SODIUM ARISTOLOCHATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H10NO7.Na
Molecular Weight	363.2536
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].COC1=C2C=C(C3=C(C4=C(OCO4)C=C3C([O-])=O)C2=CC=C1)[N+]([O-])=O

InChI

InChIKey=BQVOPWJSBBMGBR-UHFFFAOYSA-M

InChI=1S/C17H11NO7.Na/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13;/h2-6H,7H2,1H3,(H,19,20);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

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

Molecular Formula	C17H10NO7
Molecular Weight	340.2638
Charge	-1
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27080942 | Pharmaceuticals. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, No. 100A. retrieved from https://www.ncbi.nlm.nih.gov/books/NBK304331

Aristolochic acid (AA-I), a naturally occurring nitrophenanthrene carboxylic acid, commonly found in the plant family Aristolochiaceae, that are used in traditional Chinese medicine. Aristolochic acid exhibits nephrotoxic, carcinogenic, and mutagenic activities and can cause aristolochic acid nephropathy, and urothelial malignancies. The FDA has issued a strong warning to consumers to avoid herbs containing the chemical aristolochic acid. The mechanisms underlying AA-I toxicity in the kidneys are poorly understood. However, was found a protein α-actinin-4 that is inhibited by AA-I, resulting in kidney disease.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
ATP-binding cassette sub-family G member 2 16 Target ID: Q9UNQ0\|\|\|Q86V64 Gene ID: 9429.0 Gene Symbol: ABCG2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26183576	Substrate 661
Alpha-actinin-4 2 Target ID: O43707 Gene ID: 81.0 Gene Symbol: ACTN4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27080942	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Arachidonic acid released by phospholipase A(2) activation triggers Ca(2+)-dependent apoptosis through the mitochondrial pathway.	2004-06-11	15070903
Fanconi's syndrome and subsequent progressive renal failure caused by a Chinese herb containing aristolochic acid.	2004-06	15189173
Aristolochic acid nephropathy: what we know and what we have to do.	2004-06	15189168
Regulation of Na+ transport by aldosterone: signaling convergence and cross talk between the PI3-K and MAPK1/2 cascades.	2004-06	15039143
Insecticidal activity of chemical constituents from Aristolochia pubescens against Anticarsia gemmatalis larvae.	2004-04	15119605
Transcriptional activation of Igl, the gene for indole formation in Zea mays: a structure-activity study with elicitor-active N-acyl glutamines from insects.	2004-04	15110684
DNA adducts and p53 mutations in a patient with aristolochic acid-associated nephropathy.	2004-04	15042566
Purification of a Class B1 platelet aggregation inhibitor phospholipase A2 from Indian cobra (Naja Naja) venom.	2004-03	15134835
NMR regulatory analysis: determination and characterization of Chinese-herb aristolochic acids.	2004-03	15074585
Mediating of caspase-independent apoptosis by cadmium through the mitochondria-ROS pathway in MRC-5 fibroblasts.	2004-02-01	14743397
[Cellular mechanism of renal proximal tubular epithelial cell injury induced by aristolochic acid I and aristololactam I].	2004-02	14970885
Herbal bioactivation: the good, the bad and the ugly.	2004-01-09	14672753
Phospholipase C, but not InsP3 or DAG, -dependent activation of the muscarinic receptor-operated cation current in guinea-pig ileal smooth muscle cells.	2004-01	14662735
An easy and rapid method to determine aristolochic acids I and II with high sensitivity.	2004-01	13680054
Transgene-derived hepatocyte growth factor attenuates reactive renal fibrosis in aristolochic acid nephrotoxicity.	2003-12	14605273
Analysis of aristolochic acid in nine sources of Xixin, a traditional Chinese medicine, by liquid chromatography/atmospheric pressure chemical ionization/tandem mass spectrometry.	2003-11-24	14623612
Determination of aristolochic acids by capillary electrophoresis.	2003-11-05	14596334
H2O2-induced platelet aggregation and increase in intracellular Ca2+ concentration are blocked by inhibitors of intracellular signaling.	2003-11	14640963
Aristolochic acid nephropathy and the peritoneum: Functional, structural, and molecular studies.	2003-11	14531824
Aristolochic acid, an herbal carcinogen, sold on the Web after FDA alert.	2003-10-16	14561805
Human cytosolic enzymes involved in the metabolic activation of carcinogenic aristolochic acid: evidence for reductive activation by human NAD(P)H:quinone oxidoreductase.	2003-10	12869422
Effect of indomethacin on force responses and sarcoplasmic reticulum function in skinned skeletal muscle fibers and cytosolic [Ca2+] in myotubes.	2003-10	12814911
Arachidonic acid regulates surface expression of epithelial sodium channels.	2003-09-19	12837767
Role of phospholipase A2 activation and calcium in CYP2E1-dependent toxicity in HepG2 cells.	2003-09-05	12813050
The nephrotoxicity of Aristolochia manshuriensis in rats is attributable to its aristolochic acids.	2003-09	14586714
Bid activates multiple mitochondrial apoptotic mechanisms in primary hepatocytes after death receptor engagement.	2003-09	12949730
[Clinical analysis of two children with aristolochic acid nephropathy].	2003-07	14746690
[A comparative study of manchurian Dutchmanspipe and antibiotics induced acute tubular necrosis in renal cellular biological features].	2003-05	12800411
[Provide against possible trouble--on knowledge, prevention and treatment of adverse drug reactions].	2003-05	12800410
Effects of dexfenfluramine on aristolochic acid nephrotoxicity in a rat model for Chinese-herb nephropathy.	2003-04	12698237
The role of phospholipases A2 in the stimulation of neutrophil motility by cobra venoms.	2003-03	12657315
Zona pellucida induces activation of phospholipase A2 during acrosomal exocytosis in guinea pig spermatozoa.	2003-03	12604641
Enzymatic activity and inhibition of the neurotoxic complex vipoxin from the venom of Vipera ammodytes meridionalis.	2003-02-04	12562098
The importance of a histology-based diagnosis of interstitial nephropathy in two patients with renal insufficiency.	2003-02	12543907
Invasive urothelial carcinoma after exposure to Chinese herbal medicine containing aristolochic acid may occur without severe renal failure.	2003-02	12543902
Detection of aristolochic acid in Chinese phytomedicines and dietary supplements used as slimming regimens.	2003-01	12453725
Involvement of phosphatidic acid in both degranulation and oxidative activity in fMet-Leu-Phe stimulated polymorphonuclear leukocytes.	2003	12876387
Aristolochic acid and 'Chinese herbs nephropathy': a review of the evidence to date.	2003	12495362
Antithrombin activity of some constituents from Origanum vulgare.	2002-12	12490231
Bradykinin increases permeability by calcium and 5-lipoxygenase in the ECV304/C6 cell culture model of the blood-brain barrier.	2002-10-25	12384249
Is aristolochic acid a risk factor for Balkan endemic nephropathy-associated urothelial cancer?	2002-10-10	12216081
Determination of aristolochic acid I and II in North American species of Asarum and Aristolochia.	2002-10	12426949
Mechanism of endothelin-1-induced cytosolic Ca(2+) mobility in cultured H9c2 myocardiac ventricular cells.	2002-10	12135702
Structural basis of phospholipase A2 inhibition for the synthesis of prostaglandins by the plant alkaloid aristolochic acid from a 1.7 A crystal structure.	2002-09-10	12206661
[Aristolochic acid induced transdifferentiation and apoptosis in human tubular epithelial cells in vitro].	2002-09	12411187
An LC/DAD-UV/MS method for the rapid detection of aristolochic acid in plant preparations.	2002-09	12357407
Contribution of different taste cells and signaling pathways to the discrimination of "bitter" taste stimuli by an insect.	2002-08-15	12177223
[Comparison among families of Mutong].	2002-06	12774628
[Influence of long-term use of low dose caulis Aristolochiae manshuriensis on partial nephrectomized rats].	2002-06	12585193
[Current status of injury caused by Chinese herbal medicine and its counter measure].	2001-01	12577382

Patents

Sample Use Guides

In Vivo Use Guide

The FDA has issued a strong warning to consumers to avoid herbs containing the chemical aristolochic acid

Route of Administration: Oral

In Vitro Use Guide

It was studied the mechanism of aristolochic acid I (AA-I) nephrotoxicity by analyzing the uptake, subcellular distribution, and intracellular targets of AA-I in the human kidney cell line HK-2 using immunocytochemistry, immunoprecipitation, and LC-MS/MS. In HK-2 cells incubated with 20 ug/mL AA-I for different periods of time (up to 12 h). AA-I was detected by a specific monoclonal antibody (MAb) against AA-I, both in the cytoplasm and nuclei. Nuclear localization depended on the exposure time. A protein with the molecular weight of 100 kDa was immunoprecipitated with the anti-AA-I MAb from the AA-I-treated cell lysates and was identified by LC-MS/MS as alpha-actinin-4

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:08:36 GMT 2025` Edited by `admin` on `Mon Mar 31 22:08:36 GMT 2025`
Record UNII	KTM3D3H78E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM ARISTOLOCHATE

Common Name

English

ARISTOLOCHIC ACID, SODIUM SALT

Preferred Name

English

Aristolochic acid, sodium salt [WHO-DD]

Common Name

English

ARISTOLOCHIC ACID I, SODIUM SALT

Common Name

English

SODIUM ARISTOLOCHATE-I

Common Name

English

PHENANTHRO(3,4-D)-1,3-DIOXOLE-5-CARBOXYLIC ACID, 8-METHOXY-6-NITRO-, SODIUM SALT (1:1)

Systematic Name

English

PHENANTHRO(3,4-D)-1,3-DIOXOLE-5-CARBOXYLIC ACID, 8-METHOXY-6-NITRO-, SODIUM SALT

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

233-463-4