Aristolochic acid

Aristolochic acid
IUPAC name 8-methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
other names Aristolochic acid I Aristinic acid Aristolochia yellow Aristolochic acid A Aristolochin Aristolochine Descresept Isoaristolochic acid Tardolyt TR 1736 Aristolochic acid II Aristolochic acid B
Identifiers
CAS number	313-67-7
PubChem	2236
ChemSpider	2149
SMILES	[O-][N+](=O)c1cc4c(c2c1c(C(=O)O)cc3OCOc23)cccc4OC
InChI	1/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)
InChI key	BBFQZRXNYIEMAW-UHFFFAOYAG
Properties
Molecular formula	C17H11NO7
Molar mass	341.27 g mol−1
Density	? g/cm3
Melting point	260 - 265 °C
Boiling point	°C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aristolochic acid is a rodent carcinogen found in Aristolochia and Asarum, both in the Aristolochiaceae family of plants. Aristolochic acid is composed of a ~1:1 mixture of two forms, aristolochic acid I and aristolochic acid II.

In addition to its carcinogenicity, aristolochic acid is also highly nephrotoxic and may be a causative agent in Balkan nephropathy. Aristolochic acid is linked to increase in urinary tract cancers as well. However, despite these well-documented dangers, aristolochic acid still is present sometimes in herbal remedies (such as for weight loss), primarily because of substitution of innocuous herbs with Aristolochia species.

The following substitutions (not a complete list) with Aristolochia species have been reported:

• Stephania tetrandra (reported in Belgium).
• Solanum lyratum 白毛藤 báimáoténg (pak mo tang), also known as 白英 báiyīng (reported in Hong Kong).
• Various Akebia species (Akebiae Caulis) 木通 mùtōng (reported in Mainland China).

See also

• List of herbs with known adverse effects

References

• FDA Warns Consumers to Discontinue Use of Botanical Products that Contain Aristolochic acid. April 11, 2001.
• FDA Concerned About Botanical Products, Including Dietary Supplements, Containing Aristolochic Acid May 2000.
• Health Canada advising not to use products labelled to contain Aristolochia. August 2001. Website - http://www.hc-sc.gc.ca/ahc-asc/media/advisories-avis/2001/2001_91_e.html
• Wing-Tat Poon, Chi-Kong Lai, Albert Yan-Wo Chan, 2007. "Aristolochic Acid Nephropathy: The Hong Kong Perspective." Hong Kong Journal of Nephrology, 9(1):7-14.
• Lai M., 2009. Journal of National Cancer Institute. doi:10.1093/jnci/djp467. (Short summary published as "Chinese herbal products containing aristolochic acid were associated with urinary tract cancer" in "HemOnc today", page 28, dated 2010-01-25.)

External links

• Complete list of warnings from the US Food and Drug Administration

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