p-Aminohippuric acid
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p-Aminohippuric acid
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CAS No:
61-78-9
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Formula:
C9H10N2O3
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Chemical Name:
p-Aminohippuric acid
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Synonyms:
Glycine,N-(4-aminobenzoyl)-;Hippuric acid,p-amino-;N-(4-Aminobenzoyl)glycine;N-(p-Aminobenzoyl)glycine;PAH;p-Aminohippuric acid;4-Aminohippuric acid;(p-Aminobenzoyl)glycine;PAH (amino acid);4-Aminobenzoylglycine;N-(4-Aminobenzoyl)aminoacetic acid;NSC 13064;NSC 7550;(4-Aminobenzoylamino)acetic acid;2-[(4-Aminobenzoyl)amino]acetic acid;2-(4-Aminobenzamido)aceticacid;2-[(4-Aminophenyl)formamido]acetic acid
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CAS No:
Description
4-Aminohippuric acid is a diagnostic agent, useful in medical tests involving the kidney, used in the measurement of renal plasma flow.
Solid
P-aminohippuric acid is an N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow. It has a role as a Daphnia magna metabolite. It is a conjugate acid of a p-aminohippurate.|The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.
p-Aminohippuric acid Basic Attributes
194.19
194.19
1213676
200-518-9
Y79XT83BJ9
758232|13064|7550
DTXSID7022590
NEEDLES FROM HOT WATER|PRISMS FROM WATER|WHITE, CRYSTALLINE POWDER
V - Various
2924299090
Characteristics
92.42000
-0.58
Off-white to grayish Crystalline Powder
1.39 g/cm3
198-199 °C
517.2±35.0 °C at 760 mmHg
266.6±25.9 °C
1.620
soluble in alcohol, chloroform, benzene, and acetone. Insoluble in water, ether, carbon, and tetrachloride.
−20°C
3.83None
3.83|PKA: 4.0
153.7 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|147.55 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|155.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
AQ SOLN ARE ALKALINE /P-AMINOHIPPURIC ACID SODIUM/|Forms a water-soluble sodium salt.
Safety Information
NONH for all modes of transport
3
36/37/38-20/21/22
37/39-26-36
Xi,Xn
Discolors on exposure to light
P264, P270, P280, P301+P310, P302+P352, P312, P321, P322, P330, P361, P363, P405, P501
H301
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P280, P301+P310, P302+P352, P312, P321, P322, P330, P361, P363, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
The intravenous LD50 in female mice is 7.22 g/kg.
...DRUGS THAT SHARE A COMMON EXCRETORY PATHWAY WITH PAH (EG, PENICILLIN), THOSE THAT INHIBIT RENAL TUBULAR TRANSPORT (EG, PROBENECID), OR THOSE THAT HAVE A URICOSURIC EFFECT (EG, SALICYLATES) CAN INTERFERE WITH PAH CLEARANCE.|RENAL EXCRETION OF HALOFENATE IS...DIMINISHED BY...P-AMINOHIPPURATE /IN CHIMPANZEES/ @ ALL OBSERVED URINARY PH VALUES.|Patients receiving drugs that employ the same tubular excretory mechanism as PAH may exhibit mutually decreased excretion of the drugs because of competitive inhibition. Agents that share a common excretory mechanism include diuretics, iodopyracet, penicillin, phenolsulfonphthalein, probenecid, and saliclyates.|Agents that interfere with calorimetric analytical procedures, including procaine, sulfonamides, and thiazolsulfone, prevent accurate urinary measurements of PAH.
Drug Information
Used to measure effective renal plasma flow (ERPF) and to determine the functional capacity of the tubular excretory mechanism.
Aminohippurate sodium (PAH) is used in plasma concentrations of 10-20 ug/ml to estimate effective renal plasma flow (ERPF) which is an index of renal function. In these low plasma concentrations, PAH is extracted almost completely from the plasma with each passage through functional renal tissue, and the value obtained for PAH clearance is accepted as being numerically equal to the ERPF. In plasma concentration of 400-600 ug/ml, PAH is used in conjunction with glomerular filtration rate (GFR) measurements to estimate the functional capacity of the renal tubular secretory mechanism. Since PAH is excreted both by tubular secretion and glomerular filtration, tubular transport capacity can be determined by comparing PAH excretion with values for GFR obtained by inulin clearance. Although this test may be the best quantitative measure of functioning nephron mass, its complexity prevents its widespread use. PAH clearance tests are more accurate but also more complex than phenolsulfonphthalein excretion tests for evaluation of renal blood flow. In most clinical situations, simpler (although less precise) methods of renal function evaluation are used.|MEDICATION: DIAGNOSTIC AID (RENAL FUNCTION DETERMINATION) /SRP: NOT COMMONLY USED IN RENAL FUNCTION TEST/
AT PLASMA LEVELS USED TO MEASURE MAX TUBULAR SECRETION, PAH SIGNIFICANTLY INCR SODIUM, POTASSIUM, & PHOSPHORUS CLEARANCE IN HUMAN VOLUNTEERS. AT LEVELS USED TO MEASURE RENAL PLASMA FLOW, IT INCREASED ONLY SODIUM CLEARANCE.|MANY WORKERS ROUTINELY USE CLEARANCE OF PAH AS AN ESTIMATE OF RENAL PLASMA FLOW. ...PRACTICE /WAS NOT RECOMMENDED/ FOR 3 REASONS: 1) RENAL EXTRACTION OF PAH IS...VARIABLE EVEN WHEN PLASMA CONCN IS LOW, 2) PAH IS REABSORBED, 3) PAH MAY SUPPRESS RENAL TRANSPORT OF TEST DRUG IF IT IS A WEAK ORGANIC ACID.|WHEN PLASMA CONCN OF PAH ARE RAISED RAPIDLY, PATIENTS MAY EXPERIENCE NAUSEA OR VOMITING & A SENSATION OF SUDDEN WARMTH, SYMPTOMS THAT CAN BE AVOIDED BY INFUSING DRUG MORE SLOWLY.|Adverse reactions which have been reported in association with the administration of aminohippurate sodium (PAH) include nausea, vomiting, cramps, vasomotor disturbances, flushing, tingling, a sensation of warmth, and the desire to defecate or urinate during or shortly after administration of the drug.|PAH must be administered with caution in patients with low cardiac reserve, since a rapid increase in plasma volume may precipitate congestive heart failure. The large dose required to achieve the plasma concentrations necessary for the determination of the maximum tubular secretion should be administered slowly and with caution, and the patient should be continuously observed for any adverse reactions. PAH is contraindicated in patients with known hypersensitivity to the drug or any ingredient in the formulation.
Aminohippurate (p-aminohippuric acid, PAH, PAHA) is the glycine amide of p-aminobenzoic acid. It is filtered by the glomeruli and is actively secreted by the proximal tubules. At low plasma concentrations (1.0 to 2.0 mg/100 mL), an average of 90 percent of aminohippurate is cleared by the kidneys from the renal blood stream in a single circulation. It is ideally suited for measurement of ERPF since it has a high clearance, is essentially nontoxic at the plasma concentrations reached with recommended doses, and its analytical determination is relatively simple and accurate. Aminohippurate is also used to measure the functional capacity of the renal tubular secretory mechanism or transport maximum (TmPAH). This is accomplished by elevating the plasma concentration to levels (40-60 mg/100 mL) sufficient to saturate the maximal capacity of the tubular cells to secrete aminohippurate. Inulin clearance is generally measured during TmPAH determinations since glomerular filtration rate (GFR) must be known before calculations of secretory Tm measurements can be done.
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)
EXCRETION OF P-AMINOHIPPURIC ACID DURING SWEATING IN MAN: SWEAT/PLASMA RATIO: 0.02; PKA= 3.8. /FROM TABLE/|1.4% OF DOSE OF P-AMINOHIPPURIC ACID IS EXCRETED IN BILE OF RAT AFTER 3 HR. /FROM TABLE/|BILIARY EXCRETION OF 4-AMINOHIPPURIC ACID IN DIFFERENT SPECIES: % OF DOSE EXCRETED IN 3 HR: RAT 3.3; GUINEA PIG 6.7; RABBIT 3.0; DOG 3.4; CAT 0.7; HEN 0.5. /FROM TABLE/|SERUM EXTRACTION RATIO...FROM DOG RENAL CORTEX.../IS/ 0.74 FOR P-AMINOHIPPURIC ACID...|For more Absorption, Distribution and Excretion (Complete) data for P-AMINOHIPPURIC ACID (8 total), please visit the HSDB record page.
YIELDS P-ACETAMIDOHIPPURIC ACID IN PIGS: GYRD-HANSEN, N & F RASMUSSEN, ACTA PHYSIOL SCAND, 80, 249 (1970). /FROM TABLE/|ORALLY ADMIN PAH GAVE RISE TO P-AMINOBENZOIC ACID, P-AMINOHIPPURIC ACID, P-ACETYLAMINOBENZOIC ACID, P-ACETYLAMINOHIPPURIC ACID, & P-ACETYLAMINOBENZOYLGLUCURONIC ACID IN URINE. WHEN ADMIN IV, ONLY P-ACETYLAMINOHIPPURIC ACID & UNCHANGED P-AMINOHIPPURIC ACID WERE EXCRETED.
The biologic half-life of PAH in patients with normal renal function is 24 minutes.
Aminohippurate is filtered by the renal glomeruli and secreted into the urine by the proximal tubules. By measuring the amount of drug in the urine it is possible to determine functional capacity and effective renal plasma flow.|P-AMINOHIPPURATE (PAH) IS PROTOTYPE FOR AN AGENT EXCRETED BY ORGANIC ACID TRANSPORT SYSTEM...LOCATED IN PROXIMAL CONVOLUTED TUBULES...PROTEIN-BOUND TOXICANTS ARE FULLY AVAIL FOR ACTIVE TRANSPORT. /PROCESS HAS/...ALL CHARACTERISTICS OF ACTIVE TRANSPORT SYSTEM; THEREFORE VARIOUS COMPD COMPETE WITH ONE ANOTHER FOR SECRETION.
4 Aminohippuric Acid
p-Aminohippuric acid Use and Manufacturing
...BY REDN OF P-NITROHIPPURIC ACID.|BY REACTING P-NITROBENZOYL CHLORIDE WITH GLYCINE & THEN REDUCING THE P-NITRO GROUP WITH TIN & HYDROCHLORIC ACID.
4-Aminohippuric Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders.
NEPHROTEST. /P-AMINOHIPPURIC ACID SODIUM/|GRADE: USP.
Glycine, N-(4-aminobenzoyl)-: INACTIVE
TLC USED FOR THE DETERMINATION OF P-AMINOHIPPURIC ACID (PAH).|URINE & SERUM SAMPLES CAN BE ANALYZED DIRECTLY WITHOUT SOLVENT EXTRACTION OR PRETREATMENT.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:194.19
XLogP3:-0.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:194.06914219
Monoisotopic Mass:194.06914219
Topological Polar Surface Area:92.4
Heavy Atom Count:14
Complexity:222
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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