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Details

Stereochemistry ACHIRAL
Molecular Formula C20H13Cl2F2N3O5S
Molecular Weight 516.302
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OGLEMILAST

SMILES

CS(=O)(=O)NC1=CC2=C(OC3=C2C(=CC=C3OC(F)F)C(=O)NC4=C(Cl)C=NC=C4Cl)C=C1

InChI

InChIKey=OKFDRAHPFKMAJH-UHFFFAOYSA-N
InChI=1S/C20H13Cl2F2N3O5S/c1-33(29,30)27-9-2-4-14-11(6-9)16-10(3-5-15(18(16)31-14)32-20(23)24)19(28)26-17-12(21)7-25-8-13(17)22/h2-8,20,27H,1H3,(H,25,26,28)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800021503

Oglemilast (GRC-3886), is a potent and selective PDE4 inhibitor (IC50: 2.5 nM (PDE4B) and 1.7 nM (PDE4D)). Oglemilast is in phase II clinical trials for the treatment of asthma and chronic obstructive pulmonary disease (COPD). Oglemilast was originally developed by Glenmark Pharmaceuticals, and licensed to Forest (acquired by Actavis in 2014) for the rights in North America in 2004. Teijin Pharma obtained the rights of the compound in Japan in 2005.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.5 nM [IC50]
1.7 nM [IC50]
Conditions
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Can the anti-inflammatory potential of PDE4 inhibitors be realized: guarded optimism or wishful thinking?
2008 Oct
Novel N-indolylmethyl substituted olanzapine derivatives: their design, synthesis and evaluation as PDE4B inhibitors.
2013 Apr 7
Patents

Sample Use Guides

15mg oral administration, once per day
Route of Administration: Oral
In Vitro Use Guide
Oglemilast (GRC-3886) inhibited PDE4 enzyme with an IC50 value of 1.4 nM and exhibited > 7,000-fold selectivity over other PDE (PDE1–11) families. In human whole blood assays, oglemilast inhibited LPS-induced TNFα production with an IC50 value of 190 nM.
Name Type Language
OGLEMILAST
INN   WHO-DD  
INN  
Official Name English
N-(3,5-DICHLOROPYRIDIN-4-YL)-4-(DIFLUOROMETHOXY)-8-((METHYLSULFONYL)AMINO)DIBENZO(B,D)FURAN-1-CARBOXAMIDE
Systematic Name English
oglemilast [INN]
Common Name English
GRC 3845
Code English
Oglemilast [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C744
Created by admin on Fri Dec 15 16:08:44 GMT 2023 , Edited by admin on Fri Dec 15 16:08:44 GMT 2023
Code System Code Type Description
CAS
778576-62-8
Created by admin on Fri Dec 15 16:08:44 GMT 2023 , Edited by admin on Fri Dec 15 16:08:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID70999058
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DRUG BANK
DB12375
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SMS_ID
300000034264
Created by admin on Fri Dec 15 16:08:44 GMT 2023 , Edited by admin on Fri Dec 15 16:08:44 GMT 2023
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INN
8675
Created by admin on Fri Dec 15 16:08:44 GMT 2023 , Edited by admin on Fri Dec 15 16:08:44 GMT 2023
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PUBCHEM
11387409
Created by admin on Fri Dec 15 16:08:44 GMT 2023 , Edited by admin on Fri Dec 15 16:08:44 GMT 2023
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FDA UNII
67GXQ6WCC6
Created by admin on Fri Dec 15 16:08:44 GMT 2023 , Edited by admin on Fri Dec 15 16:08:44 GMT 2023
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NCI_THESAURUS
C87376
Created by admin on Fri Dec 15 16:08:44 GMT 2023 , Edited by admin on Fri Dec 15 16:08:44 GMT 2023
PRIMARY