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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H35F10O20P
Molecular Weight 1116.7052
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAFLUPOSIDE

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C3=CC(OC)=C(OP(O)(O)=O)C(OC)=C3)C4=C(C=C5OCOC5=C4)[C@@]2([H])O[C@@H]6O[C@]7([H])CO[C@@H](C)O[C@@]7([H])[C@H](OC(=O)COC8=C(F)C(F)=C(F)C(F)=C8F)[C@H]6OC(=O)COC9=C(F)C(F)=C(F)C(F)=C9F

InChI

InChIKey=RTJVUHUGTUDWRK-CSLCKUBZSA-N
InChI=1S/C45H35F10O20P/c1-13-64-9-22-39(70-13)42(72-23(56)10-65-40-33(52)29(48)27(46)30(49)34(40)53)43(73-24(57)11-66-41-35(54)31(50)28(47)32(51)36(41)55)45(71-22)74-37-16-7-19-18(68-12-69-19)6-15(16)25(26-17(37)8-67-44(26)58)14-4-20(62-2)38(21(5-14)63-3)75-76(59,60)61/h4-7,13,17,22,25-26,37,39,42-43,45H,8-12H2,1-3H3,(H2,59,60,61)/t13-,17+,22-,25-,26+,37-,39-,42+,43-,45+/m1/s1

HIDE SMILES / InChI

Molecular Formula C45H35F10O20P
Molecular Weight 1116.7052
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Tafluposide (also known as F 11782) is an epipodophyllotoxin derivative patented by Pierre Fabre Medicament as an antitumor agent. Tafluposide acts as a catalytic inhibitor of topoisomerases I and II, that capable of completely inhibiting the DNA-binding activity of topoisomerase. In preclinical models single or multiple i.p. doses of Tafluposide proves highly active against the s.c. grafted B16 melanoma, significantly increasing survival and inhibiting tumor growth. Tafluposide inhibits the number of pulmonary metastatic foci of the melanoma by 99%. In human tumor xenograft studies, multiple i.p. doses of Tafluposide results in major inhibitory activity against breast) tumors, as well as causing definite tumor regression. Significant activity was also recorded Tafluposide against the refractory lung xenografts.

Approval Year

PubMed

PubMed

TitleDatePubMed
F 11782, a novel catalytic inhibitor of topoisomerases I and II, induces atypical, yet cytotoxic DNA double-strand breaks in CHO-K1 cells.
2002 Jan-Feb
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:27:11 UTC 2023
Edited
by admin
on Fri Dec 15 16:27:11 UTC 2023
Record UNII
QN043X3ZDW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAFLUPOSIDE
INN  
INN  
Official Name English
4-((5R,5AR,8AR,9S)-9-((4,6-O-((1R)-ETHYLIDENE)-2,3-BIS-O-((PENTAFLUOROPHENOXY)ACETYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-6-OXO-5,5A,6,8,8A,9-HEXAHYDROFURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-5-YL)-2,6-DIMETHOXYPHENYL DIHYDROGEN PHOSPHATE
Common Name English
tafluposide [INN]
Common Name English
F-11782
Code English
Classification Tree Code System Code
NCI_THESAURUS C1748
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
NCI_THESAURUS C1331
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
Code System Code Type Description
SMS_ID
300000034315
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
INN
8099
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
MESH
C405744
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL2103895
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
NCI_THESAURUS
C152490
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
FDA UNII
QN043X3ZDW
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID50170767
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
CAS
179067-42-6
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
PUBCHEM
9877073
Created by admin on Fri Dec 15 16:27:11 UTC 2023 , Edited by admin on Fri Dec 15 16:27:11 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY