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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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About This Item

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

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

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.

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 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).

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kerryn McCluskie et al.
The Journal of pharmacology and experimental therapeutics, 319(1), 468-476 (2006-07-25)
Phosphodiesterase type 4 (PDE(4)) inhibitors are currently being evaluated as potential therapies for inflammatory airway diseases. However, this class of compounds has been shown to cause an arteritis/vasculitis of unknown etiology in rats and cynomolgus monkeys. Studies in rodents have
C Méhats et al.
The Journal of clinical endocrinology and metabolism, 86(11), 5358-5365 (2001-11-10)
Elevation of cAMP content resulting from stimulation of the receptor-adenylyl cyclase complex is involved in maintaining the quiescence of the human myometrium during pregnancy. The magnitude of this elevation is critically influenced by the rate of cAMP hydrolysis by phosphodiesterase
Yu Zhao et al.
The Journal of pharmacology and experimental therapeutics, 305(2), 565-572 (2003-04-22)
Piclamilast is a type 4 phosphodiesterase (PDE4) inhibitor with equal affinity for the high-affinity rolipram binding site (HARBS) and low-affinity rolipram binding site (LARBS). The binding of [(3)H]piclamilast to preparations of rat brain and peripheral tissue was investigated and compared
L Wollin et al.
Pulmonary pharmacology & therapeutics, 19(5), 343-352 (2005-11-01)
Roflumilast is an oral, once-daily phosphodiesterase 4 (PDE4) inhibitor with anti-inflammatory activity. We compared the anti-inflammatory effects of roflumilast with those of PDE4 inhibitors rolipram, piclamilast, and cilomilast in ovalbumin (OVA)-sensitized and challenged Brown-Norway rats. Animals were treated orally 1h
Sean D McKenna et al.
Endocrinology, 146(1), 208-214 (2004-09-28)
Phosphodiesterases (PDEs) are a family of enzymes that hydrolyze cyclic nucleotides to render them biologically inactive. As such, these enzymes are critical regulators of signal transduction pathways that use cyclic nucleotides as second messengers. PDE4 is one such member that
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