toceranib

{{Short description|Chemical compound used in the treatment of tumors}}

{{Use dmy dates|date=July 2024}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

{{Infobox drug

| image = Toceranib.svg

| width =

| alt =

| image2 = Toceranib ball-and-stick xray 2020.png

| width2 = 260

| alt2 = Ball-and-stick model of the toceranib molecule

| caption =

| pronounce =

| tradename = Palladia

| Drugs.com = {{drugs.com|vet|palladia}}

| MedlinePlus =

| DailyMedID = Toceranib

| pregnancy_AU =

| pregnancy_AU_comment =

| pregnancy_category=

| routes_of_administration = By mouth

| class = Antineoplastic agent

| ATCvet = yes

| ATC_prefix = L01

| ATC_suffix = EX90

| ATC_supplemental =

| legal_AU =

| legal_AU_comment =

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| legal_BR_comment =

| legal_CA = Rx-only

| legal_CA_comment =

| legal_DE =

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| legal_UK =

| legal_UK_comment =

| legal_US = Rx-only

| legal_US_comment =

| legal_EU = Rx-only

| legal_EU_comment = {{cite web | title=Palladia EPAR | website=European Medicines Agency | date=1 October 2009 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/palladia | access-date=1 July 2024}}

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| bioavailability = 77%

| protein_bound = 91%-93%

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| elimination_half-life = 16 h

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| index2_label = as salt

| CAS_number = 356068-94-5

| CAS_number2 = 874819-74-6

| CAS_supplemental =

| PubChem = 5329106

| PubChem2 = 16034840

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID = 4486268

| ChemSpiderID2 = 13163443

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 59L7Y0530C

| UNII2 = 24F9PF7J3R

| KEGG = D08503

| KEGG2 = D08544

| ChEBI =

| ChEMBL = 13608

| ChEMBL2 = 2103833

| NIAID_ChemDB =

| PDB_ligand = BWC

| synonyms =

| 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

| C=22 | H=25 | F=1 | N=4 | O=2

| SMILES = Fc1ccc2c(c1)/C(C(=O)N2)=C/c4c(c(C(=O)NCCN3CCCC3)c([nH]4)C)C

| StdInChI = 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-

| StdInChI_comment =

| StdInChIKey = SRSGVKWWVXWSJT-ATVHPVEESA-N

| density =

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}}

Toceranib (INN{{cite journal | vauthors = ((World Health Organization)) | year = 2009 | title = International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 62 | journal = WHO Drug Information | volume = 23 | issue = 2 | hdl = 10665/74420 | hdl-access = free | author-link = World Health Organization }}), 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.{{cite journal | vauthors = London CA, Malpas PB, Wood-Follis SL, Boucher JF, Rusk AW, Rosenberg MP, Henry CJ, Mitchener KL, Klein MK, Hintermeister JG, Bergman PJ, Couto GC, Mauldin GN, Michels GM | title = Multi-center, placebo-controlled, double-blind, randomized study of oral toceranib phosphate (SU11654), a receptor tyrosine kinase inhibitor, for the treatment of dogs with recurrent (either local or distant) mast cell tumor following surgical excision | journal = Clinical Cancer Research | volume = 15 | issue = 11 | pages = 3856–3865 | date = June 2009 | pmid = 19470739 | doi = 10.1158/1078-0432.CCR-08-1860 | doi-access = free }} It is the first medication developed specifically for the treatment of cancer in dogs.{{cite press release | title=FDA: First Drug to Treat Cancer in Dogs Approved | website=U.S. Food and Drug Administration (FDA) | date=3 June 2009 | url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm164118.htm | archive-url=https://web.archive.org/web/20100722024040/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm164118.htm | archive-date=22 July 2010 | url-status=dead | access-date=2 October 2021}} {{PD-notice}}{{cite web | title=Palladia New Animal Drug Application | website=U.S. Food and Drug Administration (FDA) | date=22 May 2009 | url=http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM164091.pdf | archive-url=https://web.archive.org/web/20101116092912/http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM164091.pdf | archive-date=16 November 2010 | url-status=dead | access-date=2 October 2021}} It is used as its phosphate salt, toceranib phosphate. It was developed by SUGEN as SU11654,{{cite news | title=In Trials for New Cancer Drugs, Family Pets Are Benefiting, Too | website=The New York Times | date=24 November 2006 | url=https://www.nytimes.com/2006/11/24/business/24cancer.html | access-date=2 October 2021 | archive-date=27 February 2021 | archive-url=https://web.archive.org/web/20210227062619/https://www.nytimes.com/2006/11/24/business/24cancer.html | url-status=live }} 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.

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