AMINOHIPPURATE SODIUM

US Previously Marketed

First approved in 1944

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H9N2O3.Na
Molecular Weight	216.1691
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].NC1=CC=C(C=C1)C(=O)NCC([O-])=O

InChI

InChIKey=UNZMYCAEMNVPHX-UHFFFAOYSA-M

InChI=1S/C9H10N2O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C9H9N2O3
Molecular Weight	193.1794
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/005619s021lbl.pdf

Aminohippurate (p-aminohippuric acid, PAH, PAHA) is the glycine amide of p-aminobenzoic acid. Aminohippuric acid sodium salt is an agent to measure effective renal plasma flow (ERPF).

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Renal function tests 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/005619s021lbl.pdf	Diagnostic		Approved 8429	AMINOHIPPURATE SODIUM Approved Use Estimation of effective renal plasma flow. Measurement of the functional capacity of the renal tubular secretory mechanism. Launch Date 1944

C_max

Value	Dose	Co-administered	Analyte	Population
250 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16844357/	30 mg/kg single, intravenous dose: 30 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		AMINOHIPPURIC ACID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
880 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16844357/	30 mg/kg single, intravenous dose: 30 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		AMINOHIPPURIC ACID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.67 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16844357/	30 mg/kg single, intravenous dose: 30 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		AMINOHIPPURIC ACID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599 OAT3 642	OAT1 326 MRP1 107 MRP2 205 MRP4 77 OAT3 339

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 603	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0003269700946335?via%3Dihub	yes [IC50 8.8 uM]		yes (co-administration study) Comment: co-administered with adefovir as substrate. See https://pubmed.ncbi.nlm.nih.gov/24747579/ Sources: https://www.sciencedirect.com/science/article/abs/pii/S0003269700946335?via%3Dihub
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11669456/	yes [Ki 19.6 uM]		yes (co-administration study) Comment: co-administered with benzylpenicillin as substrate. See https://pubmed.ncbi.nlm.nih.gov/24747579/ Sources: https://pubmed.ncbi.nlm.nih.gov/11669456/

Drug as victim

Target	Modality	Activity
MRP1 107	substrate 3367 Sources: https://www.kidney-international.org/article/S0085-2538(15)46912-1/fulltext	yes
MRP2 205	substrate 3367 Sources: https://www.kidney-international.org/article/S0085-2538(15)46912-1/fulltext	yes
MRP4 77	substrate 3367 Sources: https://jasn.asnjournals.org/content/15/11/2828.long	yes
OAT1 326	substrate 3367 Sources: https://dmd.aspetjournals.org/content/dmd/early/2018/05/07/dmd.118.081729.full.pdf#page=28 Page: 28.0	yes
OAT3 339	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11306713/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY443883	https://www.001chemical.com/chem/61-78-9
3B Scientific (Wuhan) Corp	3B3-011351	http://www.3bsc.com/index/pro_info.php?id=33850
AA Blocks	AA00E8TT	http://www.aablocks.com/goods/Goods/detail?id=AA00E8TT
AHH Chemical co.,ltd	MT-41082	http://www.ahhchemical.com/product/MT-41082.html
AK Scientific, Inc. (AKSCI)	X6859	http://www.aksci.com/item_detail.php?cat=X6859
Aaron Chemicals	AR00E9LL	http://www.aaronchem.com/61-78-9
AbMole Bioscience	M2359	http://www.abmole.com/products/4-aminohippuric-acid.html
Acadechem	ACDS-033060	http://www.acadechemical.com/product/107759
Achemica	ACMC-1AY8I	http://www.achemica.com/prodinfo/?id=28015
Achemo Scientific Limited	AC-20241	http://www.achemo.com/search/?Keyword= 61-78-9
Achemtek	0102-026143	http://www.achemtek.com/61-78-9
Acros Organics	AC153800100	https://www.fishersci.com/shop/products/4-aminohippuric-acid-99-acros-organics-1/AC153800100
Acros Organics	AC153800250	https://www.fishersci.com/shop/products/4-aminohippuric-acid-99-acros-organics-1/AC153800250
Acros Organics	AC153801000	https://www.fishersci.com/shop/products/4-aminohippuric-acid-99-acros-organics-1/AC153801000
Acros Organics	AC153805000	https://www.fishersci.com/shop/products/4-aminohippuric-acid-99-acros-organics/AC153805000
Adooq BioScience	A16384	https://www.adooq.com/4-aminohippuric-acid.html
Alfa Chemistry	AP61789	https://reagents.alfa-chemistry.com/product/aminohippuric-acid-cas-61-78-9-14137.html
Alfa Chemistry	1219805-41-0	https://www.alfa-chemistry.com/cas_1219805-41-0.htm
Alinda	ALBB-025851	http://alinda.ru/finechem_en_.html?i=ALBB-025851
Angel Pharmatech	AG110204	http://www.angelpharmatech.com/61-78-9.html
Angene	AGN-PC-0JK653	http://www.angenechemical.com/productshow/AGN-PC-0JK653.html
Anward	ANW-33944	http://www.anward.com/pro_result/15217
ApexBio Technology	B1873	http://www.apexbt.com/4-aminohippuric-acid.html
Aurora Fine Chemicals LLC	A00.150.687	http://online.aurorafinechemicals.com/info?ID=A00.150.687
Aurora Fine Chemicals LLC	K00.228.648	http://online.aurorafinechemicals.com/info?ID=K00.228.648
Aurum Pharmatech LLC	R1187	http://www.Aurumpharmatech.com/Product/ProductDetails/R1187
Avantor Inc	200017-368	https://us.vwr.com/store/product/7515598/4-aminohippuric-acid
BLD Pharm	BD6633	http://www.bldpharm.com/products/61-78-9.html
BioChemPartner	BCP04299	http://www.biochempartner.com/61-78-9-BCP04299
BioCrick	BCC4753	http://www.biocrick.com/4-Aminohippuric-Acid-BCC4753.html
BioSynth	W-203306	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-203306.html
Chem Scene	CS-4816	http://www.chemscene.com/61-78-9.html
ChemMol	49416528	http://www.chemmol.com/chemmol/49416528.html
Chemspace	CSSB00000211586	https://chem-space.com/CSSB00000211586
Clearsynth	CS-EB-00096	https://www.clearsynth.com/en/CSEB00096.html
Clearsynth	CS-T-03336	https://www.clearsynth.com/en/CST03336.html
Clearsynth	CS-T-48038	https://www.clearsynth.com/en/CST48038.html
DC Chemicals	DC37415	http://www.dcchemicals.com//product_show-Aminohippuric_acid.html
Debye Scientific	DB-053989	http://www.debyesci.com/cas_61-78-9.html
Finetech	FT-0617576	http://www.finetechnology-ind.com/prod/detail/pub/61-78-9.html
Finetech	FT-0622289	http://www.finetechnology-ind.com/prod/detail/pub/94-16-6.html
Glentham Life Sciences	GM0535	http://www.glentham.com/products/product/GM0535/
Hairui	HR34179	http://www.hairuichem.com/en/product/61-78-9.html
Lab Network	LN00194187	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00194187
Matrix Scientific	157279	https://www.matrixscientific.com/157279.html
MedChem Express	HY-B1306	https://www.medchemexpress.com/4-Aminohippuric-acid.html
Molcore	MC443883	https://www.molcore.com/product/61-78-9
MuseChem	I004333	https://www.musechem.com/product/I004333.html
Nextpeptide	NP16316	http://www.nextpeptide.com/61-78-9.html
Oakwood	238888	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=119887&ExtHyperLink=1
Otava	1375749	https://search.otavachemicals.com/#!/search?query=1375749&type=code&base=dbb
Parchem	48712	https://www.parchem.com/chemical-supplier-distributor/2-(4-Aminobenzamido)acetic-acid-048712.aspx
Sigma-Aldrich	08090_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/08090?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A1422_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a1422?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1025351_USP	https://www.sigmaaldrich.com/catalog/product/usp/1025351?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017403	http://www.sinfoobiotech.com/product/1020801
Smolecule	S518515	http://www.smolecule.com/products/s518515
TCI (Tokyo Chemical Industry)	A0313	http://www.tcichemicals.com/eshop/en/us/commodity/A0313/index.html
THE BioTek	bt-259353	https://www.thebiotek.com/product/inhibitors/bt-259353
Vesino Industrial Co Ltd	VZ28181	http://www.vsnchem.com/goto/product/37429/
VladaChem	VL274206-100G	https://www.vladachem.com/product.php?products=61-78-9
Yuhao Chemical	XJ0008	http://www.chemyuhao.com/61-78-9.html
abcr GmbH	AB129133	http://www.abcr.com/shop/en/AB129133
iChemical	EBD33884	http://www.ichemical.com/chemicals/cas-61-78-9
mcule	MCULE-9532170257	https://mcule.com/MCULE-9532170257/

PubMed

Title	Date	PubMed
Transport of ochratoxin A by renal multispecific organic anion transporter 1.	1999 Jun	10336520
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
Renal function of children exposed to cyclosporin in utero.	2000 Oct	11007824
Assessment of postabsorptive renal glucose metabolism in humans with multiple glucose tracers.	2001 Apr	11289038
Inducible nitric oxide synthase and glomerular hemodynamics in rats with liver cirrhosis.	2001 Aug	11457721
Long-term follow-up of renal function in recipients and donors following pediatric kidney transplantation.	2001 Dec	11793080
Net flux of folates and vitamin B12 through the gastrointestinal tract and the liver of lactating dairy cows.	2001 Dec	11749680
Alternative high-performance liquid chromatographic assay for p-aminohippuric acid (PAH): effect of aging on PAH excretion in the isolated perfused rat kidney.	2001 Dec	11600282
Effect of familial hypertension on glomerular hemodynamics and tubulo-glomerular feedback after uninephrectomy.	2001 Feb	11243302
Modulation by cyclic AMP and phorbol myristate acetate of cephaloridine-induced injury in rat renal cortical slices.	2001 Jan	11243575
Ambulatory blood pressure and heart rate in relation to kidney structure and metabolic control in adolescents with Type I diabetes.	2001 Jul	11508271
High-throughput multi-analyte screening for renal disease using capillary electrophoresis.	2001 Jul	11377062
Effects of different nickel compounds on the transport of para-aminohippurate ion by rat renal cortical slices.	2001 Jul 6	11489358
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes.	2001 Jun	11356905
Modulation of the basolateral and apical step of transepithelial organic anion secretion in proximal tubular opossum kidney cells. Acute effects of epidermal growth factor and mitogen-activated protein kinase.	2001 May 4	11278330
The hippurate ratio as an indicator of functional hepatic reserve for resection of hepatocellular carcinoma in cirrhotic patients.	2001 May-Jun	11360056
Cationic amino acids involved in dicarboxylate binding of the flounder renal organic anion transporter.	2001 Oct	11562399
Characterization of the mechanisms involved in the gender differences in p-aminohippurate renal elimination in rats.	2001 Sep	11599782
Increased renal tubular sodium reabsorption during exercise-induced hypervolemia in humans.	2001 Sep	11509520
Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells.	2001 Sep	11504818
Sex differences in p-aminohippuric acid transport in rat kidney: role of membrane fluidity and expression of OAT1.	2002 Apr	12083373
Endothelin ETA receptor-subtype specific antagonism does not mitigate the acute systemic or renal effects of exogenous angiotensin II in humans.	2002 Apr	11952807
Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport.	2002 Feb	11883641
Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake.	2002 Jan	11815391
Complementary effects of adenosine and angiotensin II in hypoxemia-induced renal dysfunction in the rabbit.	2002 Jul 5	12074937
Pharmacological characterization of the ATP-dependent low K(m) guanosine 3',5'-cyclic monophosphate (cGMP) transporter in human erythrocytes.	2002 Mar 1	11911846
Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.	2002 May	11967025
Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus.	2002 May	11961115

Patents

Sample Use Guides

In Vivo Use Guide

6 to 10 mg/kg

Route of Administration: Intravenous

In Vitro Use Guide

The hOAT1-transformed cells were incubated in 200 ml of Dulbecco's PBS containing 5 mM D-glucose, 10 uM D-[3H]-mannitol and 10 uM [14C]-aminohippuric acid, for 10 min at room temperature.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:19:47 GMT 2023` Edited by `admin` on `Fri Dec 15 16:19:47 GMT 2023`
Record UNII	SUO3KVS1O9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMINOHIPPURATE SODIUM

Systematic Name

English

AMINOHIPPURATE

Systematic Name

English

SODIUM P-AMINOHIPPURATE [JAN]

Common Name

English

.RHO.-AMINOHIPPURIC ACID SODIUM SALT [MI]

Common Name

English

Aminohippurate sodium [WHO-DD]

Common Name

English

P-AMINOHIPPURATE

Common Name

English

MONOSODIUM P-AMINOHIPPURATE

Common Name

English

AMINOHIPPURATE SODIUM [ORANGE BOOK]

Common Name

English

AMINOHIPPURATE SODIUM [USP IMPURITY]

Common Name

English

AMINOHIPPURATE [VANDF]

Common Name

English

SODIUM P-AMINOHIPPURATE

Common Name

English

GLYCINE, N-(4-AMINOBENZOYL)-, MONOSODIUM SALT

Common Name

English

AMINOHIPPURATE SODIUM [VANDF]

Common Name

English

.RHO.-AMINOHIPPURIC ACID SODIUM SALT

Common Name

English

SODIUM AMINOHIPPURATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1937