methyl (13S,15S,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

• ChemBase ID: 194
• Molecular Formular: C43H55N5O7
• Molecular Mass: 753.9261
• Monoisotopic Mass: 753.41014913
• SMILES: O[C@]1([C@@H]2N(c3c([C@@]42[C@H]2N(CC4)CC=C[C@]2([C@H]1O)CC)cc(c(OC)c3)[C@]1(C[C@H]2C[C@](O)(CN(C2)CCc2c1[nH]c1c2cccc1)CC)C(=O)OC)C)C(=O)N
• Canonical 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)N)O)(CC)C=CC1
• InChI: InChI=1S/C43H55N5O7/c1-6-39(52)21-25-22-42(38(51)55-5,33-27(13-17-47(23-25)24-39)26-11-8-9-12-30(26)45-33)29-19-28-31(20-32(29)54-4)46(3)35-41(28)15-18-48-16-10-14-40(7-2,34(41)48)36(49)43(35,53)37(44)50/h8-12,14,19-20,25,34-36,45,49,52-53H,6-7,13,15-18,21-24H2,1-5H3,(H2,44,50)/t25-,34+,35-,36-,39+,40-,41-,42+,43+/m1/s1
• InChIKey: HHJUWIANJFBDHT-KOTLKJBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (13S,15S,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraene-13-carboxylate; methyl (13S,15S,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-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-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
• IUPAC Traditional name: vindesine; DVA
• Brand Name: DAVA; Eldesine; Eldisine
• Synonyms: Vindesine Sulfate; Desacetylvinblastine Amide Sulfate; Vindesine

Database IDs

• CAS Number: 59917-39-4
• PubChem SID: 46504548; 160963657
• PubChem CID: 40839
• CHEBI ID: 36373
• ATC CODE: L01CA03
• CHEMBL: 219146
• Chemspider ID: 37302
• DrugBank ID: DB00309
• KEGG ID: D01769
• Unique Ingredient Identifier: RSA8KO39WH
• Wikipedia Title: Vindesine

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.342998
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.6965613
• LogD (pH = 7.4): 0.8213256
• Log P: 2.7891831
• Molar Refractivity: 210.3222 cm^3
• Polarizability: 82.5302 Å^3
• Polar Surface Area: 164.82 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.53
• LOG S: -4.03
• Solubility (Water): 7.00e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.9

Pharmacology Properties

• Admin Routes: Intravenous
• Excretion: Biliary and renal
• Half Life: 24 hours
• Metabolism: Hepatic (CYP3A4-mediated)
• Protein Bound: 65-75%
• Legal Status: Rx-only
• Pregnancy Category: D (Australia)

DETAILS

DrugBank - DB00309

• Drug Groups: approved
• Description: Vinblastine derivative with antineoplastic activity against cancer. Major side effects are myelosuppression and neurotoxicity. Vindesine is used extensively in chemotherapy protocols (antineoplastic combined chemotherapy protocols). [PubChem]
• Indication: For the treatment of acute leukaemia, malignant lymphoma, Hodgkin's disease, acute erythraemia and acute panmyelosis
• Pharmacology: Vindesine is indicated for the treatment of acute lymphocytic leukemia of childhood that is resistant to vincristine and non-oat cell lung cancer.Vindesine causes the arrest of cells in metaphase mitosis. It is three times more potent than vincristine and nearly 10 times more potent than vinblastine in causing mitotic arrest in in vitro studies at doses designed to arrest from 10 to 15% of the cells in mitosis. Vindesine and vincristine are approximately equipotent at dose levels that arrest 40 to 50% of the cells in mitosis. Unlike vinblastine, vindesine produces very few postmetaphase cells. Vindesine has demonstrated activity in patients who have relapsed while receiving multiple-agent treatment that included vincristine.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Half Life: 24 hours.
• Protein Binding: 65-75%
• External Links: Wikipedia; RxList