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Details

Stereochemistry ACHIRAL
Molecular Formula C22H20ClN2O4S.Na
Molecular Weight 466.913
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VERCIRNON SODIUM

SMILES

[Na+].CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)[N-]C2=C(C=C(Cl)C=C2)C(=O)C3=CC=[N+]([O-])C=C3

InChI

InChIKey=RWWYDQSZJIFTES-UHFFFAOYSA-M
InChI=1S/C22H21ClN2O4S.Na/c1-22(2,3)16-4-7-18(8-5-16)30(28,29)24-20-9-6-17(23)14-19(20)21(26)15-10-12-25(27)13-11-15;/h4-14H,1-3H3,(H,24,26);/q;+1/p-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 C22H21ClN2O4S
Molecular Weight 444.931
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27926729 | https://www.ncbi.nlm.nih.gov/pubmed/20660125 | https://www.ncbi.nlm.nih.gov/pubmed/20582872

Vercirnon (GSK-1605786, CCX-282, nTraficet-EN) is a selective, and potent antagonist of human CCR9. Vercirnon binds to the intracellular side of the receptor, exerting allosteric antagonism and preventing G-protein coupling. CCR9 is a tissue-specific lymphocyte trafficking molecule that selectively attracts both B- and T-cells to the small gut. Inhibition of CCR9 by GSK-1605786 may inhibit B- and T-cell entry to the small gut and ameliorate inflammation while leaving immune function at other anatomical sites unaffected. Vercirnon is an orally bioavailable, anti-inflammatory agent that is being developed by ChemoCentryx for treatment of inflammatory bowel disease with an initial focus in Crohn's disease. A pivotal phase III programme of vercirnon was initiated in patients with moderate-to-severe Crohn's disease, however, the programme was suspended when the first pivotal trial failed to meet its primary endpoint. Phase II trials for ulcerative colitis and celiac disease were conducted, however investigations for ulcerative colitis were suspended while no further development has been reported for celiac disease.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
993.4 ng/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VERCIRNON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14929 ng × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VERCIRNON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16.3 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VERCIRNON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

phase III trial for the treatment of Crohn's disease dosage is 500mg once-daily or twice-daily (NCT01277666)
Route of Administration: Oral
Vercirnon (CCX282-B) inhibited CCR9-mediated Ca(2+) mobilization and chemotaxis on Molt-4 cells with IC(50) values of 5.4 and 3.4 nM, respectively. In the presence of 100% human serum, CCX282-B inhibited CCR9-mediated chemotaxis with an IC(50) of 33 nM, and the addition of α1-acid glycoprotein did not affect its potency. CCX282-B inhibited chemotaxis of primary CCR9-expressing cells to CCL25 with an IC(50) of 6.8 nM. CCX282-B was an equipotent inhibitor of CCL25-directed chemotaxis of both splice forms of CCR9 (CCR9A and CCR9B) with IC(50) values of 2.8 and 2.6 nM, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:34:28 GMT 2023
Edited
by admin
on Fri Dec 15 15:34:28 GMT 2023
Record UNII
9NQF0M8R0M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VERCIRNON SODIUM
USAN  
USAN  
Official Name English
GSK1605786A
Code English
Vercirnon sodium [WHO-DD]
Common Name English
GSK-1605786A
Code English
VERCIRNON SODIUM [USAN]
Common Name English
BENZENESULFONAMIDE, N-(4-CHLORO-2-((1-OXIDO-4-PYRIDINYL)CARBONYL)PHENYL)-4-(1,1-DIMETHYLETHYL)-, SODIUM SALT (1:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C63817
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
Code System Code Type Description
EVMPD
SUB180521
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
PRIMARY
USAN
YY-94
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL2178578
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
PRIMARY
PUBCHEM
140650927
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
PRIMARY
SMS_ID
100000166361
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
PRIMARY
CAS
886214-18-2
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
PRIMARY
NCI_THESAURUS
C152859
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
PRIMARY
FDA UNII
9NQF0M8R0M
Created by admin on Fri Dec 15 15:34:28 GMT 2023 , Edited by admin on Fri Dec 15 15:34:28 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY