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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.CC[C@]1(O)C[C@@H]2CN(C1)CCC3=C(NC4=C3C=CC=C4)[C@@](C2)(C(=O)OC)C5=CC6=C(C=C5OC)N(C)[C@@H]7[C@]68CCN9CC=C[C@](CC)([C@@H]89)[C@@H](O)[C@]7(O)C(N)=O

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 H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C43H55N5O7
Molecular Weight 753.9261
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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.
2003-04
Adaptive intrapatient dose escalation of cisplatin in combination with low-dose vp16 in patients with nonsmall cell lung cancer.
2003-03-24
Regulatory approvals of pediatric oncology drugs: previous experience and new initiatives.
2003-03-15
Gemcitabine and vinorelbine followed by docetaxel in patients with advanced non-small-cell lung cancer: a multi-institutional phase II trial of nonplatinum sequential triplet combination chemotherapy (JMTO LC00-02).
2003-02-10
Randomised phase III trial of irinotecan combined with cisplatin for advanced non-small-cell lung cancer.
2003-02-10
[Cost-effectiveness analysis: a reader's guide].
2003-02
Deoxycoformycin-containing combination chemotherapy for adult T-cell leukemia-lymphoma: Japan Clinical Oncology Group Study (JCOG9109).
2003-02
[Current status of the neo-adjuvant and adjuvant therapy for the resectable non-small cell lung cancer].
2003-02
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).
2003-02
Treatment of metastatic malignant melanoma with dacarbazine plus tamoxifen, or vindesine plus tamoxifen: a prospective randomized study.
2003-02
Chemotherapy for malignant pleural mesothelioma: past results and recent developments.
2003-01-27
Feasibility of combination chemotherapy with cisplatin and etoposide for haemodialysis patients with lung cancer.
2003-01-13
Identification and quantitation of antineoplastic compounds in chemotherapeutic infusion bags by use of HPTLC: application to the vinca-alkaloids.
2003-01-01
Role of gemcitabine in the treatment of advanced and metastatic breast cancer.
2003
Immunophenotypical markers, ultrastructure and chemosensitivity profile of metastatic melanoma cells.
2002-12-05
Triplet chemotherapy with vinorelbine, gemcitabine, and cisplatin for advanced non-small cell lung cancer: a phase II study.
2002-12-02
[Comparison of NP and MVP regimen in treatment of advanced non-small cell lung cancer].
2002-12
[Phase II clinical trial of nedaplatin in advanced non-small cell lung cancer].
2002-12
Cisplatin-based chemotherapy regimen (DECAV) for uterine sarcomas.
2002-11-26
[Chemosensitivity testing of oral and maxillofacial cancer with biopsy specimens].
2002-11
[Radio-chemotherapy combination in locally advanced, inoperable, non-small cell bronchial cancers].
2002-11
[New therapeutic options for mesothelioma].
2002-11
Is first-line single-agent mitoxantrone in the treatment of high-risk metastatic breast cancer patients as effective as combination chemotherapy? No difference in survival but higher quality of life were found in a multicenter randomized trial.
2002-11
Platinum drugs in the treatment of non-small-cell lung cancer.
2002-10-07
[Pharmacologic study of intraperitoneal docetaxel in gastric cancer patients with peritoneal dissemination].
2002-10
Induction chemotherapy before operation for multiple endobronchial squamous cell carcinoma of the lung.
2002-10
Advances in diagnosis and management of oligodendroglioma.
2002-10
Primary effect of chemotherapy on the transcription profile of AIDS-related Kaposi's sarcoma.
2002-09-02
Optimization of the separation of Vinca alkaloids by nonaqueous capillary electrophoresis.
2002-08-30
The case for the introduction of new chemotherapy agents in the treatment of advanced non small cell lung cancer in the wake of the findings of The National Institute of Clinical Excellence (NICE).
2002-08-27
Concurrent administration of Docetaxel and Stealth liposomal doxorubicin with radiotherapy in non-small cell lung cancer : excellent tolerance using subcutaneous amifostine for cytoprotection.
2002-08-12
Analysis of O(6)-methylguanine-DNA methyltransferase in melanoma tumours in patients treated with dacarbazine-based chemotherapy.
2002-08
Vinorelbine plus cisplatin versus cisplatin plus vindesine and mitomycin C in stage IIIB-IV non-small cell lung carcinoma: a prospective randomized study.
2002-08
In vitro pharmacological characterizations of the anti-angiogenic and anti-tumor cell migration properties mediated by microtubule-affecting drugs, with special emphasis on the organization of the actin cytoskeleton.
2002-08
Dose-escalation study of weekly irinotecan and daily carboplatin with concurrent thoracic radiotherapy for unresectable stage III non-small cell lung cancer.
2002-07-29
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.
2002-07
[A case of multiple myeloma with infiltration into skeletal muscle after injections of a granulocyte-colony stimulating-factor].
2002-07
Factors predictive of early death in patients receiving high-dose CHOP (ACVB regimen) for aggressive non-Hodgkin's lymphoma: a GELA study.
2002-07
[Chemoradiotherapy in locally advanced cancers of the uterine neck. Retrospective study of 92 patients treated at the Institute Curie between 1986 and 1998]].
2002-06
Mydriasis after the treatment of vindesine in a patient with acute promyelocytic leukemia.
2002-06
A phase III randomized trial comparing vindesine and cisplatin with or without ifosfamide in patients with advanced non-small-cell lung cancer: long-term follow-up results and analysis of prognostic factors.
2002-06
Shortened first-line high-dose chemotherapy for patients with poor-prognosis aggressive lymphoma.
2002-05-15
[ Early anti-cancer drugs].
2002-05
Change in pharmacokinetic and pharmacodynamic behavior of gemcitabine in human tumor xenografts upon entrapment in vesicular phospholipid gels.
2002-05
Loading anticancer drugs into HDL as well as LDL has little affect on properties of complexes and enhances cytotoxicity to human carcinoma cells.
2002-04-23
[Antitumor activity of combination treatment combining gemcitabine with topotecin against human lung cancer xenografted in nude mice].
2002-04
Study of therapy resistance in cancer cells with functional proteome analysis.
2002-03
Novel aspects of natural and modified vinca alkaloids.
2002-01
[Neuron-specific enolase (NSE) serum level as a prognostic factor in non-small cell lung cancer].
2002
[Clinical observation on effect of chemotherapy combined with Chinese medicine in treating advanced tumor patients and on immunologic parameters].
2001-12
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 Mon Mar 31 17:46:14 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:14 GMT 2025
Record UNII
CPH2U7DNDY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FILDESIN
Preferred Name English
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
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 Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
NCI_THESAURUS C932
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID0049074
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
CHEBI
32295
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
SMS_ID
100000087883
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
NSC
245467
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL219146
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
EVMPD
SUB05102MIG
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
DRUG BANK
DBSALT000440
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
CAS
59917-39-4
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
FDA UNII
CPH2U7DNDY
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
NCI_THESAURUS
C935
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
ECHA (EC/EINECS)
261-984-7
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
PUBCHEM
76958180
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY
MERCK INDEX
m11454
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
PRIMARY Merck Index
RXCUI
11205
Created by admin on Mon Mar 31 17:46:14 GMT 2025 , Edited by admin on Mon Mar 31 17:46:14 GMT 2025
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