VINFORMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C46H54N4O10
Molecular Weight	822.9418
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12O[C@@]1(CC)CN3C[C@]2([H])C[C@@](C(=O)OC)(C4=C(CC3)C5=CC=CC=C5N4)C6=C(OC)C=C7N(C=O)[C@]8([H])[C@]9(CCN%10CC=C[C@@](CC)([C@@H](OC(C)=O)[C@]8(O)C(=O)OC)[C@@]9%10[H])C7=C6

InChI

InChIKey=GLDSBTCHEGZWCV-NVDFJPPOSA-N

InChI=1S/C46H54N4O10/c1-7-42-15-11-17-49-19-16-44(37(42)49)30-20-31(34(56-4)21-33(30)50(25-51)38(44)46(55,41(54)58-6)39(42)59-26(3)52)45(40(53)57-5)22-27-23-48(24-43(8-2)36(27)60-43)18-14-29-28-12-9-10-13-32(28)47-35(29)45/h9-13,15,20-21,25,27,36-39,47,55H,7-8,14,16-19,22-24H2,1-6H3/t27-,36+,37-,38+,39+,42+,43-,44+,45-,46-/m0/s1

HIDE SMILES / InChI

Description
Sources: Zhang Lixin, Demain Arnold L., Natural Products: Drug Discovery and Therapeutic Medicine, p. 184, retrieved from: https://books.google.ru/books?id=iP0i7x_38ZwC&pg=PA184&lpg=PA184&dq=VINFORMIDE&source=bl&ots=U878D4nJwk&sig=ACfU3U3IXH0TwpkFR68oYLYug7IZVYIm7Q&hl=ru&sa=X&ved=2ahUKEwiAnrO4pqvjAhVGxMQBHX-mDaQQ6AEwDnoECAgQAQ#v=onepage&q=VINFORMIDE&f=false | https://www.ncbi.nlm.nih.gov/pubmed/348087

Vinformide (also known as N-formylleurosine), an N-formyl analog of leurosine possesses antineoplastic activity. This drug was studied for the treatment of lymphoma, leukemia and Hodkin’s disease. However, studies were discontinued, because vinformide exerted an acute cardiotoxic side effect.

Approval Year

PubMed

Title	Date	PubMed
Phase I and II studies with hexitol derivatives, formyl-leurosine and ftorafur.	1978	348087
[Neurotoxicity of formyl leurosine. An experimental and clinical study (author's transl)].	1979 Jul-Aug	539376
[Neurotoxicity of formyl leurosine. An experimental and clinical study (author's transl)].	1979 Jul-Aug	232962
Prevention of cardiac damage induced by formyl-leurosine, a potent cytostatic agent, by radio-detoxified endotoxin (Tolerin) in dogs.	1984 Aug	6490357

Sample Use Guides

In Vivo Use Guide

Six patients received one to three 5-day courses of formyl leurosine (FLR; VINFORMIDE). The total dose of FLR administered ranged from 15 to 131 mg (mean 83 mg).

Route of Administration: Intravenous

Name

Type

Language

VINFORMIDE

Official Name

English

FORMYLLEUROSINE [EP IMPURITY]

Common Name

English

VINCRISTINE SULFATE IMPURITY G [EP IMPURITY]

Common Name

English

METHYL (3AR,4R,5S,5AR,10BR,13AR)-4-(ACETYLOXY)-3A-ETHYL-9-((1AS,11S,13S,13AR)-1A-ETHYL-11-(METHOXYCARBONYL)-1A,4,5,10,11,12,13,13A-OCTAHYDRO-2H-3,13-METHANO-OXIRENO(9,10)AZACYCLOUNDECINO(5,4-B)INDOL-11-YL)-6-FORMYL-5-HYDROXY-8-METHOXY-3A,4,5,5A,6,11,12,1

Systematic Name

English

N-DEMETHYL-N-FORMYLLEUROSINE

Common Name

English

NSC-269419

Code

English

vinformide [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C274