Aminohippuric acid

Aminohippurate
Clinical data
Other names	PAH, PAHA, Aminohippurate, 4-Aminohippuric acid , N-(4-Aminobenzoyl)glycine, para-Aminohippurate
ATC code	V04CH30 (WHO) ;
Identifiers
	IUPAC name (4-Aminobenzamido)acetic acid;
CAS Number	61-78-9 ; 94-16-6 (sodium salt);
PubChem CID	2148;
IUPHAR/BPS	4810;
DrugBank	DB00345 ;
ChemSpider	2063 ;
UNII	Y79XT83BJ9;
KEGG	D06890 ;
ChEBI	CHEBI:104011 ;
ChEMBL	ChEMBL463 ;
NIAID ChemDB	019143;
CompTox Dashboard (EPA)	DTXSID7022590 ;
ECHA InfoCard	100.000.472
Chemical and physical data
Formula	C9H10N2O3
Molar mass	194.190 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1ccc(N)cc1)NCC(=O)O;
	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) ; Key:HSMNQINEKMPTIC-UHFFFAOYSA-N ;
	(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 that is not naturally found in humans; it needs to be IV infused before diagnostic use.

Uses

Diagnostics

PAH is useful for the measurement of renal plasma flow.[1]

The renal extraction ratio of PAH in a normal individual is approximately 0.92.[2] This means that unlike inulin and creatinine, which are filtered in the glomerulus and ignored by the rest of the kidney, aminohippuric acid is both filtered and secreted, being almost entirely removed from the bloodstream in a normal kidney.

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.[3]

Other

pK_a = 3.83

References

Costanzo L (2007). Physiology (4th ed.). Philadelphia: Lippincott Williams and Wilkins. pp. 156–160.
Reubi FC (September 1953). "Glomerular filtration rate, renal blood flow and blood viscosity during and after diabetic coma". Circulation Research. 1 (5): 410–3. doi:10.1161/01.res.1.5.410. PMID 13082682.
Beyer KH, Flippin H, Verwey WF, Woodward R (1944-12-16). "The effect of para-aminohippuric acid on plasma concentration of penicillin in man". Journal of the American Medical Association. 126 (16): 1007–1009. doi:10.1001/jama.1944.02850510015003.

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[1] Costanzo L (2007). Physiology (4th ed.). Philadelphia: Lippincott Williams and Wilkins. pp. 156–160.

[pmid13082682-2] Reubi FC (September 1953). "Glomerular filtration rate, renal blood flow and blood viscosity during and after diabetic coma". Circulation Research. 1 (5): 410–3. doi:10.1161/01.res.1.5.410. PMID 13082682.

[3] Beyer KH, Flippin H, Verwey WF, Woodward R (1944-12-16). "The effect of para-aminohippuric acid on plasma concentration of penicillin in man". Journal of the American Medical Association. 126 (16): 1007–1009. doi:10.1001/jama.1944.02850510015003.