ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
化工社オープンプロジェクト:[email protected]AIアクセス:llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
  1. ホーム
  2. /化合物

4-アミノ馬尿酸

p-Aminohippuric acid

HCID 2148
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
61-78-9
標準SMILES
Nc1ccc(C(=O)NCC(=O)O)cc1
InChIKey
HSMNQINEKMPTIC-UHFFFAOYSA-N
分子式
C9H10N2O3
平均分子量
194.19 g/mol
単同位体質量
194.06914219

概要

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.

名称と識別子

優先名称
p-Aminohippuric acid
IUPAC
2-[(4-aminobenzoyl)amino]acetic acid
現地名
4-アミノ馬尿酸
英語名
4-Aminohippuric acid
分子式
C9H10N2O3
分子量
194.19

名称と別名

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
名称をさらに表示
4-アミノ馬尿酸N-(4-アミノベンゾイル)グリシンP-アミノ馬尿酸p-アミノ馬尿酸(4-〃)P‐アミノ馬尿酸アミノ馬尿酸P-アミノ馬尿酸, 結晶パラアミノ馬尿酸N-(p-アミノベンゾイル)グリシン(4-アミノベンゾイル)アミノ酢酸2-[(4-アミノフェニル)ホルムアミド]酢酸(4-アミノベンゾイルアミノ)酢酸[(4-アミノベンゾイル)アミノ]酢酸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

物性

構造計算による物性

XLogP
-0.9
極性表面積
92.4 Ų
水素結合供与体数
3
水素結合受容体数
4
回転可能結合数
3
重原子数
14
形式電荷
0
複雑度
222

実験および物理化学的性質

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

Log P= -0.89

-0.89

Color/Form · 3 件

NEEDLES FROM HOT WATER

PRISMS FROM WATER

WHITE, CRYSTALLINE POWDER

Solubility · 6 件

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 件

199-200 °C

198-199 °C

198.5 °C

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

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

Solid

Stability/Shelf LifeDiscolors on exposure to light

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 2 件

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 件

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%)

安全と保護具

Disposal Methods · 1 件

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.

化学と産業

薬理情報

ATC Code · 2 件

V - Various

QV - Various

Pharmacodynamics · 1 件

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 件

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 件

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.

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
61-78-9
PubChem CID
2148
DTXSID
DTXSID7022590
ChEMBL
CHEMBL463
ChEBI
CHEBI:104011
UNII
Y79XT83BJ9
EC Number
200-518-9
Nikkaji
J38.133K
Dissociation Constants · 2 件

3.83

PKA: 4.0

Collision Cross Section · 2 件

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 件

AQ SOLN ARE ALKALINE /P-AMINOHIPPURIC ACID SODIUM/

Forms a water-soluble sodium salt.

物理化学的性質

融点
199 · 199-200 °C (dec.)(lit.)
沸点
330.62 °C · 330.62°C (rough estimate)
比重(密度)
1.356 · 1.356
屈折率
1.56 · 1.5600 (estimate)
貯蔵温度
30 °C · Store below +30°C.
溶解性
33 mg/ml; · DMF: 33 mg/ml; DMF:PBS (pH7.2) (1:30): 0.03 mg/ml; DMSO: 20 mg/ml
外見
結晶性粉末
酸解離定数(Pka)
3.8 · pKa 3.8 (Uncertain)
色
オフホワイトからグレイッシュ
PH
3 · 3.0-3.5 (20g/l, H2O, 20℃)
水溶解度
エタノール、クロロホルム、ベンゼン、アセトンに可溶。水、エーテル、炭素、四塩化物に不溶。
Merck
14 · 14,442
BRN
1213676 · 1213676
主な用途
細胞分析
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 データベース
61 · 61-78-9(CAS DataBase Reference)
EPAの化学物質情報
P-Aminohippuric acid (61-78-9)

化学的性質

化学的特性off-white to greyish crystalline powder

毒性情報

Interactions · 4 件

...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 件

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.

法規制情報

FDA Requirements · 1 件

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).

安全データ

F
8-9-23
wgk
3
tsca
TSCA listed
hs_code
29242990
risk_code
36/37/38-20/21/22
化審法
(9)-111
hazard_code
Xi,Xn
safety_code
37/39-26-36
ストレージクラス
11 - Combustible Solids
有毒物質データの
61-78-9(Hazardous Substances Data)
MeSH Pharmacological Classification · 1 件

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 件

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

用途と製造

Uses · 3 件

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

INTERMEDIATE

MEDICATION

Methods of Manufacturing · 2 件

...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 件

NEPHROTEST. /P-AMINOHIPPURIC ACID SODIUM/

GRADE: USP.

General Manufacturing InformationGlycine, N-(4-aminobenzoyl)-: INACTIVE
応用分野 · 4 件

用途有機合成原料、腎臓機能診断薬原料。

説明4-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.

使用4-Aminohippuric Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders.

一般的な説明Renal tubules secretes para amino hippuric acid/PAH.

調製方法

純化方法Crystallise the acid from H2O. It is soluble in organic solvents. [Cohen & McGilvery J Biol Chem 169 119 1945, 171 121 1947, Meunzen et al. J Biol Chem 26 469 1926, Beilstein 14 III 1069, 14 IV 1152.]

上流・下流製品情報

上流原料

4-ニトロベンゾイル クロリドグリシンすず塩酸

サプライヤー100 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
上海攀鸿化工科技有限公司021-56491756 13512199871 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
上海耐士化工科技有限公司400-188-0725 +86 21 34310725 13611771617
天津希恩思生化科技有限公司400 638 7771 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海昶奇生化科技有限公司13671867139
Clearsynth Labs Limited+91-22-26355700 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
苏州亚科科技股份有限公司0512-87182055 13451648594 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
明科实业(上海)有限公司+86-021-20980300 +86-13167252998 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海馨远医药科技有限公司021-24206007 13764915196 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
深圳利斯康医药科技有限公司0755-89396905 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
補足説明 · 1 件

定義ChEBI: 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.