ANHYDROVINBLASTINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C46H56N4O8
Molecular Weight	792.9588
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12N3CC[C@@]14C5=CC(=C(OC)C=C5N(C)[C@@]4([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]6(C[C@H]7C[N@](CC(CC)=C7)CCC8=C6NC9=CC=CC=C89)C(=O)OC

InChI

InChIKey=FFRFGVHNKJYNOV-ZCIMLLHDSA-N

InChI=1S/C46H56N4O8/c1-8-28-21-29-24-45(41(52)56-6,37-31(15-19-49(25-28)26-29)30-13-10-11-14-34(30)47-37)33-22-32-35(23-36(33)55-5)48(4)39-44(32)17-20-50-18-12-16-43(9-2,38(44)50)40(58-27(3)51)46(39,54)42(53)57-7/h10-14,16,21-23,29,38-40,47,54H,8-9,15,17-20,24-26H2,1-7H3/t29-,38-,39+,40+,43+,44+,45-,46-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C46H56N4O8
Molecular Weight	792.9588
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800011729 | https://www.ncbi.nlm.nih.gov/pubmed/12655441

Anhydrovinblastine (AVLB) is a semisynthetic vinca alkaloid, which can safely be administered every 3 weeks at a dose of 21 mg/m2. Anhydrovinblastine is a cell cycle-specific anti-mitotic agent whose anti-tumour activity is directly related to its ability to bind tightly to tubulin and inhibit its polymerization into microtubules. Anhydrovinblastine has been used in trials studying the treatment of adult solid rumor, but this research has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Phase I and pharmacokinetic study of anhydrovinblastine every 3 weeks in patients with refractory solid tumors.	2003 Mar	12655441
Stereoselective conversion of anhydrovinblastine into vinblastine utilizing an anti-vinblastine monoclonal antibody as a chiral mould.	2006 May	16651762
Inhibitors of tubulin polymerization: synthesis and biological evaluation of hybrids of vindoline, anhydrovinblastine and vinorelbine with thiocolchicine, podophyllotoxin and baccatin III.	2008 Jun 1	18468444

Patents

Sample Use Guides

In Vivo Use Guide

Solid tumor: A total of 51 courses were administered at doses of 2.5, 5, 10, 16.5, 21, 25 and 30 mg/m2 in one, three, one, three, six, six and one patient respectively. Results: Grade 2 infusional hypertension, anemia, and dizziness were noted at 16.5 mg/m2. At 25 mg/m2, two of six evaluable patients had DLT. DLT was grade 4 constipation, neutropenia and grade 3 nausea/vomiting. At 21 mg/m2 one of six evaluable patients had DLT (grade 3 nausea/vomiting). This dose was the MTD. The recommended phase II dose is 21 mg/m2.

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:52 GMT 2023` Edited by `admin` on `Fri Dec 15 15:37:52 GMT 2023`
Record UNII	5B622U08B3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANHYDROVINBLASTINE

Common Name

English

(+)-ANHYDROVINBLASTINE

Common Name

English

VINCALEUKOBLASTINE, 3',4'-DIDEHYDRO-4'-DEOXY-

Common Name

English

3',4'-DIDEHYDROISOLEUROSINE

Common Name

English

F-81097

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67422