Tigilanol tiglate

Tigilanol tiglate
Clinical data
Trade namesStelfonta
Other namesEBC-46
License data
Routes of
administration		Injection
ATCvet code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Identifiers
  • (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
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC30H42O10
Molar mass562.656 g·mol−1
3D model (JSmol)
  • 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=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 ☒N
  • Key:YLQZMOUMDYVSQR-YUKITULJSA-N ☒N
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Tigilanol tiglate (USAN;[1] ), 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.[2] 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.[citation needed]

Initially, the synthesis was only used to confirm the structure and is possible via the Wender synthesis.[3] In 2022, the Wender group reported an efficient semi-synthesis of tigilanol tiglate from phorbol (12% overall yield over 12 steps).[4]

Tigilanol tiglate was approved for use in dogs in the European Union in January 2020.[5] 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.[5]

  1. ^ "United States Adopted Name (USAN) Drug Finder" (PDF). United States Adopted Names. American Medical Association. Retrieved 20 February 2017.
  2. ^ "FDA Approves First Intratumoral Injection to Treat Non-Metastatic Mast Cell Tumors in Dogs". FDA. 20 November 2020.
  3. ^ Wender PA, Kogen H, Lee HY, Munger JD, Wilhelm RS, Williams PD (1989). "Studies on tumor promoters. 8. The synthesis of phorbol". Journal of the American Chemical Society. 111 (24): 8957–8958. doi:10.1021/ja00206a050.
  4. ^ Wender PA, Gentry ZO, Fanelli DJ, Luu-Nguyen QH, McAteer OD, Njoo E (December 2022). "Practical synthesis of the therapeutic leads tigilanol tiglate and its analogues". Nature Chemistry. 14 (12): 1421–1426. Bibcode:2022NatCh..14.1421W. doi:10.1038/s41557-022-01048-2. PMC 10079359. PMID 36192432. S2CID 252693934.
  5. ^ a b "Stelfonta EPAR". European Medicines Agency (EMA). 7 November 2019. Retrieved 13 May 2020. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.