Rolapitant

Rolapitant (INN, trade name Varubi /vəˈruːbi/ və-ROO-bee in the US and Varuby in the European Union) is a drug originally developed by Schering-Plough and licensed for clinical development by Tesaro, which acts as a selective NK1 receptor antagonist (antagonist for the NK1 receptor). It has been approved as a medication for the treatment of chemotherapy-induced nausea and vomiting (CINV) after clinical trials showed it to have similar or improved efficacy and some improvement in safety over existing drugs for this application.

Rolapitant
Clinical data
Pronunciation/roʊˈlæpɪtænt/ roh-LAP-i-tant
Trade namesVarubi (US), Varuby (EU)
Other namesSCH 619734
AHFS/Drugs.comMonograph
MedlinePlusa615041
License data
Routes of
administration		By mouth (tablets), intravenous
Drug classNK1 receptor antagonists, antiemetics
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilitynearly 100%
Protein binding99.8%
MetabolismCYP3A4
MetabolitesC4-pyrrolidine-hydroxylated rolapitant (major)
Elimination half-life169–183 hours
ExcretionFeces (52–89%), urine (9–20%)
Identifiers
  • (5S,8S)-8-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)- 8-phenyl-1,7-diazaspiro[4.5]decan-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.243.022
Chemical and physical data
FormulaC25H26F6N2O2
Molar mass500.485 g·mol−1
3D model (JSmol)
  • FC(F)(F)c(c4)cc(C(F)(F)F)cc4C(C)OCC3(c2ccccc2)NCC1(CC3)NC(=O)CC1
  • InChI=1S/C25H26F6N2O2/c1-16(17-11-19(24(26,27)28)13-20(12-17)25(29,30)31)35-15-23(18-5-3-2-4-6-18)10-9-22(14-32-23)8-7-21(34)33-22/h2-6,11-13,16,32H,7-10,14-15H2,1H3,(H,33,34)/t16-,22-,23-/m1/s1
  • Key:FIVSJYGQAIEMOC-ZGNKEGEESA-N
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