fluticasone-enhanced IP-10 release in airway epithelial cells. COPD 20080201
Bronchiolar chemokine expression is different after single versus repeated cigarette smoke exposure. Respiratory research 20080101
New drugs targeting Th2 lymphocytes in asthma. Journal of occupational medicine and toxicology (London, England) 20080101
Effects of phosphodiesterase 4 inhibition on alveolarization and hyperoxia toxicity in newborn rats. PloS one 20080101
The efficacy and safety of cilomilast in COPD. Forward. Drugs 20080101
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Pharmacological control of neutrophil-mediated inflammation: strategies targeting calcium handling by activated polymorphonuclear leukocytes. Drug design, development and therapy 20080101
Pulmonary epithelium, cigarette smoke, and chronic obstructive pulmonary disease. International journal of chronic obstructive pulmonary disease 20071201
Treating COPD with PDE 4 inhibitors. International journal of chronic obstructive pulmonary disease 20071201
Future therapeutic treatment of COPD: struggle between oxidants and cytokines. International journal of chronic obstructive pulmonary disease 20070901
Phosphodiesterase 4 inhibitors augment levels of glucocorticoid receptor in B cell chronic lymphocytic leukemia but not in normal circulating hematopoietic cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20070815
PDE4B5, a novel, super-short, brain-specific cAMP phosphodiesterase-4 variant whose isoform-specifying N-terminal region is identical to that of cAMP phosphodiesterase-4D6 (PDE4D6). The Journal of pharmacology and experimental therapeutics 20070801
L-454,560, a potent and selective PDE4 inhibitor with in vivo efficacy in animal models of asthma and cognition. Biochemical pharmacology 20070615
Differential effects of phosphodiesterase PDE-3/PDE-4-specific inhibitors on vasoconstriction and cAMP-dependent vasorelaxation following balloon angioplasty. American journal of physiology. Heart and circulatory physiology 20070601
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Effects of cyclosporin A and cilomilast on activated canine, murine and human keratinocytes. Veterinary dermatology 20070401
Highly selective phosphodiesterase 4 inhibitors for the treatment of allergic skin diseases and psoriasis. Inflammation & allergy drug targets 20070301
SAR of a series of 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines as potent inhibitors of human eosinophil phosphodiesterase. Journal of medicinal chemistry 20070125
Selective inhibitors for phosphodiesterase 3 and 4 in antigen-induced increase of cough reflex sensitivity in guinea pigs. Pulmonary pharmacology & therapeutics 20070101
Evaluation of oral corticosteroids and phosphodiesterase-4 inhibitor on the acute inflammation induced by inhaled lipopolysaccharide in human. Pulmonary pharmacology & therapeutics 20070101
Phosphodiesterase-4 inhibitors as a novel approach for the treatment of respiratory disease: cilomilast. Expert opinion on investigational drugs 20070101
Cyclic AMP signalling pathways in the regulation of uterine relaxation. BMC pregnancy and childbirth 20070101
Maternal allergic contact dermatitis causes increased asthma risk in offspring. Respiratory research 20070101
Bronchial epithelial spheroids: an alternative culture model to investigate epithelium inflammation-mediated COPD. Respiratory research 20070101
Airways disease: phenotyping heterogeneity using measures of airway inflammation. Allergy, asthma, and clinical immunology : official journal of the Canadian Society of Allergy and Clinical Immunology 20070101
The phosphodiesterase type IV inhibitor cilomilast decreases pro-inflammatory cytokine production from primary bronchial epithelial cells in lung transplantation patients. The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20061201
Evaluation of PDE4 inhibition for COPD. International journal of chronic obstructive pulmonary disease 20061201
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Phosphodiesterase 4 inhibition of beta2-integrin adhesion caused by leukotriene B4 and TNF-alpha in human neutrophils. The European respiratory journal 20061101
Phosphodiesterase 4 inhibitors modulate beta2-adrenoceptor agonist-induced human airway hyperresponsiveness. Life sciences 20061012
Effects of ciclamilast, a new PDE 4 PDE4 inhibitor, on airway hyperresponsiveness, PDE4D expression and airway inflammation in a murine model of asthma. European journal of pharmacology 20061010
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Cilomilast, tacrolimus and rapamycin modulate dendritic cell function in the elicitation phase of allergic contact dermatitis. The British journal of dermatology 20050701
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Evidence for a role of phosphodiesterase 4 in lipopolysaccharide-stimulated prostaglandin E2 production and matrix metalloproteinase-9 activity in human amniochorionic membranes. Journal of immunology (Baltimore, Md. : 1950) 20050615
Identification and characterization of PDE4A11, a novel, widely expressed long isoform encoded by the human PDE4A cAMP phosphodiesterase gene. Molecular pharmacology 20050601
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Effects of phosphodiesterase 4 inhibitor on cough response in guinea pigs sensitized and challenged with ovalbumin. Chinese medical journal 20041101
TARC and RANTES, but not CTACK, are induced in two models of allergic contact dermatitis. Effects of cilomilast and diflorasone diacetate on T-cell-attracting chemokines. The British journal of dermatology 20041001
Role of PDE4 in superoxide anion generation through p44/42MAPK regulation: a cAMP and a PKA-independent mechanism. British journal of pharmacology 20040901
Lack of pharmacokinetic interactions between cilomilast and theophylline or smoking in healthy volunteers. Journal of clinical pharmacology 20040901
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PDE4 inhibition: a novel approach for the treatment of inflammatory bowel disease. Trends in pharmacological sciences 20040801
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Cytokines modulate cilomilast response in lung fibroblasts. Clinical immunology (Orlando, Fla.) 20040601
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Anti-inflammatory and utero-relaxant effects in human myometrium of new generation phosphodiesterase 4 inhibitors. Biology of reproduction 20040201
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In vivo efficacy in airway disease models of N-(3,5-dichloropyrid-4-yl)-[1-(4-fluorobenzyl)-5-hydroxy-indole-3-yl]-glyoxylic acid amide (AWD 12-281), a selective phosphodiesterase 4 inhibitor for inhaled administration. The Journal of pharmacology and experimental therapeutics 20031001
AWD 12-281, a highly selective phosphodiesterase 4 inhibitor, is effective in the prevention and treatment of inflammatory reactions in a model of allergic dermatitis. The Journal of pharmacy and pharmacology 20030801
Effect of cilomilast (Ariflo) on TNF-alpha, IL-8, and GM-CSF release by airway cells of patients with COPD. Thorax 20030701
Synthesis and structure-activity relationships of cis-tetrahydrophthalazinone/pyridazinone hybrids: a novel series of potent dual PDE3/PDE4 inhibitory agents. Journal of medicinal chemistry 20030508
Inhibitor binding to type 4 phosphodiesterase (PDE4) assessed using [3H]piclamilast and [3H]rolipram. The Journal of pharmacology and experimental therapeutics 20030501
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Does a single dose of the phosphodiesterase 4 inhibitor, cilomilast (15 mg), induce bronchodilation in patients with chronic obstructive pulmonary disease? Pulmonary pharmacology & therapeutics 20030101
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20030101
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Phosphodiesterase 4 inhibitor cilomilast inhibits fibroblast-mediated collagen gel degradation induced by tumor necrosis factor-alpha and neutrophil elastase. American journal of respiratory cell and molecular biology 20021001
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20021001
Benefit of phosphodiesterase 4 inhibitors as supplemental therapy after lung transplantation concerning their antiproliferative effects: an experimental study using a heterotopic rodent model. Transplantation 20020815
Pharmacology of N-(3,5-dichloro-1-oxido-4-pyridinyl)-8-methoxy-2-(trifluoromethyl)-5-quinoline carboxamide (SCH 351591), a novel, orally active phosphodiesterase 4 inhibitor. The Journal of pharmacology and experimental therapeutics 20020701
Effects of the phosphodiesterase 4 inhibitors SB 207499 and AWD 12-281 on the inflammatory reaction in a model of allergic dermatitis. European journal of pharmacology 20020620
Novel selective PDE4 inhibitors. 3. In vivo antiinflammatory activity of a new series of N-substituted cis-tetra- and cis-hexahydrophthalazinones. Journal of medicinal chemistry 20020606
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Discovery of L-791,943: a potent, selective, non emetic and orally active phosphodiesterase-4 inhibitor. Bioorganic & medicinal chemistry letters 20020603
PDE4 inhibitors attenuate fibroblast chemotaxis and contraction of native collagen gels. American journal of respiratory cell and molecular biology 20020601
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Pharmacological profile of a novel phosphodiesterase 4 inhibitor, 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridin-6-yl)-benzoic acid (NVP-ABE171), a 1,7-naphthyridine derivative, with anti-inflammatory activities. The Journal of pharmacology and experimental therapeutics 20020401
Synthesis and biological evaluation of imidazol-2-one and 2-cyanoiminoimidazole derivatives: novel series of PDE4 inhibitors. Bioorganic & medicinal chemistry letters 20020225
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Synthesis of 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridine-6-yl)-benzoic acid: a potent and selective phosphodiesterase type 4D inhibitor. Bioorganic & medicinal chemistry letters 20020121
Cyclic AMP-specific phosphodiesterase 4 inhibitors promote ABCA1 expression and cholesterol efflux. Biochemical and biophysical research communications 20020118
Phthalazine PDE4 inhibitors. Part 3: the synthesis and in vitro evaluation of derivatives with a hydrogen bond acceptor. Bioorganic & medicinal chemistry letters 20020107
Update on the therapeutic potential of PDE4 inhibitors. Expert opinion on investigational drugs 20020101
Cilomilast (Ariflo) does not potentiate the cardiovascular effects of inhaled salbutamol. Pulmonary pharmacology & therapeutics 20020101
Warfarin pharmacodynamics unaffected by cilomilast. The Annals of pharmacotherapy 20011201
Effects of inhibition of PDE4 and TNF-alpha on local and remote injuries following ischaemia and reperfusion injury. British journal of pharmacology 20011101
Cilomilast: a breath of relief? Trends in molecular medicine 20011001
An overview of the pharmacokinetics of cilomilast (Ariflo), a new, orally active phosphodiesterase 4 inhibitor, in healthy young and elderly volunteers. Journal of clinical pharmacology 20010901
Novel selective PDE4 inhibitors. 1. Synthesis, structure-activity relationships, and molecular modeling of 4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-ones and analogues. Journal of medicinal chemistry 20010802
Novel selective PDE4 inhibitors. 2. Synthesis and structure-activity relationships of 4-aryl-substituted cis-tetra- and cis-hexahydrophthalazinones. Journal of medicinal chemistry 20010802
The next generation of PDE4 inhibitors. Current opinion in chemical biology 20010801
Cilomilast, a selective phosphodiesterase-4 inhibitor for treatment of patients with chronic obstructive pulmonary disease: a randomised, dose-ranging study. Lancet (London, England) 20010728
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Bioavailability of the oral selective phosphodiesterase 4 inhibitor cilomilast. Pharmacotherapy 20010601
Cilomilast: pharmacokinetic and pharmacodynamic interactions with digoxin. Clinical therapeutics 20010601
Requirement of additional adenylate cyclase activation for the inhibition of human eosinophil degranulation by phosphodiesterase IV inhibitors. European journal of pharmacology 20010406
Anti-inflammatory and immunomodulatory potential of the novel PDE4 inhibitor roflumilast in vitro. The Journal of pharmacology and experimental therapeutics 20010401
In vivo efficacy in airway disease models of roflumilast, a novel orally active PDE4 inhibitor. The Journal of pharmacology and experimental therapeutics 20010401
Syntheses and evaluation of pyrido[2,3-dlpyrimidine-2,4-diones as PDE 4 inhibitors. Bioorganic & medicinal chemistry letters 20010312
Phthalazine PDE4 inhibitors. Part 2: the synthesis and biological evaluation of 6-methoxy-1,4-disubstituted derivatives. Bioorganic & medicinal chemistry letters 20010108
Comparison of PDE 4 inhibitors, rolipram and SB 207499 (ariflo), in a rat model of pulmonary neutrophilia. Pulmonary pharmacology & therapeutics 20010101
Ariflo (SB 207499), a second generation phosphodiesterase 4 inhibitor for the treatment of asthma and COPD: from concept to clinic. Pulmonary pharmacology & therapeutics 19990101
SB 207499 (Ariflo), a second generation phosphodiesterase 4 inhibitor, reduces tumor necrosis factor alpha and interleukin-4 production in vivo. The Journal of pharmacology and experimental therapeutics 19981101
SB 207499 (Ariflo), a potent and selective second-generation phosphodiesterase 4 inhibitor: in vitro anti-inflammatory actions. The Journal of pharmacology and experimental therapeutics 19980101
Properties