Vindesine sulfate

Names

[ Name ]:
Vindesine sulfate

[Synonym ]:
2H-3,7-Methanoazacycloundecino[5,4-b]indole-9-carboxylic acid, 9-[(2β,3β,4β,5α,12β,19α)-3-(aminocarbonyl)-6,7-didehydro-3,4-dihydroxy-16-methoxy-1-methylaspidospermidin-15-yl]-5-et hyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-, methyl ester, (5S,7S,9S)-, sulfate (1:1) (salt)
methyl (5S,7S,9S)-9-[(2β,3β,4β,5α,12β,19α)-3-carbamoyl-3,4-dihydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidin-15-yl]-5-ethyl-5-hydroxy-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methanoazacycloundecino[5,4-b]indole-9-carboxylate sulfate (1:1)
Vindesine Sulfate Salt
2H-3,7-methanoazacycloundecino[5,4-b]indole-9-carboxylic acid, 9-[(2β,3β,4β,5α,12β,19α)-3-(aminocarbonyl)-6,7-didehydro-3,4-dihydroxy-16-methoxy-1-methylaspidospermidin-15-yl]-5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-, methyl ester, (5S,7S,9S)-, sulfate (1:1) (salt)
Vindesine sulphate
Methyl (13S,15S,17S)-13-[(2β,3β,4β,5α,12β,19α)-3-carbamoyl-3,4-dihydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidin-15-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0.0]nonadeca-4(12),5,7,9-tetraene-13-carboxylate sulfate (1:1)

Biological Activity

[Description]:

Vindesine sulfate is a potent tubulin inhibitor with an Ki of 0.110 µM. Vindesine sulfate shows anti-proliferation effect in vitro. Vindesine sulfate shows antitumor effect in vivo[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[In Vitro]

Vindesine sulfate inhibits L-cells growth and shows about 25% inhibition at 40 nM[1].

[References]

[1]. Jordan MA, et al. Comparison of the effects of vinblastine, vincristine, vindesine, and vinepidine on microtubule dynamics and cell proliferation in vitro. Cancer Res. 1985 Jun;45(6):2741-7.

Chemical & Physical Properties

[ Density]:
1.41 g/cm3

[ Melting Point ]:
>250ºC

[ Molecular Formula ]:
C₄₃H₅₇N₅O₁₁S

[ Molecular Weight ]:
852.00

[ Exact Mass ]:
851.377502

[ PSA ]:
247.80000

[ LogP ]:
3.80150

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
deionized water: ≥50mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YY8090000

CAS REGISTRY NUMBER :: 59917-39-4

LAST UPDATED :: 199706

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C43-H55-N5-O7.H2-O4-S

MOLECULAR WEIGHT :: 852.11

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1050 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Gastrointestinal - hypermotility, diarrhea Kidney, Ureter, Bladder - urine volume increased

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1790 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1920 ug/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Kidney, Ureter, Bladder - urine volume increased Blood - normocytic anemia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3500 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Gastrointestinal - hypermotility, diarrhea Kidney, Ureter, Bladder - urine volume increased

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6300 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1250 ug/kg/33D-I

TOXIC EFFECTS :: Endocrine - other changes Blood - changes in bone marrow (not otherwise specified) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 1250 ug/kg

SEX/DURATION :: male 10 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 28 nmol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 38,2886,1978

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R40

[ Safety Phrases ]:
26-36

[ RIDADR ]:
UN 1544

[ RTECS ]:
YY8090000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
2942000000

Customs

[ HS Code ]: 2942000000

Articles

Validated HILIC-MS/MS assay for determination of vindesine in human plasma: Application to a population pharmacokinetic study

J. Pharm. Biomed. Anal. 96 , 31-6, (2014)

Mean plasma concentration–time profiles of intravenous injection of 3mg Vindesine Sulfate for Injection to 100 unrelated Chinese Han subjects with hematological malignant disorders.

Young patients with non-germinal center B-cell-like diffuse large B-cell lymphoma benefit from intensified chemotherapy with ACVBP plus rituximab compared with CHOP plus rituximab: analysis of data from the Groupe d'Etudes des Lymphomes de l'Adulte/lymphoma study association phase III trial LNH 03-2B.

J. Clin. Oncol. 32(35) , 3996-4003, (2014)

To determine whether any tumor biomarkers could account for the survival advantage observed in the LNH 03-2B trial among patients with diffuse large B-cell lymphoma (DLBCL) and low-intermediate risk a...

Reovirus cell entry requires functional microtubules.

MBio 4 , (2013)

Mammalian reovirus binds to cell-surface glycans and junctional adhesion molecule A and enters cells by receptor-mediated endocytosis in a process dependent on β1 integrin. Within the endocytic compar...