144035-83-6
144035-83-6 structure
- Name: Piclamilast
- Chemical Name: piclamilast
- CAS Number: 144035-83-6
- Molecular Formula: C18H18Cl2N2O3
- Molecular Weight: 381.253
- Catalog: Signaling Pathways Metabolic Enzyme/Protease Phosphodiesterase (PDE)
- Create Date: 2017-08-11 16:38:12
- Modify Date: 2024-01-08 16:37:49
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Piclamilast (RP 73401) is a phosphodiesterase 4 (PDE4) inhibitor, with IC50 values of 16 nM and 2 nM in pig aorta and eosinophil soluble, respectively[1][2][3][4].
| Name | piclamilast |
|---|---|
| Synonyms |
3-(cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide
3-cyclopentyloxy-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide Piclamilast 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridinyl)-4-methoxybenzamide Cpodpmb Benzamide, 3-(cyclopentyloxy)-N-(3,5-dichloro-4-pyridinyl)-4-methoxy- 3-(Cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide |
| Description | Piclamilast (RP 73401) is a phosphodiesterase 4 (PDE4) inhibitor, with IC50 values of 16 nM and 2 nM in pig aorta and eosinophil soluble, respectively[1][2][3][4]. |
|---|---|
| Related Catalog | |
| Target |
PDE4:16 nM (IC50, in pig aorta) PDE4:2 nM (IC50, in eosinophil soluble) PDE1:>100 μM (IC50) PDE2:40 μM (IC50) PDE3:>100 μM (IC50) PDE5:14 μM (IC50) |
| In Vitro | Piclamilast (RP 73401, 1 μM, 30 min) significantly inhibits the changes in 23 genes via mechanisms involving AP-1 activation and c-Jun phosphorylation at Ser63[2]. Piclamilast (RP 73401) exhibits IC50 values >100 μM, 40 μM, >100 μM, 14 μM for PDE1, PDE2, PDE3 and PDE5. Respectively[4]. RT-PCR[2] Cell Line: Human A549 type II lung epithelial cells. Concentration: 1 μM (H2O2 200 μM). Incubation Time: 30 min. Result: Prevented H2O2 -induced changes in gene expression levels in A549 cells. Cell Viability Assay[3] Cell Line: NB4 cells. Concentration: 30 μM. Incubation Time: 3 days. Result: Exerted a significant enhancing effect on the induction of STAT1 observed in ATRA-treated NB4 cells. Caused a significant increase in the number of cells expressing NBT-R activity. |
| In Vivo | Piclamilast (RP 73401, 10 mg/kg, 30 min) alone does not affect the MST of leukemia-bearing animals. Piclamilast combined with ATRA (HY-14649) significantly more effective than ATRA alone in increasing the MST (40 days; interval 34–45 days) of leukemia-bearing animals[3]. Animal Model: SCID mice[3]. Dosage: 10 mg/kg (combined with ATRA (HY-14649)). Administration: Injection daily. Result: Significantly more effective than ATRA alone in increasing the MST (40 days; interval 34–45 days) of leukemia-bearing animals. |
| References |
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 447.8±45.0 °C at 760 mmHg |
| Molecular Formula | C18H18Cl2N2O3 |
| Molecular Weight | 381.253 |
| Flash Point | 224.6±28.7 °C |
| Exact Mass | 380.069458 |
| PSA | 63.68000 |
| LogP | 5.25 |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.626 |
| Symbol |
GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H315-H319-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| Hazard Codes | Xi |
| RIDADR | NONH for all modes of transport |
|
~85%
144035-83-6 |
| Literature: Cook, David C.; Jones, Ronald H.; Kabir, Humayun; Lythgoe, David J.; McFarlane, Ian M.; Pemberton, Clive; Thatcher, Alan A.; Thompson, David M.; Walton, John B. Organic Process Research and Development, 1998 , vol. 2, # 3 p. 157 - 168 |
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144035-83-6 |
| Literature: Journal of Medicinal Chemistry, , vol. 37, # 11 p. 1696 - 1703 |
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144035-83-6 |
| Literature: Journal of Medicinal Chemistry, , vol. 37, # 11 p. 1696 - 1703 |
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144035-83-6 |
| Literature: Journal of Medicinal Chemistry, , vol. 37, # 11 p. 1696 - 1703 |
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144035-83-6 |
| Literature: Journal of Medicinal Chemistry, , vol. 37, # 11 p. 1696 - 1703 |
| Precursor 6 | |
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| DownStream 0 | |