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Vinblastine

February 15, 2024

Not to be confused with vincristine.

Vinblastine (VBL), sold under the brand name Velban among others, is a chemotherapy medication, typically used with other medications, to treat a number of types of cancer.[1] This includes Hodgkin's lymphoma, non-small-cell lung cancer, bladder cancer, brain cancer, melanoma, and testicular cancer.[1] It is given by injection into a vein.[1]

Vinblastine
Clinical data
Trade namesVelban, Velbe, others
Other namesvincaleukoblastine
AHFS/Drugs.comMonograph
MedlinePlusa682848
License data
Pregnancy
category
  • AU: D
Routes of
administration		intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailabilityn/a
MetabolismLiver (CYP3A4-mediated)
Elimination half-life24.8 hours (terminal)
ExcretionBiliary and kidney
Identifiers
  • dimethyl (2β,3β,4β,5α,12β,19α)-15-[(5S,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methanoazacycloundecino[5,4-b]indol- 9-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3,4-dicarboxylate
CAS Number
  • 865-21-4 Y
PubChem CID
  • 241903
DrugBank
  • DB00570 Y
ChemSpider
  • 211446 Y
UNII
  • 5V9KLZ54CY
KEGG
  • D08675 Y
ChEBI
  • CHEBI:27375 Y
ChEMBL
  • ChEMBL159 N
NIAID ChemDB
  • 002673
CompTox Dashboard (EPA)
  • DTXSID8021430
ECHA InfoCard100.011.577
Chemical and physical data
FormulaC46H58N4O9
Molar mass810.989 g·mol−1
3D model (JSmol)
  • Interactive image
  • [H][C@]89CN(CCc1c([nH]c2ccccc12)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@@]5([H])[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]7(CC)C=CCN6CC[C@]45[C@@]67[H])C8)C[C@](O)(CC)C9
  • 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+/m1/s1 Y
  • Key:JXLYSJRDGCGARV-XQKSVPLYSA-N Y
 NY (what is this?)  (verify)

Most people experience some side effects.[1] Commonly it causes a change in sensation, constipation, weakness, loss of appetite, and headaches.[1] Severe side effects include low blood cell counts and shortness of breath.[1] It should not be given to people who have a current bacterial infection.[1] Use during pregnancy will likely harm the baby.[1] Vinblastine works by blocking cell division.[1]

Vinblastine was isolated in 1958.[2] An example of a natural herbal remedy that has since been developed into a conventional medicine, vinblastine was originally obtained from the Madagascar periwinkle.[3] It is on the World Health Organization's List of Essential Medicines.[4]

Medical uses edit

Vinblastine is a component of a number of chemotherapy regimens, including ABVD for Hodgkin lymphoma.[5] It is also used to treat histiocytosis according to the established protocols of the Histiocytosis Association.

Side effects edit

Adverse effects of vinblastine include hair loss, loss of white blood cells and blood platelets, gastrointestinal problems, high blood pressure, excessive sweating, depression, muscle cramps, vertigo and headaches.[6][1] As a vesicant, vinblastine can cause extensive tissue damage and blistering if it escapes from the vein from improper administration.[7]

Pharmacology edit

Vinblastine is a vinca alkaloid[8][2][9] and a chemical analogue of vincristine.[10][11] It binds tubulin, thereby inhibiting the assembly of microtubules.[12] Vinblastine treatment causes M phase specific cell cycle arrest by disrupting microtubule assembly and proper formation of the mitotic spindle and the kinetochore, each of which are necessary for the separation of chromosomes during anaphase of mitosis. Toxicities include bone marrow suppression (which is dose-limiting), gastrointestinal toxicity, potent vesicant (blister-forming) activity, and extravasation injury (forms deep ulcers). Vinblastine paracrystals may be composed of tightly packed unpolymerized tubulin or microtubules.[13]

Vinblastine is reported to be an effective component of certain chemotherapy regimens, particularly when used with bleomycin and methotrexate in VBM chemotherapy for Stage IA or IIA Hodgkin lymphomas. The inclusion of vinblastine allows for lower doses of bleomycin and reduced overall toxicity with larger resting periods between chemotherapy cycles.[14]

Mechanism of action edit

 
The complex of tubulin and vinblastine. Vinblastine is shown in yellow.

Microtubule-disruptive drugs like vinblastine, colcemid, and nocodazole have been reported to act by two mechanisms.[15] At very low concentrations they suppress microtubule dynamics and at higher concentrations they reduce microtubule polymer mass. Recent findings indicate that they also produce microtubule fragments by stimulating microtubule minus-end detachment from their organizing centers. Dose-response studies further indicate that enhanced microtubule detachment from spindle poles correlate best with cytotoxicity.[16] But research into the mechanism is still ongoing as recent studies also show vinblastine inducing apoptosis that is phase-independent in certain leukemias.[17]

Pharmacokinetics edit

Vinblastine appears to be a peripherally selective drug due to limited brain uptake caused by binding to P-glycoprotein.[18][19]

Isolation and synthesis edit

Vinblastine may be isolated from the Madagascar Periwinkle (Catharanthus roseus), its only known biological producer,[20] along with several of its precursors, catharanthine and vindoline. Extraction is costly and yields of vinblastine and its precursors are low, although procedures for rapid isolation with improved yields avoiding auto-oxidation have been developed. Enantioselective synthesis has been of considerable interest in recent years, as the natural mixture of isomers is not an economical source for the required C16'S, C14'R stereochemistry of biologically active vinblastine. Initially, the approach depends upon an enantioselective Sharpless epoxidation, which sets the stereochemistry at C20. The desired configuration around C16 and C14 can then be fixed during the ensuing steps. In this pathway, vinblastine is constructed by a series of cyclization and coupling reactions which create the required stereochemistry. The overall yield may be as great as 22%, which makes this synthetic approach more attractive than extraction from natural sources, whose overall yield is about 10%.[21] Stereochemistry is controlled through a mixture of chiral agents (Sharpless catalysts), and reaction conditions (temperature, and selected enantiopure starting materials).[22] Due to difficulty of stereochemical restraints in total synthetic processes, other semi-synthetic methods from precursors, catharanthine and vindoline, continue to be developed.[23]

History edit

Vinblastine was first isolated by Robert Noble and Charles Thomas Beer at the University of Western Ontario from the Madagascar periwinkle plant. Vinblastine's utility as a chemotherapeutic agent was first suggested by its effect on the body when an extract of the plant was injected in rabbits to study the plant's supposed anti-diabetic effect. (A tea made from the plant was a folk-remedy for diabetes.) The rabbits died from a bacterial infection, due to a decreased number of white blood cells, so it was hypothesized that vinblastine might be effective against cancers of the white blood cells such as lymphoma.[24] It was approved by FDA in 1965.[12]

See also edit

References edit

  1. ^ a b c d e f g h i j "Vinblastine Sulfate". The American Society of Health-System Pharmacists. from the original on 2015-01-02. Retrieved Jan 2, 2015.
  2. ^ a b Ravina E (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1. Aufl. ed.). Weinheim: Wiley-VCH. p. 157. ISBN 9783527326693. from the original on 2017-08-01.
  3. ^ Liljefors T, Krogsgaard-Larsen P, Madsen U (2002). Textbook of Drug Design and Discovery (Third ed.). CRC Press. p. 550. ISBN 9780415282888. from the original on 2016-12-20.
  4. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  5. ^ Rueda Domínguez A, Márquez A, Gumá J, Llanos M, Herrero J, de Las Nieves MA, et al. (December 2004). "Treatment of stage I and II Hodgkin's lymphoma with ABVD chemotherapy: results after 7 years of a prospective study". Annals of Oncology. 15 (12): 1798–1804. doi:10.1093/annonc/mdh465. PMID 15550585.
  6. ^ "Vinblastine sulfate- vinblastine sulfate injection". DailyMed. 31 December 2019. Retrieved 15 April 2020.
  7. ^ "Vinblastine". Chemocare. Retrieved 12 November 2021.
  8. ^ van Der Heijden R, Jacobs DI, Snoeijer W, Hallard D, Verpoorte R (March 2004). "The Catharanthus alkaloids: pharmacognosy and biotechnology". Current Medicinal Chemistry. 11 (5): 607–628. doi:10.2174/0929867043455846. PMID 15032608.
  9. ^ Cooper R, Deakin JJ (2016). "Africa's gift to the world". Botanical Miracles: Chemistry of Plants That Changed the World. CRC Press. pp. 46–51. ISBN 9781498704304. from the original on 2017-08-01.
  10. ^ Keglevich P, Hazai L, Kalaus G, Szántay C (May 2012). "Modifications on the basic skeletons of vinblastine and vincristine". Molecules. 17 (5): 5893–5914. doi:10.3390/molecules17055893. PMC 6268133. PMID 22609781.
  11. ^ Sears JE, Boger DL (March 2015). "Total synthesis of vinblastine, related natural products, and key analogues and development of inspired methodology suitable for the systematic study of their structure-function properties". Accounts of Chemical Research. 48 (3): 653–662. doi:10.1021/ar500400w. PMC 4363169. PMID 25586069.
  12. ^ a b Altmann KH (2009). "Preclinical Pharmacology and Structure-Activity Studies of Epothilones". In Mulzer JH (ed.). The Epothilones: An Outstanding Family of Anti-Tumor Agents: From Soil to the Clinic. Springer Science & Business Media. pp. 157–220. ISBN 9783211782071. from the original on 2017-09-11.
  13. ^ Starling D (January 1976). "Two ultrastructurally distinct tubulin paracrystals induced in sea-urchin eggs by vinblastine sulphate" (PDF). Journal of Cell Science. 20 (1): 79–89. doi:10.1242/jcs.20.1.79. PMID 942954. (PDF) from the original on 2014-01-13.
  14. ^ Gobbi PG, Broglia C, Merli F, Dell'Olio M, Stelitano C, Iannitto E, et al. (December 2003). "Vinblastine, bleomycin, and methotrexate chemotherapy plus irradiation for patients with early-stage, favorable Hodgkin lymphoma: the experience of the Gruppo Italiano Studio Linfomi". Cancer. 98 (11): 2393–2401. doi:10.1002/cncr.11807. hdl:11380/4847. PMID 14635074. S2CID 21376280.
  15. ^ Jordan MA, Wilson L (April 2004). "Microtubules as a target for anticancer drugs". Nature Reviews. Cancer. 4 (4): 253–265. doi:10.1038/nrc1317. PMID 15057285. S2CID 10228718.
  16. ^ Yang H, Ganguly A, Cabral F (October 2010). "Inhibition of cell migration and cell division correlates with distinct effects of microtubule inhibiting drugs". The Journal of Biological Chemistry. 285 (42): 32242–32250. doi:10.1074/jbc.M110.160820. PMC 2952225. PMID 20696757.
  17. ^ Salerni BL, Bates DJ, Albershardt TC, Lowrey CH, Eastman A (April 2010). "Vinblastine induces acute, cell cycle phase-independent apoptosis in some leukemias and lymphomas and can induce acute apoptosis in others when Mcl-1 is suppressed". Molecular Cancer Therapeutics. 9 (4): 791–802. doi:10.1158/1535-7163.MCT-10-0028. PMC 2852489. PMID 20371726.
  18. ^ Schinkel AH (April 1999). "P-Glycoprotein, a gatekeeper in the blood-brain barrier". Adv Drug Deliv Rev. 36 (2–3): 179–194. doi:10.1016/s0169-409x(98)00085-4. PMID 10837715.
  19. ^ Tsuji A (October 1998). "P-glycoprotein-mediated efflux transport of anticancer drugs at the blood-brain barrier". Ther Drug Monit. 20 (5): 588–90. doi:10.1097/00007691-199810000-00024. PMID 9780140.
  20. ^ Zhu J, Wang M, Wen W, Yu R (January 2015). "Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus". Pharmacognosy Reviews. 9 (17): 24–28. doi:10.4103/0973-7847.156323. PMC 4441158. PMID 26009689.
  21. ^ Kuehne ME, Matson PA, Bornmann WG (1991). "Enantioselective Syntheses of Vinblastine, Leurosidine, Vincovaline, and 20'-epi-Vincovaline". Journal of Organic Chemistry. 56 (2): 513–528. doi:10.1021/jo00002a008.
  22. ^ Yokoshima S, Tokuyama H, Fukuyama T (2009). "Total Synthesis of (+)-Vinblastine: Control of the Stereochemistry at C18′". The Chemical Record. 10 (2): 101–118. doi:10.1002/tcr.200900025. PMID 20394103.
  23. ^ Verma A, Laakso I, Seppänen-Laakso T, Huhtikangas A, Riekkola ML (July 2007). "A simplified procedure for indole alkaloid extraction from Catharanthus roseus combined with a semi-synthetic production process for vinblastine". Molecules. 12 (7): 1307–1315. doi:10.3390/12071307. PMC 6149338. PMID 17909486.
  24. ^ Noble RL, Beer CT, Cutts JH (December 1958). "Role of chance observations in chemotherapy: Vinca rosea". Annals of the New York Academy of Sciences. 76 (3): 882–894. Bibcode:1958NYASA..76..882N. doi:10.1111/j.1749-6632.1958.tb54906.x. PMID 13627916. S2CID 34879726.

External links edit

  • "Vinblastine". Drug Information Portal. U.S. National Library of Medicine.

February 15, 2024
vinblastine, confused, with, vincristine, sold, under, brand, name, velban, among, others, chemotherapy, medication, typically, used, with, other, medications, treat, number, types, cancer, this, includes, hodgkin, lymphoma, small, cell, lung, cancer, bladder,. Not to be confused with vincristine Vinblastine VBL sold under the brand name Velban among others is a chemotherapy medication typically used with other medications to treat a number of types of cancer 1 This includes Hodgkin s lymphoma non small cell lung cancer bladder cancer brain cancer melanoma and testicular cancer 1 It is given by injection into a vein 1 VinblastineClinical dataTrade namesVelban Velbe othersOther namesvincaleukoblastineAHFS Drugs comMonographMedlinePlusa682848License dataUS DailyMed VinblastinePregnancycategoryAU DRoutes ofadministrationintravenousATC codeL01CA01 WHO Legal statusLegal statusAU S4 Prescription only CA only UK POM Prescription only US only In general Prescription only Pharmacokinetic dataBioavailabilityn aMetabolismLiver CYP3A4 mediated Elimination half life24 8 hours terminal ExcretionBiliary and kidneyIdentifiersIUPAC name dimethyl 2b 3b 4b 5a 12b 19a 15 5S 9S 5 ethyl 5 hydroxy 9 methoxycarbonyl 1 4 5 6 7 8 9 10 octahydro 2H 3 7 methanoazacycloundecino 5 4 b indol 9 yl 3 hydroxy 16 methoxy 1 methyl 6 7 didehydroaspidospermidine 3 4 dicarboxylateCAS Number865 21 4 YPubChem CID241903DrugBankDB00570 YChemSpider211446 YUNII5V9KLZ54CYKEGGD08675 YChEBICHEBI 27375 YChEMBLChEMBL159 NNIAID ChemDB002673CompTox Dashboard EPA DTXSID8021430ECHA InfoCard100 011 577Chemical and physical dataFormulaC 46H 58N 4O 9Molar mass810 989 g mol 13D model JSmol Interactive imageSMILES H C 89CN CCc1c nH c2ccccc12 C C O OC c3cc4c cc3OC N C C 5 H C O C O OC C H OC C O C 7 CC C CCN6CC C 45 C 67 H C8 C C O CC C9InChI 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 m1 s1 YKey JXLYSJRDGCGARV XQKSVPLYSA N Y N Y what is this verify Most people experience some side effects 1 Commonly it causes a change in sensation constipation weakness loss of appetite and headaches 1 Severe side effects include low blood cell counts and shortness of breath 1 It should not be given to people who have a current bacterial infection 1 Use during pregnancy will likely harm the baby 1 Vinblastine works by blocking cell division 1 Vinblastine was isolated in 1958 2 An example of a natural herbal remedy that has since been developed into a conventional medicine vinblastine was originally obtained from the Madagascar periwinkle 3 It is on the World Health Organization s List of Essential Medicines 4 Contents 1 Medical uses 2 Side effects 3 Pharmacology 3 1 Mechanism of action 3 2 Pharmacokinetics 4 Isolation and synthesis 5 History 6 See also 7 References 8 External linksMedical uses editVinblastine is a component of a number of chemotherapy regimens including ABVD for Hodgkin lymphoma 5 It is also used to treat histiocytosis according to the established protocols of the Histiocytosis Association Side effects editAdverse effects of vinblastine include hair loss loss of white blood cells and blood platelets gastrointestinal problems high blood pressure excessive sweating depression muscle cramps vertigo and headaches 6 1 As a vesicant vinblastine can cause extensive tissue damage and blistering if it escapes from the vein from improper administration 7 Pharmacology editVinblastine is a vinca alkaloid 8 2 9 and a chemical analogue of vincristine 10 11 It binds tubulin thereby inhibiting the assembly of microtubules 12 Vinblastine treatment causes M phase specific cell cycle arrest by disrupting microtubule assembly and proper formation of the mitotic spindle and the kinetochore each of which are necessary for the separation of chromosomes during anaphase of mitosis Toxicities include bone marrow suppression which is dose limiting gastrointestinal toxicity potent vesicant blister forming activity and extravasation injury forms deep ulcers Vinblastine paracrystals may be composed of tightly packed unpolymerized tubulin or microtubules 13 Vinblastine is reported to be an effective component of certain chemotherapy regimens particularly when used with bleomycin and methotrexate in VBM chemotherapy for Stage IA or IIA Hodgkin lymphomas The inclusion of vinblastine allows for lower doses of bleomycin and reduced overall toxicity with larger resting periods between chemotherapy cycles 14 Mechanism of action edit nbsp The complex of tubulin and vinblastine Vinblastine is shown in yellow Microtubule disruptive drugs like vinblastine colcemid and nocodazole have been reported to act by two mechanisms 15 At very low concentrations they suppress microtubule dynamics and at higher concentrations they reduce microtubule polymer mass Recent findings indicate that they also produce microtubule fragments by stimulating microtubule minus end detachment from their organizing centers Dose response studies further indicate that enhanced microtubule detachment from spindle poles correlate best with cytotoxicity 16 But research into the mechanism is still ongoing as recent studies also show vinblastine inducing apoptosis that is phase independent in certain leukemias 17 Pharmacokinetics edit Vinblastine appears to be a peripherally selective drug due to limited brain uptake caused by binding to P glycoprotein 18 19 Isolation and synthesis editVinblastine may be isolated from the Madagascar Periwinkle Catharanthus roseus its only known biological producer 20 along with several of its precursors catharanthine and vindoline Extraction is costly and yields of vinblastine and its precursors are low although procedures for rapid isolation with improved yields avoiding auto oxidation have been developed Enantioselective synthesis has been of considerable interest in recent years as the natural mixture of isomers is not an economical source for the required C16 S C14 R stereochemistry of biologically active vinblastine Initially the approach depends upon an enantioselective Sharpless epoxidation which sets the stereochemistry at C20 The desired configuration around C16 and C14 can then be fixed during the ensuing steps In this pathway vinblastine is constructed by a series of cyclization and coupling reactions which create the required stereochemistry The overall yield may be as great as 22 which makes this synthetic approach more attractive than extraction from natural sources whose overall yield is about 10 21 Stereochemistry is controlled through a mixture of chiral agents Sharpless catalysts and reaction conditions temperature and selected enantiopure starting materials 22 Due to difficulty of stereochemical restraints in total synthetic processes other semi synthetic methods from precursors catharanthine and vindoline continue to be developed 23 History editVinblastine was first isolated by Robert Noble and Charles Thomas Beer at the University of Western Ontario from the Madagascar periwinkle plant Vinblastine s utility as a chemotherapeutic agent was first suggested by its effect on the body when an extract of the plant was injected in rabbits to study the plant s supposed anti diabetic effect A tea made from the plant was a folk remedy for diabetes The rabbits died from a bacterial infection due to a decreased number of white blood cells so it was hypothesized that vinblastine might be effective against cancers of the white blood cells such as lymphoma 24 It was approved by FDA in 1965 12 See also editDoxorubicin MimosineReferences edit a b c d e f g h i j Vinblastine Sulfate The American Society of Health System Pharmacists Archived from the original on 2015 01 02 Retrieved Jan 2 2015 a b Ravina E 2011 The evolution of drug discovery from traditional medicines to modern drugs 1 Aufl ed Weinheim Wiley VCH p 157 ISBN 9783527326693 Archived from the original on 2017 08 01 Liljefors T Krogsgaard Larsen P Madsen U 2002 Textbook of Drug Design and Discovery Third ed CRC Press p 550 ISBN 9780415282888 Archived from the original on 2016 12 20 World Health Organization 2023 The selection and use of essential medicines 2023 web annex A World Health Organization model list of essential medicines 23rd list 2023 Geneva World Health Organization hdl 10665 371090 WHO MHP HPS EML 2023 02 Rueda Dominguez A Marquez A Guma J Llanos M Herrero J de Las Nieves MA et al December 2004 Treatment of stage I and II Hodgkin s lymphoma with ABVD chemotherapy results after 7 years of a prospective study Annals of Oncology 15 12 1798 1804 doi 10 1093 annonc mdh465 PMID 15550585 Vinblastine sulfate vinblastine sulfate injection DailyMed 31 December 2019 Retrieved 15 April 2020 Vinblastine Chemocare Retrieved 12 November 2021 van Der Heijden R Jacobs DI Snoeijer W Hallard D Verpoorte R March 2004 The Catharanthus alkaloids pharmacognosy and biotechnology Current Medicinal Chemistry 11 5 607 628 doi 10 2174 0929867043455846 PMID 15032608 Cooper R Deakin JJ 2016 Africa s gift to the world Botanical Miracles Chemistry of Plants That Changed the World CRC Press pp 46 51 ISBN 9781498704304 Archived from the original on 2017 08 01 Keglevich P Hazai L Kalaus G Szantay C May 2012 Modifications on the basic skeletons of vinblastine and vincristine Molecules 17 5 5893 5914 doi 10 3390 molecules17055893 PMC 6268133 PMID 22609781 Sears JE Boger DL March 2015 Total synthesis of vinblastine related natural products and key analogues and development of inspired methodology suitable for the systematic study of their structure function properties Accounts of Chemical Research 48 3 653 662 doi 10 1021 ar500400w PMC 4363169 PMID 25586069 a b Altmann KH 2009 Preclinical Pharmacology and Structure Activity Studies of Epothilones In Mulzer JH ed The Epothilones An Outstanding Family of Anti Tumor Agents From Soil to the Clinic Springer Science amp Business Media pp 157 220 ISBN 9783211782071 Archived from the original on 2017 09 11 Starling D January 1976 Two ultrastructurally distinct tubulin paracrystals induced in sea urchin eggs by vinblastine sulphate PDF Journal of Cell Science 20 1 79 89 doi 10 1242 jcs 20 1 79 PMID 942954 Archived PDF from the original on 2014 01 13 Gobbi PG Broglia C Merli F Dell Olio M Stelitano C Iannitto E et al December 2003 Vinblastine bleomycin and methotrexate chemotherapy plus irradiation for patients with early stage favorable Hodgkin lymphoma the experience of the Gruppo Italiano Studio Linfomi Cancer 98 11 2393 2401 doi 10 1002 cncr 11807 hdl 11380 4847 PMID 14635074 S2CID 21376280 Jordan MA Wilson L April 2004 Microtubules as a target for anticancer drugs Nature Reviews Cancer 4 4 253 265 doi 10 1038 nrc1317 PMID 15057285 S2CID 10228718 Yang H Ganguly A Cabral F October 2010 Inhibition of cell migration and cell division correlates with distinct effects of microtubule inhibiting drugs The Journal of Biological Chemistry 285 42 32242 32250 doi 10 1074 jbc M110 160820 PMC 2952225 PMID 20696757 Salerni BL Bates DJ Albershardt TC Lowrey CH Eastman A April 2010 Vinblastine induces acute cell cycle phase independent apoptosis in some leukemias and lymphomas and can induce acute apoptosis in others when Mcl 1 is suppressed Molecular Cancer Therapeutics 9 4 791 802 doi 10 1158 1535 7163 MCT 10 0028 PMC 2852489 PMID 20371726 Schinkel AH April 1999 P Glycoprotein a gatekeeper in the blood brain barrier Adv Drug Deliv Rev 36 2 3 179 194 doi 10 1016 s0169 409x 98 00085 4 PMID 10837715 Tsuji A October 1998 P glycoprotein mediated efflux transport of anticancer drugs at the blood brain barrier Ther Drug Monit 20 5 588 90 doi 10 1097 00007691 199810000 00024 PMID 9780140 Zhu J Wang M Wen W Yu R January 2015 Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus Pharmacognosy Reviews 9 17 24 28 doi 10 4103 0973 7847 156323 PMC 4441158 PMID 26009689 Kuehne ME Matson PA Bornmann WG 1991 Enantioselective Syntheses of Vinblastine Leurosidine Vincovaline and 20 epi Vincovaline Journal of Organic Chemistry 56 2 513 528 doi 10 1021 jo00002a008 Yokoshima S Tokuyama H Fukuyama T 2009 Total Synthesis of Vinblastine Control of the Stereochemistry at C18 The Chemical Record 10 2 101 118 doi 10 1002 tcr 200900025 PMID 20394103 Verma A Laakso I Seppanen Laakso T Huhtikangas A Riekkola ML July 2007 A simplified procedure for indole alkaloid extraction from Catharanthus roseus combined with a semi synthetic production process for vinblastine Molecules 12 7 1307 1315 doi 10 3390 12071307 PMC 6149338 PMID 17909486 Noble RL Beer CT Cutts JH December 1958 Role of chance observations in chemotherapy Vinca rosea Annals of the New York Academy of Sciences 76 3 882 894 Bibcode 1958NYASA 76 882N doi 10 1111 j 1749 6632 1958 tb54906 x PMID 13627916 S2CID 34879726 External links edit Vinblastine Drug Information Portal U S National Library of Medicine Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Vinblastine amp oldid 1206070483, wikipedia, wiki, book, books, library,

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