Rolapitant

Rolapitant
Clinical data
Pronunciation	/roʊˈlæpɪtænt/ roh-LAP-i-tant
Trade names	Varubi (US), Varuby (EU)
Other names	SCH 619734
AHFS/Drugs.com	Monograph
MedlinePlus	a615041
License data	EU EMA: by INN; US DailyMed: Rolapitant;
Routes of; administration	By mouth (tablets), intravenous
Drug class	NK1 receptor antagonists, antiemetics
ATC code	A04AD14 (WHO) ;
Legal status
Legal status	US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	nearly 100%
Protein binding	99.8%
Metabolism	CYP3A4
Metabolites	C4-pyrrolidine-hydroxylated rolapitant (major)
Elimination half-life	169–183 hours
Excretion	Feces (52–89%), urine (9–20%)
Identifiers
	IUPAC name (5S,8S)-8-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)- 8-phenyl-1,7-diazaspiro[4.5]decan-2-one;
CAS Number	552292-08-7 ;
PubChem CID	10311306;
IUPHAR/BPS	5749;
DrugBank	DB09291 ;
ChemSpider	8486772;
UNII	NLE429IZUC;
KEGG	D10742; as HCl: D08988;
ChEBI	CHEBI:90908 ;
CompTox Dashboard (EPA)	DTXSID90203740 ;
ECHA InfoCard	100.243.022
Chemical and physical data
Formula	C25H26F6N2O2
Molar mass	500.485 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)c(c4)cc(C(F)(F)F)cc4C(C)OCC3(c2ccccc2)NCC1(CC3)NC(=O)CC1;
	InChI 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;

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.

Clinical data

Pronunciation	/roʊˈlæpɪtænt/ roh-LAP-i-tant
Trade names	Varubi (US), Varuby (EU)
Other names	SCH 619734
AHFS/Drugs.com	Monograph
MedlinePlus	a615041
License data	EU EMA: by INN US DailyMed: Rolapitant
Routes of administration	By mouth (tablets), intravenous
Drug class	NK1 receptor antagonists, antiemetics
ATC code	A04AD14 (WHO)
Legal status
Legal status	US: ℞-only EU: Rx-only
Pharmacokinetic data
Bioavailability	nearly 100%
Protein binding	99.8%
Metabolism	CYP3A4
Metabolites	C4-pyrrolidine-hydroxylated rolapitant (major)
Elimination half-life	169–183 hours
Excretion	Feces (52–89%), urine (9–20%)
Identifiers
IUPAC name (5S,8S)-8-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)- 8-phenyl-1,7-diazaspiro[4.5]decan-2-one
CAS Number	552292-08-7^Y
PubChem CID	10311306
IUPHAR/BPS	5749
DrugBank	DB09291^Y
ChemSpider	8486772
UNII	NLE429IZUC
KEGG	D10742 as HCl: D08988
ChEBI	CHEBI:90908^Y
CompTox Dashboard (EPA)	DTXSID90203740
ECHA InfoCard	100.243.022
Chemical and physical data
Formula	C₂₅H₂₆F₆N₂O₂
Molar mass	500.485 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c(c4)cc(C(F)(F)F)cc4C(C)OCC3(c2ccccc2)NCC1(CC3)NC(=O)CC1
InChI 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