Lapachol

Lapachol
Image illustrative de l’article Lapachol
Identification
Nom UICPA 4-hydroxy-3-(3-méthylbut-2-ényl)naphtaléne-1,2-dione
No CAS 84-79-7
No ECHA 100.001.421
No CE 201-563-7
PubChem 3884
SMILES
InChI
Apparence cristaux jaunes
Propriétés chimiques
Formule C15H14O3  [Isomères]
Masse molaire[1] 242,269 9 ± 0,013 9 g/mol
C 74,36 %, H 5,82 %, O 19,81 %,
Propriétés physiques
T° fusion 139,5 °C[2]
Écotoxicologie
DL50 487 mg·kg-1 (souris, oral)[3]
400 mg·kg-1 (souris, i.p.)[4]
LogP 3,130[2]
Unités du SI et CNTP, sauf indication contraire.
modifier 

Le lapachol est un composé organique naturellement présent dans l'arbre lapacho[5], d'où il tire d'ailleurs son nom. Chimiquement, c'est un dérivé de la naphtoquinone, proche de la vitamine K.

Certains l'ont étudié comme possible traitement de certains types de cancers, mais il a été trouvé que son potentiel dans ce domaine est faible, dû aux effets secondaires qu'engendre sa toxicité[6],[7],[8],[9].

Notes et références

  1. ↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
  2. ↑ a et b (en) « Lapachol », sur ChemIDplus, consulté le 30 avril 2011
  3. ↑ Toxicology and Applied Pharmacology. Vol. 17, Pg. 1, 1970. PMID
  4. ↑ Journal of Medicinal Chemistry. Vol. 26, Pg. 570, 1983.
  5. ↑ Record, Samuel J., Lapachol, Tropical Woods (1925), 1 7-9.
  6. ↑ (en) Felício AC, Chang CV, Brandão MA, Peters VM, Guerra Mde O, « Fetal growth in rats treated with lapachol », Contraception, vol. 66, no 4,‎ , p. 289–93 (PMID 12413627, DOI 10.1016/S0010-7824(02)00356-6)
  7. ↑ Oral toxicology studies with lapachol. Morrison, Robert K.; Brown, Donald Emerson; Oleson, Jerome J.; Cooney, David A. Toxicology and Applied Pharmacology (1970), 17(1), 1-11.
  8. ↑ (en) Guerra Mde O, Mazoni AS, Brandão MA, Peters VM, « Toxicology of Lapachol in rats: embryolethality », Brazilian journal of biology = Revista brasleira de biologia, vol. 61, no 1,‎ , p. 171–4 (PMID 11340475)
  9. ↑ (en) de Cássia da Silveira E Sá R, de Oliveira Guerra M, « Reproductive toxicity of lapachol in adult male Wistar rats submitted to short-term treatment », Phytotherapy research : PTR, vol. 21, no 7,‎ , p. 658–62 (PMID 17421057, DOI 10.1002/ptr.2141)

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