Toceranib phosphate| CAS#874819-74-6 | 356068-94-5

MedKoo Cat#: 205738 | Name: Toceranib phosphate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Toceranib, also known as PHA-291639 and SU 11654, is a receptor tyrosine kinase inhibitor and is used in the treatment of canine mast cell tumor also called mastocytoma. Toceranib phosphate was approved for dog.

Chemical Structure

Toceranib phosphate

CAS#874819-74-6 (phosphate)

Theoretical Analysis

MedKoo Cat#: 205738

Name: Toceranib phosphate

CAS#: 874819-74-6 (phosphate)

Chemical Formula: C22H28FN4O6P

Exact Mass: 0.0000

Molecular Weight: 494.46

Elemental Analysis: C, 53.44; H, 5.71; F, 3.84; N, 11.33; O, 19.41; P, 6.26

Price and Availability

Size	Price	Availability
50mg	USD 100.00	Ready to ship
100mg	USD 150.00	Ready to ship
250mg	USD 325.00	Ready to ship
500mg	USD 585.00	Ready to ship
1g	USD 950.00	Ready to ship
2g	USD 1,650.00	Ready to Ship
5g	USD 3,450.00	Ready to Ship

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Related CAS #

874819-74-6 (phosphate) 356068-94-5 (free base)

Synonym

PHA-291639; PHA291639; PHA 291639; SU-11654; SU 11654; SU11654; Toceranib; Toceranib phosphate; Brand name: Palladia.

IUPAC/Chemical Name

(Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrole-3-carboxamide phosphate.

InChi Key

AOORBROPMMRREB-HBPAQXCTSA-N

InChi Code

InChI=1S/C22H25FN4O2.H3O4P/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;1-5(2,3)4/h5-6,11-12,25H,3-4,7-10H2,1-2H3,(H,24,29)(H,26,28);(H3,1,2,3,4)/b17-12-;

SMILES Code

O=C(C1=C(C)NC(/C=C2C(NC3=C\2C=C(F)C=C3)=O)=C1C)NCCN4CCCC4.O=P(O)(O)O

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Related CAS# 256068-94-5 ( Toceranib phosphate) 356068-94-5 ( Toceranib free base).

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T7K08C24

QC Data

View QC data: current batch, Lot#T7K08C24

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Toceranib phosphate inhibits PDGFR, VEGFR, and Kit with Kis of 5 and 6 nM for PDGFRβ and Flk-1/KDR, respectively.

In vitro activity:

The functional effects of toceranib phosphate (TOC) on six canine osteosarcoma (OSA) cell lines were evaluated by transwell, wound healing and colony formation assays. TOC inhibited cell growth of all cell lines, but reduced invasion and migration was only observed in Penny and Wall cell lines. Overall, the results demonstrate that TOC is able to slightly inhibit cell growth in vitro. Reference: Vet Comp Oncol. 2020 Mar;18(1):117-127. https://onlinelibrary.wiley.com/doi/abs/10.1111/vco.12562

In vivo activity:

An orthotopic xenograft model of canine OSA was used to evaluate the effects of TOC. In mice engrafted with Penny cells and subjected to TOC treatment, decreased tumour growth was observed, and PDGFRs and c-Kit mRNA were downregulated. Immunohistochemical analyses demonstrated a significant reduction of Ki67 staining in treated mice when compared to controls. The results demonstrate that TOC significantly reduced tumour size and the Ki67 index without modifying apoptosis markers in vivo. Reference: Vet Comp Oncol. 2020 Mar;18(1):117-127. https://onlinelibrary.wiley.com/doi/abs/10.1111/vco.12562

	Solvent	mg/mL	mM
Solubility
	DMSO	2.2	4.51
	Water	1.1	2.12

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 494.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Sánchez-Céspedes R, Accornero P, Miretti S, Martignani E, Gattino F, Maniscalco L, Gola C, Iussich S, Martano M, Morello E, Buracco P, Aresu L, Maria R. In vitro and in vivo effects of toceranib phosphate on canine osteosarcoma cell lines and xenograft orthotopic models. Vet Comp Oncol. 2020 Mar;18(1):117-127. doi: 10.1111/vco.12562. Epub 2019 Dec 15. PMID: 31816142.

In vitro protocol:

In vivo protocol:

1: Frezoulis P, Harper A. The role of toceranib phosphate in dogs with non-mast cell neoplasia: A systematic review. Vet Comp Oncol. 2022 Jun;20(2):362-371. doi: 10.1111/vco.12799. Epub 2022 Jan 17. PMID: 34981886. 2: Sheppard-Olivares S, Bello NM, Wood E, Szivek A, Biller B, Hocker S, Wouda RM. Toceranib phosphate in the treatment of canine thyroid carcinoma: 42 cases (2009-2018). Vet Comp Oncol. 2020 Dec;18(4):519-527. doi: 10.1111/vco.12571. Epub 2020 Feb 13. PMID: 32012432. 3: Wiles V, Hohenhaus A, Lamb K, Zaidi B, Camps-Palau M, Leibman N. Retrospective evaluation of toceranib phosphate (Palladia) in cats with oral squamous cell carcinoma. J Feline Med Surg. 2017 Feb;19(2):185-193. doi: 10.1177/1098612X15622237. Epub 2016 Jul 9. PMID: 26755491; PMCID: PMC10816576. 4: Sheppard-Olivares S, Bello NM, Johannes CM, Hocker SE, Biller B, Husbands B, Snyder E, McMillan M, McKee T, Wouda RM. Toceranib phosphate in the management of canine insulinoma: A retrospective multicentre study of 30 cases (2009-2019). Vet Rec Open. 2022 Jan 20;9(1):e27. doi: 10.1002/vro2.27. PMID: 35079406; PMCID: PMC8776903. 5: Berger EP, Johannes CM, Post GS, Rothchild G, Shiu KB, Wetzel S, Fox LE. Retrospective evaluation of toceranib phosphate (Palladia) use in cats with mast cell neoplasia. J Feline Med Surg. 2018 Feb;20(2):95-102. doi: 10.1177/1098612X17695898. Epub 2017 Mar 1. PMID: 29172873; PMCID: PMC11129263. 6: Lew FH, McQuown B, Borrego J, Cunningham S, Burgess KE. Retrospective evaluation of canine heart base tumours treated with toceranib phosphate (Palladia): 2011-2018. Vet Comp Oncol. 2019 Dec;17(4):465-471. doi: 10.1111/vco.12491. Epub 2019 Jun 18. PMID: 31069932. 7: Yamazaki H, Tanaka T, Mie K, Nishida H, Miura N, Akiyoshi H. Assessment of postoperative adjuvant treatment using toceranib phosphate against adenocarcinoma in dogs. J Vet Intern Med. 2020 May;34(3):1272-1281. doi: 10.1111/jvim.15768. Epub 2020 Apr 8. PMID: 32267594; PMCID: PMC7255667. 8: Rosario CO, Musser ML, Yuan L, Mochel JP, Talbott J, Johannes CM, Berger EP. Retrospective evaluation of toceranib phosphate (Palladia) use in the treatment of feline pancreatic carcinoma. Can Vet J. 2023 Dec;64(12):1143-1148. PMID: 38046430; PMCID: PMC10637710. 9: Musser ML, Johannes CM. Toceranib phosphate (Palladia) for the treatment of canine exocrine pancreatic adenocarcinoma. BMC Vet Res. 2021 Aug 11;17(1):269. doi: 10.1186/s12917-021-02978-8. PMID: 34380474; PMCID: PMC8356392. 10: Heaton CM, Fernandes AFA, Jark PC, Pan X. Evaluation of toceranib for treatment of apocrine gland anal sac adenocarcinoma in dogs. J Vet Intern Med. 2020 Mar;34(2):873-881. doi: 10.1111/jvim.15706. Epub 2020 Jan 24. PMID: 31977135; PMCID: PMC7096647. 11: Remerowski SM, Herrera CL, Donnelly LL. Toceranib phosphate-associated nephrotic syndrome in a dog: a case report. BMC Vet Res. 2021 Apr 7;17(1):146. doi: 10.1186/s12917-021-02850-9. PMID: 33827545; PMCID: PMC8028059. 12: Coto GM, Musser ML, Tropf MA, Ward JL, Seo YJ, Mochel JP, Johannes CM. A Multi-Institutional Retrospective Analysis of Toceranib Phosphate for Presumed or Confirmed Canine Aortic Body Chemodectomas. Front Vet Sci. 2021 Feb 5;8:635057. doi: 10.3389/fvets.2021.635057. PMID: 33614771; PMCID: PMC7892462. 13: Osada H, Okazawa T, Kushida K, Kishimoto M, Ikeda M, Kondo H, Kimura J, Ohmori K. Toceranib phosphate and firocoxib-mediated partial response in a dog with advanced intranasal sarcoma. J Vet Med Sci. 2023 Sep 20;85(9):1004-1009. doi: 10.1292/jvms.22-0542. Epub 2023 Aug 2. PMID: 37532540; PMCID: PMC10539811. 14: Gregory J, Thomason J, Hocker S. Toceranib phosphate resolves right heart obstruction secondary to a heart base neoplasm in a dog. J Vet Cardiol. 2022 Dec;44:38-42. doi: 10.1016/j.jvc.2022.09.003. Epub 2022 Sep 30. PMID: 36356366. 15: Jackson AE. In this issue - May 2019: West Nile virus in horses · Treating horses with dexamethasone via nebulisation · Animal hoarding in NSW · Dangers of powdered washing soda for emesis in dogs · Pneumocystis in a dog following toceranib phosphate · Oxalate nephrosis in koalas. Aust Vet J. 2019 May;97(5):129-130. doi: 10.1111/avj.12818. PMID: 31025324. 16: Kishi K, Yonezawa T, Kaji N, Goto M, Nonoshita Y, Iio A, Tsuru Y, Hori M. Toceranib phosphate (Palladia) reverses type 1 diabetes by preserving islet function in mice. J Vet Med Sci. 2023 Jul 17;85(7):781-789. doi: 10.1292/jvms.23-0154. Epub 2023 May 31. PMID: 37258127; PMCID: PMC10372262. 17: Hicks KA, Leeper HJ, Curran KM. Retrospective evaluation of toceranib phosphate (Palladia) in the treatment of canine carcinomatosis and mesothelioma. Vet Comp Oncol. 2024 Jun;22(2):245-254. doi: 10.1111/vco.12972. Epub 2024 Apr 15. PMID: 38622074. 18: Burgess KE, DeRegis CJ. Urologic Oncology. Vet Clin North Am Small Anim Pract. 2019 Mar;49(2):311-323. doi: 10.1016/j.cvsm.2018.11.006. Epub 2019 Jan 8. PMID: 30635132. 19: Merino-Gutierrez V, Borrego JF, Puig J, Hernández A, Clemente-Vicario F. Treatment of advanced-stage canine nasal carcinomas with toceranib phosphate: 23 cases (2015-2020). J Small Anim Pract. 2021 Oct;62(10):881-885. doi: 10.1111/jsap.13387. Epub 2021 Jun 16. PMID: 34131916. 20: Ehling TJ, Klein MK, Smith L, Prescott D, Haney S, Looper J, LaDue T, Brawner W, Fidel J, Shiomitsu K, Green E, Saba C, Turek M, Farrelly J. A prospective, multi-centre, Veterinary Radiation Therapy Oncology Group study reveals potential efficacy of toceranib phosphate (Palladia) as a primary or adjuvant agent in the treatment of canine nasal carcinoma. Vet Comp Oncol. 2022 Mar;20(1):293-303. doi: 10.1111/vco.12776. Epub 2021 Oct 26. PMID: 34655275.