CAS 865-21-4|Vinblastine|Rozevin|Vincaleucoblastine|Velbe|Vinblastin|Vinblastina [Dcit]|Vinblastinum [INN-Latin]|Velban|Vincoblastine|methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,1...

General Information

Structure

Molecular Formula

C₄₆H₅₈N₄O₉

Molecular Mass

810.97412

Exact Mass

810.42037946

Charge

InChI

InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1

InChIKey

JXLYSJRDGCGARV-XQKSVPLYSA-N

Canonic Smiles

COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1

Isomeric Smiles

c1c2c(cc(c1OC)[C@@]1(c3[nH]c4ccccc4c3CCN3C[C@](C[C@@H](C3)C1)(O)CC)C(=O)OC)[C@@]13CCN4CC=C[C@@]([C@@H]34)(CC)[C@@H](OC(=O)C)[C@@](O)([C@@H]1N2C)C(=O)OC

Calculated Properties

JChem

LogD (pH = 7.4)

1.81

LogD (pH = 5.5)

-1.67

Log P

4.18

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

8.86

Polar Surface Area

154.10

Polarizability

87.47

Molar Refractivity

222.42

LOG S

-4.03

Data Source

Names and Identifiers

IUPAC Traditional name

vincaleukoblastine vinblastine methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

Brand Name

Vinblastina [Dcit]NincaluicolflastineVinblastinVincoblastineVincaleucoblastineVinblastine SulfateVincaleucoblastinVinblastinum [INN-Latin]VincaleukoblastineVelbanRozevinVelbe

IUPAC name

methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

Synonyms

VinblastinevincaleukoblastineVLBvincaleukoblastine(+)-vinblastine(2ALPHA,2'BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE

International Nonproprietary Name (INN)

vinblastinavinblastinumvinblastine

Names and Identifiers

Registration numbers

CHEMBL

PubChem CID

Chemspider ID

KEGG ID

ATC CODE

Medline Plus

Unique Ingredient Identifier

5V9KLZ54CY

CHEBI ID

27375CHEBI:27375CHEBI:46447CHEBI:27287CHEBI:9983

CAS Number

865-21-4

DrugBank ID

DB00570

Wikipedia Title

Vinblastine

PubChem SID

4650455016096391514717661

MetaboLights Database

MTBLS379MTBLS142

UniProt Database

P07305Q8VWZ7Q6V4H0P98183Q06034Q99T13Q9ZTK5

BKMS React Database

127062125884

PubMed Citation Links

1187896615917812228687582558606935404502275184422666076220394103

BRENDA Database

7.6.2.2

Drug Central Database

2,823

BindingDB Database

227643

KEGG DRUG Database

D08675

SureChEMBL Database

SCHEMBL6146SCHEMBL17813675

Beilstein Number

4779207

Patent number

WO2007098183

BRENDA Ligand Database

HMDB Database

PDBeChem Database

KNApSAcK Database

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

3.9

Solubility

Negligible

Pharmacology Properties

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00570

Drug Groups

approved

Description

Antitumor alkaloid isolated from Vinca rosea. (Merck, 11th ed.)

Indication

For treatment of breast cancer, testicular cancer, lymphomas, neuroblastoma, Hodgkin's and non-Hodgkin's lymphomas, mycosis fungoides, histiocytosis, and Kaposi's sarcoma.

Pharmacology

Vinblastine is a vinca alkaloid antineoplastic agent. The vinca alkaloids are structurally similar compounds comprised of 2 multiringed units: vindoline and catharanthine. The vinca alkaloids have become clinically useful since the discovery of their antitumour properties in 1959. Initially, extracts of the periwinkle plant (Catharanthus roseus) were investigated because of putative hypoglycemic properties, but were noted to cause marrow suppression in rats and antileukemic effects in vitro. Vinblastine has some immunosuppressant effect. The vinca alkaloids are considered to be cell cycle phase-specific.

Toxicity

Oral, mouse: LD₅₀ = 423 mg/kg; Oral, rat: LD₅₀ = 305 mg/kg.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic. Metabolism of vinblastine has been shown to be mediated by hepatic cytochrome P450 3A isoenzymes.

Half Life

Triphasic: 35 min, 53 min, and 19 hours

Protein Binding

98-99%

Elimination

The major route of excretion may be through the biliary system.

References

• Starling D: Two ultrastructurally distinct tubulin paracrystals induced in sea-urchin eggs by vinblastine sulphate. J Cell Sci. 1976 Jan;20(1):79-89. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Wikipedia

Vinblastine

Molecule Details

References

PubChem Literature

From Data Sources

• Starling D: Two ultrastructurally distinct tubulin paracrystals induced in sea-urchin eggs by vinblastine sulphate. J Cell Sci. 1976 Jan;20(1):79-89. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

Brand Name

Vinblastina [Dcit]NincaluicolflastineVinblastinVincoblastineVincaleucoblastineVinblastine SulfateVincaleucoblastinVinblastinum [INN-Latin]VincaleukoblastineVelbanRozevinVelbe

IUPAC name

Synonyms

VinblastinevincaleukoblastineVLBvincaleukoblastine(+)-vinblastine(2ALPHA,2'BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE

International Nonproprietary Name (INN)

vinblastinavinblastinumvinblastine

Registration numbers

CHEMBL

PubChem CID

Chemspider ID

KEGG ID

ATC CODE

Medline Plus

Unique Ingredient Identifier

5V9KLZ54CY

CHEBI ID

27375CHEBI:27375CHEBI:46447CHEBI:27287CHEBI:9983

CAS Number

865-21-4

DrugBank ID

DB00570

Wikipedia Title

Vinblastine

PubChem SID

4650455016096391514717661

MetaboLights Database

MTBLS379MTBLS142

UniProt Database

P07305Q8VWZ7Q6V4H0P98183Q06034Q99T13Q9ZTK5

BKMS React Database

127062125884

PubMed Citation Links

1187896615917812228687582558606935404502275184422666076220394103

BRENDA Database

7.6.2.2

Drug Central Database

2,823

BindingDB Database

227643

KEGG DRUG Database

D08675

SureChEMBL Database

SCHEMBL6146SCHEMBL17813675

Beilstein Number

4779207

Patent number

WO2007098183

BRENDA Ligand Database

HMDB Database

PDBeChem Database

KNApSAcK Database

Properties

Physical Property

Hydrophobicity(logP)

3.9

Solubility

Negligible

Pharmacology Properties

Molecule Details

DrugBank

DB00570

Drug Groups

approved

Description

Antitumor alkaloid isolated from Vinca rosea. (Merck, 11th ed.)

Indication

For treatment of breast cancer, testicular cancer, lymphomas, neuroblastoma, Hodgkin's and non-Hodgkin's lymphomas, mycosis fungoides, histiocytosis, and Kaposi's sarcoma.

Pharmacology

Toxicity

Oral, mouse: LD₅₀ = 423 mg/kg; Oral, rat: LD₅₀ = 305 mg/kg.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic. Metabolism of vinblastine has been shown to be mediated by hepatic cytochrome P450 3A isoenzymes.

Half Life

Triphasic: 35 min, 53 min, and 19 hours

Protein Binding

98-99%

Elimination

The major route of excretion may be through the biliary system.

References

• Starling D: Two ultrastructurally distinct tubulin paracrystals induced in sea-urchin eggs by vinblastine sulphate. J Cell Sci. 1976 Jan;20(1):79-89. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Wikipedia

Vinblastine

References

PubChem Literature

From Data Sources

• Starling D: Two ultrastructurally distinct tubulin paracrystals induced in sea-urchin eggs by vinblastine sulphate. J Cell Sci. 1976 Jan;20(1):79-89. Pubmed

Bioactivity

PubChem BioAssay

Molecule

ID:452