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MedKoo Cat#: 563422 | Name: Piclamilast
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Description:

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

Piclamilast is a benzamide which serves as a selective PDE4 inhibitor. Piclamilast is studied for its applications in treating DMH-induced colorectal cancer (CRC).

Chemical Structure

Piclamilast
Piclamilast
CAS#144035-83-6

Theoretical Analysis

MedKoo Cat#: 563422

Name: Piclamilast

CAS#: 144035-83-6

Chemical Formula: C18H18Cl2N2O3

Exact Mass: 380.0694

Molecular Weight: 381.25

Elemental Analysis: C, 56.71; H, 4.76; Cl, 18.60; N, 7.35; O, 12.59

Price and Availability

Size Price Availability Quantity
5mg USD 395.00
25mg USD 825.00
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Related CAS #
No Data
Synonym
Piclamilast; RP-73401; RP 73-401; RP 73401; RP 73 401; RP73401; RP 73401;
IUPAC/Chemical Name
3-(Cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide
InChi Key
RRRUXBQSQLKHEL-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H18Cl2N2O3/c1-24-15-7-6-11(8-16(15)25-12-4-2-3-5-12)18(23)22-17-13(19)9-21-10-14(17)20/h6-10,12H,2-5H2,1H3,(H,21,22,23)
SMILES Code
O=C(NC1=C(Cl)C=NC=C1Cl)C2=CC=C(OC)C(OC3CCCC3)=C2
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
Shelf Life
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Piclamilast (RP 73401) is a phosphodiesterase 4 (PDE4) inhibitor, with IC50 values of 16 nM and 2 nM.
In vitro activity:
This study analysed the effects of piclamilast, a selective PDE4 inhibitor, on modulating the global gene expression profile in A549 cells exposed to H(2)O(2). The results indicate that H(2)O(2) modified the expression of several genes related to apoptosis, cell cycle control and cell signalling, including IL8, FAS, HIG2, CXCL2, CDKN25 and JUNB. Piclamilast pre-treatment significantly inhibited the changes in 23 genes via mechanisms involving AP-1 activation and c-Jun phosphorylation at Ser63. Reference: Free Radic Res. 2012 May;46(5):690-9. https://pubmed.ncbi.nlm.nih.gov/22360706/
In vivo activity:
RP 73401 (0.4-400 micrograms kg-1, intratracheally (i.t.) on lactose) inhibited antigen-induced bronchospasm in previously sensitized conscious guinea-pigs (ID50: 7 +/- 1 micrograms kg-1) and in anaesthetized rats (ID50: 100 +/- 25 micrograms kg-1). Rolipram inhibited the antigen-induced bronchospasm in guinea-pigs with an ID50 of 5 +/- 1 micrograms kg-1. In guinea-pig bronchoalveolar lavage (BAL) fluid, total inflammatory cell and eosinophil numbers were reduced by RP 73401 (ID50s: 3.9 +/- 0.8 micrograms kg-1 and 3.2 +/- 0.7 micrograms kg-1, respectively). In the rat, inflammatory cell numbers are less affected. Only the highest dose of RP 73401 (400 micrograms kg-1) significantly inhibited eosinophil influx (41 +/- 16% inhibition). Reference: Br J Pharmacol. 1994 Dec;113(4):1423-31. https://pubmed.ncbi.nlm.nih.gov/7889300/
Solvent mg/mL mM comments
Solubility
DMSO 38.1 100.00
Ethanol 7.6 20.00
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 381.25 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. Mata M, Pallardo F, Morcillo EJ, Cortijo J. Piclamilast inhibits the pro-apoptotic and anti-proliferative responses of A549 cells exposed to H(2)O(2) via mechanisms involving AP-1 activation. Free Radic Res. 2012 May;46(5):690-9. doi: 10.3109/10715762.2012.669040. Epub 2012 Mar 15. PMID: 22360706. 2. Parrella E, Gianni' M, Cecconi V, Nigro E, Barzago MM, Rambaldi A, Rochette-Egly C, Terao M, Garattini E. Phosphodiesterase IV inhibition by piclamilast potentiates the cytodifferentiating action of retinoids in myeloid leukemia cells. Cross-talk between the cAMP and the retinoic acid signaling pathways. J Biol Chem. 2004 Oct 1;279(40):42026-40. doi: 10.1074/jbc.M406530200. Epub 2004 Jul 28. PMID: 15292163. 3. Abdel-Wahab BA, Alqhtani H, Walbi IA, Albarqi HA, Aljadaan AM, Khateeb MM, Hassanein EHM. Piclamilast mitigates 1,2-dimethylhydrazine induced colon cancer in rats through modulation of Ras/PI3K/Akt/mTOR and NF-κβ signaling. Chem Biol Interact. 2021 Dec 1;350:109686. doi: 10.1016/j.cbi.2021.109686. Epub 2021 Oct 7. PMID: 34627785. 4. Raeburn D, Underwood SL, Lewis SA, Woodman VR, Battram CH, Tomkinson A, Sharma S, Jordan R, Souness JE, Webber SE, et al. Anti-inflammatory and bronchodilator properties of RP 73401, a novel and selective phosphodiesterase type IV inhibitor. Br J Pharmacol. 1994 Dec;113(4):1423-31. doi: 10.1111/j.1476-5381.1994.tb17156.x. PMID: 7889300; PMCID: PMC1510545.
In vitro protocol:
1. Mata M, Pallardo F, Morcillo EJ, Cortijo J. Piclamilast inhibits the pro-apoptotic and anti-proliferative responses of A549 cells exposed to H(2)O(2) via mechanisms involving AP-1 activation. Free Radic Res. 2012 May;46(5):690-9. doi: 10.3109/10715762.2012.669040. Epub 2012 Mar 15. PMID: 22360706. 2. Parrella E, Gianni' M, Cecconi V, Nigro E, Barzago MM, Rambaldi A, Rochette-Egly C, Terao M, Garattini E. Phosphodiesterase IV inhibition by piclamilast potentiates the cytodifferentiating action of retinoids in myeloid leukemia cells. Cross-talk between the cAMP and the retinoic acid signaling pathways. J Biol Chem. 2004 Oct 1;279(40):42026-40. doi: 10.1074/jbc.M406530200. Epub 2004 Jul 28. PMID: 15292163.
In vivo protocol:
1. Abdel-Wahab BA, Alqhtani H, Walbi IA, Albarqi HA, Aljadaan AM, Khateeb MM, Hassanein EHM. Piclamilast mitigates 1,2-dimethylhydrazine induced colon cancer in rats through modulation of Ras/PI3K/Akt/mTOR and NF-κβ signaling. Chem Biol Interact. 2021 Dec 1;350:109686. doi: 10.1016/j.cbi.2021.109686. Epub 2021 Oct 7. PMID: 34627785. 2. Raeburn D, Underwood SL, Lewis SA, Woodman VR, Battram CH, Tomkinson A, Sharma S, Jordan R, Souness JE, Webber SE, et al. Anti-inflammatory and bronchodilator properties of RP 73401, a novel and selective phosphodiesterase type IV inhibitor. Br J Pharmacol. 1994 Dec;113(4):1423-31. doi: 10.1111/j.1476-5381.1994.tb17156.x. PMID: 7889300; PMCID: PMC1510545.
1: Oh KK, Yoon SJ, Song SH, Park JH, Kim JS, Kim DJ, Suk KT. The synchronized feature of Saururus chinensis and gut microbiota against T2DM, NAFLD, obesity and hypertension via integrated pharmacology. Artif Cells Nanomed Biotechnol. 2024 Dec;52(1):278-290. doi: 10.1080/21691401.2024.2350475. Epub 2024 May 11. PMID: 38733373. 2: Lim I, Masutani T, Hashitani H, Chess-Williams R, Sellers D. Inhibition of PDE-4 isoenzyme attenuates frequency and overall contractility of agonist-evoked ureteral phasic contractions. Pharmacol Res Perspect. 2024 Feb;12(1):e1175. doi: 10.1002/prp2.1175. PMID: 38339883; PMCID: PMC10858371. 3: Giuzio F, Bonomo MG, Catalano A, Infantino V, Salzano G, Monné M, Geronikaki A, Petrou A, Aquaro S, Sinicropi MS, Saturnino C. Potential PDE4B inhibitors as promising candidates against SARS-CoV-2 infection. Biomol Concepts. 2023 Nov 1;14(1). doi: 10.1515/bmc-2022-0033. PMID: 37909122. 4: Zheng Y, Schroeder S, Kanev GK, Botros SS, William S, Sabra AA, Maes L, Caljon G, Gil C, Martinez A, Salado IG, Augustyns K, Edink E, Sijm M, de Heuvel E, de Esch IJP, van der Meer T, Siderius M, Sterk GJ, Brown D, Leurs R. To Target or Not to Target Schistosoma mansoni Cyclic Nucleotide Phosphodiesterase 4A? Int J Mol Sci. 2023 Apr 6;24(7):6817. doi: 10.3390/ijms24076817. PMID: 37047792; PMCID: PMC10095301. 5: Wan Q, Xu C, Zhu L, Zhang Y, Peng Z, Chen H, Rao H, Zhang E, Wang H, Chu F, Ning X, Yang X, Yuan J, Wu Y, Huang Y, Hu S, Liu DP, Wang M. Targeting PDE4B (Phosphodiesterase-4 Subtype B) for Cardioprotection in Acute Myocardial Infarction via Neutrophils and Microcirculation. Circ Res. 2022 Aug 19;131(5):442-455. doi: 10.1161/CIRCRESAHA.122.321365. Epub 2022 Jul 28. PMID: 35899614. 6: Kaur A, Singh TG, Khan H, Kumar M, Singh N, Abdel-Daim MM. Neuroprotective Effect of Piclamilast-Induced Post-Ischemia Pharmacological Treatment in Mice. Neurochem Res. 2022 Aug;47(8):2230-2243. doi: 10.1007/s11064-022-03609-w. Epub 2022 Apr 28. PMID: 35482135. 7: Abdel-Wahab BA, Alqhtani H, Walbi IA, Albarqi HA, Aljadaan AM, Khateeb MM, Hassanein EHM. Piclamilast mitigates 1,2-dimethylhydrazine induced colon cancer in rats through modulation of Ras/PI3K/Akt/mTOR and NF-κβ signaling. Chem Biol Interact. 2021 Dec 1;350:109686. doi: 10.1016/j.cbi.2021.109686. Epub 2021 Oct 7. PMID: 34627785. 8: Aragon IV, Boyd A, Abou Saleh L, Rich J, McDonough W, Koloteva A, Richter W. Inhibition of cAMP-phosphodiesterase 4 (PDE4) potentiates the anesthetic effects of Isoflurane in mice. Biochem Pharmacol. 2021 Apr;186:114477. doi: 10.1016/j.bcp.2021.114477. Epub 2021 Feb 18. PMID: 33609559; PMCID: PMC8052286. 9: McDonough W, Aragon IV, Rich J, Murphy JM, Abou Saleh L, Boyd A, Koloteva A, Richter W. PAN-selective inhibition of cAMP-phosphodiesterase 4 (PDE4) induces gastroparesis in mice. FASEB J. 2020 Sep;34(9):12533-12548. doi: 10.1096/fj.202001016RR. Epub 2020 Aug 1. PMID: 32738081; PMCID: PMC7954513. 10: McDonough W, Rich J, Aragon IV, Abou Saleh L, Boyd A, Richter A, Koloteva A, Richter W. Inhibition of type 4 cAMP-phosphodiesterases (PDE4s) in mice induces hypothermia via effects on behavioral and central autonomous thermoregulation. Biochem Pharmacol. 2020 Oct;180:114158. doi: 10.1016/j.bcp.2020.114158. Epub 2020 Jul 20. PMID: 32702371; PMCID: PMC7606724. 11: Zheng XY, Chen JC, Xie QM, Chen JQ, Tang HF. Anti‑inflammatory effect of ciclamilast in an allergic model involving the expression of PDE4B. Mol Med Rep. 2019 Mar;19(3):1728-1738. doi: 10.3892/mmr.2019.9802. Epub 2019 Jan 2. PMID: 30628641. 12: Sisson TH, Christensen PJ, Muraki Y, Dils AJ, Chibucos L, Subbotina N, Tohyama K, Horowitz JC, Matsuo T, Bailie M, Nikam S, Hazama M. Phosphodiesterase 4 inhibition reduces lung fibrosis following targeted type II alveolar epithelial cell injury. Physiol Rep. 2018 Jun;6(12):e13753. doi: 10.14814/phy2.13753. PMID: 29952109; PMCID: PMC6021279. 13: Nio Y, Tanaka M, Hirozane Y, Muraki Y, Okawara M, Hazama M, Matsuo T. Phosphodiesterase 4 inhibitor and phosphodiesterase 5 inhibitor combination therapy has antifibrotic and anti-inflammatory effects in mdx mice with Duchenne muscular dystrophy. FASEB J. 2017 Dec;31(12):5307-5320. doi: 10.1096/fj.201700249R. Epub 2017 Aug 10. PMID: 28798156. 14: Vang AG, Basole C, Dong H, Nguyen RK, Housley W, Guernsey L, Adami AJ, Thrall RS, Clark RB, Epstein PM, Brocke S. Differential Expression and Function of PDE8 and PDE4 in Effector T cells: Implications for PDE8 as a Drug Target in Inflammation. Front Pharmacol. 2016 Aug 23;7:259. doi: 10.3389/fphar.2016.00259. PMID: 27601994; PMCID: PMC4993990. 15: Seimetz M, Parajuli N, Pichl A, Bednorz M, Ghofrani HA, Schermuly RT, Seeger W, Grimminger F, Weissmann N. Cigarette Smoke-Induced Emphysema and Pulmonary Hypertension Can Be Prevented by Phosphodiesterase 4 and 5 Inhibition in Mice. PLoS One. 2015 Jun 9;10(6):e0129327. doi: 10.1371/journal.pone.0129327. PMID: 26058042; PMCID: PMC4461257. 16: Patel BS, Prabhala P, Oliver BG, Ammit AJ. Inhibitors of Phosphodiesterase 4, but Not Phosphodiesterase 3, Increase β2-Agonist-Induced Expression of Antiinflammatory Mitogen-Activated Protein Kinase Phosphatase 1 in Airway Smooth Muscle Cells. Am J Respir Cell Mol Biol. 2015 May;52(5):634-40. doi: 10.1165/rcmb.2014-0344OC. PMID: 25296132. 17: Felding J, Sørensen MD, Poulsen TD, Larsen J, Andersson C, Refer P, Engell K, Ladefoged LG, Thormann T, Vinggaard AM, Hegardt P, Søhoel A, Nielsen SF. Discovery and early clinical development of 2-{6-[2-(3,5-dichloro-4-pyridyl)acetyl]-2,3-dimethoxyphenoxy}-N-propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis. J Med Chem. 2014 Jul 24;57(14):5893-903. doi: 10.1021/jm500378a. Epub 2014 Jul 1. PMID: 24984230. 18: Blednov YA, Benavidez JM, Black M, Harris RA. Inhibition of phosphodiesterase 4 reduces ethanol intake and preference in C57BL/6J mice. Front Neurosci. 2014 May 27;8:129. doi: 10.3389/fnins.2014.00129. PMID: 24904269; PMCID: PMC4034339. 19: Van Ly D, De Pedro M, James P, Morgan L, Black JL, Burgess JK, Oliver BG. Inhibition of phosphodiesterase 4 modulates cytokine induction from toll like receptor activated, but not rhinovirus infected, primary human airway smooth muscle. Respir Res. 2013 Nov 15;14(1):127. doi: 10.1186/1465-9921-14-127. PMID: 24237854; PMCID: PMC3832400. 20: Woodring JL, Bland ND, Ochiana SO, Campbell RK, Pollastri MP. Synthesis and assessment of catechol diether compounds as inhibitors of trypanosomal phosphodiesterase B1 (TbrPDEB1). Bioorg Med Chem Lett. 2013 Nov 1;23(21):5971-4. doi: 10.1016/j.bmcl.2013.08.057. Epub 2013 Aug 21. PMID: 24042005; PMCID: PMC3825250.