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MedKoo Cat#: 500450 | Name: Cilomilast
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cilomilast (Ariflo, SB-207,499) is a drug which was developed for the treatment of respiratory disorders such as asthma and Chronic Obstructive Pulmonary Disease (COPD). It is orally active and acts as a selective Phosphodiesterase-4 inhibitor. Clinical trial results showed reasonable efficacy for treating COPD, but side effects were problematic and it is unclear whether cilomalast will be marketed, or merely used in the development of newer drugs. Cilomilast is a second-generation PDE4 inhibitor with antiinflammatory effects that target bronchoconstriction, mucus hypersecretion, and airway remodeling associated with COPD.

Chemical Structure

Cilomilast
Cilomilast
CAS#153259-65-5

Theoretical Analysis

MedKoo Cat#: 500450

Name: Cilomilast

CAS#: 153259-65-5

Chemical Formula: C20H25NO4

Exact Mass: 343.1784

Molecular Weight: 343.42

Elemental Analysis: C, 69.95; H, 7.34; N, 4.08; O, 18.64

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
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Related CAS #
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Synonym
SB 207499; SB-207499; SB207499. Cilomilast; Ariflo.
IUPAC/Chemical Name
cis-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid
InChi Key
CFBUZOUXXHZCFB-LDTOLXSISA-N
InChi Code
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)/t14-,20+
SMILES Code
O=C([C@H]1CC[C@](C2=CC=C(OC)C(OC3CCCC3)=C2)(C#N)CC1)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>5 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
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Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cilomilast (SB-207499) is an inhibitor of Phosphodiesterase 4 (PDE4), with IC50s of ~100 and 120 nM for LPDE4 and HPDE4, respectively.
In vitro activity:
It was found that cilomilast enhances the osteoblastic differentiation of MSCs equally well as rolipram in primary cultured MSCs. Reference: Biochimie. 2012 Nov;94(11):2360-5. https://pubmed.ncbi.nlm.nih.gov/22706281/
In vivo activity:
As shown in Figure 3, KIM-1 and NGAL expression was markedly increased in the UUO mouse group according to western blot and qRT-PCR analyses, which was attenuated by cilomilast treatment (Figures 3A,B). The trend of NGAL change measured by immunohistochemistry was consistent with that of the protein and mRNA levels (Figure 3C). These data suggested that the amelioration of tubular injury after cilomilast treatment could protect tubular integrity and attenuate subsequent pathological events. Reference: Front Med (Lausanne). 2020; 7: 626140. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7859332/
Solvent mg/mL mM comments
Solubility
Ethanol 35.0 101.92
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 343.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. 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 Nov;94(11):2360-5. doi: 10.1016/j.biochi.2012.05.031. Epub 2012 Jun 15. PMID: 22706281. 2. 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. doi: 10.1016/j.cellimm.2011.02.004. Epub 2011 Feb 20. PMID: 21382614. 3. Xu M, Li S, Wang J, Huang S, Zhang A, Zhang Y, Gu W, Yu X, Jia Z. Cilomilast Ameliorates Renal Tubulointerstitial Fibrosis by Inhibiting the TGF-β1-Smad2/3 Signaling Pathway. Front Med (Lausanne). 2021 Jan 21;7:626140. doi: 10.3389/fmed.2020.626140. PMID: 33553218; PMCID: PMC7859332. 4. McLean JH, Smith A, Rogers S, Clarke K, Darby-King A, Harley CW. A phosphodiesterase inhibitor, cilomilast, enhances cAMP activity to restore conditioned odor preference memory after serotonergic depletion in the neonate rat. Neurobiol Learn Mem. 2009 Jul;92(1):63-9. doi: 10.1016/j.nlm.2009.02.003. Epub 2009 Feb 20. PMID: 19233302.
In vitro protocol:
1. 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 Nov;94(11):2360-5. doi: 10.1016/j.biochi.2012.05.031. Epub 2012 Jun 15. PMID: 22706281. 2. 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. doi: 10.1016/j.cellimm.2011.02.004. Epub 2011 Feb 20. PMID: 21382614.
In vivo protocol:
1. Xu M, Li S, Wang J, Huang S, Zhang A, Zhang Y, Gu W, Yu X, Jia Z. Cilomilast Ameliorates Renal Tubulointerstitial Fibrosis by Inhibiting the TGF-β1-Smad2/3 Signaling Pathway. Front Med (Lausanne). 2021 Jan 21;7:626140. doi: 10.3389/fmed.2020.626140. PMID: 33553218; PMCID: PMC7859332. 2. McLean JH, Smith A, Rogers S, Clarke K, Darby-King A, Harley CW. A phosphodiesterase inhibitor, cilomilast, enhances cAMP activity to restore conditioned odor preference memory after serotonergic depletion in the neonate rat. Neurobiol Learn Mem. 2009 Jul;92(1):63-9. doi: 10.1016/j.nlm.2009.02.003. Epub 2009 Feb 20. PMID: 19233302.
1: 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. [Epub ahead of print] PubMed PMID: 22706281. 2: 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. PubMed PMID: 21382614. 3: 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. PubMed PMID: 20496830. 4: McLean JH, Smith A, Rogers S, Clarke K, Darby-King A, Harley CW. A phosphodiesterase inhibitor, cilomilast, enhances cAMP activity to restore conditioned odor preference memory after serotonergic depletion in the neonate rat. Neurobiol Learn Mem. 2009 Jul;92(1):63-9. Epub 2009 Feb 20. PubMed PMID: 19233302. 5: Harada D, Ikeda Y, Nosaka Y, Kobayashi K, Manabe H. Curative effects of phosphodiesterase 4 inhibitors cilomilast, roflumilast, and rolipram in dermatitis mouse model. J Dermatol Sci. 2008 Sep;51(3):215-9. Epub 2008 Jun 9. PubMed PMID: 18539440. 6: Reddy PJ, Aksoy MO, Yang Y, Li XX, Ji R, Kelsen SG. Inhibition by salmeterol and cilomilast of fluticasone-enhanced IP-10 release in airway epithelial cells. COPD. 2008 Feb;5(1):5-11. PubMed PMID: 18259970. 7: Rennard S, Knobil K, Rabe KF, Morris A, Schachter N, Locantore N, Canonica WG, Zhu Y, Barnhart F. The efficacy and safety of cilomilast in COPD. Drugs. 2008;68 Suppl 2:3-57. doi: 10.2165/0003495-200868002-00002. Review. PubMed PMID: 19105585. 8: Agusti A. The efficacy and safety of cilomilast in COPD. Forward. Drugs. 2008;68 Suppl 2:1-2. doi: 10.2165/0003495-200868002-00001. PubMed PMID: 19105584. 9: Bäumer W, Kietzmann M. Effects of cyclosporin A and cilomilast on activated canine, murine and human keratinocytes. Vet Dermatol. 2007 Apr;18(2):107-14. PubMed PMID: 17355425. 10: Murphy DM, Ward C, Forrest IA, Pritchard G, Jones D, Stovold R, Fisher AJ, Cawston TE, Lordan JL, Corris PA. The phosphodiesterase type IV inhibitor cilomilast decreases pro-inflammatory cytokine production from primary bronchial epithelial cells in lung transplantation patients. J Heart Lung Transplant. 2006 Dec;25(12):1436-40. PubMed PMID: 17178338