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Details

Stereochemistry ACHIRAL
Molecular Formula C22H23N3O2S.CH4O3S
Molecular Weight 489.6106
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CJ-13610 MESYLATE

SMILES

Cc1nccn1-c2ccc(cc2)Sc3cccc(c3)C4(CCOCC4)C(=N)O.CS(=O)(=O)O

InChI

InChIKey=WRQQAESBKZTAFL-UHFFFAOYSA-N
InChI=1S/C22H23N3O2S.CH4O3S/c1-16-24-11-12-25(16)18-5-7-19(8-6-18)28-20-4-2-3-17(15-20)22(21(23)26)9-13-27-14-10-22;1-5(2,3)4/h2-8,11-12,15H,9-10,13-14H2,1H3,(H2,23,26);1H3,(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula C22H23N3O2S
Molecular Weight 393.5038
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula CH4O3S
Molecular Weight 96.1068
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

4-(3-((4-(2-Methyl-1H-Imidaz-1-yl)Phenyl)Sulfanyl)Phenyl)Tetrahydro-2H-Pyran-4-Carboxamide, better known as CJ13610, is an orally active inhibitor of 5-lipoxygenase. Originally discovered by deCode Genetics, and later developed by Pfizer, CJ13610 has shown promise in preclinical models for pain. The compound was investigated in phase II clinical trials for asthma and chronic obstructive pulmonary disease; however, these efforts have been discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P09917
Gene ID: 240
Gene Symbol: ALOX5
Target Organism: Homo sapiens (Human)
0.569999999999999951 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Optimization of imidazole 5-lipoxygenase inhibitors and selection and synthesis of a development candidate.
2005 Aug
Comparative protection against liver inflammation and fibrosis by a selective cyclooxygenase-2 inhibitor and a nonredox-type 5-lipoxygenase inhibitor.
2007 Dec
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: the referenced study was conducted in rat
Male Sprague-Dawley rats were induced to inflammatory paw pain by subcutaneous injection of a 0.1 mL 1% suspension of carrageenan in saline. Prophylactic treatment with CJ-13610 (1 h before carrageenan) dose-dependently reversed mechanical hyperalgesia by 38 + 7%, 46 + 3% and 90 + 4% with 1, 10 and 30 mg/kg respectively. The CJ-13610 dose was delivered as a 1 mL oral gavage in a vehicle containing 0.5% methylcellulose and 0.025% Tween-20.
Route of Administration: Oral
Human blood was collected in 10 mL heparinized tubes and pooled and dispensed into 384 well experimental plates. Varying concentrations of CJ13610 were dissolved in DMSO, and 2 micro-L was added to each well. CJ13610 was preincubated with blood at room temperature for 10 minutes, followed by stimulation with 40 micro-M calcium ionophore and 30 micro-M arachidonic acid dissolved in 60% ethanol (intended to stimulate maximum leukotriene production). After 15 minute incubation at 37 deg-C blood was centrifuged and leukotriene levels measured from the supernatant. CJ13610 was found to have an IC50 of 0.57 micro-M against the production of leukotrienes.
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:38:23 UTC 2021
Edited
by admin
on Sat Jun 26 00:38:23 UTC 2021
Record UNII
TJY190LBT9
Record Status Validated (UNII)
Record Version
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Name Type Language
CJ-13610 MESYLATE
Code English
4-(3-(4-(2-METHYLIMIDAZOL-1-YL)PHENYLTHIO))PHENYL-3,4,5,6-TETRAHYDRO-2H-PYRAN-4-CARBOXAMIDE MESYLATE
Common Name English
2H-PYRAN-4-CARBOXAMIDE, TETRAHYDRO-4-(3-((4-(2-METHYL-1H-IMIDAZOL-1-YL)PHENYL)THIO)PHENYL)-, METHANESULFONATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
249296-43-3
Created by admin on Sat Jun 26 00:38:23 UTC 2021 , Edited by admin on Sat Jun 26 00:38:23 UTC 2021
PRIMARY
PUBCHEM
9935274
Created by admin on Sat Jun 26 00:38:23 UTC 2021 , Edited by admin on Sat Jun 26 00:38:23 UTC 2021
PRIMARY
FDA UNII
TJY190LBT9
Created by admin on Sat Jun 26 00:38:23 UTC 2021 , Edited by admin on Sat Jun 26 00:38:23 UTC 2021
PRIMARY
Related Record Type Details
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PARENT -> SALT/SOLVATE