Toceranib

Toceranib (INN^[2]), sold under the brand name Palladia, is a receptor tyrosine kinase inhibitor that is used in the treatment of canine mast cell tumor also called mastocytoma.^[3] It is the first medication developed specifically for the treatment of cancer in dogs.^[4][5] It is used as its phosphate salt, toceranib phosphate. It was developed by SUGEN as SU11654,^[6] a sister compound to sunitinib, which was later approved for human therapies. Toceranib is a tyrosine kinase inhibitor and works in two ways: by killing tumor cells and by cutting off the blood supply to the tumor.^[4]

Toceranib

Clinical data
Trade names	Palladia
AHFS/Drugs.com	Veterinary Use
License data	US DailyMed: Toceranib
Routes of administration	By mouth
Drug class	Antineoplastic agent
ATCvet code	QL01EX90 (WHO)
Legal status
Legal status	CA: ℞-only US: ℞-only EU: Rx-only[1]
Pharmacokinetic data
Bioavailability	77%
Protein binding	91%-93%
Elimination half-life	16 h
Identifiers
IUPAC name 5-[(5Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-N-[2-(pyrrolidin-1-yl)ethyl]-1H-pyrrole-3-carboxamide
CAS Number	356068-94-5 as salt: 874819-74-6
PubChem CID	5329106 as salt: 16034840
ChemSpider	4486268 as salt: 13163443
UNII	59L7Y0530C as salt: 24F9PF7J3R
KEGG	D08503 as salt: D08544
ChEMBL	ChEMBL13608 as salt: ChEMBL2103833
PDB ligand	BWC (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID50189076
Chemical and physical data
Formula	C22H25FN4O2
Molar mass	396.466 g·mol−1
3D model (JSmol)	Interactive image
SMILES Fc1ccc2c(c1)/C(C(=O)N2)=C/c4c(c(C(=O)NCCN3CCCC3)c([nH]4)C)C
InChI InChI=1S/C22H25FN4O2/c1-13-19(12-17-16-11-15(23)5-6-18(16)26-21(17)28)25-14(2)20(13)22(29)24-7-10-27-8-3-4-9-27/h5-6,11-12,25H,3-4,7-10H2,1-2H3,(H,24,29)(H,26,28)/b17-12- Key:SRSGVKWWVXWSJT-ATVHPVEESA-N

The most common side effects include diarrhea, decrease or loss of appetite, lameness, weight loss, and blood in the stool.^[4]

Veterinary uses

Toceranib is indicated to treat canine cutaneous (skin-based) mast cell tumors, a type of cancer responsible for about one out of five cases of canine skin tumors.^[4] It is approved to treat the tumors with or without regional lymph node involvement.^[4]