DARBUFELONE MESYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H24N2O2S.CH4O3S
Molecular Weight	428.566
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)\C=C2/SC(=N)NC2=O

InChI

InChIKey=BAZGFSKJAVQJJI-CHHCPSLASA-N

InChI=1S/C18H24N2O2S.CH4O3S/c1-17(2,3)11-7-10(8-12(14(11)21)18(4,5)6)9-13-15(22)20-16(19)23-13;1-5(2,3)4/h7-9,21H,1-6H3,(H2,19,20,22);1H3,(H,2,3,4)/b13-9-;

HIDE SMILES / InChI

Molecular Formula	C18H24N2O2S
Molecular Weight	332.46
Charge	0
Count

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

Molecular Formula	CH4O3S
Molecular Weight	96.106
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/11412128 | https://www.ncbi.nlm.nih.gov/pubmed/8295221 | https://www.ncbi.nlm.nih.gov/pubmed/20352217 | http://en.pharmacodia.com/web/drug/1_3130.html

Darbufelone mesylate is a dual inhibitor of cellular prostaglandin and leukotriene production. Darbufelone potently inhibits PGHS-2 (IC50 = 0.19 uM) but is much less potent with PGHS-1 (IC50= 20 uM). Darbufelone is a dual inhibitor of cellular PGF2R and LTB4 production. Darbufelone is orally active and nonulcerogenic in animal models of inflammation and arthritis. Darbufelone mesylate was in phase III clinical trials by Pfizer and Zhuhai United Laboratories for the treatment of rheumatoid arthritis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11412128	Inhibitor 8297		0.19 µM [IC50]
Arachidonate 5-lipoxygenase 49 Target ID: CHEMBL312 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8295221	Inhibitor 8297		0.77 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatic diseases 30 Sources: http://adisinsight.springer.com/drugs/800004636 https://www.pharmacodia.com/yaodu/html/v1/chemicals/2cf7926aeec52fbe4f1a6ae2a1770329.html	Primary		Phase III 656	Unknown Approved Use Unknown
Lung cancer 69 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20352217	Primary		Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	R022	https://aksci.com/item_detail.php?cat=R022
AOBIOUS INC	AOB5070	http://aobious.com/aobious/search?search_query=AOB5070
AbovChem LLC	HY-101438A	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-101438A
Alfa Chemistry	ACM139340560	http://www.alfa-chemistry.com/search.aspx?q=ACM139340560
Angene	AGN-PC-0PO0N2	http://www.angenechemical.com/productshow/AGN-PC-0PO0N2.html
AsisChem	P04687	https://asischem.com/catalogsearch/result/?q=P04687
BOC Sciences	139226-28-1	http://www.bocsci.com/description.asp?cas=139226-28-1
BOC Sciences	139340-56-0	http://www.bocsci.com/description.asp?cas=139340-56-0
BioSynth	J-501626	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501626
Chem Scene	CS-0021331	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0021331
MolPort	MolPort-035-681-321	https://www.molport.com/shop/molecule-link/MolPort-035-681-321
MuseChem	I006382	https://www.musechem.com/product/I006382.html
MuseChem	M116908	https://www.musechem.com/product/M116908.html
ShangHai Biochempartner	BCP09753	http://www.biochempartner.com/search_BCP09753
ShangHai Biochempartner	BCP23976	http://www.biochempartner.com/search_BCP23976
eMolecules	275088870	https://orderbb.emolecules.com/search/#?query=275088870
eMolecules	45820085	https://orderbb.emolecules.com/search/#?query=45820085
eMolecules	49260268	https://orderbb.emolecules.com/search/#?query=49260268
eMolecules	68831866	https://orderbb.emolecules.com/search/#?query=68831866
mcule	MCULE-2117997566	https://mcule.com/MCULE-2117997566/
mcule	MCULE-7722973115	https://mcule.com/MCULE-7722973115/
mcule	MCULE-8203564467	https://mcule.com/MCULE-8203564467/

PubMed

Title	Date	PubMed
Synthesis and biological evaluation of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors.	2010 Dec 15	21055929
Dual inhibition of COX-2/5-LOX blocks colon cancer proliferation, migration and invasion in vitro.	2016 Mar	26707712

Patents

Sample Use Guides

In Vivo Use Guide

Mice were administered Darbufelone by gavage at doses of 20, 40, and 80 mg/kg/day. When mice are treated with Darbufelone at dosage of 80 mg/kg/day, the tumor volumes decrease in a time-dependent manner. In contrast, lower dose of Darbufelone (20 or 40 mg/kg/day) dos not show any significant inhibition of tumor weight.

Route of Administration: Oral

In Vitro Use Guide

In cyclooxygenase assays following a 15-min incubation of enzyme with inhibitor, darbufelone potently inhibits PGHS-2 (IC(50) = 0.19 uM) but is much less potent with PGHS-1 (IC(50) = 20 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:28:11 GMT 2023` Edited by `admin` on `Fri Dec 15 16:28:11 GMT 2023`
Record UNII	5I2Y40C5PX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DARBUFELONE MESYLATE

Official Name

English

DARBUFELONE MESILATE

Common Name

English

5-[(Z)-3,5-Di-tert-butyl-4-hydroxybenzylidene]-2-imino-4-thiazolidinone monomethanesulfonate (salt)

Common Name

English

(Z)-2-AMINO-5-((3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXYPHENYL)METHYLENE)-4(5H)-THIAZOLONE MONOMETHANESULPHONATE (SALT)

Common Name

English

DARBUFELONE MESYLATE [USAN]

Common Name

English

(Z)-2-AMINO-5-((3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXYPHENYL)METHYLENE)-4(5H)-THIAZOLONE MONOMETHANESULFONATE (SALT)

Common Name

English

5-((Z)-3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENE)-2-IMINO-4-THIAZOLIDINONE MONOMETHANESULPHONATE (SALT)

Common Name

English

CI-1004

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1323