OGLEMILAST SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H12Cl2F2N3O5S.Na
Molecular Weight	538.284
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CS(=O)(=O)[N-]C1=CC2=C(OC3=C(OC(F)F)C=CC(C(=O)NC4=C(Cl)C=NC=C4Cl)=C23)C=C1

InChI

InChIKey=QGLDQTFMBKMDCG-UHFFFAOYSA-N

InChI=1S/C20H12Cl2F2N3O5S.Na/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;/h2-8,20H,1H3,(H,25,26,28);/q-1;+1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C20H13Cl2F2N3O5S
Molecular Weight	516.302
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23436140
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 4B 11 Target ID: CHEMBL275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23436140	Inhibitor 8297		2.5 nM [IC50]
Phosphodiesterase 4D 14 Target ID: CHEMBL288 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23436140	Inhibitor 8297		1.7 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 174 Sources: http://adisinsight.springer.com/drugs/800021503 https://clinicaltrials.gov/ct2/show/NCT00671073	Primary		Phase II 1132	Unknown Approved Use Unknown
Asthma 241 Sources: http://adisinsight.springer.com/drugs/800021503 https://clinicaltrials.gov/ct2/show/NCT00859404	Primary		Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461

Drug as perpetrator

Target	Modality	Activity
P-gp 1650	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363678335	inconclusive [IC50 20.5962 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363678335	yes [IC50 0.3379 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=363678335	yes
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=363678335	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY114381	https://www.001chemical.com/chem/search?q=DY114381
1PlusChem LLC	1P005RQM	https://www.1pchem.com/search?query=1P005RQM
AK Scientific	2205AC	https://aksci.com/item_detail.php?cat=2205AC
Angene	AGN-PC-0UCFNQ	http://www.angenechemical.com/productshow/AGN-PC-0UCFNQ.html
BLD Pharm	BD236356	http://www.bldpharm.com/search/Search.html?keyword=BD236356
BOC Sciences	778576-62-8	http://www.bocsci.com/description.asp?cas=778576-62-8
Chem Scene	CS-0844	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0844
Matrix Scientific	95742	http://www.matrixscientific.com/095742.html
MedChem Express	HY-15178	https://www.medchemexpress.com/search.html?q=HY-15178&ft=&fa=&fp=
MolPort	MolPort-023-332-467	https://www.molport.com/shop/molecule-link/MolPort-023-332-467
Molcore	MC114381	http://www.molcore.com/CatMC114381.html
Molnova	M15938	https://www.molnova.com/en/serch-list.html?keywords=M15938
Wonderchem	WD06POT	http://www.wonder-chem.com/search.html?text=WD06POT
eMolecules	44467058	https://orderbb.emolecules.com/search/#?query=44467058
mcule	MCULE-6636991180	https://mcule.com/MCULE-6636991180/

PubMed

Title	Date	PubMed
Can the anti-inflammatory potential of PDE4 inhibitors be realized: guarded optimism or wishful thinking?	2008 Oct	18660832
Novel N-indolylmethyl substituted olanzapine derivatives: their design, synthesis and evaluation as PDE4B inhibitors.	2013 Apr 7	23436140

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:30:55 GMT 2023` Edited by `admin` on `Fri Dec 15 15:30:55 GMT 2023`
Record UNII	0J3S7PC0H3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OGLEMILAST SODIUM

Common Name

English

1-DIBENZOFURANCARBOXAMIDE, N-(3,5-DICHLORO-4-PYRIDINYL)-4-(DIFLUOROMETHOXY)-8-((METHYLSULFONYL)AMINO)-, MONOSODIUM SALT

Common Name

English

GRC 3886

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C744