EPOFOLATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C67H92N16O22S3
Molecular Weight	1569.736
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1CCC[C@@H]2[C@H](C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(\C)=C\C3=CSC(C)=N3)N2CCOC(=O)OCCSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(O)=O)NC(=O)CC[C@H](NC(=O)C4=CC=C(NCC5=CN=C6N=C(N)NC(=O)C6=N5)C=C4)C(O)=O)C(O)=O

InChI

InChIKey=TURJYGRXEJIBGT-OCOMGVANSA-N

InChI=1S/C67H92N16O22S3/c1-32-9-7-11-45-46(26-47(33(2)23-38-30-106-35(4)74-38)105-52(90)27-48(84)67(5,6)55(92)34(3)54(32)91)83(45)19-20-103-66(102)104-21-22-107-108-31-44(63(100)101)80-60(96)43(25-51(88)89)79-58(94)40(10-8-18-71-64(68)69)77-59(95)42(24-50(86)87)76-49(85)17-16-41(62(98)99)78-57(93)36-12-14-37(15-13-36)72-28-39-29-73-56-53(75-39)61(97)82-65(70)81-56/h12-15,23,29-30,32,34,40-48,54,72,84,91H,7-11,16-22,24-28,31H2,1-6H3,(H,76,85)(H,77,95)(H,78,93)(H,79,94)(H,80,96)(H,86,87)(H,88,89)(H,98,99)(H,100,101)(H4,68,69,71)(H3,70,73,81,82,97)/b33-23+/t32-,34+,40-,41-,42-,43-,44-,45+,46-,47-,48-,54-,83?/m0/s1

HIDE SMILES / InChI

Molecular Formula	C67H92N16O22S3
Molecular Weight	1569.736
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25380635 | https://adisinsight.springer.com/drugs/800023742

Epofolate (BMS-753493) is a folate conjugate of the epothilone analog BMS-748285 that was designed to selectively target folate receptor expressing cancer cells. In Phase I/IIa pharmacokinetic and safety studies epofolate was generally tolerable and toxicities known to be associated with epothilone class of anticancer agents were common, although peripheral neuropathy and neutropenia appear to have been less frequent and less severe as compared to epothilones. Antitumor activity was not demonstrated and further development of BMS-753493 has been discontinued.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
Degradation of BMS-753493, a novel epothilone folate conjugate anticancer agent.	2013 Sep	23039020
A phase I pharmacokinetic and safety analysis of epothilone folate (BMS-753493), a folate receptor targeted chemotherapeutic agent in humans with advanced solid tumors.	2015 Apr	25380635
Tissue distribution and tumor uptake of folate receptor-targeted epothilone folate conjugate, BMS-753493, in CD2F1 mice after systemic administration.	2016 Sep	27709015

Patents

Sample Use Guides

In Vivo Use Guide

BMS-753493 was investigated in two parallel multi-institutional first-in-human phase I/IIa studies in patients with advanced solid tumors. In Study 1, patients were treated on a schedule of once daily dosing of BMS-753493 administered on Days 1, 4, 8 and 11 every 21 days with a starting dose of 5 mg daily and in Study 2, patients were treated once daily on Days 1-4 every 21 days, with a starting dose of 2.5 mg daily. Results A total of 65 patients were treated across the two studies. The maximum tolerated dose (MTD) was 26 mg in Study 1 and 15 mg in Study 2.

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:19:11 GMT 2023` Edited by `admin` on `Fri Dec 15 19:19:11 GMT 2023`
Record UNII	Q3XAW4B1DP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPOFOLATE

Common Name

English

BMS-753493

Code

English

BMS753493

Code

English

Code System Code Type Description

DRUG BANK

DB12266