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4-아미노히푸릭-d4산

p-Aminohippuric acid

HCID 178749375
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
1219805-41-0
표준 SMILES
Nc1ccc(C(=O)NCC(=O)O)cc1
InChIKey
HSMNQINEKMPTIC-UHFFFAOYSA-N
분자식
C9H10N2O3
평균 분자량
194.19 g/mol

개요

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.

이름 및 식별자

우선 이름
p-Aminohippuric acid
IUPAC
2-[(4-aminobenzoyl)amino]acetic acid
현지명
4-아미노히푸릭-d4산
영어명
4-AMinohippuric-d4 Acid
분자식
C9H10N2O3
분자량
194.19

이름 및 동의어

4-Aminohippuric acid61-78-9aminohippuric acidP-AMINOHIPPURIC ACIDN-(4-Aminobenzoyl)glycineGlycine, N-(4-aminobenzoyl)-Pahapara-Aminohippuric acidNefrotestN-(p-Aminobenzoyl)glycinePAH (amino acid)N-(para-aminobenzoyl)glycine
이름 더 보기
4-아미노히푸릭-d4산4-AMinohippuric-d4 AcidAminohippuric-13C6 acid[2H4]-4-Aminohippuric AcidN-(4-Aminobenzoyl-D4)Glycine (Standard)2-[(4-amino-2,3,5,6-tetradeuterio-benzoyl)amino]acetic acid
Hippuric acid, p-amino-paraaminohippuric acid2-[(4-aminobenzoyl)amino]acetic acidN-(p-Aminobenzoyl)aminoacetic acidAminohippuric acid, p-DTXSID70225902-[(4-aminophenyl)formamido]acetic acidNSC-13064

데이터베이스 식별자

CAS
1219805-41-0
ChEMBL
CHEMBL463
ChEBI
CHEBI:104011
UNII
Y79XT83BJ9
EC Number
200-518-9
Nikkaji
J38.133K

물성

구조 계산 물성

XLogP
-0.9
극성 표면적
92.4 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
4
회전 가능 결합 수
3
무거운 원자 수
14
형식 전하
0
복잡도
222

실험 및 물리화학적 성질

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

Log P= -0.89

-0.89

Color/Form · 3건

NEEDLES FROM HOT WATER

PRISMS FROM WATER

WHITE, CRYSTALLINE POWDER

Solubility · 6건

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 · 3건

199-200 °C

198-199 °C

198.5 °C

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

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

Solid

Stability/Shelf LifeDiscolors on exposure to light

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 2건

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 · 1건

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%)

안전 및 보호

Disposal Methods · 1건

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.

화학 및 산업

약리 정보

ATC Code · 2건

V - Various

QV - Various

Pharmacodynamics · 1건

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 · 2건

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 · 2건

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.

관련 반응

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화합물 노트

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Dissociation Constants · 2건

3.83

PKA: 4.0

Collision Cross Section · 2건

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 · 2건

AQ SOLN ARE ALKALINE /P-AMINOHIPPURIC ACID SODIUM/

Forms a water-soluble sodium salt.

물리화학적 성질

녹는점
246 °C · >246°C (dec.)
저장 조건
Room Temperature
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
고체
색상
미색부터 베이지까지

독성 정보

Interactions · 4건

...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 · 5건

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.

규제 정보

FDA Requirements · 1건

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).

MeSH Pharmacological Classification · 1건

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 · 5건

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

용도 및 제조

Uses · 3건

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

INTERMEDIATE

MEDICATION

Methods of Manufacturing · 2건

...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 · 2건

NEPHROTEST. /P-AMINOHIPPURIC ACID SODIUM/

GRADE: USP.

General Manufacturing InformationGlycine, N-(4-aminobenzoyl)-: INACTIVE

응용 분야

용도Labelled4-AMinohippuric-d4 Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders.