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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H55N5O7.H2O4S
Molecular Weight 852.005
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VINDESINE SULFATE

SMILES

OS(O)(=O)=O.[H][C@@]12N3CC[C@@]14C5=CC(=C(OC)C=C5N(C)[C@@]4([H])[C@](O)([C@H](O)[C@]2(CC)C=CC3)C(N)=O)[C@]6(C[C@@]7([H])CN(C[C@](O)(CC)C7)CCC8=C6NC9=C8C=CC=C9)C(=O)OC

InChI

InChIKey=COFJBSXICYYSKG-OAUVCNBTSA-N
InChI=1S/C43H55N5O7.H2O4S/c1-6-39(52)21-25-22-42(38(51)55-5,33-27(13-17-47(23-25)24-39)26-11-8-9-12-30(26)45-33)29-19-28-31(20-32(29)54-4)46(3)35-41(28)15-18-48-16-10-14-40(7-2,34(41)48)36(49)43(35,53)37(44)50;1-5(2,3)4/h8-12,14,19-20,25,34-36,45,49,52-53H,6-7,13,15-18,21-24H2,1-5H3,(H2,44,50);(H2,1,2,3,4)/t25-,34-,35+,36+,39-,40+,41+,42-,43-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C43H55N5O7
Molecular Weight 753.9261
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Vindesine (desacetyl vinblastine amide sulfate) is a synthetic derivative of vinblastine. Vindesine acts by causing the arrest of cells in metaphase mitosis through its inhibition tubulin mitotic funcitoning. Vindesine is an anti-neoplastic drug for intravenous use which can be used alone or in combination with other oncolytic drugs. Information available at present suggests that Eldisine as a single agent may be useful for the treatment of: acute lymphoblastic leukaemia of childhood resistant to other drugs; blastic crises of chronic myeloid leukaemia; malignant melanoma unresponsive to other forms of therapy; advanced carcinoma of the breast, unresponsive to appropriate endocrine surgery and/or hormonal therapy. Adverse effects associated with the use of vindesine include cellulitis and phlebitis, gastrointestinal bleeding, chills, and fever. It may increase the neuropathy associated with Charcot-Marie-Tooth syndrome. Vindesine may interact with mitomycin-C (brand name Mutamycin), causing acute bronchospasm within minutes or hours following administration. Phenytoin (brand name Dilantin) may also interact with vindesine, leading to decreased serum levels of phenytoin.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Eldisine
Primary
Eldisine
Primary
Eldisine
Primary
Eldisine

PubMed

Sample Use Guides

In Vivo Use Guide
The usual dose is 3 milligrams for every square metre of the body surface. The maximum total weekly dosage for which data exists is 4mg/m2
Route of Administration: Intravenous
In Vitro Use Guide
Human small cell lung cancer H69 (104 cells/ml) cells were seeded into a 96-well microplate in a volume of 180 ul. A 20-ul aliquot of various concentrations of vindesine was added to each well. The IC50 of H69 for vindesine was estimated as 5.5 nM.
Substance Class Chemical
Record UNII
CPH2U7DNDY
Record Status Validated (UNII)
Record Version