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Revision as of 15:58, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{drugbox}} taken from revid 457795730 of page Vindesine for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Revision as of 15:58, 10 January 2012 edit undoBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{drugbox}} taken from revid 456953721 of page Vinorelbine for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').Next edit →
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} {{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457794905 | verifiedrevid = 402875554
| IUPAC_name = methyl (5''S'',7''S'',9''S'')- 9-- 5-ethyl- 5-hydroxy- 1,4,5,6,7,8,9,10-octahydro- 2''H''- 3,7-methanoazacycloundecinoindole- 9-carboxylate
| IUPAC_name = 4-(acetyloxy)- 6,7-didehydro- 15-((2''R'',6''R'',8''S'')-4-ethyl- 1,3,6,7,8,9-hexahydro- 8-(methoxycarbonyl)- 2,6-methano- 2''H''-azecino(4,3-''b'')indol-8-yl)- 3-hydroxy- 16-methoxy- 1-methyl- methyl ester,
| image = Vindesin.svg | image = Vinorelbine.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Navelbine
| Drugs.com = {{drugs.com|CONS|vindesine}} | Drugs.com = {{drugs.com|monograph|navelbine}}
| MedlinePlus = a695013
| pregnancy_AU = D | pregnancy_AU = D
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = D
| legal_UK = POM
| pregnancy_category =
| legal_status = Rx-only | legal_US = Rx-only
| routes_of_administration = ] | routes_of_administration = ], oral


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 43 ± 14% (oral)<ref name = Marty>{{cite journal | author = Marty M, Fumoleau P, Adenis A, Rousseau Y, Merrouche Y, Robinet G, Senac I, Puozzo C | title = Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors | journal = Ann Oncol | volume = 12 | issue = 11 | pages = 1643–9 | year = 2001 | pmid = 11822766 | doi = 10.1023/A:1013180903805}}</ref>
| bioavailability =
| protein_bound = 65-75% | protein_bound = 79 to 91%
| metabolism = ] (]-mediated) | metabolism = ] (]-mediated)
| elimination_half-life = 24 hours | elimination_half-life = 27.7 to 43.6 hours
| excretion = Biliary and ] | excretion = Fecal (46%) and ] (18%)


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 59917-39-4 | CAS_number = 71486-22-1
| ATC_prefix = L01 | ATC_prefix = L01
| ATC_suffix = CA03 | ATC_suffix = CA04
| PubChem = 5311497
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChEMBL = 219146
| PubChem = 40839 | DrugBank = DB00361
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB00309
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 37302 | ChemSpiderID = 4470974
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|changed|FDA}}
| UNII = RSA8KO39WH | UNII = Q6C979R91Y
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D01769 | KEGG = D08680
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 607994 -->
| ChEBI = 36373
| C=45 | H=54 | N=4 | O=8

| molecular_weight = 778.932 g/mol
<!--Chemical data-->
| smiles = O=C(OC)4(c2nc1ccccc1c2CN3CC(=C/(C3)C4)\CC)c5c(OC)cc6c(c5)89(N6C)(O)(C(=O)OC)(OC(=O)C)7(/C=C\CN(78)CC9)CC
| C=43 | H=55 | N=5 | O=7
| InChI = 1/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
| molecular_weight = 753.926 g/mol
| InChIKey = GBABOYUKABKIAF-IELIFDKJBG
| smiles = O=C(OC)4(c2c(c1ccccc1n2)CCN3C(O)(CC)C(C3)C4)c5c(OC)cc6c(c5)89(N6C)(O)(C(=O)N)(O)7(/C=C\CN(78)CC9)CC
| InChI = 1/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-KOTLKJBCBW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HHJUWIANJFBDHT-KOTLKJBCSA-N | StdInChIKey = GBABOYUKABKIAF-IELIFDKJSA-N
}} }}

Revision as of 15:58, 10 January 2012

This page contains a copy of the infobox ({{drugbox}}) taken from revid 456953721 of page Vinorelbine with values updated to verified values.
WikiProject Chemicals/Chembox validation/VerifiedDataSandbox
Clinical data
Trade namesNavelbine
AHFS/Drugs.comMonograph
MedlinePlusa695013
Pregnancy
category
  • AU: D
Routes of
administration
intravenous, oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability43 ± 14% (oral)
Protein binding79 to 91%
MetabolismHepatic (CYP3A4-mediated)
Elimination half-life27.7 to 43.6 hours
ExcretionFecal (46%) and renal (18%)
Identifiers
IUPAC name
  • 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,
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC45H54N4O8
Molar mass778.932 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C(OC)4(c2nc1ccccc1c2CN3CC(=C/(C3)C4)\CC)c5c(OC)cc6c(c5)89(N6C)(O)(C(=O)OC)(OC(=O)C)7(/C=C\CN(78)CC9)CC
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
  • Key:GBABOYUKABKIAF-IELIFDKJSA-N
  (what is this?)  (verify)
  1. Marty M, Fumoleau P, Adenis A, Rousseau Y, Merrouche Y, Robinet G, Senac I, Puozzo C (2001). "Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors". Ann Oncol. 12 (11): 1643–9. doi:10.1023/A:1013180903805. PMID 11822766.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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