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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H53NO14
Molecular Weight 807.8792
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-EPIDOCETAXEL

SMILES

[H][C@@]12C[C@@H](O)[C@@]3(C)C(=O)[C@H](O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C5=CC=CC=C5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C6=CC=CC=C6

InChI

InChIKey=ZDZOTLJHXYCWBA-MQOKZWAMSA-N
InChI=1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27+,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1

HIDE SMILES / InChI

Molecular Formula C43H53NO14
Molecular Weight 807.8792
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

7-epidocetaxel (4-epidocetaxel) is an epimer of antitumor agent docetaxel (TAXOTERE). The presence of 7-epidocetaxel in docetaxel injection and in vivo epimerisation has been reported to be the cause for development of tumor resistance to chemotherapy including docetaxel by inducing tumor cell protein cytochrome P450 1B1.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

B16F10 experimental metastasis model using C57BL/6 mice injected with Taxotere® containing 10% 7-epimer showed higher weight loss as compared to Taxotere® containing no epimer at single dose of 40 mg/kg indicating higher systemic toxicity. Incubation of PEGylated liposomes with phosphate buffer saline (pH 7.4) containing 0.1% w/v Tween-80 for 48 h showed better resistance to docetaxel degradation when compared with Taxotere® injection indicating better in vivo stability of liposomal docetaxel. In addition, PEGylated liposomes showed enhanced in vitro cytotoxicity, against A549 and B16F10 cells, than Taxotere®.
Route of Administration: Parenteral
7-epidocetaxel, which is in equilibrium with docetaxel as a minor compound in solutions, was a potent activator of rhCYP1B1, with a >7-fold increase of EROD activity at 10 microM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:59:21 UTC 2023
Edited
by admin
on Fri Dec 15 16:59:21 UTC 2023
Record UNII
BVQ8BYC7MI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-EPIDOCETAXEL
Common Name English
5.BETA.,20-EPOXY-1,7.ALPHA.,10.BETA.-TRIHYDROXY-9-OXOTAX-11-ENE-2.ALPHA.,4,13.ALPHA.-TRIYL 4-ACETATE 2-BENZOATE 13-((2R,3S)-3-(((1,1-DIMETHYLETHOXY)CARBONYL)AMINO)-2-HYDROXY-3-PHENYLPROPANOATE)
Common Name English
4-EPI-DOCETAXEL
Common Name English
7-EPIDOCETAXEL
Common Name English
7-EPITAXOTERE
Common Name English
DOCETAXEL IMPURITY C
Common Name English
DOCETAXEL TRIHYDRATE IMPURITY C [EP IMPURITY]
Common Name English
DOCETAXEL IMPURITY, 4-EPIDOCETAXEL- [USP IMPURITY]
Common Name English
7-EPI-DOCETAXEL
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID30165318
Created by admin on Fri Dec 15 16:59:21 UTC 2023 , Edited by admin on Fri Dec 15 16:59:21 UTC 2023
PRIMARY
FDA UNII
BVQ8BYC7MI
Created by admin on Fri Dec 15 16:59:21 UTC 2023 , Edited by admin on Fri Dec 15 16:59:21 UTC 2023
PRIMARY
CAS
153381-68-1
Created by admin on Fri Dec 15 16:59:21 UTC 2023 , Edited by admin on Fri Dec 15 16:59:21 UTC 2023
PRIMARY
PUBCHEM
58510442
Created by admin on Fri Dec 15 16:59:21 UTC 2023 , Edited by admin on Fri Dec 15 16:59:21 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP