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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 443384241 |
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| verifiedrevid = 443661015 |
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| IUPAC_name = 2-acetic acid |
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| IUPAC_name = (4-Aminobenzamido)acetic acid <!-- the locant '2' for acetic acid is not cited --> |
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| image = aminohippuric acid.png |
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| image = aminohippuric acid.png |
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| synonyms = PAH, PAHA, Aminohippurate, 4-Aminohippuric acid , N-(4-Aminobenzoyl)glycine, para-Aminohippurate |
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| drug_name = Aminohippurate |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| IUPHAR_ligand = 4810 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 61-78-9 |
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| CAS_supplemental = <br>{{CAS|94-16-6}} (sodium salt) <!-- CAS verified--> |
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| ATC_prefix = V04 |
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| ATC_suffix = CH30 |
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| PubChem = 2148 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00345 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2063 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = Y79XT83BJ9 |
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| UNII = Y79XT83BJ9 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D06890 |
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| KEGG = D06890 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChI = 1/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) |
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| ChEBI = 104011 |
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| InChIKey = HSMNQINEKMPTIC-UHFFFAOYAW |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 463 |
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| NIAID_ChemDB = 019143 |
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<!--Chemical data--> |
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| C=9 | H=10 |
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| N=2 | O=3 |
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| smiles = O=C(c1ccc(N)cc1)NCC(=O)O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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) |
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| StdInChI = 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HSMNQINEKMPTIC-UHFFFAOYSA-N |
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| StdInChIKey = HSMNQINEKMPTIC-UHFFFAOYSA-N |
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| synonyms = PAH, PAHA, Aminohippurate, 4-Aminohippuric acid , N-(4-Aminobenzoyl)glycine, para-Aminohippurate |
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| CAS_number = 61-78-9 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 463 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_supplemental = <br>94-16-6 (sodium salt) <!-- CAS verified--> |
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| ATC_prefix = V04 |
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| ATC_suffix = CH30 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 104011 |
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| PubChem = 2148 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2063 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00345 |
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| C=9|H=10|N=2|O=3 |
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| molecular_weight = 194.19 g/mol |
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| smiles = O=C(c1ccc(N)cc1)NCC(=O)O |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| ⚫ |
| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Aminohippuric acid''' or '''para-aminohippuric acid''' ('''PAH'''), a derivative of ], is a diagnostic agent useful in medical tests involving the ] used in the measurement of ]. It is an ] derivative of the ] ] and ]. |
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'''Aminohippuric acid''' or '''''para''-aminohippuric acid''' ('''PAH'''), a derivative of ], is a diagnostic agent useful in medical tests involving the ] used in the measurement of ]. It is an ] derivative of the ] ] and ] that is not naturally found in humans; it needs to be IV infused before diagnostic use. |
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==Uses== |
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==Uses== |
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===Diagnostics=== |
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===Diagnostics=== |
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PAH is useful for the measurement of renal plasma flow.<ref>{{cite book | last = Costanzo | first = Linda | name-list-style = vanc | title = Physiology | edition = 4th | location = Philadelphia | publisher = Lippincott Williams and Wilkins | date = 2007 | pages = 156–160 }}</ref> |
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PAH is useful for the measurement of renal plasma flow because it is secreted primarily by the ]; only 20-30% is filtered by the ].<ref name='0002-9513/48'>{{cite journal|title=Effect of 20,60 and 120 minutes of renal ischemia on glomerular and tubular function|journal=Am J Physiol|date=1948-02-29|first=R. A.|last=Phillips|coauthors=P. B. Hamilton|volume=152|issue=3|pages=523–30|issn=0002-9513|id= |url=http://ajplegacy.physiology.org/cgi/content/citation/152/3/523|format=PDF|accessdate=2008-03-20|pmid=18863150 }}</ref> PAH is completely filtered from ] in the ] and not reabsorbed by the tubules, in a manner identical to ]. PAH differs from inulin in that the fraction of PAH that bypasses the glomerulus and enters the nephron's tubular cells (via the ]) is completely secreted. Thus, ] of PAH is useful in calculation of renal plasma flow (RPF), which empirically is (1 − ]) × ]. 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%.<ref>Costanzo, Linda. Physiology, 4th Edition. Philadelphia: Lippincott Williams and Wilkins, 2007. Page 156-160.</ref> |
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The ] of PAH in a normal individual is approximately 0.92.<ref name="pmid13082682">{{cite journal | author = Reubi, François C. | title = Glomerular filtration rate, renal blood flow and blood viscosity during and after diabetic coma | journal = ] | volume = 1 | issue = 5 | pages = 410–3 | date = 1953-04-29 | pmid = 13082682 | doi = | issn = 00097330 | url=http://circres.ahajournals.org/cgi/content/abstract/1/5/410 | accessdate = 2008-03-19}}</ref> |
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The ] of PAH in a normal individual is approximately 0.92.<ref name="pmid13082682">{{cite journal | vauthors = Reubi FC | title = Glomerular filtration rate, renal blood flow and blood viscosity during and after diabetic coma | journal = Circulation Research | volume = 1 | issue = 5 | pages = 410–3 | date = September 1953 | pmid = 13082682 | doi = 10.1161/01.res.1.5.410 | doi-access = free }}</ref> This means that unlike ] and ], which are filtered in the ] 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. |
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===Pharmaceuticals=== |
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===Pharmaceuticals=== |
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Aminohippuric acid is often used as the ] ] 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. |
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Aminohippuric acid is often used as the ] ] 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.<ref>{{cite journal | vauthors = Beyer KH, Flippin H, Verwey WF, Woodward R |date=1944-12-16 |title= The effect of para-aminohippuric acid on plasma concentration of penicillin in man |journal=Journal of the American Medical Association |volume=126 |issue=16 |pages=1007–1009 |doi= 10.1001/jama.1944.02850510015003 }}</ref> |
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==Other== |
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==Other== |
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In ]s, the ] ], which is extraordinarily ] to ]s, interferes with the renal transport of ] via the PAH channel.<ref name="pmid18727958">{{cite journal | author = Naidoo V, Swan GE | title = Diclofenac toxicity in Gyps vulture is associated with decreased uric acid excretion and not renal portal vasoconstriction | journal = Comp. Biochem. Physiol. C Toxicol. Pharmacol. | volume = 149| issue = 3| pages = 269–74| year = 2008 | month = August | pmid = 18727958 | doi = 10.1016/j.cbpc.2008.07.014 | url = | issn = }}</ref> |
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pKa = 3.83 |
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] = 3.83 |
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==See also== |
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== See also == |
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==References== |
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== References == |
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{{reflist}} |
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