Vindesine

Vindesine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	AU: D;
Routes of; administration	Intravenous
ATC code	L01CA03 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	65-75%
Metabolism	Hepatic (CYP3A4-mediated)
Elimination half-life	24 hours
Excretion	Biliary and renal
Identifiers
	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;
CAS Number	53643-48-4 ; as salt: 59917-39-4 ;
PubChem CID	40839;
DrugBank	DB00309 ;
ChemSpider	37302 ;
UNII	RSA8KO39WH; as salt: CPH2U7DNDY ;
KEGG	D01769 ;
ChEBI	CHEBI:36373 ;
ChEMBL	ChEMBL219146 ;
CompTox Dashboard (EPA)	DTXSID6023739 ;
ECHA InfoCard	100.053.330
Chemical and physical data
Formula	C43H55N5O7
Molar mass	753.941 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	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 ; Key:HHJUWIANJFBDHT-KOTLKJBCSA-N ;
	(verify)

Vindesine, also termed Eldisine, is a semisynthetic vinca alkaloid derived from the flowering plant Catharanthus roseus.^[1] 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.^[2] 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.^[3]

References

^ Mondal A, Gandhi A, Fimognari C, Atanasov AG, Bishayee A (September 2019). "Alkaloids for cancer prevention and therapy: Current progress and future perspectives". European Journal of Pharmacology. 858: 172472. doi:10.1016/j.ejphar.2019.172472. PMID 31228447.
^ Martino E, Casamassima G, Castiglione S, Cellupica E, Pantalone S, Papagni F, Rui M, Siciliano AM, Collina S (September 2018). "Vinca alkaloids and analogues as anti-cancer agents: Looking back, peering ahead". Bioorganic & Medicinal Chemistry Letters. 28 (17): 2816–2826. doi:10.1016/j.bmcl.2018.06.044. PMID 30122223.
^ https://www.cancerresearchuk.org/about-cancer/cancer-in-general/treatment/cancer-drugs/drugs/vindesine

Clinical data


AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	AU: D
Routes of administration	Intravenous
ATC code	L01CA03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	65-75%
Metabolism	Hepatic (CYP3A4-mediated)
Elimination half-life	24 hours
Excretion	Biliary and renal
Identifiers
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
CAS Number	53643-48-4 as salt: 59917-39-4
PubChem CID	40839
DrugBank	DB00309
ChemSpider	37302
UNII	RSA8KO39WH as salt: CPH2U7DNDY
KEGG	D01769
ChEBI	CHEBI:36373
ChEMBL	ChEMBL219146
CompTox Dashboard (EPA)	DTXSID6023739
ECHA InfoCard	100.053.330
Chemical and physical data
Formula	C₄₃H₅₅N₅O₇
Molar mass	753.941 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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 Key:HHJUWIANJFBDHT-KOTLKJBCSA-N
(verify)