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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

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
Resistance against migrating ascaris suum larvae in pigs immunized with infective eggs or adult worm antigens.
2001 Jun
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
Serum mineral levels in children with intestinal parasitic infection.
2003
Anthelmintic treatment in horses: the extra-label use of products and the danger of under-dosing.
2003 Jun
Population-S benzimidazole- and tetrahydropyrimidine-resistant small strongyles in a pony herd in Kentucky (1977-1999): effects of anthelmintic treatment on the parasites as determined in critical tests.
2003 Nov
Appendiceal enterobius vermicularis infestation associated with right-sided chronic pelvic pain.
2004 Apr-Jun
Studies on the development of taste-masked suspension of chloroquine.
2004 Dec
Schistosomiasis and soil-transmitted helminthiasis: common drugs for treatment and control.
2004 Feb
Presence of immunoglobulins and antigens in serum, lung and small intestine in Ascaris suum infected and immunised pigs.
2004 Jan 5
Adverse drug reactions to anthelmintics.
2004 Mar
Common intestinal parasites.
2004 Mar 1
Management of biliary ascariasis in pregnancy.
2005 Oct
Target animal safety and tolerance study of pyrantel pamoate paste (19.13% w/w pyrantel base) administered orally to horses.
2005 Winter
Cyathostomes in horses in Canada resistant to pyrantel salts and effectively removed by moxidectin.
2006 Aug 31
Pinning down pinworms.
2006 May
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
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
The little-known scenario of anthelmintic resistance in equine cyathostomes in Italy.
2008 Dec
Controlling soil-transmitted helminthiasis in pre-school-age children through preventive chemotherapy.
2008 Mar 26
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
Fixed drug eruption resulting from fluconazole use: a case report.
2009 Jul 6
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 Thu Jul 06 11:00:06 UTC 2023
Edited
by admin
on Thu Jul 06 11:00:06 UTC 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 Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1493000
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
SMS_ID
100000079735
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
WIKIPEDIA
PAMOIC ACID
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
FDA UNII
7RRQ8QZ38N
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
NSC
30188
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
EVMPD
SUB14746MIG
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
PUBCHEM
8546
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
CHEBI
50186
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID9048984
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
CAS
130-85-8
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-998-0
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
MESH
C004368
Created by admin on Thu Jul 06 11:00:08 UTC 2023 , Edited by admin on Thu Jul 06 11:00:08 UTC 2023
PRIMARY
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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