VINZOLIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C48H58ClN5O9
Molecular Weight	884.455
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@]1(O)C[C@@H]2CN(C1)CCC3=C(NC4=C3C=CC=C4)[C@@](C2)(C(=O)OC)C5=CC6=C(C=C5OC)N(C)[C@@H]7[C@]68CCN9CC=C[C@](CC)([C@@H]89)[C@@H](OC(C)=O)[C@@]7%10OC(=O)N(CCCl)C%10=O

InChI

InChIKey=MMRCWWRFYLZGAE-ZBZRSYSASA-N

InChI=1S/C48H58ClN5O9/c1-7-44(59)24-29-25-47(42(57)61-6,37-31(14-19-52(26-29)27-44)30-12-9-10-13-34(30)50-37)33-22-32-35(23-36(33)60-5)51(4)39-46(32)16-20-53-18-11-15-45(8-2,38(46)53)40(62-28(3)55)48(39)41(56)54(21-17-49)43(58)63-48/h9-13,15,22-23,29,38-40,50,59H,7-8,14,16-21,24-27H2,1-6H3/t29-,38-,39+,40+,44-,45+,46+,47-,48-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3965155 | https://www.ncbi.nlm.nih.gov/pubmed/2272767 | https://www.ncbi.nlm.nih.gov/pubmed/6498855

Vinzolidine (also known as LY104208), a semisynthetic vinblastine derivative that was developed as an antitumor agent. Vinzolidine participated in clinical trials phase II in the oral formulation in patients with lymphoma, particularly Hodgkin's disease. In addition, it was studied in patients with Kaposi's sarcoma, non-small cell lung cancer, colorectal cancer, and breast cancer. It was found significant side effects included neurotoxicity and dose-related myelosuppression. As a result, was suggested intravenous route of administration for vinzolidine could be more safely. However, the phase I trial of intravenous vinzolidine was shown no antitumor activity. The further development of this drug was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Adenocarcinoma of unknown primary: retrospective analysis of chemosensitivity of 313 freshly explanted tumors in a tumor cloning system.	1995	7499107
Phase I trial of intravenous vinzolidine (LY 104208) given on a biweekly dosing schedule.	1990-08	2272767
Oral vinzolidine as therapy for Kaposi's sarcoma and carcinomas of lung, breast, and colon/rectum.	1985	3965155
Phase II trial of vinzolidine, an oral vinca alkaloid, in Hodgkin's disease and non-Hodgkin's lymphoma.	1984-11	6498855

Sample Use Guides

In Vivo Use Guide

intravenous: the maximum tolerated dose (MTD) on this schedule was 9.0 mg/m2 with unpredictable leukopenia oral: substantial variations in morbidity were observed among the patients, some patients receiving doses up to 45 mg/m2 without toxicity while others had severe hematologic toxicity at doses as low as 25 mg/m2.

Route of Administration: Other

Name

Type

Language

VINZOLIDINE

Official Name

English

vinzolidine [INN]

Preferred Name

English

Classification Tree Code System Code

NCI_THESAURUS

C932