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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 of TIGILANOL TIGLATE

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

HIDE SMILES / InChI

Molecular Formula C30H42O10
Molecular Weight 562.6485
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 12
E/Z Centers 1
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Optimising intratumoral treatment of head and neck squamous cell carcinoma models with the diterpene ester Tigilanol tiglate.
2019 Feb
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:11:52 GMT 2023
Edited
by admin
on Sat Dec 16 10:11:52 GMT 2023
Record UNII
R1ZJT87990
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIGILANOL TIGLATE
USAN   INN  
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
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
Code System Code Type Description
RXCUI
2478456
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
SMS_ID
100000177173
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
INN
10517
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
PUBCHEM
92135637
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
FDA UNII
R1ZJT87990
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
USAN
DE-22
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
WIKIPEDIA
EBC-46
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID601029530
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
NCI_THESAURUS
C152622
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
DAILYMED
R1ZJT87990
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
MERCK INDEX
m12202
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
CAS
943001-56-7
Created by admin on Sat Dec 16 10:11:52 GMT 2023 , Edited by admin on Sat Dec 16 10:11:52 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY