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

• ChemBase ID: 130457
• Molecular Formular: C45H54N4O8
• Molecular Mass: 778.93226
• Monoisotopic Mass: 778.39416471
• SMILES: O=C(OC)[C@]1(c2[nH]c3ccccc3c2CN2CC(=C[C@@H](C2)C1)CC)c1c(OC)cc2c(c1)[C@@]13[C@@H](N2C)[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@@]2(C=CCN([C@H]12)CC3)CC
• Canonical SMILES: CCC1=C[C@H]2CN(C1)Cc1c3ccccc3[nH]c1[C@@](C2)(C(=O)OC)c1cc2c(cc1OC)N([C@@H]1[C@@]32CCN2[C@H]3[C@@](CC)(C=CC2)[C@H]([C@]1(O)C(=O)OC)OC(=O)C)C
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^3,^1^1.0^4,^9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-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-tetraene-10-carboxylate
• IUPAC Traditional name: vinorelbine
• Brand Name: Navelbine
• Synonyms: Vinorelbine

Database IDs

• CAS Number: 71486-22-1
• PubChem SID: 162224736
• PubChem CID: 5311497
• ATC CODE: L01CA04
• CHEMBL: 607994
• Chemspider ID: 4470974
• DrugBank ID: DB00361
• KEGG ID: D08680
• Unique Ingredient Identifier: Q6C979R91Y
• Wikipedia Title: Vinorelbine
• Medline Plus: a695013

CALCULATED PROPERTIES

• Acid pKa: 10.868411
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.86895776
• LogD (pH = 7.4): 2.6344895
• Log P: 4.6482043
• Molar Refractivity: 216.9875 cm^3
• Polarizability: 85.129105 Å^3
• Polar Surface Area: 133.87 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: intravenous, oral
• Bioavailability: 43 ± 14% (oral)
• Excretion: Fecal (46%) and renal (18%)
• Half Life: 27.7 to 43.6 hours
• Metabolism: Hepatic (CYP3A4-mediated)
• Protein Bound: 79 to 91%
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: D (Australia); D (US)