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

Details

Stereochemistry ACHIRAL
Molecular Formula C23H16O6
Molecular Weight 388.3695
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PAMOIC ACID

SMILES

OC(=O)C1=CC2=C(C=CC=C2)C(CC3=C4C=CC=CC4=CC(C(O)=O)=C3O)=C1O

InChI

InChIKey=WLJNZVDCPSBLRP-UHFFFAOYSA-N
InChI=1S/C23H16O6/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h1-10,24-25H,11H2,(H,26,27)(H,28,29)

HIDE SMILES / InChI

Molecular Formula C23H16O6
Molecular Weight 388.3695
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/27064272 | https://www.ncbi.nlm.nih.gov/pubmed/20580560

Pamoic acid, also called embonic acid, is a naphthoic acid derivative, used as a counter ion of a drug compound to increase the solubility of the drug in water. Pamoic acid has agonist activity for the orphan G protein-coupled receptor GPR35 by which it activates ERK and beta-arrestin2, and causes antinociceptive activity. Although (like other drug salts) it has been considered an inactive compound by the FDA.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
79.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A phase II trial with new triptorelin sustained release formulations in prostatic carcinoma.
2001
Pharmacokinetic disposition and faecal excretion of pyrantel embonate following oral administration in horses.
2001 Feb
Chemotherapy of enterobiasis (oxyuriasis).
2001 Feb
Continuance of studies on Population S benzimidazole-resistant small strongyles in a Shetland pony herd in Kentucky: effect of pyrantel pamoate (1992-1999).
2001 Jan 20
Hepatobiliary and pancreatic ascariasis.
2001 Mar
Vitamin B12 and folic acid in children with intestinal parasitic infection.
2002 Apr
Ziprasidone and migraine headache.
2002 Aug
Effects of imipramine on ion channels and proliferation of IGR1 melanoma cells.
2002 Jul 15
Strongyloides stercoralis infection with bloody pericardial effusion in a non-immunosuppressed patient.
2002 Jun
Immediate hypersensitivity reaction associated with the rapid infusion of Crotalidae polyvalent immune Fab (ovine).
2002 Jun
Synergistic effects of pyrantel and the febantel metabolite fenbendazole on adult Toxocara canis.
2003 Jul
Anthelmintic treatment in horses: the extra-label use of products and the danger of under-dosing.
2003 Jun
A modified critical test for the efficacy of pyrantel pamoate for Anoplocephala perfoliata in equids.
2004 Apr
Schistosomiasis and soil-transmitted helminthiasis: common drugs for treatment and control.
2004 Feb
Common intestinal parasites.
2004 Mar 1
Necator americanus: optimization of the golden hamster model for testing anthelmintic drugs.
2005 Dec
Management of biliary ascariasis in pregnancy.
2005 Oct
Cyathostomes in horses in Canada resistant to pyrantel salts and effectively removed by moxidectin.
2006 Aug 31
Strongyle egg shedding consistency in horses on farms using selective therapy in Denmark.
2006 Feb 18
Coprological study on intestinal helminths in Swiss dogs: temporal aspects of anthelminthic treatment.
2006 Mar
Comparison of various anthelmintic therapies for the treatment of Trypanoxyuris microon infection in owl monkeys (Aotus nancymae).
2007 Apr
Field evaluation of the efficacy and the safety of a combination of oxantel/pyrantel/praziquantel in the treatment of naturally acquired gastrointestinal nematode and/or cestode infestations in dogs in Europe.
2007 Apr 10
Occurrence of anthelmintic resistant equine cyathostome populations in central and southern Italy.
2007 Dec 14
Revalidation and rationale for high pKa values of unconjugated bilirubin.
2007 May 2
Upcoming agents for the treatment of schizophrenia: mechanism of action, efficacy and tolerability.
2008
Anthelmintic prescribing patterns of a sample of general practitioners from selected areas in the colombo district of sri lanka.
2008 Apr
Influence of Bi 58 Nowy (38% dimethoate) on pyrantel embonate concentration in the liver of rats.
2009
The old and new therapeutic approaches to the treatment of giardiasis: where are we?
2009
Olanzapine pamoate - blockbuster or damp squib?
2009 Apr
Field effectiveness of pyrantel and failure of Parascaris equorum egg count reduction following ivermectin treatment in Italian horse farms.
2009 Apr 6
Synergistic effect of febantel and pyrantel embonate in elimination of Giardia in a gerbil model.
2009 Aug
Treatment of naturally occurring, asymptomatic Giardia sp. in dogs with Drontal Plus flavour tablets.
2009 Aug
Fixed drug eruption resulting from fluconazole use: a case report.
2009 Jul 6
Comparison of treatment completion rates for olanzapine pamoate and risperidone microspheres.
2009 Jun
Second-generation antipsychotic long-acting injections: systematic review.
2009 Nov
Patient perspectives in the development and use of long-acting antipsychotics in schizophrenia: focus on olanzapine long-acting injection.
2009 Nov 29
The control of hookworm infection in China.
2009 Sep 24
Diagnosis and control of anthelmintic-resistant Parascaris equorum.
2009 Sep 25
Anthelmintic resistance in cyathostomin populations from horse yards in Italy, United Kingdom and Germany.
2009 Sep 25
Patents

Sample Use Guides

Abdominal Constriction Test in Mice were used for Pamoic acid activity evaluation. Four groups of 10 male, Swiss-Webster mice (30–35 g; Ace Animals, Inc., Boyertown, PA) were used. They were then injected with saline or one of three doses of pamoic acid disodium (25, 50, and 100 mg/kg s.c.). Twenty minutes later, each mouse was challenged with 0.6% acetic acid (0.30 ml/30 g animal i.p.) and, after an additional 5 min, was observed over the subsequent 10 min for abdominal writhing behavior.
Route of Administration: Other
U2OS cells transiently expressing human GPR35b and _arr2-GFP or HEK 293 cells transiently expressing mouse GPR35 and beta arr2-GFP were used 48 h after transfection. U2OS cells permanently expressing HA-GPR35a and _arr2-GFP (UGPR35_) were used for most experiments. Cells were plated onto coverslips, placed in 24-well plates, and pretreated for 1 h with 0.02 mg/ml poly-Dlysine. Cells were maintained at 37°C in 5% CO2 until ready for experiments (80–85% confluent) and washed once with HBSS before drug application and experiments were performed in HBSS. Agonist stimulated redistribution of _arr2-GFP was assessed after drug treatment for 40 min. Experiments involving antagonist were done with 15 min preincubation of antagonist for both the stable UGPR35 cells and the transiently transfected mouse GPR35 HEK293 cells. To examine reversibility of the antagonist, cells were preincubated with 100 nM CID2745687 for 10 min, then washed with HBSS five times for 5 min each before adding 1 mkM pamoic acid. Cells were then fixed with 4% paraformaldehyde for 20 min at room temperature followed by three washes with HBSS.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:13:16 GMT 2023
Edited
by admin
on Sat Dec 16 05:13:16 GMT 2023
Record UNII
7RRQ8QZ38N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PAMOIC ACID
MI   USP-RS   WHO-DD  
Common Name English
Pamoic acid [WHO-DD]
Common Name English
4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLIC ACID)
Systematic Name English
4,4'-METHYLENEDI(3-HYDROXY-2-NAPHTHOIC ACID)
Systematic Name English
PAMOIC ACID [MI]
Common Name English
PYRANTEL EMBONATE RELATED COMPOUND PAMOIC ACID [USP IMPURITY]
Common Name English
PAMOIC ACID [USP-RS]
Common Name English
NSC-30188
Code English
EMBONIC ACID
Common Name English
Code System Code Type Description
MERCK INDEX
m8376
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1493000
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
SMS_ID
100000079735
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
WIKIPEDIA
PAMOIC ACID
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
FDA UNII
7RRQ8QZ38N
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
NSC
30188
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
EVMPD
SUB14746MIG
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
PUBCHEM
8546
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
CHEBI
50186
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID9048984
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
CAS
130-85-8
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-998-0
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
MESH
C004368
Created by admin on Sat Dec 16 05:13:18 GMT 2023 , Edited by admin on Sat Dec 16 05:13:18 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
NO peak value listed in USP-NF
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP