ARHALOFENATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H17ClF3NO4
Molecular Weight	415.791
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NCCOC(=O)[C@H](OC1=CC=CC(=C1)C(F)(F)F)C2=CC=C(Cl)C=C2

InChI

InChIKey=BJBCSGQLZQGGIQ-QGZVFWFLSA-N

InChI=1S/C19H17ClF3NO4/c1-12(25)24-9-10-27-18(26)17(13-5-7-15(20)8-6-13)28-16-4-2-3-14(11-16)19(21,22)23/h2-8,11,17H,9-10H2,1H3,(H,24,25)/t17-/m1/s1

HIDE SMILES / InChI

Description
Sources: http://ard.bmj.com/content/71/Suppl_3/450.3 | https://www.ncbi.nlm.nih.gov/pubmed/19404482

Arhalofenate is a uricosuric drug which lowers serum urate by blocking its reabsorption by the proximal tubules of the kidney. Arhalofenate activity is mediated by inhibition of URAT1, OAT4 and OAT10. Additionally, arhalofenate has been suggested to exert potent anti-inflammatory activity. Arhalofenate has completed Phase 2 and is ready to advance to Phase 3 as a novel potential treatment for gout. The drug was also tested in patients with type 2 diabetes mellitus (phase III study), where it demonstrated its ability to lower glucose level, acting as a selective, partial PPAR-gamma agonist. However, the development of arhalofenate as an anti-diabetic drug was terminated.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Solute carrier family 22 member 12 10 Target ID: Q96S37\|\|\|Q96DT2 Gene ID: 116085.0 Gene Symbol: SLC22A12 Target Organism: Homo sapiens (Human) Sources: http://ard.bmj.com/content/71/Suppl_3/450.3	Inhibitor 8297	92.0 µM [IC50]
Solute carrier family 22 member 11 12 Target ID: Q9NSA0 Gene ID: 55867.0 Gene Symbol: SLC22A11 Target Organism: Homo sapiens (Human) Sources: http://ard.bmj.com/content/71/Suppl_3/450.3	Inhibitor 8297	2.6 µM [IC50]
Solute carrier family 22 member 13 2 Target ID: Q9Y226 Gene ID: 9390.0 Gene Symbol: SLC22A13 Target Organism: Homo sapiens (Human) Sources: http://ard.bmj.com/content/71/Suppl_3/450.3	Inhibitor 8297	53.0 µM [IC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: P37231\|\|\|Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19404482	Partial Agonist 290	12.0 µM [EC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19404482\|https://www.ncbi.nlm.nih.gov/pubmed/19389808\|https://www.ncbi.nlm.nih.gov/pubmed/18815616	Partial Agonist 290

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gout 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26989892	Primary		Phase II 1132	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: https://www.clinicaltrials.gov/ct2/show/NCT00353587	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
140 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27980008	800 mg 1 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARHALOFENATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2960 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27980008	800 mg 1 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARHALOFENATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
50 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27980008	800 mg 1 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARHALOFENATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030	unhealthy, ADULT n = 51 Health Status: unhealthy Condition: gout Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 51 Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030	Disc. AE: Abdominal pain, Headache... AEs leading to discontinuation/dose reduction: Abdominal pain (2%) Headache (2%) Skin rash (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030

AEs

AE	Significance	Dose	Population
Abdominal pain	2% Disc. AE	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030	unhealthy, ADULT n = 51 Health Status: unhealthy Condition: gout Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 51 Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030
Headache	2% Disc. AE	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030	unhealthy, ADULT n = 51 Health Status: unhealthy Condition: gout Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 51 Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030
Skin rash	2% Disc. AE	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030	unhealthy, ADULT n = 51 Health Status: unhealthy Condition: gout Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 51 Sources: https://pubmed.ncbi.nlm.nih.gov/26989892 Page: p.2030

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	26718-25-2	http://www.alfa-chemistry.com/search.aspx?q=26718-25-2
BOC Sciences	26718-25-2
ChemShuttle	139050	https://www.chemshuttle.com/catalogsearch/result/?q=139050
Compound Cloud	12082259
Compound Cloud	33584
Lan Pharmatech	LQT-B04043
Lan Pharmatech	LQT-B14870
MuseChem	I002754	https://www.musechem.com/product/I002754.html
Norris Pharm	NSZB-A235090
Norris Pharm	NSZB-A242660
Tetrahedron	TS69750	http://www.thsci.com/search.do?q=TS69750
eMolecules	50418047	https://orderbb.emolecules.com/search/#?query=50418047
mcule	MCULE-1116084857	https://mcule.com/MCULE-1116084857/

PubMed

Title	Date	PubMed
A Randomized, Double-Blind, Active- and Placebo-Controlled Efficacy and Safety Study of Arhalofenate for Reducing Flare in Patients With Gout.	2016 Aug	26989892

Patents

Sample Use Guides

In Vivo Use Guide

In a clinical trial, patients with gout received 600 mg arhalofenate or 800 mg arhalofenate. In patients with type 2 diabetes mellitus, the dose was 200, 400 or 600 mg given once daily for 16 weeks.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

ARHALOFENATE

Official Name

English

CB-102

Code

English

BENZENEACETIC ACID, 4-CHLORO-.ALPHA.-(3-(TRIFLUOROMETHYL)PHENOXY)-, 2-(ACETYLAMINO)ETHYL ESTER, (-)-

Common Name

English

arhalofenate [INN]

Common Name

English

JNJ-39659100

Code

English

Arhalofenate [WHO-DD]

Common Name

English

ARHALOFENATE [USAN]

Common Name

English

M-102

Code

English

(-)-2-(ACETYLAMINO)ETHYL (2R)-(4-CHLOROPHENYL)(3-(TRIFLUOROMETHYL)PHENOXY)ACETATE

Systematic Name

English

MBX-102

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C921