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Aristolochic acid information


Aristolochic acid I
Aristolochic acid molecule
Names
Preferred IUPAC name
8-Methoxy-6-nitro-2H-phenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
Other names
Aristinic acid; Aristolochia yellow; Aristolochic acid A; Aristolochin;Aristolochine; Descresept; Tardolyt;TR 1736
Identifiers
CAS Number
  • 313-67-7 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL93353 checkY
ChemSpider
  • 2149 checkY
KEGG
  • C08469 checkY
PubChem CID
  • 2236
UNII
  • 94218WFP5T checkY
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) checkY
    Key: BBFQZRXNYIEMAW-UHFFFAOYSA-N checkY
  • 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
SMILES
  • [O-][N+](=O)c1cc4c(c2c1c(C(=O)O)cc3OCOc23)cccc4OC
Properties
Chemical formula
C17H11NO7
Molar mass 341.275 g·mol−1
Appearance yellow powder
Melting point 260 to 265 °C (500 to 509 °F; 533 to 538 K)
Solubility in water
Slightly soluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Aristolochic acids (English: /əˌrɪstəˈlkɪk/) are a family of carcinogenic, mutagenic, and nephrotoxic phytochemicals commonly found in the flowering plant family Aristolochiaceae (birthworts). Aristolochic acid (AA) I is the most abundant one.[1] The family Aristolochiaceae includes the genera Aristolochia and Asarum (wild ginger), which are commonly used in Chinese herbal medicine.[2][3] Although these compounds are widely associated with kidney problems, liver and urothelial cancers, the use of AA-containing plants for medicinal purposes has a long history. The FDA has issued warnings regarding consumption of AA-containing supplements.

  1. ^ Wu, Tian-Shung; et al. (2005). "Chemical constituents and pharmacology of Aristolochia species". In Rahman, Atta-ur (ed.). Studies in Natural Products Chemistry: Bioactive Natural Products (Part L). Gulf Professional Publishing. p. 863. ISBN 978-0-444-52171-2.
  2. ^ Heinrich M, Chan J, Wanke S, Neinhuis C, Simmonds MS (August 2009). "Local uses of Aristolochia species and content of nephrotoxic aristolochic acid 1 and 2--a global assessment based on bibliographic sources". J Ethnopharmacol. 125 (1): 108–44. doi:10.1016/j.jep.2009.05.028. PMID 19505558.
  3. ^ Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack (ed.). Adverse Drug Reactions. Springer. p. 123. ISBN 978-3-642-00662-3.

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Aristolochic acid

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Aristolochic acids (English: /əˌrɪstəˈloʊkɪk/) are a family of carcinogenic, mutagenic, and nephrotoxic phytochemicals commonly found in the flowering...

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Balkan endemic nephropathy

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Romania, and Bulgaria. It is caused by small long-term doses of aristolochic acid in the diet. The disease primarily affects people 30 to 60 years of...

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Aristolochia

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ancient medicine, Aristolochia is known to contain the lethal toxin aristolochic acid. The Bencao Gangmu, compiled by Li Shi-Zhen in the latter part of...

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Asarum canadense

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contains aristolochic acid, a carcinogenic compound. The United States Food and Drug Administration warns that consumption of aristolochic acid-containing...

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Battus philenor hirsuta

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aristolochic acid. The larvae sequester the toxin, and both the juvenile and adult butterflies have high and toxic concentrations of the aristolochic...

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Ginger

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contains aristolochic acid, a carcinogenic compound. The United States Food and Drug Administration warns that consumption of aristolochic acid-containing...

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Aristolochia grandiflora

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plant. The use of this plant poses a risk as it contains the toxin aristolochic acid which is carcinogenic. The USDA has banned all products containing...

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Aristolochia indica

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1:1 mixture of two forms, aristolochic acid I and aristolochic acid II. In addition to its carcinogenicity, aristolochic acid is also highly nephrotoxic...

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Aristolochia macrophylla

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the past few decades for the discovery of a potent compound called aristolochic acid, which has been the focus of debate due its harmful side effects....

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Battus philenor

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butterfly gets its common name. This plant genus is known to have active aristolochic acids, which pipevine swallowtail larvae sequester and use for defensive...

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IARC group 1 Carcinogens

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treated Phenacetin, analgesic mixtures containing Plants containing aristolochic acid Polychlorinated biphenyls, dioxin-like, with a Toxicity Equivalency...

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medicines suspected of containing aristolochic acid, unless laboratory testing indicated they were negative for aristolochic acid. The traditional route of ingestion...

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Swallowtail butterfly

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List of herbs with known adverse effects

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Magazine. 2012. "Aristolochic Acid: FDA Concerned About Botanical Products, Including Dietary Supplements, Containing Aristolochic Acid". FDA. 2001. Daniele...

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Asarum

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consuming Asarum, as it is nephrotoxic and contains the potent carcinogen aristolochic acid. The birthwort family also contains the genus Aristolochia, known...

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Nephrotoxicity

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Demeclocycline Foscarnet Lead, Uranium, mercury, and cadmium salts Aristolochic acid, found in some plants and in some herbal supplements derived from...

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Bladder cancer

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of aristolochic acid present in many Chinese herbal medications has been shown to cause urothelial carcinoma and kidney failure. Aristolochic acid activates...

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Transitional epithelium

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carcinogens in the urine and is a leading cause of bladder cancer. Aristolochic acid, a compound found in plants of the family Aristolochiaceae, also causes...

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Aristolochia rotunda

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polyxena). Eating the leaves of the plant the larvae this insect ingest aristolochic acid that make them poisonous to birds. This plant is common in Mediterranean...

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Aristolochia didyma

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an Ayahuasca session. Caution is required; injuries are linked to aristolochic acid contained in some species of this family, as in Belgium incorrect...

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List of traditional Chinese medicines

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Aristolochia californica

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metabolites known as aristolochic acids. Aristolochic acids are compounds that are composed of nitrophenanthrene carboxylic acids that have been utilized...

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Aristolochia clematitis

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the plant are also reported. The link between kidney failure and aristolochic acid, which the plant contains, was discovered after a clinic for obesity...

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Uddanam nephropathy

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Balkan endemic nephropathy was found to be caused by chronic intake of aristolochic acid, while the causes of Mesoamerican nephropathy that occurs in sugar...

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Assembly theory

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Synthesis of aristolochic acid. Complex molecules require many steps to be synthesized. And the more steps are required to synthesize a particular molecule...

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Opsin

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function not only as photoreceptors, but also as chemoreceptors for aristolochic acid. These opsins still have Lys2967.43 like other opsins. However, if...

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Phytochemical

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phytochemicals are known phytotoxins that are toxic to humans; for example aristolochic acid is carcinogenic at low doses. Some phytochemicals are antinutrients...

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Methylglyoxal

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acetone and threonine. Illustrative of the myriad pathways to MGO, aristolochic acid caused 12-fold increase of methylglyoxal from 18 to 231 μg/mg of kidney...

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Doctrine of signatures

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but is carcinogenic and very damaging to the kidneys, owing to its aristolochic acid content. As a defense against predation, many plants contain toxic...

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Pachliopta aristolochiae

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Aristolochia, family Aristolochiaceae, and they sequester toxins such as aristolochic acid in their bodies. This makes the adults toxic to vertebrate predators...

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