3790 Cyclopiazonic acid Cyclopiazonic acid (CPA) is a myxotoxin originally isolated from Penicillium cyclopium and subsequently from Penicillium griseofulvum, Penicillium camembertii, Aspergillus flavus and Aspergillus versicolor. It is often found co-occurring with aflatoxins. CPA is a natural contaminant of corn, peanuts, and sunflowers, as well as various types of cheese, sausages, and salamis. It may also occur in eggs, milk and meats from animal that have consumed CPA-contaminated feed and is toxic in high concentrations. (L1961, A2999) 18172-33-3 2908 C20H20N2O3 White powder. Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Cyclopiazonic acid is potent and specific inhibitor of the endoplasmic and sarcoplasmic reticulum Ca+-dependent ATPases, which are essential for calcium reuptake in the muscle contraction-relaxation cycle. CPA blocks the calcium access channel and rigidifies a subset of transmembrane helices in a nonnative configuration that is incompatible with calcium binding. Inhibition of Ca2+-ATPases results in cell death through the activation of stress-response and apoptotic pathways within the endoplasmic reticulum and mitochondria. CPA can also induce both secretion and mRNA levels of proinflammatory cytokines, likely leading to macrophage activation and immunotoxic effects. In addition, it has been shown to be mutagenic and genotoxic. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (A2998, A2999, A3001, A3014) LD50: 13 mg/kg (Intraperitoneal, Mouse) (A3000) LD50: 2.3 mg/kg (Intraperitoneal, Rat) (A3001) No indication of carcinogenicity to humans (not listed by IARC). Cyclopiazonic acid (CPA) is a myxotoxin originally isolated from Penicillium cyclopium and subsequently from Penicillium griseofulvum, Penicillium camembertii, Aspergillus flavus and Aspergillus versicolor. It is often found co-occurring with aflatoxins. CPA is a natural contaminant of corn, peanuts, and sunflowers, as well as various types of cheese, sausages, and salamis. It may also occur in eggs, milk and meats from animal that have consumed CPA-contaminated feed. (L1961, A2999) Cyclopiazonic acid affects muscle function and may also be immunotoxic, genotoxic, and mutagenic. (A2999, A3000, A3001) Animals studies have shown cyclopiazonic acid to cause symptoms such as tremors, convulsions, dyspnoea, hypokinesia, hypothermia, sedation, tachycardia, and tachypnoea. (A3000) 2010-05-05T19:41:24Z 2026-04-03T05:06:43Z http://en.wikipedia.org/wiki/Cyclopiazonic_acid true CC(=O)C1=C(O)N2C(C3C(CC4=C5C(NC=C35)=CC=C4)C2(C)C)C1=O C20H20N2O3 InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,25H,7H2,1-3H3 RLOAZVAJNNPPDI-UHFFFAOYSA-N 336.3844 336.147392516 Exogenous Solid 2805 CHEM002705 DTXSID00891798 NS00018336 5-acetyl-6-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),5,11(18),12,14-pentaen-4-one