Triptolide

Not to be confused with Triptonide, another derivative of Tripterygium wilfordii.
Triptolide
Names
Preferred IUPAC name
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,9bS)-6-Hydroxy-8b-methyl-6a-(propan-2-yl)-3b,4,4a,5a,6,6a,7a,7b,8a,8b,9,10-dodecahydrotris(oxireno)[2′,3′:4b,5;2′′,3′′:6,7;2′′′,3′′′:8a,9]phenanthro[1,2-c]furan-1(3H)-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.208.723 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1
    Key: DFBIRQPKNDILPW-CIVMWXNOSA-N
  • CC(C)[C@@]12[C@@H](O1)[C@H]3[C@@]4(O3)[C@]5(CCC6=C([C@@H]5C[C@H]7[C@]4([C@@H]2O)O7)COC6=O)C
Properties
C20H24O6
Molar mass 360.406 g·mol−1
0.017 mg/mL[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Triptolide is a diterpenoid epoxide which is produced by the thunder god vine, Tripterygium wilfordii. It has in vitro and in vivo activities against mouse models of polycystic kidney disease[2] and pancreatic cancer, but its physical properties[3] and severe toxicity[4] limit its therapeutic potential. Consequently, a synthetic water-soluble prodrug, minnelide, is being studied clinically instead.[3][5]

Triptolide is a component of ContraPest, a contraceptive pest control liquid used to reduce rat populations in the United States.

  1. ^ Patil, Satish; Lis, Lev G.; Schumacher, Robert J.; Norris, Beverly J.; Morgan, Monique L.; Cuellar, Rebecca A. D.; Blazar, Bruce R.; Suryanarayanan, Raj; Gurvich, Vadim J.; Georg, Gunda I. (10 December 2015). "Phosphonooxymethyl Prodrug of Triptolide: Synthesis, Physicochemical Characterization, and Efficacy in Human Colon Adenocarcinoma and Ovarian Cancer Xenografts". Journal of Medicinal Chemistry. 58 (23): 9334–9344. doi:10.1021/acs.jmedchem.5b01329. PMC 4678411. PMID 26596892.
  2. ^ Leuenroth, Stephanie (2007). "Triptolide is a traditional Chinese medicine-derived inhibitor of polycystic kidney disease". PNAS. 104 (11): 4389–4394. Bibcode:2007PNAS..104.4389L. doi:10.1073/pnas.0700499104. PMC 1838612. PMID 17360534.
  3. ^ a b Chugh, Rohit (2012). "A Preclinical Evaluation of Minnelide as a Therapeutic Agent Against Pancreatic Cancer". Science Translational Medicine. 4 (156): 156ra139. doi:10.1126/scitranslmed.3004334. PMC 3656604. PMID 23076356.
  4. ^ Liu Q. (2011). "Triptolide and its expanding multiple pharmacological functions". International Immunopharmacology. 11 (3): 377–383. doi:10.1016/j.intimp.2011.01.012. PMID 21255694.
  5. ^ "Study of Minnelide in Patients With Advanced GI Tumors". Retrieved 6 October 2016.