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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
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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: doi:10.1016/B978-008055232-3.62854-5 | http://www.encyclopedia.com/medicine/drugs/pharmacology/vindesine

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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Eldisine

Approved Use

Vindesine is used primarily to treat acute lymphocytic leukemia.
Primary
Eldisine

Approved Use

Eldisine as a single agent may be useful for the treatment of blastic crises of chronic myeloid leukaemia.
Primary
Eldisine

Approved Use

Eldisine as a single agent may be useful for the treatment of malignant melanoma unresponsive to other forms of therapy
Primary
Eldisine

Approved Use

Eldisine as a single agent may be useful for the treatment of advanced carcinoma of the breast, unresponsive to appropriate endocrine surgery and/or hormonal therapy
PubMed

PubMed

TitleDatePubMed
Cisplatin, vindesine, mitomycin-C and 13-cis retinoic acid in the treatment of advanced non small cell lung cancer. A phase II pilot study.
2000 May-Jun
A clinical, molecular and cytogenetic study of 12 cases of human herpesvirus 8 associated primary effusion lymphoma in HIV-infected patients.
2001
Expense and benefit of neoadjuvant treatment in squamous cell carcinoma of the esophagus.
2001
Biodegradation of the antineoplastics vindesine, vincristine, and vinblastine and their toxicity against bacteria in the aquatic environment.
2001
Adenovirus-mediated p16 gene transfer changes the sensitivity to taxanes and Vinca alkaloids of human ovarian cancer cells.
2001 Jul-Aug
Chemotherapy and concomitant irradiation in inflammatory breast cancer.
2001 Jul-Aug
[A case of primary malignant fibrous histiocytoma of the lung].
2001 Mar
Pathologic and clinical features of 77 Hodgkin's lymphoma patients treated in a lymphoma protocol (LNH87): a GELA study.
2001 Mar
[Treatment for elderly lung cancer patients by anticancer drugs and possible use of target based drugs].
2001 May
A new G-CSF-supported combination chemotherapy, LSG15, for adult T-cell leukaemia-lymphoma: Japan Clinical Oncology Group Study 9303.
2001 May
The role of mitomycin in the treatment of non-small cell lung cancer: a systematic review with meta-analysis of the literature.
2001 May 4
A case with HER2-overexpressing breast cancer completely responded to humanized anti-HER2 monoclonal antibody.
2001 Nov
Modifications in the "upper" velbenamine part of the Vinca alkaloids have major implications for tubulin interacting activities.
2001 Sep
[Neuron-specific enolase (NSE) serum level as a prognostic factor in non-small cell lung cancer].
2002
A phase II study of continuous concurrent thoracic radiotherapy in combination with mitomycin, vindesine and cisplatin in unresectable stage III non-small cell lung cancer.
2002 Apr
Trimodality treatment in Stage III nonsmall cell lung carcinoma: prrognostic impact of K-ras mutations after neoadjuvant therapy.
2002 Apr 1
[Comparison of NP and MVP regimen in treatment of advanced non-small cell lung cancer].
2002 Dec
[Phase II clinical trial of nedaplatin in advanced non-small cell lung cancer].
2002 Dec
Immunophenotypical markers, ultrastructure and chemosensitivity profile of metastatic melanoma cells.
2002 Dec 5
[Hypercalcemia mediated by parathyroid hormone-related protein in the blastic phase of chronic myelogenous leukemia].
2002 Feb
Treatment of acute lymphoblastic leukemia in the elderly: an evaluation of interferon alpha given as a single agent after complete remission.
2002 Jan
Dose-intensified accelerated vindesine-ifosfamide-cisplatin (VIP) chemotherapy followed by high-dose accelerated hyperfractionated radiotherapy in patients with pathologically proven stage IIIB non-small cell lung cancer: a feasibility study.
2002 Jul
[A case of multiple myeloma with infiltration into skeletal muscle after injections of a granulocyte-colony stimulating-factor].
2002 Jul
Dose-escalation study of weekly irinotecan and daily carboplatin with concurrent thoracic radiotherapy for unresectable stage III non-small cell lung cancer.
2002 Jul 29
[Chemoradiotherapy in locally advanced cancers of the uterine neck. Retrospective study of 92 patients treated at the Institute Curie between 1986 and 1998]].
2002 Jun
Shortened first-line high-dose chemotherapy for patients with poor-prognosis aggressive lymphoma.
2002 May 15
[Chemosensitivity testing of oral and maxillofacial cancer with biopsy specimens].
2002 Nov
Induction of long-term remission of a relapsed childhood B-acute lymphoblastic leukemia with rituximab chimeric anti-CD20 monoclonal antibody and autologous stem cell transplantation.
2003 Apr
[Cost-effectiveness analysis: a reader's guide].
2003 Feb
Deoxycoformycin-containing combination chemotherapy for adult T-cell leukemia-lymphoma: Japan Clinical Oncology Group Study (JCOG9109).
2003 Feb
[Current status of the neo-adjuvant and adjuvant therapy for the resectable non-small cell lung cancer].
2003 Feb
A randomized trial comparing induction chemotherapy followed by surgery with surgery alone for patients with stage IIIA N2 non-small cell lung cancer (JCOG 9209).
2003 Feb
Identification and quantitation of antineoplastic compounds in chemotherapeutic infusion bags by use of HPTLC: application to the vinca-alkaloids.
2003 Jan 1
Chemotherapy for malignant pleural mesothelioma: past results and recent developments.
2003 Jan 27
Regulatory approvals of pediatric oncology drugs: previous experience and new initiatives.
2003 Mar 15
Patents

Sample Use Guides

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
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
Created
by admin
on Fri Dec 15 15:05:42 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:42 GMT 2023
Record UNII
CPH2U7DNDY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VINDESINE SULFATE
EP   JAN   MART.   USAN   VANDF   WHO-DD  
USAN  
Official Name English
VINDESINE SULFATE SALT
MI  
Common Name English
VINCALEUKOBLASTINE, 3-(AMINOCARBONYL)-O(SUP 4)-DEACETYL-3-DE(METHOXYCARBONYL)SULPHATE (1:1) (SALT)
Common Name English
LY-099094
Code English
3-CARBAMOYL-4-DEACETYL-3-DE(METHOXYCARBONYL)VINCALEUKOBLASTINE SULPHATE (1:1) (SALT)
Common Name English
VINDESINE SULFATE [EP IMPURITY]
Common Name English
3-Carbamoyl-4-deacetyl-3-de(methoxycarbonyl)vincaleukoblastine sulfate (1:1) (salt)
Common Name English
VINDESINE SULFATE [MART.]
Common Name English
FILDESIN
Brand Name English
Vindesine sulfate [WHO-DD]
Common Name English
NSC-245467
Code English
LY099094
Code English
VINDESINE SULFATE [JAN]
Common Name English
VINDESINE SULPHATE
Common Name English
VINDESINE SULFATE [EP MONOGRAPH]
Common Name English
VINDESINE SULFATE [USAN]
Common Name English
VINDESINE SULFATE [VANDF]
Common Name English
VINCALEUKOBLASTINE, 3-(AMINOCARBONYL)-O(SUP 4)-DEACETYL-3-DE(METHOXYCARBONYL)SULFATE (1:1) (SALT)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67422
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
NCI_THESAURUS C932
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID0049074
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
CHEBI
32295
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
SMS_ID
100000087883
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
NSC
245467
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL219146
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
EVMPD
SUB05102MIG
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
DRUG BANK
DBSALT000440
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
CAS
59917-39-4
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
FDA UNII
CPH2U7DNDY
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
NCI_THESAURUS
C935
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
ECHA (EC/EINECS)
261-984-7
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
PUBCHEM
76958180
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY
MERCK INDEX
m11454
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY Merck Index
RXCUI
11205
Created by admin on Fri Dec 15 15:05:42 GMT 2023 , Edited by admin on Fri Dec 15 15:05:42 GMT 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY