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 Y
KEGG	C08469 Y
ChEMBL	CHEMBL93353 Y
Jmol-3D images	Image 1
SMILES [O-][N+](=O)c1cc4c(c2c1c(C(=O)O)cc3OCOc23)cccc4OC
InChI 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) Y Key: BBFQZRXNYIEMAW-UHFFFAOYSA-N Y 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) Key: BBFQZRXNYIEMAW-UHFFFAOYAG
Properties
Molecular formula	C17H11NO7
Molar mass	341.27 g mol−1
Density	1.571g/cm3
Melting point	260 - 265 °C
Boiling point	615.5°C @760mmHg
Solubility in water	slightly soluble in water
Hazards
Flash point	326°C
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aristolochic acids are a family of carcinogenic, mutagenic, and nephrotoxic compounds commonly found in the Aristolochiaceae family of plants, including Aristolochia and Asarum, which are commonly used in Chinese herbal medicine.^[1] Aristolochic acid I is the most abundant of the aristolochic acids and is found in almost all Aristolochia species.^[2] Aristolochic acids are often accompanied by aristolactams.^[3]

Aristolochic acids may be a causative agent in Balkan nephropathy.^[4][5] Exposure to aristolochic acid is associated with a high incidence of uroepithelial tumorigenesis.^[6]

Aristolochic acids are slightly soluble in water, have a melting point between 281 and 286 degrees celsius,^[7] and have a bitter flavor.^[8]

See also

• List of herbs with known adverse effects
• Stephania tetrandra

References

1. ^ Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack. Adverse Drug Reactions. Springer. p. 123. ISBN 9783642006623. http://books.google.com/books?id=0NhAFmL2Q08C&pg=PA123. 
2. ^ Wu, Tian-Shung et al. (2005). "Chemical constituents and pharmacology of Aristolochia species". In Rahman, Atta-ur. Studies in Natural Products Chemistry: Bioactive Natural Products (Part L). Gulf Professional Publishing. p. 863. ISBN 9780444521712. http://books.google.com/books?id=UBHng8FfwgIC&pg=PA863. 
3. ^ Wink, Michael & Schimmer, Oskar (1999). "Modes of action of defensive secondary metabolites". In Wink, Michael. Functions of plant secondary metabolites and their exploitation in biotechnology. CRC Press. p. 75. ISBN 9780849340864. http://books.google.com/books?id=eFQgSjZIu8EC&pg=PA75. 
4. ^ Geacintov, Nicholas E. & Broyde, Suse, ed (2010). "Introduction and perspectives on the Chemistry and Biology of DNA Damage". The Chemical Biology of DNA Damage. Wiley-VCH. p. 7. ISBN 9783527322954. http://books.google.com/books?id=PueBA8SiPdAC&pg=PA7. 
5. ^ Wild, Chris et al., ed (2008). Molecular epidemiology of chronic diseases. John Wiley & Sons. p. 113. ISBN 9780470027431. http://books.google.com/books?id=w86iv6ib-zcC&pg=PA113. 
6. ^ Ronco, Claudio et al., ed (2008). Critical care nephrology. Elsevier Health Sciences. p. 1699. ISBN 9781416042525. http://books.google.com/books?id=XkKn96HThzEC&pg=PA1699. 
7. ^ Barceloux, Donald G. (2008). "Aristolochic acid and Chinese Herb nephropathy". Medical toxicology of natural substances: foods, fungi, medicinal herbs, plants, and venomous animals. John Wiley & Sons. p. 384. ISBN 9780471727613. http://books.google.com/books?id=HWUzlp_V6uIC&pg=PA384. 
8. ^ Offermanns, S. & Amara, Susan G., ed (2006). Reviews of physiology, biochemistry and pharmacology, Volume 154. Birkhäuser. p. 56. ISBN 9783540303848. http://books.google.com/books?id=2CgsRIL2lGAC&pg=PA56. 

Further reading

• Aronson, J.K. (2008). "Aristolochicae". Meyler's side effects of herbal medicines. Elsevier. p. 55. ISBN 9780444532695. http://books.google.com/books?id=ibxfK1l6oXoC&pg=PA55. 
• 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.)
• Mills, Simon & Bone, Kerry (2005). "Aristolochic Acid Nephropathy". The essential guide to herbal safety. Elsevier Health Sciences. p. 15. ISBN 9780443071713. http://books.google.com/books?id=85M0N8UioCcC&pg=PA15. 
• 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.

External links

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