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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

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
Electron and video-light microscopy analysis of the in vitro effects of pyrantel pamoate on Giardia lamblia.
2001 Jan
Resistance against migrating ascaris suum larvae in pigs immunized with infective eggs or adult worm antigens.
2001 Jun
Hepatobiliary and pancreatic ascariasis.
2001 Mar
Vitamin B12 and folic acid in children with intestinal parasitic infection.
2002 Apr
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
Expulsion of small strongyle nematodes (cyathostomin spp) following deworming of horses on a stud farm in Sweden.
2003 Aug 14
Growth of Enterobius vermicularis in a chimpanzee after anthelmintic treatment.
2003 Jun
Management of drug-resistant cyathostominosis on a breeding farm in central North Carolina.
2003 May
A modified critical test for the efficacy of pyrantel pamoate for Anoplocephala perfoliata in equids.
2004 Apr
Benzimidazole resistance in cyathostomin populations on horse farms in western Anatolia, Turkey.
2004 Aug
Presence of immunoglobulins and antigens in serum, lung and small intestine in Ascaris suum infected and immunised pigs.
2004 Jan 5
Common intestinal parasites.
2004 Mar 1
Identification of small molecule synthetic inhibitors of DNA polymerase beta by NMR chemical shift mapping.
2004 Sep 17
Poor efficacy of the most commonly used anthelmintics in sport horse nematodes in Morocco in relation to resistance.
2005 Dec
Reversal of a full-length mutant huntingtin neuronal cell phenotype by chemical inhibitors of polyglutamine-mediated aggregation.
2005 Jan 13
Field studies on endoparasites of Thoroughbred foals on seven farms in central Kentucky in 2004.
2006 Apr
[A case of drug eruption induced by hydroxyzine pamoate].
2006 Jan
The impact of concurrent and treated Ancylostoma ceylanicum hookworm infections on the immunogenicity of a recombinant hookworm vaccine in hamsters.
2006 Jan 1
Coprological study on intestinal helminths in Swiss dogs: temporal aspects of anthelminthic treatment.
2006 Mar
High transmission rates restore expression of genetically determined susceptibility of mice to nematode infections.
2006 May
Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35.
2006 Sep 18
Comparison of various anthelmintic therapies for the treatment of Trypanoxyuris microon infection in owl monkeys (Aotus nancymae).
2007 Apr
Pyrvinium targets the unfolded protein response to hypoglycemia and its anti-tumor activity is enhanced by combination therapy.
2008
Anthelmintic prescribing patterns of a sample of general practitioners from selected areas in the colombo district of sri lanka.
2008 Apr
Structural insights on the pamoic acid and the 8 kDa domain of DNA polymerase beta complex: towards the design of higher-affinity inhibitors.
2008 Apr 16
Micromolar concentration of kynurenic acid in rat small intestine.
2008 Aug
Highly pathogenic avian influenza virus (H5N1) infection in red foxes fed infected bird carcasses.
2008 Dec
Evaluation of parasiticidal activity of fenbendazole, ivermectin, oxibendazole, and pyrantel pamoate in horse foals with emphasis on ascarids (Parascaris equorum) in field studies on five farms in Central Kentucky in 2007.
2008 Jul
Field studies indicating reduced activity of ivermectin on small strongyles in horses on a farm in Central Kentucky.
2008 Jun
Controlling soil-transmitted helminthiasis in pre-school-age children through preventive chemotherapy.
2008 Mar 26
Education and imaging. Gastrointestinal: ascariasis.
2008 Nov
Gateways to clinical trials.
2008 Oct
Influence of Bi 58 Nowy (38% dimethoate) on pyrantel embonate concentration in the liver of rats.
2009
Olanzapine pamoate - blockbuster or damp squib?
2009 Apr
Ascariasis-associated worm encephalopathy in a young child.
2009 Apr
Field effectiveness of pyrantel and failure of Parascaris equorum egg count reduction following ivermectin treatment in Italian horse farms.
2009 Apr 6
Treatment of naturally occurring, asymptomatic Giardia sp. in dogs with Drontal Plus flavour tablets.
2009 Aug
Density-dependent effects on the weight of female Ascaris lumbricoides infections of humans and its impact on patterns of egg production.
2009 Feb 10
Olanzapine pamoate: a stick in time? A review of the efficacy and safety profile of a new depot formulation of a second-generation antipsychotic.
2009 Jan
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.
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
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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
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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
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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
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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