Pamoic acid

Pamoic acid[1]
Names
	Preferred IUPAC name 4,4'-Methylenebis(3-hydroxynaphthalene-2-carboxylic acid)
	Other names 4,4'-Methylenebis(3-hydroxy-2-naphthoic acid); Embonic acid
Identifiers
CAS Number	130-85-8 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	901319
ChEBI	CHEBI:50186;
ChEMBL	ChEMBL177880 ;
ChemSpider	8228 ;
ECHA InfoCard	100.004.545
EC Number	204-998-0;
IUPHAR/BPS	2920;
MeSH	Pamoic+acid
PubChem CID	8546;
RTECS number	QL2180000;
UNII	7RRQ8QZ38N ;
CompTox Dashboard (EPA)	DTXSID9048984 ;
	InChI 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) Key: WLJNZVDCPSBLRP-UHFFFAOYSA-N ;
	SMILES OC(=O)C1=CC2=CC=CC=C2C(CC2=C(O)C(=CC3=CC=CC=C23)C(O)=O)=C1O; C1=CC=C2C(=C1)C=C(C(=C2CC3=C(C(=CC4=CC=CC=C43)C(=O)O)O)O)C(=O)O;
Properties
Chemical formula	C23H16O6
Molar mass	388.375 g·mol−1
Melting point	≥300 °C
log P	6.169
Acidity (pKa)	2.675
Hazards
Main hazards	Causes skin irritation; Causes serious eye irritation; May cause respiratory irritation
EU classification (DSD) (outdated)	Xi
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26 S36
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Pamoic acid, also called embonic acid, is a naphthoic acid derivative. Salts and esters of pamoic acid are known as pamoates or embonates. It can be prepared by the reaction of 2-hydroxy-3-naphthoic acid with formaldehyde.

In pharmacology, the salt form of pamoic acid (pamoate ion) can be used as a counterion of a drug compound to affect the dissolution rate of the drug.[2] The presence of multiple oxygen atoms enables significant hydrogen bonding to occur. Hydrogen bonds facilitate the dissolution of compounds in water. Pharmaceutical drugs formulated this way include cycloguanil pamoate, hydroxyzine pamoate, imipramine pamoate, olanzapine pamoate hydrate, oxantel pamoate, pyrantel pamoate, and pyrvinium pamoate.

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.[3][4]

References

Merck Index, 12th Edition, 7136.
Saesmaa, T; Tötterman, AM (1990). "Dissolution studies on ampicillin embonate and amoxycillin embonate". Journal of pharmaceutical and biomedical analysis. 8 (1): 61–5. doi:10.1016/0731-7085(90)80007-c. PMID 2102266.
Zhao, P.; Sharir, H.; Kapur, A.; Cowan, A.; Geller, E. B.; Adler, M. W.; Seltzman, H. H.; Reggio, P. H.; et al. (2010). "Targeting of the Orphan Receptor GPR35 by Pamoic Acid: A Potent Activator of Extracellular Signal-Regulated Kinase and -Arrestin2 with Antinociceptive Activity". Molecular Pharmacology. 78 (4): 560–8. doi:10.1124/mol.110.066746. PMC 2981393. PMID 20826425.
Neubig, Richard R (2010). "Mind your salts: when the inactive constituent isn't". Molecular Pharmacology. 78 (4): 558–9. doi:10.1124/mol.110.067645. PMID 20651116.

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[Merck-1] Merck Index, 12th Edition, 7136.

[2] Saesmaa, T; Tötterman, AM (1990). "Dissolution studies on ampicillin embonate and amoxycillin embonate". Journal of pharmaceutical and biomedical analysis. 8 (1): 61–5. doi:10.1016/0731-7085(90)80007-c. PMID 2102266.

[3] Zhao, P.; Sharir, H.; Kapur, A.; Cowan, A.; Geller, E. B.; Adler, M. W.; Seltzman, H. H.; Reggio, P. H.; et al. (2010). "Targeting of the Orphan Receptor GPR35 by Pamoic Acid: A Potent Activator of Extracellular Signal-Regulated Kinase and -Arrestin2 with Antinociceptive Activity". Molecular Pharmacology. 78 (4): 560–8. doi:10.1124/mol.110.066746. PMC 2981393. PMID 20826425.

[4] Neubig, Richard R (2010). "Mind your salts: when the inactive constituent isn't". Molecular Pharmacology. 78 (4): 558–9. doi:10.1124/mol.110.067645. PMID 20651116.