FIBOFLAPON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C38H43N3O4S
Molecular Weight	637.831
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=CC=C(C=N1)C2=CC=C(CN3C(CC(C)(C)C(O)=O)=C(SC(C)(C)C)C4=C3C=CC(OCC5=NC=C(C)C=C5)=C4)C=C2

InChI

InChIKey=DFQGDHBGRSTTHX-UHFFFAOYSA-N

InChI=1S/C38H43N3O4S/c1-8-44-34-18-14-28(22-40-34)27-12-10-26(11-13-27)23-41-32-17-16-30(45-24-29-15-9-25(2)21-39-29)19-31(32)35(46-37(3,4)5)33(41)20-38(6,7)36(42)43/h9-19,21-22H,8,20,23-24H2,1-7H3,(H,42,43)

HIDE SMILES / InChI

Description
Sources: http://www.biospace.com/News/amira-pharmaceuticals-inc-announces-am103-and/187186http://adisinsight.springer.com/drugs/800027280
Curator's Comment: Description was created based on several sources, including http://www.generon.co.uk/amine-oxides-1830/gsk2190915-sodium-salt-gsk-2190915a-231013117.html https://www.ncbi.nlm.nih.gov/pubmed/23331559

Fiboflapon sodium (GSK2190915) is a high affinity 5-lipoxygenase-activating protein inhibitor being developed for the treatment of asthma. The compound was originally developed by Amira Pharmaceuticals. Fiboflapon sodium (GSK2190915) exhibits excellent preclinical toxicology and pharmacokinetics in rat and dog. GSK2190915 also demonstrated an extended pharmacodynamic effect in a rodent bronchoalveolar lavage (BAL) model. Oral administration of Fiboflapon sodium (GSK2190915) (1 mg/kg) resulted in sustained inhibition of ex vivo ionophore-challenged whole blood LTB4 biosynthesis with >90% inhibition for up to 12 h and an EC50 of approximately 7 nM. When rat lungs were challenged in vivo with calcium-ionophore, Fiboflapon sodium inhibited LTB4 and cysteinyl leukotriene (CysLT) production with ED50s of 0.12 mg/kg and 0.37 mg/kg, respectively. Fiboflapon sodium is in Phase-II for Asthma (Adjunctive treatment) in Poland, Ukraine, Bulgaria, USA, United Kingdom and Canada (PO).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-lipoxygenase activating protein 7 Target ID: CHEMBL4550 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22059882	Inhibitor 8297		2.9 nM [IC50]
5-lipoxygenase activating protein 7 Target ID: CHEMBL4550 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=22059882	Inhibitor 8297		2.9 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://clinicaltrials.gov/ct2/show/NCT01471665	Primary		Phase II 1132	Unknown Approved Use Unknown
Asthma 241 Sources: https://clinicaltrials.gov/ct2/show/NCT00748306	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P008U2Q	https://www.1pchem.com/search?query=1P008U2Q
1PlusChem LLC	1P00GUP7	https://www.1pchem.com/search?query=1P00GUP7
AbovChem LLC	HY-15874A	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-15874A
ApexBio Technology	B4905	https://www.apexbt.com/catalogsearch/result/?q=B4905
BLD Pharm	BD629975	http://www.bldpharm.com/search/Search.html?keyword=BD629975
BLD Pharm	BD631035	http://www.bldpharm.com/search/Search.html?keyword=BD631035
Chem Scene	CS-3604	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3604
ChemShuttle	140121	https://www.chemshuttle.com/catalogsearch/result/?q=140121
MedChem Express	HY-15874	https://www.medchemexpress.com/search.html?q=HY-15874&ft=&fa=&fp=
MolPort	MolPort-046-417-103	https://www.molport.com/shop/molecule-link/MolPort-046-417-103
MolPort	MolPort-046-417-104	https://www.molport.com/shop/molecule-link/MolPort-046-417-104
Molnova	M10690	https://www.molnova.com/en/serch-list.html?keywords=M10690
Molnova	M16702	https://www.molnova.com/en/serch-list.html?keywords=M16702
MuseChem	I005562	https://www.musechem.com/product/I005562.html
MuseChem	I006622	https://www.musechem.com/product/I006622.html
eMolecules	50550828	https://orderbb.emolecules.com/search/#?query=50550828
mcule	MCULE-4250296441	https://mcule.com/MCULE-4250296441/
mcule	MCULE-4876509472	https://mcule.com/MCULE-4876509472/

PubMed

Title	Date	PubMed
Pharmacology of AM803, a novel selective five-lipoxygenase-activating protein (FLAP) inhibitor in rodent models of acute inflammation.	2010 Aug 25	20519143
The 5-lipoxygenase-activating protein inhibitor, GSK2190915, attenuates the early and late responses to inhaled allergen in mild asthma.	2013 Feb	23331559

Patents

Sample Use Guides

In Vivo Use Guide

Patients receive 100mg of GSK2190915 (FIBOFLAPON) once daily for up to 16 days followed by a wash out period of at least 14 days before they cross over onto the placebo arm of the study.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

FIBOFLAPON

Official Name

English

AM803

Code

English

FIBOFLAPON [USAN]

Common Name

English

fiboflapon [INN]

Common Name

English

Fiboflapon [WHO-DD]

Common Name

English

GSK-2190915

Code

English

3-(3-(TERT-BUTYLSULFANYL)-1-((4-(6-ETHOXYPYRIDIN-3-YL)PHENYL)METHYL)-5-((5-METHYLPYRIDIN-2-YL)METHOXY)-1H-INDOL-2-YL)-2,2-DIMETHYLPROPANOIC ACID

Systematic Name

English

AM-803

Code

English

1H-INDOLE-2-PROPANOIC ACID, 3-((1,1-DIMETHYLETHYL)THIO)-1-((4-(6-ETHOXY-3-PYRIDINYL)PHENYL)METHYL)-.ALPHA.,.ALPHA.-DIMETHYL-5-((5-METHYL-2-PYRIDINYL)METHOXY)-

Common Name

English

GSK2190915

Code

English

Code System Code Type Description

DRUG BANK

DB06346