Tigilanol tiglate

Tigilanol tiglate
Clinical data
Trade names	Stelfonta
Other names	EBC-46
License data	US DailyMed: Tigilanol tiglate;
Routes of; administration	Injection
ATCvet code	QL01XX91 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Identifiers
	IUPAC name (1aR,1bR,1cS,2aR,3S,3aS,6aS,6bR,7R,8R,8aS)-3,3a,6b-Trihydroxy-2a-(hydroxymethyl)-1,1,5,7-tetramethyl-8a-{[(2S)-2-methylbutanoyl]oxy}-4-oxo-1a,1b,1c,2a,3,3a,4,6a,6b,7,8,8a-dodecahydro-1H-cyclopropa[5', 6']benzo[1',2':7,8]azuleno[5,6-b]oxiren-8-yl-(2E)-2-methyl-2-butenoate;
CAS Number	943001-56-7 ;
PubChem CID	23627739;
ChemSpider	32079087 ;
UNII	R1ZJT87990;
KEGG	D11191;
Chemical and physical data
Formula	C30H42O10
Molar mass	562.656 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(C)C(=O)O[C@@]12[C@@H](C1(C)C)[C@@H]3[C@H]4[C@](O4)([C@H]([C@]5([C@H]([C@]3([C@@H]([C@H]2OC(=O)/C(=C/C)/C)C)O)C=C(C5=O)C)O)O)CO;
	InChI InChI=1S/C30H42O10/c1-9-13(3)23(33)38-21-16(6)28(36)17-11-15(5)20(32)29(17,37)25(35)27(12-31)22(39-27)18(28)19-26(7,8)30(19,21)40-24(34)14(4)10-2/h9,11,14,16-19,21-22,25,31,35-37H,10,12H2,1-8H3/b13-9+/t14?,16-,17+,18-,19-,21-,22+,25-,27+,28+,29-,30-/m1/s1 ; Key:YLQZMOUMDYVSQR-YUKITULJSA-N ;
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Tigilanol tiglate (USAN; ), sold under the brand name Stelfonta is a medication used to treat dogs with non-metastatic, skin-based (cutaneous) mast cell tumors (MCTs). The FDA is also approving Stelfonta to treat non-metastatic MCTs located under the dog's skin (subcutaneous), in particular areas of a dog's leg. Stelfonta is injected directly into the MCT (intratumoral injection). Stelfonta works by activating a protein that spreads throughout the treated tumor, which disintegrates tumor cells.

It is a tiglien-3-on derivative, with a tigliane backbone. Since the substance is obtained by extraction, impurities with other tiglian-3-one derivatives are possible.

Initially, the synthesis was only used to confirm the structure and is possible via the Wender synthesis. In 2022, the Wender group reported an efficient semi-synthesis of tigilanol tiglate from phorbol (12% overall yield over 12 steps).

Tigilanol tiglate was approved for use in dogs in the European Union in January 2020. It is indicated for the treatment of non-resectable, non-metastatic (WHO staging) subcutaneous mast cell tumors located at or distal to the elbow or the hock, and non-resectable, non metastatic cutaneous mast cell tumors in dogs.