Aminohippuric acid (original) (raw)
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Chemical compound
Aminohippurate
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| 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  Y 94-16-6 (sodium salt) |
| PubChem CID | 2148 |
| IUPHAR/BPS | 4810 |
| DrugBank | DB00345 Y |
| ChemSpider | 2063 Y |
| UNII | Y79XT83BJ9 |
| KEGG | D06890 Y |
| ChEBI | CHEBI:104011 Y |
| ChEMBL | ChEMBL463 Y |
| 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) YKey:HSMNQINEKMPTIC-UHFFFAOYSA-N Y |
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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.
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.
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]
p_K_a = 3.83
- ^ 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.