Aminohippuric acid

Chemical compound
  • V04CH30 (WHO)
Identifiers
  • (4-Aminobenzamido)acetic acid
CAS Number
  • 61-78-9 checkY
    94-16-6 (sodium salt)
PubChem CID
  • 2148
IUPHAR/BPS
  • 4810
DrugBank
  • DB00345 checkY
ChemSpider
  • 2063 checkY
UNII
  • Y79XT83BJ9
KEGG
  • D06890 checkY
ChEBI
  • CHEBI:104011 checkY
ChEMBL
  • ChEMBL463 checkY
NIAID ChemDB
  • 019143
CompTox Dashboard (EPA)
  • DTXSID7022590 Edit this at Wikidata
ECHA InfoCard100.000.472 Edit this at WikidataChemical and physical dataFormulaC9H10N2O3Molar mass194.190 g·mol−13D model (JSmol)
  • Interactive image
  • 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) checkY
  • Key:HSMNQINEKMPTIC-UHFFFAOYSA-N checkY
  (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

pKa = 3.83

See also

References

  1. ^ Costanzo L (2007). Physiology (4th ed.). Philadelphia: Lippincott Williams and Wilkins. pp. 156–160.
  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.
  • v
  • t
  • e
Creating urine
Secretion
Reabsorption
Filtration
Other functions
Hormones
Fluid balance
Acid–base balance
Assessment and measurement
Other