NAVARIXIN ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H26N2O5
Molecular Weight	410.4629
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC[C@@H](NC1=C(CC2=C(O)C(=CC=C2)C(=O)N(C)C)C(=O)C1=O)C3=CC=C(C)O3

InChI

InChIKey=IXBYSXNOKFHHDR-QGZVFWFLSA-N

InChI=1S/C23H26N2O5/c1-5-7-17(18-11-10-13(2)30-18)24-19-16(21(27)22(19)28)12-14-8-6-9-15(20(14)26)23(29)25(3)4/h6,8-11,17,24,26H,5,7,12H2,1-4H3/t17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H26N2O5
Molecular Weight	410.4629
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800022619 | https://www.ncbi.nlm.nih.gov/pubmed/17181143 | https://www.ncbi.nlm.nih.gov/pubmed/17496166

Merck & Co. and Ligand Pharmaceuticals are collaborating in the development of navarixin, an oral CXCR2/CXCR1 antagonist, for the treatment of solid tumours. Navarixin is a potent, allosteric antagonist of both CXCR1 and CXCR2, with Kd values of 41 nM for cynomolgus CXCR1 and 0.20 nM, 0.20 nM, 0.08 nM for mouse, rat and cynomolgus monkey CXCR2, respectivelly. Navarixin has also been investigated for the treatment of asthma, chronic obstructive pulmonary disease, psoriasis, but this research has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Interleukin-8 receptor B 8 Target ID: CHEMBL2434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17496166	Antagonist 2778		0.97 nM [IC50]
Interleukin-8 receptor A 4 Target ID: CHEMBL4029 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17496166	Antagonist 2778		43.0 nM [IC50]

PubMed

Title	Date	PubMed
Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5- methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123): a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist.	2006 Dec 28	17181143
Future therapeutic treatment of COPD: struggle between oxidants and cytokines.	2007	18229560
Pharmacological characterization of Sch527123, a potent allosteric CXCR1/CXCR2 antagonist.	2007 Aug	17496166
International Union of Basic and Clinical Pharmacology. [corrected]. LXXXIX. Update on the extended family of chemokine receptors and introducing a new nomenclature for atypical chemokine receptors.	2014	24218476

Patents

Sample Use Guides

In Vivo Use Guide

Psoriasis: Navarixin 30 mg administered orally once daily for 28 days.

Route of Administration: Oral

In Vitro Use Guide

Navarixin is a potent, allosteric antagonist of both CXCR1 and CXCR2, with Kd values of 41 nM for cynomolgus CXCR1 and 0.20 nM, 0.20 nM, 0.08 nM for mouse, rat and cynomolgus monkey CXCR2, respectivelly.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:47:57 GMT 2023` Edited by `admin` on `Fri Dec 15 19:47:57 GMT 2023`
Record UNII	4GMU5HUX5I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAVARIXIN ANHYDROUS

Common Name

English

BENZAMIDE, 2-HYDROXY-N,N-DIMETHYL-3-((2-(((1R)-1-(5-METHYL-2-FURANYL)PROPYL)AMINO)-3,4-DIOXO-1-CYCLOBUTEN-1-YL)AMINO)-

Systematic Name

English

3-((3-((DIMETHYLAMINO)CARBONYL)-2-HYDROXYPHENYL)AMINO)-4-(((R)-1-(5-METHYLFURAN-2-YL)PROPYL)AMINO)CYCLOBUT-3-ENE-1,2-DIONE

Systematic Name

English

navarixin [INN]

Common Name

English

2-HYDROXY-N,N-DIMETHYL-3-((2-(((1R)-1-(5-METHYLFURAN-2-YL)PROPYL)AMINO)-3,4-DIOXOCYCLOBUT-1-EN-1-YL)AMINO)BENZAMIDE

Systematic Name

English

SCH527123

Code

English

Navarixin [WHO-DD]

Common Name

English

MK7123

Code

English

SCH-527123

Code

English

MK-7123

Code

English

Code System Code Type Description

FDA UNII

4GMU5HUX5I