Cilomilast
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MedKoo CAT#: 500450

CAS#: 153259-65-5

Description: 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

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Cilomilast
CAS# 153259-65-5

Theoretical Analysis

MedKoo Cat#: 500450
Name: Cilomilast
CAS#: 153259-65-5
Chemical Formula: C20H25NO4
Exact Mass: 343.17836
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
5.0mg USD 250.0 2 Weeks
10.0mg USD 450.0 2 Weeks
25.0mg USD 950.0 2 Weeks
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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: >95% (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

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

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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



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