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

CC[C@H](C)C(=O)O[C@]12[C@H]([C@@H]3[C@@H]4O[C@]4(CO)[C@@H](O)[C@@]5(O)[C@@H](C=C(C)C5=O)[C@@]3(O)[C@H](C)[C@H]1OC(=O)C(\C)=C\C)C2(C)C

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

HIDE SMILES / InChI

Molecular Formula	C30H42O10
Molecular Weight	562.6485
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	1
Optical Activity	UNSPECIFIED

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
Optimising intratumoral treatment of head and neck squamous cell carcinoma models with the diterpene ester Tigilanol tiglate.	2019-02	29667135
Progressive cutaneous viral pigmented plaques in three Hungarian Vizslas and the response of lesions to topical tigilanol tiglate gel.	2018-02	29468081
Intra-lesional injection of the novel PKC activator EBC-46 rapidly ablates tumors in mouse models.	2014	25272271

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:06:04 GMT 2025` Edited by `admin` on `Mon Mar 31 23:06:04 GMT 2025`
Record UNII	R1ZJT87990
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIGILANOL TIGLATE

Official Name

English

EBC-46

Preferred 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

(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