Tetrabenazine

Tetrabenazine
Clinical data
Trade names	Xenazine, Xentra, Nitoman, others
Other names	Ro-1-9569
AHFS/Drugs.com	Consumer Drug Information
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	N07XX06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: ℞-only;
Pharmacokinetic data
Bioavailability	Low, extensive first pass effect
Protein binding	82–85%
Metabolism	Liver (CYP2D6-mediated)
Elimination half-life	10 hours parent compound (2 to 8 hours active metabolites)
Excretion	Kidney (~75%) and fecal (7–16%)
Identifiers
	IUPAC name (SS,RR)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one;
CAS Number	58-46-8 ;
PubChem CID	6018;
IUPHAR/BPS	4834;
DrugBank	DB04844 ;
ChemSpider	5796 ;
UNII	Z9O08YRN8O;
KEGG	D08575 ;
ChEMBL	ChEMBL117785 ;
CompTox Dashboard (EPA)	DTXSID501127442 DTXSID0042614, DTXSID501127442 ;
ECHA InfoCard	100.000.348
Chemical and physical data
Formula	C19H27NO3
Molar mass	317.429 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O=C3C(CC(C)C)CN2C(c1c(cc(OC)c(OC)c1)CC2)C3;
	InChI InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3 ; Key:MKJIEFSOBYUXJB-UHFFFAOYSA-N ;
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Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorders. It is sold under the brand names Nitoman and Xenazine among others. On August 15, 2008, the US Food and Drug Administration (FDA) approved the use of tetrabenazine to treat chorea associated with Huntington's disease. Although other drugs had been used "off-label", tetrabenazine was the first approved treatment for Huntington's disease in the United States. The compound has been known since the 1950s.