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

[H][C@@]12N(C)C3=C(C=C(C(OC)=C3)[C@]4(C[C@@]5([H])CN(C[C@](O)(CC)C5)CCC6=C4NC7=CC=CC=C67)C(=O)OC)[C@@]18CCN9CC=C[C@@](CC)([C@@H](OC(C)=O)[C@@]2%10OC(=O)N(CCCl)C%10=O)[C@@]89[H]

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

Molecular Formula	C48H58ClN5O9
Molecular Weight	884.455
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Oral vinzolidine as therapy for Kaposi's sarcoma and carcinomas of lung, breast, and colon/rectum.	1985	3965155
Phase I trial of intravenous vinzolidine (LY 104208) given on a biweekly dosing schedule.	1990 Aug	2272767
Adenocarcinoma of unknown primary: retrospective analysis of chemosensitivity of 313 freshly explanted tumors in a tumor cloning system.	1995	7499107

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:52:57 GMT 2023` Edited by `admin` on `Fri Dec 15 16:52:57 GMT 2023`
Record UNII	533U947V6Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VINZOLIDINE

Official Name

English

vinzolidine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C932