4-EPIDOCETAXEL

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 Search

SMILES

CC(=O)O[C@@]12CO[C@@H]1C[C@@H](O)[C@]3(C)[C@@H]2[C@H](OC(=O)C4=CC=CC=C4)[C@]5(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C6=CC=CC=C6)C(C)=C([C@@H](O)C3=O)C5(C)C

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	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.rxlist.com/taxotere-drug.htm | https://www.ncbi.nlm.nih.gov/pubmed/23756759 | https://www.ncbi.nlm.nih.gov/pubmed/12386117 | http://onlinelibrary.wiley.com/doi/10.1002/dta.1617/abstract

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

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Is an alternative drug delivery system needed for docetaxel? The role of controlling epimerization in formulations and beyond.	2013-10	23756759
Evidence for the conversion of docetaxel into 7'-epidocetaxel in patients receiving Taxotere-based conventional chemotherapy.	2010-07	20557853
Docetaxel (Taxotere) is not metabolized by recombinant human CYP1B1 in vitro, but acts as an effector of this isozyme.	2002-11	12386117

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 18:38:58 GMT 2025` Edited by `admin` on `Mon Mar 31 18:38:58 GMT 2025`
Record UNII	BVQ8BYC7MI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4-EPI-DOCETAXEL

Preferred Name

English

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

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

SMS_ID

300000053073