Aminohippuric acid

Aminohippurate

Systematic (IUPAC) name
2-[(4-Aminobenzoyl)amino]acetic acid
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	61-78-9 94-16-6 (sodium salt)
ATC code	V04CH30
PubChem	CID 2148
DrugBank	DB00345
ChemSpider	2063 Y
UNII	Y79XT83BJ9 Y
KEGG	D06890 Y
ChEBI	CHEBI:104011 Y
ChEMBL	CHEMBL463 Y
Synonyms	PAH, PAHA, Aminohippurate, 4-Aminohippuric acid , N-(4-Aminobenzoyl)glycine, para-Aminohippurate
Chemical data
Formula	C9H10N2O3
Mol. mass	194.19 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13) Y Key:HSMNQINEKMPTIC-UHFFFAOYSA-N Y
Y(what is this?)  acid (verify)

Aminohippuric acid or para-aminohippuric acid (PAH), a derivative of hippuric acid, is a diagnostic agent useful in medical tests involving the kidney used in the measurement of renal plasma flow. It is an amide derivative of the amino acid glycine and para-aminobenzoic acid.

Uses

Diagnostics

PAH is useful for the measurement of renal plasma flow because it is secreted primarily by the renal tubules; only 20-30% is filtered by the glomerulus.^[1] PAH is completely filtered from plasma in the nephron and not reabsorbed by the tubules, in a manner identical to inulin. PAH differs from inulin in that the fraction of PAH that bypasses the glomerulus and enters the nephron's tubular cells (via the peritubular capillaries) is completely secreted. Thus, renal clearance of PAH is useful in calculation of renal plasma flow (RPF), which empirically is (1 − hematocrit) × renal blood flow. Of note, the clearance of PAH is reflective only of RPF to portions of the kidney that deal with urine formation, and thus underestimates actual RPF by about 10%.^[2]

The renal extraction ratio of PAH in a normal individual is approximately 0.92.^[3]

Pharmaceuticals

Aminohippuric acid is often used as the sodium salt sodium para-aminohippurate. During World War II, para-aminohippurate was given along with penicillin in order to prolong the time penicillin circulated in the blood. Because both penicillin and para-aminohippurate compete for the same transporter in the kidney, administering para-aminohippurate with penicillin decreased the clearance of penicillin from the body by the kidney, providing better antibacterial therapy. Transporters found in the kidney eliminate organic anions and cations from the blood by moving substances, in this case, drug metabolites, from blood into urine.

Other

In vultures, the NSAID diclofenac, which is extraordinarily toxic to vultures, interferes with the renal transport of uric acid via the PAH channel.^[4]

pKa = 3.83

See also

• PAH clearance

References

1. ^ Phillips, R. A.; P. B. Hamilton (1948-02-29). "Effect of 20,60 and 120 minutes of renal ischemia on glomerular and tubular function" (PDF). Am J Physiol 152 (3): 523–30. ISSN 0002-9513. PMID 18863150. http://ajplegacy.physiology.org/cgi/content/citation/152/3/523. Retrieved 2008-03-20. 
2. ^ Costanzo, Linda. Physiology, 4th Edition. Philadelphia: Lippincott Williams and Wilkins, 2007. Page 156-160.
3. ^ Reubi, François C. (1953-04-29). "Glomerular filtration rate, renal blood flow and blood viscosity during and after diabetic coma". Circ. Res. 1 (5): 410–3. ISSN 00097330. PMID 13082682. http://circres.ahajournals.org/cgi/content/abstract/1/5/410. Retrieved 2008-03-19. 
4. ^ Naidoo V, Swan GE (August 2008). "Diclofenac toxicity in Gyps vulture is associated with decreased uric acid excretion and not renal portal vasoconstriction". Comp. Biochem. Physiol. C Toxicol. Pharmacol. 149 (3): 269–74. doi:10.1016/j.cbpc.2008.07.014. PMID 18727958.