p-Aminohippuric acid

Log P= -0.89

-0.89

NEEDLES FROM HOT WATER

PRISMS FROM WATER

WHITE, CRYSTALLINE POWDER

Slightly soluble

SOL IN WATER /P-AMINOHIPPURIC ACID SODIUM/

1 G SOL IN 45 ML WATER

SOL IN CHLOROFORM; BENZENE; ACETONE; ALCOHOL

PRACTICALLY INSOL IN ETHER; CARBON TETRACHLORIDE

FREELY SOL IN SOLN OF ALKALI HYDROXIDES WITH SOME DECOMP

199-200 °C

198-199 °C

198.5 °C

White solid; Discolors upon exposure to light; [Hawley] Off-white or white powder; [MSDSonline]

Solid

3.83

PKA: 4.0

155.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

153.7 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

AQ SOLN ARE ALKALINE /P-AMINOHIPPURIC ACID SODIUM/

Forms a water-soluble sodium salt.

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Danger

H301 (50%): Toxic if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Glycine, N-(4-aminobenzoyl)-

Glycine, N-(4-aminobenzoyl)-: Does not have an individual approval but may be used under an appropriate group standard

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).

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.

...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-Induced Liver Injury Severity and Toxicity (DILIst)

aminohippurate

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

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).

V - Various

QV - Various

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 (Tm_PAH). 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 Tm_PAH determinations since glomerular filtration rate (GFR) must be known before calculations of secretory Tm measurements can be done.

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.

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.

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 & Hackh's Chemical Dictionary, 5th ed, p301, p499)

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.

Used as a diagnostic aid (renal function determination) and intermediate; [HSDB]

INTERMEDIATE

MEDICATION

...BY REDN OF P-NITROHIPPURIC ACID.

BY REACTING P-NITROBENZOYL CHLORIDE WITH GLYCINE & THEN REDUCING THE P-NITRO GROUP WITH TIN & HYDROCHLORIC ACID.

NEPHROTEST. /P-AMINOHIPPURIC ACID SODIUM/

GRADE: USP.