U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of SODIUM ARISTOLOCHATE

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

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

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