U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C21H19NO3S
Molecular Weight 365.445
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OTENAPROXESUL, (±)-

SMILES

COC1=CC2=CC=C(C=C2C=C1)C(C)C(=O)OC3=CC=C(C=C3)C(N)=S

InChI

InChIKey=YCNMAPLPQYQJFC-UHFFFAOYSA-N
InChI=1S/C21H19NO3S/c1-13(21(23)25-18-8-5-14(6-9-18)20(22)26)15-3-4-17-12-19(24-2)10-7-16(17)11-15/h3-13H,1-2H3,(H2,22,26)

HIDE SMILES / InChI

Molecular Formula C21H19NO3S
Molecular Weight 365.445
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800040845 https://www.ncbi.nlm.nih.gov/pubmed/27777130

ATB-346, being developed by Antibe Therapeutics, a Toronto-based pharmaceutical company, is a hydrogen sulfide-releasing non-steroidal anti-inflammatory drug (NSAID) that inhibits COX and suppresses prostaglandin production. ATB-346 exhibits anti-inflammatory, analgesic, antinociceptive, immunomodulatory, and neuroprotective activities. In vivo, this compound attenuates zymosan-induced inflammation, nociception, and immune signaling. ATB-346 also prevents ligature-induced periodontal bone loss and pathologies, potentially by suppressing increases in pro-inflammatory cytokine levels. Additionally, ATB-346 decreases edema and improves neurological function in animal models of traumatic brain injury (TBI). ATB-346 completed Phase 1 clinical studies in Q1 2015. To better understand the metabolism of ATB-346, Antibe conducted a radiolabeled study in rats at Covance Laboratories that was completed in Q4 2015. Antibe received approval from Health Canada in March 2016 to conduct a Phase 2 trial of ATB-346 in patients with osteoarthritis of the knee. Preclinical studies of ATB-346 for the treatment intestinal cancer; malignant melanoma; periodontal disorders are in progress.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

250 mg once daily
Route of Administration: Oral
Incubation of A375 cells with ATB-346 (100 uM) for 24, 48 or 72 h caused an inhibition of cell proliferation by 38.2%, 63.2% and 66%, respectively
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:04:50 GMT 2023
Edited
by admin
on Sat Dec 16 10:04:50 GMT 2023
Record UNII
3096O7WP53
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OTENAPROXESUL, (±)-
Common Name English
ATB-346
Preferred Name English
2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, 4-(AMINOTHIOXOMETHYL)PHENYL ESTER
Systematic Name English
Code System Code Type Description
DRUG BANK
DB15377
Created by admin on Sat Dec 16 10:04:50 GMT 2023 , Edited by admin on Sat Dec 16 10:04:50 GMT 2023
PRIMARY
CAS
1226895-20-0
Created by admin on Sat Dec 16 10:04:50 GMT 2023 , Edited by admin on Sat Dec 16 10:04:50 GMT 2023
PRIMARY
SMS_ID
300000010321
Created by admin on Sat Dec 16 10:04:50 GMT 2023 , Edited by admin on Sat Dec 16 10:04:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID201336751
Created by admin on Sat Dec 16 10:04:50 GMT 2023 , Edited by admin on Sat Dec 16 10:04:50 GMT 2023
PRIMARY
FDA UNII
3096O7WP53
Created by admin on Sat Dec 16 10:04:50 GMT 2023 , Edited by admin on Sat Dec 16 10:04:50 GMT 2023
PRIMARY
PUBCHEM
25065981
Created by admin on Sat Dec 16 10:04:50 GMT 2023 , Edited by admin on Sat Dec 16 10:04:50 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY