A mycotoxin anthelmintic
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Paraherquamide A

Item No. 26685

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1'R,5'aS,7'R,8'aS,9'aR)-2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-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
CAS Number
77392-58-6
Synonyms
  • (–)-Paraherquamide
  • VM 29919
Molecular Formula
C28H35N3O5
Formula Weight
493.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
λmax
226 nm
SMILES
CC(C=CO1)(C)OC2=C1C(NC([C@]34C[C@](CN(CC[C@]5(O)C)[C@]5(C6=O)C7)(N6C)[C@]7([H])C3(C)C)=O)=C4C=C2
InChi Code
InChI=1S/C28H35N3O5/c1-23(2)10-12-35-20-17(36-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31-11-9-25(5,34)28(31,22(33)30(26)6)13-18(26)24(27,3)4/h7-8,10,12,18,34H,9,11,13-15H2,1-6H3,(H,29,32)/t18-,25+,26+,27+,28-/m0/s1
InChi Key
UVZZDDLIOJPDKX-ITKQZBBDSA-N
Origin
Fungus/Penicillium simplicissimum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Paraherquamide A is a mycotoxin anthelmintic originally isolated from P. paraherquei.1 It binds to acetylcholine receptors (IC50 = 0.5 nM for head homogenates of M. domestica) and acts as an antagonist.1,2 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.3,4 It is toxic to mice (LD50 = 14.9 mg/kg).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Robertson, A.P., Clark, C.L., Burns, T.A., et al. Paraherquamide and 2-deoxy-paraherquamide distinguish cholinergic receptor subtypes in Ascaris muscle. J. Pharmacol. Exp. Ther. 302(3), 853-860 (2002).

    2. Nauen, R., Ebbinghaus, U., and Tietjen, K. Ligands of the nicotinic acetylcholine receptor as insecticides. Pest. Manag. Sci. 55(5), 608-610 (1999).

    3. Ondeyka, J.G., Goegelman, R.T., Schaeffer, J.M., et al. Novel antinematodal and antiparasitic agents from Penicillium charlesii. J. Antibiot. (Tokyo) 43(11), 1375-1379 (1990).

    4. Ostlind, D.A., Mickle, W.G., Ewanciw, D.V., et al. Efficacy of paraherquamide against immature Trichostrongylus colubriformis in the gerbil (Meriones unguiculatus). Res. Vet. Sci. 48(2), 260-261 (1990).

    5. Shoop, W.L., Haines, H.W., Eary, C.H., et al. Acute toxicity of paraherquamide and its potential as an anthelmintic. Am. J. Vet. Res. 53(11), 2032-2034 (1992).