Calanolide A

Calanolide A
Clinical data
ATC code
  • none
Pharmacokinetic data
Protein binding>97%
MetabolismHepatic (mostly CYP3A4-mediated)
Identifiers
  • (+)-[10R,11S,12S]-10,11-trans-dihydro-
    12-hydroxy-6,6,10,11-tetramethyl-4-propyl-
    2H,6H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H26O5
Molar mass370.445 g·mol−1
3D model (JSmol)
  • O=C/4Oc2c(c3OC(/C=C\c3c1O[C@@H]([C@@H](C)[C@H](O)c12)C)(C)C)\C(=C\4)CCC
  • InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1
  • Key:NIDRYBLTWYFCFV-FMTVUPSXSA-N

Calanolide A is an experimental non-nucleoside reverse transcriptase inhibitor (NNRTI). This compound was extracted from the tree Calophyllum lanigerum, of variety austrocoriaceum, in Lundu, Malaysian state of Sarawak in 1992 by United States National Cancer Institute (NCI). Due to rarity of the raw materials and low yield of the active ingredient, total synthesis of the compound was devised in 1996. For the same reason, its sister compound (-)-Calanolide B (also known as Costatolide) have been touted as replacement. As a result of the discovery of Calanolide A, Sarawak Medichem pharmaceuticals company was established as a joint venture between US-based MediChem Research Inc and Craun Research Sdn Bhd, a company owned by the Sarawak state government. In 2006, Craun Research acquired Sarawak MediChem. In 2016, Craun Research announced the completion of Phase I clinical trials for Calanolide A.