| Identification | Back Directory | [Name]
paraherquamide | [CAS]
77392-58-6 | [Synonyms]
VM 29919
paraherquamide
(-)-Paraherquamide A
Spiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-9,10'(10H)-dione, 2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-, (1'R,5'aS,7'R,8'aS,9'aR)- | [Molecular Formula]
C28H35N3O5 | [MOL File]
77392-58-6.mol | [Molecular Weight]
493.59 |
| Chemical Properties | Back Directory | [Melting point ]
244-247° (dec) | [alpha ]
D22 -28° (c = 0.43 in methanol) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble | [form ]
White to off-white powder. |
| Hazard Information | Back Directory | [Description]
Paraherquamide A is a mycotoxin anthelmintic originally isolated from P. paraherquei. It binds to acetylcholine receptors (IC50 = 0.5 nM for head homogenates of M. domestica) and acts as an antagonist. Paraherquamide A is toxic to C. elegans (LD50 = 2.5 μg/ml) and effective against T. colubriformis infection in gerbils when used at doses ranging from 0.39 to 200 mg/kg. It is toxic to mice (LD50 = 14.9 mg/kg). | [Uses]
Paraherquamide A is a selective, competitive, cholinergic antagonist. | [Uses]
Paraherquamide A was first reported as a mycotoxin related to the indole tremorgenic mycotoxins. Subsequent research identified a potent, non-toxic paralysis of nematodes which led to the metabolite's development as a candidate anthelmintic. Paraherquamide A is a selective, competitive, cholinergic antagonist that distinguishes subtypes of cholinergic receptors. | [References]
[1] ALAN P ROBERTSON. Paraherquamide and 2-deoxy-paraherquamide distinguish cholinergic receptor subtypes in Ascaris muscle.[J]. Journal of Pharmacology and Experimental Therapeutics, 2002, 302 1: 853-860. DOI: 10.1124/jpet.102.034272
[2] RALF NAUEN Klaus T Ulrich Ebbinghaus. Ligands of the nicotinic acetylcholine receptor as insecticides?[J]. Pest Management Science, 1999, 55 5: 608-610. DOI: 10.1002/(sici)1096-9063(199905)55:5<608::aid-ps967>3.0.co;2-y
[3] J G ONDEYKA. Novel antinematodal and antiparasitic agents from Penicillium charlesii. I. Fermentation, isolation and biological activity.[J]. Journal of Antibiotics, 1990, 43 11: 1375-1379. DOI: 10.7164/antibiotics.43.1375
[4] D.A. OSTLIND. Efficacy of paraherquamide against immature Trichostrongylus colubriformis in the gerbil (Meriones unguiculatus)[J]. Research in veterinary science, 1990, 48 2: Pages 260-261. DOI: 10.1016/s0034-5288(18)31003-8
[5] W L SHOOP. Acute toxicity of paraherquamide and its potential as an anthelmintic.[J]. American journal of veterinary research, 1992, 53 11: 2032-2034.
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