ORTATAXEL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C44H57NO17
Molecular Weight	871.9199
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12[C@H](OC(=O)C3=CC=CC=C3)[C@]45OC(=O)O[C@H]4[C@H](OC(=O)[C@H](O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)C(C)=C([C@@H](OC(C)=O)C(=O)[C@]1(C)[C@@H](O)C[C@H]6OC[C@@]26OC(C)=O)C5(C)C

InChI

InChIKey=BWKDAMBGCPRVPI-ZQRPHVBESA-N

InChI=1S/C44H57NO17/c1-20(2)17-25(45-38(53)61-40(6,7)8)29(49)37(52)57-30-21(3)28-31(56-22(4)46)33(50)42(11)26(48)18-27-43(19-55-27,60-23(5)47)32(42)35(58-36(51)24-15-13-12-14-16-24)44(41(28,9)10)34(30)59-39(54)62-44/h12-16,20,25-27,29-32,34-35,48-49H,17-19H2,1-11H3,(H,45,53)/t25-,26-,27+,29+,30+,31+,32-,34-,35-,42+,43-,44+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C44H57NO17
Molecular Weight	871.9199
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00044538 | https://www.ncbi.nlm.nih.gov/pubmed/30726533 | https://clinicaltrials.gov/ct2/show/NCT00054314 | https://clinicaltrials.gov/ct2/show/NCT00044538

Ortataxel (previously known as IDN 5109 or BAY59-8862), a second-generation taxane derivative that was developed as an antitumor agent. Ortataxel binds to and stabilizes tubulin molecules, thereby interfering with the dynamics of microtubule assembly/disassembly. This results in the inhibition of cell division and cellular proliferation. In addition, ortataxel modulates multi-drug resistance mechanisms and may be useful for treating multi-drug resistant tumors that express Pgp, MRP-1, and BCRP. This drug participated in phase II clinical trials in patients with advanced renal cell carcinoma and in patients with Non-Hodgkin's lymphoma. However, these studies were discontinued. Ortataxel was also involved in phase II clinical trials for patients with glioblastoma; however, in a limited number of patients, the drug produced a benefit that lasted for a long time. Besides, ortataxel successfully completed phase II trials in taxane-resistant metastatic breast cancer patients and in taxane-resistant non-small cell lung cancer patients.

Approval Year

PubMed

Title	Date	PubMed
Anti-proliferative activity of a new class of taxanes (14beta-hydroxy-10-deacetylbaccatin III derivatives) on multidrug-resistance-positive human cancer cells.	1997 Sep 4	9311603
IDN5109, a taxane with oral bioavailability and potent antitumor activity.	2000 Feb 15	10706091
Antitumor effects of IDN5109 on head and neck squamous cell carcinoma.	2006 Feb	16391850

Sample Use Guides

In Vivo Use Guide

Intravenous dose over 60 minutes every 3 weeks

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:30:53 GMT 2023` Edited by `admin` on `Fri Dec 15 15:30:53 GMT 2023`
Record UNII	8H61Y4E29N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ORTATAXEL

Official Name

English

IDN-5109

Code

English

SB-T 101131

Code

English

Ortataxel [WHO-DD]

Common Name

English

BAY-59-8862

Code

English

IDN5109

Code

English

SB-T-101131

Code

English

ortataxel [INN]

Common Name

English

BAY 59-8862

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67437