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Details

Stereochemistry ACHIRAL
Molecular Formula C23H16O6
Molecular Weight 388.3704
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PAMOIC ACID

SMILES

c1ccc2c(c1)cc(c(c2Cc3c4ccccc4cc(c3O)C(=O)O)O)C(=O)O

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 388.3704
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
Poor efficacy of the most commonly used anthelmintics in sport horse nematodes in Morocco in relation to resistance.
2005 Dec
Necator americanus: optimization of the golden hamster model for testing anthelmintic drugs.
2005 Dec
Assessment of frequency, transmission, and genitourinary complications of enterobiasis (pinworms).
2005 Oct
Target animal safety and tolerance study of pyrantel pamoate paste (19.13% w/w pyrantel base) administered orally to horses.
2005 Winter
Heart failure caused by hookworm infection possibly associated with organic food consumption.
2006
Residues of dimethoate in the liver and AchE activity in blood of rats after exposure to dimethoate, and dimethoate and pyrantel embonate.
2006
Field studies on endoparasites of Thoroughbred foals on seven farms in central Kentucky in 2004.
2006 Apr
Clinical field efficacy and safety of pyrantel pamoate paste (19.13% w/w pyrantel base) against Anoplocephala spp. in naturally infected horses.
2006 Apr 15
Comparative effects of milbemycin oxime-based and febantel-pyrantel embonate-based anthelmintic tablets on Toxocara canis egg shedding in naturally infected pups.
2006 Apr 30
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
[A case of drug eruption induced by hydroxyzine pamoate].
2006 Jan
Pyrantel pamoate resistance in horses receiving daily administration of pyrantel tartrate.
2006 Jan 1
The impact of concurrent and treated Ancylostoma ceylanicum hookworm infections on the immunogenicity of a recombinant hookworm vaccine in hamsters.
2006 Jan 1
Dose-confirmation studies of the cestocidal activity of pyrantel pamoate paste in horses.
2006 Jun 15
Coprological study on intestinal helminths in Swiss dogs: temporal aspects of anthelminthic treatment.
2006 Mar
Pinning down pinworms.
2006 May
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
Macrocyclic lactone-resistant Parascaris equorum on stud farms in Canada and effectiveness of fenbendazole and pyrantel pamoate.
2007 Apr 30
Study (1991 to 2001) of drug-resistant Population B small strongyles in critical tests in horses in Kentucky at the termination of a 40-year investigation.
2007 Aug
Chitotriosidase deficiency is not associated with human hookworm infection in a Papua New Guinean population.
2007 Dec
Occurrence of anthelmintic resistant equine cyathostome populations in central and southern Italy.
2007 Dec 14
Parasite field study in central Kentucky on thoroughbred foals (born in 2004) treated with pyrantel tartrate daily and other parasiticides periodically.
2007 Feb
A field study on the effect of some anthelmintics on cyathostomins of horses in sweden.
2007 Jan
Necrosis avidity of (99m)Tc(CO)3-labeled pamoic acid derivatives: synthesis and preliminary biological evaluation in animal models of necrosis.
2007 Nov-Dec
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
Efficacy of current drugs against soil-transmitted helminth infections: systematic review and meta-analysis.
2008 Apr 23
Micromolar concentration of kynurenic acid in rat small intestine.
2008 Aug
The little-known scenario of anthelmintic resistance in equine cyathostomes in Italy.
2008 Dec
D2 receptor occupancy of olanzapine pamoate depot using positron emission tomography: an open-label study in patients with schizophrenia.
2008 Jan
Efficacy of Drontal Flavour Plus (50 mg praziquantel, 144 mg pyrantel embonate, 150 mg febantel per tablet) against Giardia sp in naturally infected dogs.
2008 Oct
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
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
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
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:48:45 UTC 2021
Edited
by admin
on Sat Jun 26 00:48:45 UTC 2021
Record UNII
7RRQ8QZ38N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PAMOIC ACID
MI   USP-RS   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
PAMOIC ACID [USP-RS]
Common Name English
NSC-30188
Code English
PAMOIC ACID [WHO-DD]
Common Name English
PYRANTEL EMBONATE RELATED COMPOUND PAMOIC ACID [USP]
Common Name English
EMBONIC ACID
Common Name English
Code System Code Type Description
MERCK INDEX
M8376
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
PAMOIC ACID
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY
FDA UNII
7RRQ8QZ38N
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY
USP_CATALOG
1493000
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY USP-RS
EVMPD
SUB14746MIG
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY
PUBCHEM
8546
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY
EPA CompTox
130-85-8
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY
CAS
130-85-8
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-998-0
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY
MESH
C004368
Created by admin on Sat Jun 26 00:48:46 UTC 2021 , Edited by admin on Sat Jun 26 00:48:46 UTC 2021
PRIMARY
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