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SML1099

Sigma-Aldrich

Roflumilast

≥98% (HPLC), powder, phosphodiesterase 4 PDE4 inhibitor

Synonym(s):

3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide, 3-Cyclopropylmethoxy-4-difluoromethoxy-N-[3,5-dichloropyrid-4-yl]-benzamide

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About This Item

Empirical Formula (Hill Notation):
C17H14Cl2F2N2O3
CAS Number:
162401-32-3
Molecular Weight:
403.21
MDL number:
MFCD00938270
UNSPSC Code:
41106305
PubChem Substance ID:
329825476
NACRES:
NA.77

product name

Roflumilast, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

ClC1=CN=CC(Cl)=C1NC(C2=CC=C(OC(F)F)C(OCC3CC3)=C2)=O

InChI

1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24)

InChI key

MNDBXUUTURYVHR-UHFFFAOYSA-N

Gene Information

human ... PDE4A(5141) , PDE4B(5142) , PDE4C(5143) , PDE4D(5144)

Application

Roflumilast has been used to evaluate its effect on acute lung inflammation and chronic lung changes in models of cigarette exposure in mice. It is also used to investigate its therapeutic potential to ameliorate primary blast-induced deficits in long-term potentiation (LTP).

Biochem/physiol Actions

Roflumilast is a highly potent, orally active, and selective phosphodiesterase 4 (PDE4) inhibitor with an IC50 of 0.8 nM. Roflumilast has anti-inflammatory properties and is used clinically to treat COPD.

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.

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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Amparo Buenestado et al.
PloS one, 8(9), e74640-e74640 (2013-09-26)
Roflumilast is the first phosphodiesterase-4 (PDE4) inhibitor to have been approved for the treatment of COPD. The anti-inflammatory profile of PDE4 inhibitors has not yet been explored in human lung tissues. We investigated the effects of roflumilast and its active
Xiaohua Du et al.
Phytotherapy research : PTR, 33(3), 602-609 (2019-01-15)
The principal active component of isoforskolin (ISOF) is from the plant Coleus forskohlii, native to China, which has attracted much attention for its biological effects. We hypothesize that ISOF and forskolin (FSK) pretreatment attenuates inflammation induced by lipopolysaccharide (LPS) related
Phosphodiesterase-4 inhibition restored hippocampal long term potentiation after primary blast.
Vogel E W, et al.
Experimental Neurology, 293, 91-100 (2017)
Fernando J Martinez et al.
Lancet (London, England), 385(9971), 857-866 (2015-02-17)
Roflumilast reduces exacerbations in patients with severe chronic obstructive pulmonary disease. Its effect in patients using fixed combinations of inhaled corticosteroids and longacting β2 agonists is unknown. We postulated that roflumilast would reduce exacerbations in patients with severe chronic obstructive
Roflumilast fully prevents emphysema in mice chronically exposed to cigarette smoke.
Martorana P A, et al.
American Journal of Respiratory and Critical Care Medicine, 172(7), 848-853 (2005)
View All Related Papers

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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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