Vindesine

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 470630451

| IUPAC_name = methyl (5S,7S,9S)- 9-[(2β,3β,4β,5α,12β,19α)- 3-(aminocarbonyl)- 3,4-dihydroxy- 16-methoxy- 1-methyl- 6,7-didehydroaspidospermidin- 15-yl]- 5-ethyl- 5-hydroxy- 1,4,5,6,7,8,9,10-octahydro- 2H- 3,7-methanoazacycloundecino[5,4-b]indole- 9-carboxylate

| image = Vindesin.svg

| image2 = Vindesine ball-and-stick animation.gif

| tradename =

| Drugs.com = {{drugs.com|CONS|vindesine}}

| pregnancy_AU = D

| pregnancy_US =

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Intravenous

| bioavailability =

| protein_bound = 65-75%

| metabolism = Hepatic (CYP3A4-mediated)

| elimination_half-life = 24 hours

| excretion = Biliary and renal

| index2_label = Sulfate

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 59917-39-4

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = CPH2U7DNDY

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 53643-48-4

| ATC_prefix = L01

| ATC_suffix = CA03

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 219146

| PubChem = 40839

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00309

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 37302

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = RSA8KO39WH

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01769

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 36373

| C=43 | H=55 | N=5 | O=7

| smiles = O=C(OC)[C@]4(c2c(c1ccccc1[nH]2)CCN3C[C@](O)(CC)C[C@@H](C3)C4)c5c(OC)cc6c(c5)[C@@]89[C@@H](N6C)[C@@](O)(C(=O)N)[C@H](O)[C@@]7(/C=C\CN([C@@H]78)CC9)CC

| 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HHJUWIANJFBDHT-KOTLKJBCSA-N

}}

Vindesine, also termed Eldisine, is a semisynthetic vinca alkaloid derived from the flowering plant Catharanthus roseus.{{cite journal | vauthors = Mondal A, Gandhi A, Fimognari C, Atanasov AG, Bishayee A | title = Alkaloids for cancer prevention and therapy: Current progress and future perspectives | journal = European Journal of Pharmacology | volume = 858 | pages = 172472 | date = September 2019 | pmid = 31228447 | doi = 10.1016/j.ejphar.2019.172472 | s2cid = 195298770 }} Like the natural (e.g. vinblastine and vincristine) and semisynthetic vinca alkaloids (e.g. vinorelbine and vinflunine) derived from this plant, vindesine is an inhibitor of mitosis that is used as a chemotherapy drug.{{cite journal | vauthors = Martino E, Casamassima G, Castiglione S, Cellupica E, Pantalone S, Papagni F, Rui M, Siciliano AM, Collina S | title = Vinca alkaloids and analogues as anti-cancer agents: Looking back, peering ahead | journal = Bioorganic & Medicinal Chemistry Letters | volume = 28 | issue = 17 | pages = 2816–2826 | date = September 2018 | pmid = 30122223 | doi = 10.1016/j.bmcl.2018.06.044 | s2cid = 52039135 }} By inhibiting mitosis, vinedsine blocks the proliferation of cells, particularly the rapidly proliferation cells of certain types of cancer. It is used, generally in combination with other chemotherapeutic drugs, in the treatment of various malignancies such as leukaemia, lymphoma, melanoma, breast cancer, and lung cancer.{{cite web |url=https://www.cancerresearchuk.org/about-cancer/cancer-in-general/treatment/cancer-drugs/drugs/vindesine |title = Vindesine (Eldisine) {{!}} Cancer information {{!}} Cancer Research UK}}