TIGILANOL TIGLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H42O10
Molecular Weight	562.6485
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C=C(C)C(=O)[C@@]1(O)[C@H](O)[C@@]3(CO)O[C@H]3[C@@]4([H])[C@@H]5C(C)(C)[C@]5(OC(=O)[C@@H](C)CC)[C@H](OC(=O)C(\C)=C\C)[C@@H](C)[C@]24O

InChI

InChIKey=YLQZMOUMDYVSQR-FOWZUWBHSA-N

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+/m0/s1

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Description
Sources: https://qbiotics.com/index.php/research/human-health | https://www.ncbi.nlm.nih.gov/pubmed/25272271 | https://www.ncbi.nlm.nih.gov/pubmed/29667135

Tigilanol tiglate (EBC-46) is a novel small molecule diterpene ester in development as a local treatment for solid tumors. The drug is not synthetically tractable and is isolated from the Australian native plant Blushwood. Intra-lesional injection of EBC-46 causes PKC-dependent hemorrhagic necrosis, rapid tumor cell death and ultimate cure of solid tumors in pre-clinical models of cancer. QBiotics recently completed a first-in-human dose escalation safety study of tigilanol tiglate in patients across four Australian hospitals. This Phase I/IIA clinical trial was conducted in 22 patients with refractory skin and subcutis solid tumors (specifically melanoma, basal cell carcinoma, squamous cell carcinoma, breast and colorectal adenocarcinoma, angiosarcoma, fibrosarcoma, adenoid cystic sarcoma and fibroxanthoma). Currently, tigilanol tiglate is not commercially available.

Originator

Approval Year

PubMed

Title	Date	PubMed
Intra-lesional injection of the novel PKC activator EBC-46 rapidly ablates tumors in mouse models.	2014	25272271
Progressive cutaneous viral pigmented plaques in three Hungarian Vizslas and the response of lesions to topical tigilanol tiglate gel.	2018 Feb	29468081
Optimising intratumoral treatment of head and neck squamous cell carcinoma models with the diterpene ester Tigilanol tiglate.	2019 Feb	29667135

Name

Type

Language

TIGILANOL TIGLATE

Official Name

English

TIGILANOL TIGLATE [USAN]

Common Name

English

12-TIGLOYL-13-(2-METHYLBUTANOYL)-6,7-EPOXY-4,5,9,12,13,20-HEXAHYDROXY-1-TIGLIAN-3-ONE

Common Name

English

TIGILANOL TIGLATE [MI]

Common Name

English

EBC-46

Code

English

(1AR,1BR,1CS,2AR,3S,3AS,6AS,6BR,7R,8R,8AS)-3,3A,6B-TRIHYDROXY-2A-(HYDROXYMETHYL)-1,1,5,7-TETRAMETHYL-4-OXO-1,1A,1B,1C,2A,3,3A,4,6A,6B,7,8-DODECAHYDRO-8AH-CYCLOPROPA(5',6')BENZO(1',2':7,8)AZULENO(5,6-B)OXIRENE-8,8A-DIYL 8A-((2S)-2-METHYLBUTANOATE) 8-((2E)

Systematic Name

English

tigilanol tiglate [INN]

Common Name

English

(4S,5S,6R,7S,8R,9R,10S,11R,12R,13S,14R)-12-(2E)-2-METHYL-2-ENOATYL-13((2S)-2-METHYLBUTYROYL)-6,7-EPOXY-4,5,9,12,13,20-HEXAHYDROXY-1-TIGLIAEN-3-ONE

Systematic Name

English

EBI-46

Code

English

Tigilanol tiglate [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2089