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p-Aminohippuric acid

HCID 2148
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
61-78-9
Standard SMILES
Nc1ccc(C(=O)NCC(=O)O)cc1
InChIKey
HSMNQINEKMPTIC-UHFFFAOYSA-N
Molecular formula
C9H10N2O3
Average molar mass
194.19 g/mol
Monoisotopic mass
194.06914219

Overview

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.

Names & identifiers

Preferred name
p-Aminohippuric acid
IUPAC
2-[(4-aminobenzoyl)amino]acetic acid
English name
4-Aminohippuric acid
Molecular formula
C9H10N2O3
Molecular weight
194.19

Names & synonyms

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
Show more names
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

Database identifiers

CAS
61-78-9
PubChem CID
2148
DTXSID
DTXSID7022590
ChEMBL
CHEMBL463
ChEBI
CHEBI:104011
UNII
Y79XT83BJ9

Properties

Computed structural properties

XLogP
-0.9
Topological polar surface area
92.4 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
14
Formal charge
0
Complexity
222

Experimental & physicochemical properties

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

Log P= -0.89

-0.89

Color/Form · 3 items

NEEDLES FROM HOT WATER

PRISMS FROM WATER

WHITE, CRYSTALLINE POWDER

Solubility · 6 items

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 items

199-200 °C

198-199 °C

198.5 °C

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

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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

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.

Hazard information

Regulatory Information · 2 items

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 item

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%)

Safety & protection

Disposal Methods

Chemistry & industry

Pharmacology

ATC Code · 2 items

V - Various

QV - Various

Pharmacodynamics · 1 item

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 items

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 items

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.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
EC Number
200-518-9
Nikkaji
J38.133K

Solid

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

3.83

PKA: 4.0

Collision Cross Section · 2 items

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 items

AQ SOLN ARE ALKALINE /P-AMINOHIPPURIC ACID SODIUM/

Forms a water-soluble sodium salt.

Physicochemical properties

Melting point
199 · 199-200 °C (dec.)(lit.)
Boiling point
330.62 °C · 330.62°C (rough estimate)
Density
1.356 · 1.356
bulk density
380 kg/m3 · 380kg/m3
refractive index
1.56 · 1.5600 (estimate)
storage temp.
30 °C · Store below +30°C.
solubility
33 mg/ml; · DMF: 33 mg/ml; DMF:PBS (pH7.2) (1:30): 0.03 mg/ml; DMSO: 20 mg/ml
form
Crystalline Powder
pka
3.8 · pKa 3.8 (Uncertain)
color
Off-white to grayish
PH
3 · 3.0-3.5 (20g/l, H2O, 20℃)
Water Solubility
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 DataBase Reference
61 · 61-78-9(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
PAH
FDA UNII
79 XT83BJ9 · Y79XT83BJ9
EPA Substance Registry System
P-Aminohippuric acid (61-78-9)
UNSPSC Code
41116107 · 41116107
NACRES
26 · NA.26
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-20/21/22
Safety Statements
37 · 37/39-26-36
WGK Germany
3 · 3
F
8 · 8-9-23
TSCA
TSCA listed
HS Code
29242990 · 29242990
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
61 · 61-78-9(Hazardous Substances Data)
· 1 item

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.

Toxicology

Interactions · 4 items

...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 items

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.

Regulatory information

FDA Requirements · 1 item

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).

Safety data

F
8-9-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29242990
risk_code
36/37/38-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
37/39-26-36
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P305+P351+P338
Hazardous Substances Data
61-78-9(Hazardous Substances Data)
MeSH Pharmacological Classification · 1 item

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 items

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

Uses & manufacturing

Uses · 3 items

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

INTERMEDIATE

MEDICATION

Methods of Manufacturing · 2 items

...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 items

NEPHROTEST. /P-AMINOHIPPURIC ACID SODIUM/

GRADE: USP.

General Manufacturing InformationGlycine, N-(4-aminobenzoyl)-: INACTIVE
Applications · 5 items

Description4-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.

Usesmuscle relaxant (smooth)

Usesp-Aminohippuric acid has been used as infusions to measure plasma flow.

Uses4-Aminohippuric Acid is used in the measurement of renal plasma flow as a diagnostic tool which may be applied towards kidney disorders.

General DescriptionRenal tubules secretes para amino hippuric acid/PAH.

Upstream & downstream products

Upstream raw materials

4-Nitrobenzoyl chlorideGlycineTinHydrochloric acid

Suppliers100 total

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Additional notes · 1 item

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.