Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H11NO7 |
| Molecular Weight | 341.2717 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2C=C(C3=C(C4=C(OCO4)C=C3C(O)=O)C2=CC=C1)[N+]([O-])=O
InChI
InChIKey=BBFQZRXNYIEMAW-UHFFFAOYSA-N
InChI=1S/C17H11NO7/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)
| Molecular Formula | C17H11NO7 |
| Molecular Weight | 341.2717 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|---|
Target ID: Q9UNQ0|||Q86V64 Gene ID: 9429.0 Gene Symbol: ABCG2 Target Organism: Homo sapiens (Human) |
|||
Target ID: O43707 Gene ID: 81.0 Gene Symbol: ACTN4 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Arachidonic acid released by phospholipase A(2) activation triggers Ca(2+)-dependent apoptosis through the mitochondrial pathway. | 2004-06-11 |
|
| Fanconi's syndrome and subsequent progressive renal failure caused by a Chinese herb containing aristolochic acid. | 2004-06 |
|
| Aristolochic acid nephropathy: what we know and what we have to do. | 2004-06 |
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| Regulation of Na+ transport by aldosterone: signaling convergence and cross talk between the PI3-K and MAPK1/2 cascades. | 2004-06 |
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| Insecticidal activity of chemical constituents from Aristolochia pubescens against Anticarsia gemmatalis larvae. | 2004-04 |
|
| 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 |
|
| DNA adducts and p53 mutations in a patient with aristolochic acid-associated nephropathy. | 2004-04 |
|
| Purification of a Class B1 platelet aggregation inhibitor phospholipase A2 from Indian cobra (Naja Naja) venom. | 2004-03 |
|
| NMR regulatory analysis: determination and characterization of Chinese-herb aristolochic acids. | 2004-03 |
|
| Mediating of caspase-independent apoptosis by cadmium through the mitochondria-ROS pathway in MRC-5 fibroblasts. | 2004-02-01 |
|
| [Cellular mechanism of renal proximal tubular epithelial cell injury induced by aristolochic acid I and aristololactam I]. | 2004-02 |
|
| Herbal bioactivation: the good, the bad and the ugly. | 2004-01-09 |
|
| 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 |
|
| An easy and rapid method to determine aristolochic acids I and II with high sensitivity. | 2004-01 |
|
| Transgene-derived hepatocyte growth factor attenuates reactive renal fibrosis in aristolochic acid nephrotoxicity. | 2003-12 |
|
| 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 |
|
| Determination of aristolochic acids by capillary electrophoresis. | 2003-11-05 |
|
| H2O2-induced platelet aggregation and increase in intracellular Ca2+ concentration are blocked by inhibitors of intracellular signaling. | 2003-11 |
|
| Aristolochic acid nephropathy and the peritoneum: Functional, structural, and molecular studies. | 2003-11 |
|
| Aristolochic acid, an herbal carcinogen, sold on the Web after FDA alert. | 2003-10-16 |
|
| 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 |
|
| Effect of indomethacin on force responses and sarcoplasmic reticulum function in skinned skeletal muscle fibers and cytosolic [Ca2+] in myotubes. | 2003-10 |
|
| Arachidonic acid regulates surface expression of epithelial sodium channels. | 2003-09-19 |
|
| Role of phospholipase A2 activation and calcium in CYP2E1-dependent toxicity in HepG2 cells. | 2003-09-05 |
|
| The nephrotoxicity of Aristolochia manshuriensis in rats is attributable to its aristolochic acids. | 2003-09 |
|
| Bid activates multiple mitochondrial apoptotic mechanisms in primary hepatocytes after death receptor engagement. | 2003-09 |
|
| [Clinical analysis of two children with aristolochic acid nephropathy]. | 2003-07 |
|
| [A comparative study of manchurian Dutchmanspipe and antibiotics induced acute tubular necrosis in renal cellular biological features]. | 2003-05 |
|
| [Provide against possible trouble--on knowledge, prevention and treatment of adverse drug reactions]. | 2003-05 |
|
| Effects of dexfenfluramine on aristolochic acid nephrotoxicity in a rat model for Chinese-herb nephropathy. | 2003-04 |
|
| The role of phospholipases A2 in the stimulation of neutrophil motility by cobra venoms. | 2003-03 |
|
| Zona pellucida induces activation of phospholipase A2 during acrosomal exocytosis in guinea pig spermatozoa. | 2003-03 |
|
| Enzymatic activity and inhibition of the neurotoxic complex vipoxin from the venom of Vipera ammodytes meridionalis. | 2003-02-04 |
|
| The importance of a histology-based diagnosis of interstitial nephropathy in two patients with renal insufficiency. | 2003-02 |
|
| Invasive urothelial carcinoma after exposure to Chinese herbal medicine containing aristolochic acid may occur without severe renal failure. | 2003-02 |
|
| Detection of aristolochic acid in Chinese phytomedicines and dietary supplements used as slimming regimens. | 2003-01 |
|
| Involvement of phosphatidic acid in both degranulation and oxidative activity in fMet-Leu-Phe stimulated polymorphonuclear leukocytes. | 2003 |
|
| Aristolochic acid and 'Chinese herbs nephropathy': a review of the evidence to date. | 2003 |
|
| Antithrombin activity of some constituents from Origanum vulgare. | 2002-12 |
|
| Bradykinin increases permeability by calcium and 5-lipoxygenase in the ECV304/C6 cell culture model of the blood-brain barrier. | 2002-10-25 |
|
| Is aristolochic acid a risk factor for Balkan endemic nephropathy-associated urothelial cancer? | 2002-10-10 |
|
| Determination of aristolochic acid I and II in North American species of Asarum and Aristolochia. | 2002-10 |
|
| Mechanism of endothelin-1-induced cytosolic Ca(2+) mobility in cultured H9c2 myocardiac ventricular cells. | 2002-10 |
|
| 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 |
|
| [Aristolochic acid induced transdifferentiation and apoptosis in human tubular epithelial cells in vitro]. | 2002-09 |
|
| An LC/DAD-UV/MS method for the rapid detection of aristolochic acid in plant preparations. | 2002-09 |
|
| Contribution of different taste cells and signaling pathways to the discrimination of "bitter" taste stimuli by an insect. | 2002-08-15 |
|
| [Comparison among families of Mutong]. | 2002-06 |
|
| [Influence of long-term use of low dose caulis Aristolochiae manshuriensis on partial nephrectomized rats]. | 2002-06 |
|
| [Current status of injury caused by Chinese herbal medicine and its counter measure]. | 2001-01 |
Patents
Sample Use Guides
The FDA has issued a strong warning to consumers to avoid herbs containing the chemical aristolochic acid
Route of Administration:
Oral
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
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| Record UNII |
94218WFP5T
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C000228
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ARISTOLOCHIC ACID
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
