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SML0585

Sigma-Aldrich

Piclamilast

≥98% (HPLC)

Synonym(s):

3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridinyl)-4-methoxy-benzamide, N-(3,5-Dichloropyrid-4-yl)-3-cyclopentyloxy-4-methoxybenzamide, RP 73-401, RP 73401, RPR 73401

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$112.00
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$434.00

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5 MG
$112.00
25 MG
$434.00

About This Item

Empirical Formula (Hill Notation):
C18H18Cl2N2O3
CAS Number:
144035-83-6
Molecular Weight:
381.25
UNSPSC Code:
41106305
NACRES:
NA.77

$112.00

Available to ship onMay 05, 2025Details

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assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

Clc1cncc(c1NC(=O)c2cc(c(cc2)OC)OC3CCCC3)Cl

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)

InChI key

RRRUXBQSQLKHEL-UHFFFAOYSA-N

Application

Piclamilasthas been used as a phosphodiesterase-4 (PDE4) inhibitor to treat cultures at the indicated time points after blast exposure.[1]

Biochem/physiol Actions

Piclamilast is a potent and selective cyclic AMP phosphodiesterase-4 inhibitor that exhibits equal, high affinity for both the PDE4 high- and low-affinity rolipram binding states (HARBS and LARBS). Recent studies shown that piclamilast inhibits Trypanosoma brucei PDEB1 (TbrPDEB1) and TbrPDEB2.
Piclamilast is a potent and selective cyclic AMP phosphodiesterase-4 inhibitor.
Piclamilast is also known as N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-methoxybenzamide. Piclamilast regulates the cAMP (cyclic adenosine monophosphate) signaling pathway. It increases the retinoid-dependent transactivation and the degradation of retinoic acid receptor α (RARα).[2]

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
013M4722V

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Ryo Hirose et al.
European journal of pharmacology, 573(1-3), 93-99 (2007-07-31)
We employed an ex vivo [(3)H]rolipram binding experiment to elucidate the mechanism of emetic activity of phosphodiesterase 4 inhibitors. In Suncus murinus (an insectivore used for evaluation of emesis), emetic potential as well as ability to occupy the high-affinity rolipram
Edoardo Parrella et al.
The Journal of biological chemistry, 279(40), 42026-42040 (2004-08-05)
Inhibition of phosphodiesterase IV by N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-methoxybenzamide (piclamilast) enhances the myeloid differentiation induced by all-trans-retinoic acid (ATRA), retinoic acid receptor alpha (RARalpha), or retinoic acid receptor X agonists in NB4 and other retinoid-sensitive myeloid leukemia cell types. ATRA-resistant NB4.R2 cells are
Yu Zhao et al.
The Journal of pharmacology and experimental therapeutics, 307(1), 246-253 (2003-09-05)
The effects of antidepressant treatment on the high- and low-affinity rolipram binding sites on type 4 phosphodiesterase (PDE4) were determined; previous work had shown that repeated antidepressant treatment increases the overall expression of PDE4. Rats were administered different doses of
Jun-Chun Chen et al.
Acta pharmacologica Sinica, 25(9), 1171-1175 (2004-09-02)
To improve the specific activity of human phosphodiesterase 4A (PDE4A) expressed in yeast cell GL62 and investigate the effects of selective phosphodiesterase 4 (PDE4) inhibitors (ciclamilast, piclamilast, and rolipram), selective phosphodiesterase 5 (PDE5) inhibitor zaprinast, and cyclooxygenase (COX) inhibitors (aspirin
Phosphodiesterase-4 inhibition restored hippocampal long term potentiation after primary blast
Vogel EW, et al.
Experimental Neurology, 293(40), 91-100 (2017)
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