Vincristine sulfateProduct ingredient for Vincristine

Name
Vincristine sulfate
Drug Entry
Vincristine

Vincristine is an antitumor vinca alkaloid isolated from Vinca Rosea. It is marketed under several brand names, many of which have different formulations such as Marqibo (liposomal injection) and Vincasar. Vincristine is indicated for the treatment of acute leukaemia, malignant lymphoma, Hodgkin's disease, acute erythraemia, and acute panmyelosis. vincristine sulfate is often chosen as part of polychemotherapy because of lack of significant bone–marrow suppression (at recommended doses) and of unique clinical toxicity (neuropathy).

Accession Number
DBSALT000314
Structure
Synonyms
22-OXOVINCALEUKOBLASTINE SULFATE (1:1) (SALT) / Vincristine sulfate / VINCRISTINE SULFATE LIPOSOME / Vincristine sulfate liposome injection / vincristine sulfate liposomes / Vincristine sulphate
External IDs
LILLY-37231
UNII
T5IRO3534A
CAS Number
2068-78-2
Weight
Average: 923.036
Monoisotopic: 922.367023274
Chemical Formula
C46H58N4O14S
InChI Key
AQTQHPDCURKLKT-PNYVAJAMSA-N
InChI
InChI=1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1
IUPAC Name
methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(1R,13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate; sulfuric acid
SMILES
OS(O)(=O)=O.[H][C@@]12N3CC[C@@]11C4=C(C=C(OC)C(=C4)[C@]4(C[C@H]5C[N@](C[C@](O)(CC)C5)CCC5=C4NC4=CC=CC=C54)C(=O)OC)N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC
KEGG Drug
D02197
KEGG Compound
C13974
PubChem Compound
45356935
ChemSpider
4535014
ChEBI
79401
ChEMBL
CHEMBL385978
Wikipedia
Vincristine
Predicted Properties
PropertyValueSource
Water Solubility0.03 mg/mLALOGPS
logP3.36ALOGPS
logP3.13Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.85Chemaxon
pKa (Strongest Basic)8.66Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area171.17 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity221.48 m3·mol-1Chemaxon
Polarizability87.39 Å3Chemaxon
Number of Rings9Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon