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^Y
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	901319
ChEBI	CHEBI:50186
ChEMBL	ChEMBL177880^Y
ChemSpider	8228^Y
ECHA InfoCard	100.004.545
EC Number	204-998-0
IUPHAR/BPS	2920
MeSH	Pamoic+acid
PubChem	8546
RTECS number	QL2180000
UNII	7RRQ8QZ38N^Y
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)^Y Key: WLJNZVDCPSBLRP-UHFFFAOYSA-N^Y
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	388.38 g·mol⁻¹
Melting point	≥300 °C
log P	6.169
Acidity (pK_a)	2.675
Hazards
Main hazards	Causes skin irritation Causes serious eye irritation May cause respiratory irritation
EU classification (DSD)	Xi
R-phrases	R36/37/38
S-phrases	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 counter ion of a drug compound to increase the solubility of the drug in water.^[2] The presence of multiple oxygen atoms enables significant hydrogen bonding to occur. Hydrogen bonds facilitate the dissolution of compounds 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.^[3]^[4] Although (like other drug salts) it has been considered an inactive compound by the FDA, these recent data suggest that its permitted uses may need to be reexamined.

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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