Drug Information

General Information
Drug ID
DR00308
Drug Name
Vinblastine
Synonyms
(2ALPHA,2'BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE; (2xi,3beta,4'beta,19xi)-vincaleukoblastine; 1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid; NDC 0002-1452-01; Nincaluicolflastine; Rozevin; VLB; VR-8; Vinblastin; Vinblastina; Vinblastina (TN); Vinblastina [DCIT]; Vinblastine (INN); Vinblastine [INN:BAN]; Vinblastinum; Vinblastinum [INN-Latin]; Vincaleucoblastin; Vincaleucoblastine; Vincaleukoblastine; Vincoblastine
Drug Type
Small molecular drug
Indication Testicular cancer [ICD11:2C80] Approved [1]
Hodgkin lymphoma [ICD11:2B30] Approved [1]
Bladder cancer [ICD11:2C94] Approved [1]
Melanoma [ICD11:2C30] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
Formula
C46H58N4O9
Canonical SMILES
CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
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-/m0/s1
InChIKey
JXLYSJRDGCGARV-CFWMRBGOSA-N
CAS Number
CAS 865-21-4
Pharmaceutical Properties Molecular Weight 811 Topological Polar Surface Area 154
Heavy Atom Count 59 Rotatable Bond Count 10
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 12
XLogP
3.7
PubChem CID
13342
PubChem SID
103229487 ,103924566 ,104331509 ,124886802 ,126628575 ,126690312 ,127342232 ,127342233 ,134338070 ,134980402 ,136126664 ,136959342 ,137001867 ,141857134 ,152104919 ,15945566 ,162184753 ,165280031 ,16702846 ,175268513 ,178103457 ,179335179 ,184812178 ,223683512 ,223832241 ,226395766 ,24262986 ,25641143 ,29281493 ,46393695 ,48034812 ,49855966 ,50104049 ,50637221 ,57328088 ,7891062 ,8160040 ,85788295 ,92718122 ,93167219
ChEBI ID
ChEBI:27375
TTD Drug ID
D0W9MM
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
MDR3 Transporter Info Multidrug resistance protein 3 Substrate [3]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [4]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [5]
P-GP Transporter Info P-glycoprotein 1 Substrate [6]
Drug-Transporter Activity Data
Drug-Transporter Activity Data MRP2 Transporter Info Km =137.3 microM Madin-Darby canine kidney cells (MDCKII)-MRP2 [7]
P-GP Transporter Info Km =0.8 microM Chinese hamster ovary AA8 cells-MDR1 [8]
P-GP Transporter Info Km =5.71 microM High five cells-MDR1 [9]
P-GP Transporter Info Km =19 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [10]
P-GP Transporter Info Km =89.2 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [11]
P-GP Transporter Info Km =99.4 microM LLC-PK1 cells-MDR1 [12]
P-GP Transporter Info Km =253 microM Madin-Darby canine kidney (MDCK) cells-MDR1 [11]
P-GP Transporter Info Km =146 microM Oocytes-MDR1 [6]
P-GP Transporter Info Km =1.7 microM Spodoptera frugiperda (Sf9) cells-MDR1 [13]
References
1 Vinblastine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Ixabepilone, a novel microtubule-targeting agent for breast cancer, is a substrate for P-glycoprotein (P-gp/MDR1/ABCB1) but not breast cancer resistance protein (BCRP/ABCG2). J Pharmacol Exp Ther. 2011 May;337(2):423-32.
3 MDR3 P-glycoprotein, a phosphatidylcholine translocase, transports several cytotoxic drugs and directly interacts with drugs as judged by interference with nucleotide trapping. J Biol Chem. 2000 Aug 4;275(31):23530-9.
4 Development and characterization of a recombinant Madin-Darby canine kidney cell line that expresses rat multidrug resistance-associated protein 1 (rMRP1). AAPS PharmSci. 2004 Mar 9;6(1):E8.
5 Severe hypokalemia due to a possible drug-drug interaction between vinblastine and antiretrovirals in a HIV-infected patient with Hodgkin's lymphoma. Int J STD AIDS. 2017 Oct;28(12):1259-1262.
6 Xenopus laevis oocytes expressing human P-glycoprotein: probing trans- and cis-inhibitory effects on [3H]vinblastine and [3H]digoxin efflux. Pharmacol Res. 2010 Jan;61(1):76-84.
7 Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):773-9.
8 Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71.
9 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
10 Functional expression of P-glycoprotein in apical membranes of human intestinal Caco-2 cells. Kinetics of vinblastine secretion and interaction with modulators. J Biol Chem. 1993 Jul 15;268(20):14991-7.
11 Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):765-72.
12 Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35.
13 Modulation of drug-stimulated ATPase activity of human MDR1/P-glycoprotein by cholesterol. Biochem J. 2007 Jan 15;401(2):597-605.

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