Drug Details

General Information of the Drug (ID: DR7358)
Name
Vinorelbine
Synonyms
vinorelbine; 71486-22-1; Navelbine; Vinorelbinum; Exelbine; Vinorelbina; Nor-5'-anhydrovinblastine; UNII-Q6C979R91Y; Vinorelbinum [Latin]; Vinorelbina [Spanish]; Navelbine base; CHEBI:480999; KW-2307; Q6C979R91Y; Navelbine (TN); Eunades; Vinorelbine [INN:BAN]; KW 2307 base; methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(12S,14R)-16-ethyl-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaen-12-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 (2b,3b,4b,5a,12b,19a)-4-(acetyloxy)-15-[(6R,8S)-4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate; Vinorelbine (INN); Vinorelbine(Navelbine); SR-05000001504; HSDB 7665; ANX-530; SDP-012; C45H54N4O8; Vinorelbine(Navelbine)/; 5'-Noranhydrovinblastine; NVB; SCHEMBL4765; cc-469; C'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy-; CHEMBL553025; GTPL7105; DTXSID8040640; HMS2090E13; ABP000672; ZINC85536958; AKOS024457606; AT-7140; CCG-208616; DB00361; NSC 760087; NCGC00165966-03; K210; methyl (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-acetoxy-15-[(6R,8S)-4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate; FT-0657343; D08680; AB01275493-01; AB01566877_01; 486V221; SR-05000001504-1; SR-05000001504-2; Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-((2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino(4,3-b)indol-8-yl)-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-; Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-((2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino(4,3-b)indol-8-yl)-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12R,19alpha)-
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Molecular Type
Small molecule
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Clearance
The drug present in the plasma can be removed from the body at the rate of 20 mL/min/kg
Elimination
Urinary excretion of unchanged drug accounts for less than 20% of an intravenous dose, with fecal elimination accounting for an additional 30% to 60%
Half-life
The concentration or amount of drug in body reduced by one-half in 27.7 - 43.6 hours
Metabolism
The drug is metabolized via the hepatic
Unbound Fraction
The unbound fraction of drug in plasma is 0.87%
Vd
The volume of distribution (Vd) of drug is 25.4-40.1 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 1000 mg/mL
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Formula
C45H54N4O8
PubChem CID
5311497
Canonical SMILES
CCC1=CC2CC(C3=C(CN(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
InChI
1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37-,38+,39+,42+,43+,44-,45-/m0/s1
InChIKey
GBABOYUKABKIAF-IELIFDKJSA-N
CAS Number
CAS 71486-22-1
ChEBI ID
CHEBI:480999
TTD Drug ID
D01HTL
DrugBank ID
DB00361
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Gamma linolenic acid      Gossypium hirsutum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
T-47D CVCL_0553 Invasive breast carcinoma Homo sapiens
SK-BR-3 CVCL_0033 Breast adenocarcinoma Homo sapiens
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Some UFAs can be used as modulators of tumor cell chemosensitivity.
Target and Pathway
Target(s) Tubulin (TUB)  Molecule Info  [3]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7105).
Reference 2 Synergistic interaction between vinorelbine and gamma-linolenic acid in breast cancer cells. Breast Cancer Res Treat. 2002 Apr;72(3):203-19.
Reference 3 Vinca alkaloid and MDR1. Gan To Kagaku Ryoho. 2008 Jul;35(7):1086-9.
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