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4-Aminohippursure

p-Aminohippuric acid

HCID 2148
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
61-78-9
Standard-SMILES
Nc1ccc(C(=O)NCC(=O)O)cc1
InChIKey
HSMNQINEKMPTIC-UHFFFAOYSA-N
Summenformel
C9H10N2O3
Durchschnittliche Molmasse
194,19 g/mol
Monoisotopische Masse
194,06914219

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
p-Aminohippuric acid
IUPAC
2-[(4-aminobenzoyl)amino]acetic acid
Lokaler Name
4-Aminohippursure
Englischer Name
4-Aminohippuric acid
Summenformel
C9H10N2O3
Molmasse
194.19

Namen und Synonyme

4-Aminohippuric acidaminohippuric acid61-78-9P-AMINOHIPPURIC ACIDN-(4-Aminobenzoyl)glycineGlycine, N-(4-aminobenzoyl)-PahaNefrotestpara-Aminohippuric acidN-(p-Aminobenzoyl)glycinePAH (amino acid)N-(para-aminobenzoyl)glycine
Weitere Namen anzeigen
PAHPOLYNUCLEAR AROMATIC HYDROCARBONSN-glycineAminohippuricpah(aminoacid)AKOS BBS-00006940
Hippuric acid, p-amino-paraaminohippuric acid2-[(4-aminobenzoyl)amino]acetic acidN-(p-Aminobenzoyl)aminoacetic acidAminohippuric acid, p-DTXSID70225902-[(4-aminophenyl)formamido]acetic acidNSC-13064

Datenbank-Bezeichner

CAS
61-78-9
PubChem CID
2148
DTXSID
DTXSID7022590
ChEMBL
CHEMBL463
ChEBI
CHEBI:104011

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,9
Polarare Oberfläche (TPSA)
92,4 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
3
Schwere Atome
14
Formalladung
0
Komplexität
222

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Amino Carboxylic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 Einträge

Log P= -0.89

-0.89

Color/Form · 3 Einträge

NEEDLES FROM HOT WATER

PRISMS FROM WATER

WHITE, CRYSTALLINE POWDER

Solubility · 6 Einträge

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

Melting Point · 3 Einträge

199-200 °C

198-199 °C

198.5 °C

Vapor Pressure0.00000004 [mmHg]
Physical Description · 2 Einträge

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

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Regulatory Information · 2 Einträge

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

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

Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazards SummaryEmergency treatment: symptomatic drug parenteral exposure; [HSDB] May cause irritation; [MSDSonline]
FDA Requirements · 1 Eintrag

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).

Hazard Classes and CategoriesAcute Tox. 3 (50%)

Sicherheit und Schutzausrüstung

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

V - Various

QV - Various

Pharmacodynamics · 1 Eintrag

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<sub>PAH</sub>). 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<sub>PAH</sub> determinations since glomerular filtration rate (GFR) must be known before calculations of secretory Tm measurements can be done.

Mechanism of Action · 2 Einträge

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.

Biological Half-LifeThe biologic half-life of PAH in patients with normal renal function is 24 minutes.
Metabolism/Metabolites · 2 Einträge

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.

Zugehörige Reaktionen

0
Reaktionsaufzeichnung erstellen

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
UNII
Y79XT83BJ9
EC Number
200-518-9
Nikkaji
J38.133K

Solid

Stability/Shelf LifeDiscolors on exposure to light
Dissociation Constants · 2 Einträge

3.83

PKA: 4.0

Collision Cross Section · 2 Einträge

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)]

Other Experimental Properties · 2 Einträge

AQ SOLN ARE ALKALINE /P-AMINOHIPPURIC ACID SODIUM/

Forms a water-soluble sodium salt.

Physikochemische Eigenschaften

Schmelzpunkt
199 · 199-200 °C (dec.)(lit.)
Siedepunkt
330.62 °C · 330.62°C (rough estimate)
Dichte
1.356 · 1.356
Brechungsindex
1.56 · 1.5600 (estimate)
storage temp.
30 °C · Store below +30°C.
Löslichkeit
33 mg/ml; · DMF: 33 mg/ml; DMF:PBS (pH7.2) (1:30): 0.03 mg/ml; DMSO: 20 mg/ml
Aggregatzustand
Crystalline Powder
pka
3.8 · pKa 3.8 (Uncertain)
Farbe
Off-white to grayish
PH
3 · 3.0-3.5 (20g/l, H2O, 20℃)
Wasserlöslichkeit
Soluble in alcohol, chloroform, benzene, and acetone. Insoluble in water, ether, carbon, and tetrachloride.
Merck
14 · 14,442
BRN
1213676 · 1213676
Major Application
cell analysis
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)
InChIKey
HSMNQINEKMPTIC-UHFFFAOYSA-N
SMILES
Nc1ccc(cc1)C(=O)NCC(O)=O
CAS Datenbank
61 · 61-78-9(CAS DataBase Reference)
EPA chemische Informationen
P-Aminohippuric acid (61-78-9)
Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Interactions · 4 Einträge

...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 · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

aminohippurate

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity ExcerptsTHE ACUTE OR REPEATED ADMIN OF P-AMINOHIPPURIC ACID TO RATS INCREASED RENAL BLOOD FLOW & PERIPHERAL BLOOD PRESSURE, BUT ONLY THE ACUTE DOSE INCREASED HEART MINUTE VOLUME.

Regulatorische Informationen

FDA Requirements · 1 Eintrag

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).

Sicherheitsdaten

F
8-9-23
wgk
3
tsca
TSCA listed
hs_code
29242990
risk_code
36/37/38-20/21/22
hazard_code
Xi,Xn
safety_code
37/39-26-36
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
61-78-9(Hazardous Substances Data)
MeSH Pharmacological Classification · 1 Eintrag

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 &amp; Hackh&apos;s Chemical Dictionary, 5th ed, p301, p499)

Absorption, Distribution and Excretion · 5 Einträge

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.

Tissue LocationsKidney
Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 3 Einträge

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

INTERMEDIATE

MEDICATION

Methods of Manufacturing · 2 Einträge

...BY REDN OF P-NITROHIPPURIC ACID.

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

Formulations/Preparations · 2 Einträge

NEPHROTEST. /P-AMINOHIPPURIC ACID SODIUM/

GRADE: USP.

General Manufacturing InformationGlycine, N-(4-aminobenzoyl)-: INACTIVE
Anwendungen · 2 Einträge

Beschreibung4-Aminohippuric acid is a substrate for various renal transporters that has been used in the study of anion uptake in the kidney. It is a substrate for organic anion transporter 1 (OAT1; Km = 14.3 μM in X. laevis oocytes), the human inorganic phosphate transporter (NPT1; Km = 2.66 mM in HEK293 cells), and apical multidrug resistance protein (MDR2; Km = 880 μM in HEK293 cells). 4-Aminohippuric acid is a glycine amide form of 4-aminobenzoic acid . Formulations containing 4-aminohippuric acid have been used as markers to determine renal plasma flow.

Verwenden4-Aminohippuric Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

4-NitrobenzoylchloridGlycinZinnHydrogenchlorid

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.