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Wikipedia

Aminohippuric acid

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.

Aminohippurate
Clinical data
Other namesPAH, PAHA, Aminohippurate, 4-Aminohippuric acid , N-(4-Aminobenzoyl)glycine, para-Aminohippurate
ATC code
Identifiers
  • (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 InfoCard100.000.472
Chemical and physical data
FormulaC9H10N2O3
Molar mass194.190 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(c1ccc(N)cc1)NCC(=O)O
  • 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
  (verify)

Uses edit

Diagnostics edit

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 edit

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 edit

pKa = 3.83

See also edit

References edit

  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.

aminohippuric, acid, para, aminohippuric, acid, derivative, hippuric, acid, diagnostic, agent, useful, medical, tests, involving, kidney, used, measurement, renal, plasma, flow, amide, derivative, amino, acid, glycine, para, aminobenzoic, acid, that, naturally. 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 AminohippurateClinical dataOther namesPAH PAHA Aminohippurate 4 Aminohippuric acid N 4 Aminobenzoyl glycine para AminohippurateATC codeV04CH30 WHO IdentifiersIUPAC name 4 Aminobenzamido acetic acidCAS Number61 78 9 Y 94 16 6 sodium salt PubChem CID2148IUPHAR BPS4810DrugBankDB00345 YChemSpider2063 YUNIIY79XT83BJ9KEGGD06890 YChEBICHEBI 104011 YChEMBLChEMBL463 YNIAID ChemDB019143CompTox Dashboard EPA DTXSID7022590ECHA InfoCard100 000 472Chemical and physical dataFormulaC 9H 10N 2O 3Molar mass194 190 g mol 13D model JSmol Interactive imageSMILES O C c1ccc N cc1 NCC O OInChI 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 verify Contents 1 Uses 1 1 Diagnostics 1 2 Pharmaceuticals 2 Other 3 See also 4 ReferencesUses editDiagnostics edit 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 edit 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 editpKa 3 83See also editPAH clearance Ortho iodohippurateReferences edit 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 Retrieved from https en wikipedia org w index php title Aminohippuric acid amp oldid 1192854951, wikipedia, wiki, book, books, library,

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