Aristolochic acid Chemical Properties

Melting point:

260 °C

Boiling point:

476.92°C (rough estimate)

Density 

1.3162 (rough estimate)

refractive index 

1.4500 (estimate)

storage temp. 

2-8°C

solubility 

DMSO: soluble

form 

powder

pka

2.99±0.20(Predicted)

color 

yellow

InChIKey

LIDQMWRBMLSXLL-UHFFFAOYSA-N

CAS DataBase Reference

313-67-7(CAS DataBase Reference)

IARC

1 (Vol. 82, 100A) 2012, 1 (Vol. 82, 100A) 2012

Safety Information

Hazard Codes 

T

Risk Statements 

25-68-36/37/38-23/24/25-45

Safety Statements 

7-35-45-36/37/39-26-53

RIDADR 

UN 1544 6.1/PG 3

WGK Germany 

3

RTECS 

CF3325000

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29329990

Toxicity

LD50 in male, female mice, male, female rats (mg/kg): 38.4, 70.1, 82.5, 74.0 i.v.; 55.9, 106.1, 203.4, 183.9 orally (Mengs)

MSDS

• Language:English Provider:8-Methoxy-3,4-methylenedioxy-10-nitrophenanthrene-1-carboxylic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Aristolochic acid Usage And Synthesis

Description

Aristolochic acid first appeared in Chinese medicine in the fifth century AD, while it was used to treat kidney and urinary diseases, as well as gout, snakebites, and a variety of other ailments. In many of these cases, aristolochic acid was just one of the main components of the salves. In the first century, aristolochic acid was first described as a composition of ingested medicine to treat symptoms such as asthma, hiccups, pains, and spasms.

Chemical Properties

Shiny brown leaflets or a yellow or white powder.

Physical properties

Appearance: brown sheet crystal or yellow powder. Solubility: practically insoluble in water and soluble in ethanol, chloroform, ethyl ether, acetone, glacial acetic acid, and aniline. Melting point: 260–265?°C (500–509?°F; 533–538?K).

History

At a clinic in Brussels, Belgium, a group of women who had all taken the same weight loss supplement, Aristolochia fangchi, which contained aristolochic acid, was first diagnosed with aristolochic acid poisoning. Balkan endemic nephropathy (BEN) was later found to be also the result of aristolochic acid (AA) consumption. Balkan endemic nephropathy is likely caused by low-level AA exposure, possibly from the contamination of wheat flour seeds by Aristolochia clematitis. BEN falls under the umbrella of what is now known as aristolochic acid nephropathy, the prevalent symptom of AA poisoning .

Uses

PLA2 inhibitor

Uses

Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids

Uses

Aristolochic acid I is a potent phospholipase A₂ inhibitor. Aristolochic acid I induces tumor formation in rat kidneys and apoptosis in human renal proximal tubular epithelial cells.

Definition

ChEBI: A monocarboxylic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is b th carcinogenic and nephrotoxic.

Indications

Due to the widely associated kidney problems and urothelial cancers, the FDA has issued warnings regarding consumption of AA-containing supplements.

brand name

Acidum aristolchicum;Descresepet;Fago-araxin;Fluocinova;Predno-facilus haemota.

World Health Organization (WHO)

Extracts of aristolochiaceae have traditionally been used as a bitter for which a broad range of therapeutic effects has been claimed. Aristolochic acid is claimed to promote phagocytosis and to have immunostimulant activity. However, in 1981, a three-month toxicity study in rats revealed the carcinogenic potential of aristolochic acid and preparations containing this substance have since been withdrawn in several countries.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Potent phospholipase A2 inhibitor, including calcium ionophore-induced phospholipase A2 activity in neutrophils. Kidney tumor initiator in experimental animal model.

Pharmacology

In 1992, some cases of women present with a rapidly progressive renal failure after having a slimming regimen including powdered extracts of Chinese herbal preparations. This outbreak of renal failure eventually resulted in about 100 cases in 1998, 70% of them being in end-stage renal disease (ESRD) . Recent research has confirmed that the main reason leading to renal injury is aristolochic acid found in many Chinese herbs . Aristolochic acid, a potent human carcinogen from Aristolochia plants, is associated with the incidence of urothelial carcinoma in the upper urinary tract (UUC). After the metabolic activation, aristolochic acid reacted with DNA to form aristolactam (AL)-DNA adducts. Mainly pathological changes are in renal cortex, where they serve as a specific biomarker, and are also found in urothelium, where they lead to a unique mutational signature in the TP53 tumorsuppressor gene. The conclusion is that exposure to aristolochic acid gives rise to the incidence of UUC, a finding with significant implications for the global public health .

Clinical Use

Aristolochia species are nephrotoxic and carcinogenic, and FDA has issued warnings regarding consumption of AA-containing supplements.

Safety Profile

Confirmed carcinogen. Poison by ingestion, intraperitoneal, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NO,. Potentially Toxic Chemicals: April 1982." Vol. 5 No. 1: The Ministry of Health of the Federal Republic of Germany has withdrawn from the national market drugs containing aristolochic acid. The decision resulted from the demonstration of a carcinogenic potential in a three-month ingestion toxicity study undertaken in rats. Aristolochic acid is claimed to promote phagocytosis and to have immunostimulant activity. A growth-inhibiting effect on experimentally induced tumors has been described, but this effect has not been shown to have any clinical relevance. Extracts of species of Aristolochiacea have tradtionally been used as a bitter, and a broad range of therapeutic effects has been claimed.

Potential Exposure

Aristolochic acids are alkaloids used primarily as a chemical intermediate for pharmaceuticals, lab chemicals, herbal extract, drug.

Shipping

UN1544 Alkaloids, solid, n.o.s. or Alkaloid salts, solid, n.o.s. poisonous, Hazard Class: 6.1; Labels: 6.1- Poisonous materials, Technical Name Required. PG III.

Incompatibilities

Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator. All federal, state, and local environmental regulations must be observed.

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