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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27709015
Curator's Comment: Epofolate (BMS 753493) has very poor penetration into mouse brain despite showing wide distribution into other normal tissues.
Originator
Approval Year
Sample Use Guides
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
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SUBSTANCE RECORD