VLB

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

Created:	2005-03-17
Last modified:	2020-06-05

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7 entries where VLB is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	117
Chiral Atom Count	9
Bond Count	125
Aromatic Bond Count	16

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Chemical Component Summary
Name	(2ALPHA,2'BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE
Synonyms	VINBLASTINE
Systematic Name (OpenEye OEToolkits)	n/a
Formula	C₄₆ H₅₈ N₄ O₉
Molecular Weight	810.974
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(OC)C4(c2c(c1ccccc1n2)CCN3CC(O)(CC)CC(C3)C4)c5c(OC)cc6c(c5)C89C(N6C)C(O)(C(=O)OC)C(OC(=O)C)C7(C=CCN(C78)CC9)CC
SMILES	CACTVS	3.341	CC[C]1(O)C[CH]2CN(CCc3c([nH]c4ccccc34)[C](C2)(C(=O)OC)c5cc6c(cc5OC)N(C)[CH]7[C](O)([CH](OC(C)=O)[C]8(CC)C=CCN9CC[C]67[CH]89)C(=O)OC)C1
SMILES	OpenEye OEToolkits	1.5.0	CCC1(CC2CC(c3c(c4ccccc4[nH]3)CCN(C2)C1)(c5cc6c(cc5OC)N(C7C68CCN9C8C(C=CC9)(C(C7(C(=O)OC)O)OC(=O)C)CC)C)C(=O)OC)O
Canonical SMILES	CACTVS	3.341	CC[C@]1(O)C[C@@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C2)(C(=O)OC)c5cc6c(cc5OC)N(C)[C@H]7[C@](O)([C@H](OC(C)=O)[C@]8(CC)C=CCN9CC[C@]67[C@H]89)C(=O)OC)C1
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC[C@@]1(C[C@H]2C[C@@](c3c(c4ccccc4[nH]3)CC[N@](C2)C1)(c5cc6c(cc5OC)[N@@]([C@@H]7[C@]68CC[N@]9[C@H]8[C@@](C=CC9)([C@H]([C@@]7(C(=O)OC)O)OC(=O)C)CC)C)C(=O)OC)O
InChI	InChI	1.03	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-/m0/s1
InChIKey	InChI	1.03	JXLYSJRDGCGARV-CFWMRBGOSA-N

Drug Info: DrugBank

DrugBank ID	DB00570
Name	Vinblastine
Groups	approved
Description	Antitumor alkaloid isolated from Vinca rosea. (Merck, 11th ed.)
Synonyms	Vinblastine sulfate Vinblastin Vinblastinum Vincaleukoblastine Vinblastine Vinblastina
Brand Names	Vinblastine Sulfate Injection Velbe 1mg/ml Vinblastine Sulphate Injection Vinblastine Sulfate Vinblastine Sulfate Inj 1mg/ml
Indication	For treatment of breast cancer, testicular cancer, lymphomas, neuroblastoma, Hodgkin's and non-Hodgkin's lymphomas, mycosis fungoides, histiocytosis, and Kaposi's sarcoma.
Categories	Alkaloids Antimitotic Agents Antineoplastic Agents Antineoplastic Agents, Phytogenic Antineoplastic and Immunomodulating Agents BSEP/ABCB11 Inhibitors BSEP/ABCB11 Substrates BSEP/ABCB11 Substrates with a Narrow Therapeutic Index Cardiotoxic antineoplastic agents Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP3A Inducers Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inducers Cytochrome P-450 CYP3A4 Inducers (strength unknown) Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Heterocyclic Compounds, Fused-Ring Immunosuppressive Agents Indole Alkaloids Indoles Indolizidines Indolizines Mitosis Modulators Myelosuppressive Agents Narrow Therapeutic Index Drugs OATP1B1/SLCO1B1 Inhibitors P-glycoprotein inducers P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Secologanin Tryptamine Alkaloids Tubulin Modulators Vinca Alkaloids
ATC-Code	L01CA01
CAS number	865-21-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Tubulin alpha-1A chain	MRECISIHVGQAGVQIGNACWELYCLEHGIQPDGQMPSDKTIGGGDDSFN...	unknown	binder
Tubulin beta chain	MREIVHIQAGQCGNQIGAKFWEVISDEHGIDPTGTYHGDSDLQLDRISVY...	unknown	binder
Tubulin delta chain	MSIVTVQLGQCGNQIGFEVFDALLSDSHSSQGLCSMRENEAYQASCKERF...	unknown	binder
Tubulin gamma-1 chain	MPREIITLQLGQCGNQIGFEFWKQLCAEHGISPEGIVEEFATEGTDRKDV...	unknown	binder
Tubulin epsilon chain	MTQSVVVQVGQCGNQIGCCFWDLALREHAAVNQKGIYDEAISSFFRNVDT...	unknown	binder
Transcription factor AP-1	MTAKMETTFYDDALNASFLPSESGPYGYSNPKILKQSMTLNLADPVGSLK...	unknown	other/unknown
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor,inducer
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor,inducer
Multidrug resistance-associated protein 1	MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...	unknown	substrate,inhibitor,inducer
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	substrate,inhibitor,inducer
Multidrug resistance-associated protein 6	MAAPAEPCAGQGVWNQTEPEPAATSLLSLCFLRTAGVWVPPMYLWVLGPI...	unknown	inhibitor
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682