Search summary:
Session ID: 751161b8c2d7f78b88b086fe3c016100
Search Type: drug
Started at: 2009-12-08 15:43:39
Finished at: 2009-12-08 15:45:35
| Field | Result | Source |
|---|---|---|
| Name | ||
| vincristine | External | |
| Drugbank ID | ||
| DB00541 | DrugBank | |
| Description | ||
| Peripheral neuropathy can be severe, and hence a reason to avoid, reduce, or stop the use of vincristine. One of the first symptoms of peripheral neuropathy is foot drop: a person with a family history of foot drop and/or Charcot-Marie-Tooth disease (CMT) may benefit from genetic testing for CMT before taking vincristine. | Wikipedia | |
| Tubulin is a structural protein which polymerizes to form microtubules. The cell cytoskeleton and mitotic spindle, amongst other things, are made of microtubules. Vincristine binds to tubulin dimers, inhibiting assembly of microtubule structures. Disruption of the microtubules arrests mitosis in metaphase. The vinca alkaloids therefore affect all rapidly dividing cell types including cancer cells, but also intestinal epithelium and bone marrow. | Wikipedia | |
| Vincristine (brand name, Oncovin), also known as leurocristine, is a vinca alkaloid from the Catharanthus roseus (Madagascar periwinkle), formerly Vinca rosea and hence its name. It is a mitotic inhibitor, and is used in cancer chemotherapy. | Wikipedia | |
| Vincristine is a vinca alkaloid antineoplastic agent used as a treatment for various cancers including breast cancer, Hodgkin's disease, Kaposi's sarcoma, and testicular cancer. The vinca alkaloids are structurally similar compounds comprised of 2 multiringed units, vindoline and catharanthine. The vinca alkaloids have become clinically useful since the discovery of their antitumour properties in 1959. Initially, extracts of the periwinkle plant (Catharanthus roseus) were investigated because of putative hypoglycemic properties, but were noted to cause marrow suppression in rats and antileukemic effects in vitro. Vincristine binds to the microtubular proteins of the mitotic spindle, leading to crystallization of the microtubule and mitotic arrest or cell death. Vincristine has some immunosuppressant effect. The vinca alkaloids are considered to be cell cycle phase-specific. | DrugBank | |
| Chemical Kingdom | ||
| Organic | BioSpider | |
| Chemical Class | ||
| Not Available | Not Applicable | |
| Chemical Species | ||
| alkene | Checkmol | |
| alkyl aryl ether | Checkmol | |
| aromatic compound | Checkmol | |
| carboxylic acid ester | Checkmol | |
| heterocyclic compound | Checkmol | |
| tertiary alcohol | Checkmol | |
| tertiary aliphatic amine (trialkylamine) | Checkmol | |
| tertiary amine | Checkmol | |
| tertiary carboxylic acid amide | Checkmol | |
| Synonym | ||
| 2068-78-2 (SULFATE 1:1 SALT) | Pubchem | |
| 22-oxovincaleukoblastine | Pubchem | |
| Indole alkaloid | Pubchem | |
| LCR | Pubchem | |
| Leurocristine | Pubchem | |
| Liposomal vincristine | Pubchem | |
| Onco TCS | Pubchem | |
| Oncovin | FDA | |
| Oncovin (1:1 sulfate salt) | Pubchem | |
| Oncovine | Pubchem | |
| UNII-5J49Q6B70F | Pubchem | |
| VCR | Pubchem | |
| VIN | Pubchem | |
| Vincaleukoblastine, 22-oxo- | Pubchem | |
| Vincaleukoblastine, 22-oxo- 22-Oxovincaleukoblastine | Pubchem | |
| Vincasar (1:1 Sulfate Salt) | Pubchem | |
| Vincrex (1:1 sulfate salt) | Pubchem | |
| Vincristina | Pubchem | |
| Vincristina [dcit] | Pubchem | |
| Vincristine Sulphate Injection-Liq Iv 1mg/Ml | DPD | |
| Vincristine [inn:ban] | Pubchem | |
| Vincristine sulfate | Pubchem | |
| Vincristine sulfate PFS | FDA | |
| Vincristine sulphate injection | DPD | |
| Vincristinum | Pubchem | |
| Vincristinum [inn-latin] | Pubchem | |
| Vincrisul | Pubchem | |
| Vincrstine | Pubchem | |
| Vincrystine | Pubchem | |
| Vinkristin | Pubchem | |
| Z-d-val-LYS(z)-oh | Pubchem | |
| Brand Mixture | ||
| Not Available | Not Applicable | |
| CAS | ||
| 57-22-7 | DrugBank | |
| InChI Identifier | ||
InChI=1/C46H55N4O10/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/h9-13,15,20-21,26,28,37-39,55-56H,7-8,14, 16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1 |
World Wide Molecular Matrix | |
| IUPAC | ||
| Not Available | Not Applicable | |
| Chemical Formula | ||
| C46H56N4O10 | PubChem | |
| Chemical Structure | ||
 |
Molconvert | |
| Average Molecular Weight (g/mol) | ||
| 824.957640 | BioSpider | |
| Monoisotopic Molecular Weight (g/mol) | ||
| 824.399640 | BioSpider | |
| SMILES (Isomeric) | ||
O=C(OC)[C@]4(c2c(c1ccccc1n2)CCN3C[C@](O)(CC)C[C@@H](C3)C4)c5c(OC) cc6c(c5)[C@@]89[C@@H](N6C=O)[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@@]7 (/C=C\CN([C@@H]78)CC9)CC |
ChemSpider | |
| SMILES (Canonical) | ||
CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7 C(C=CC9)(C(C(C8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O |
PubChem | |
| Kegg Drug | ||
| D08679 | KEGG Compound | |
| Kegg Compound | ||
| C07204 | DrugBank | |
| Pubchem Compound ID | ||
| 5978 | DrugBank | |
| Pubchem Substance ID | ||
| 11431056 | Pubchem | |
| 14717665 | Pubchem | |
| 148816 | Pubchem | |
| 14889382 | Pubchem | |
| 26757081 | Pubchem | |
| 29224994 | Pubchem | |
| 46507033 | Pubchem | |
| 48424284 | Pubchem | |
| 49854447 | Pubchem | |
| 56312035 | Pubchem | |
| 56314177 | Pubchem | |
| 57323093 | Pubchem | |
| 598397 | Pubchem | |
| 74979043 | Pubchem | |
| 8153716 | Pubchem | |
| 9413 | Kegg | |
| OMIM ID | ||
| Not Available | Not Applicable | |
| ChEBI | ||
| 28445 | DrugBank | |
| BioCyc | ||
| Not Available | Not Applicable | |
| PharmGKB | ||
| PA451879 | DrugBank | |
| HET ID | ||
| Not Available | Not Applicable | |
| DPD ID | ||
| 02143305 | DPD | |
| 02183013 | DPD | |
| Rxlist Link | ||
| http://www.rxlist.com/cgi/generic3/vincristine.htm | DrugBank | |
| Wikipedia | ||
| vincristine | Wikipedia | |
| Pdr Health Link | ||
| Not Available | Not Applicable | |
| Melting Point | ||
| 219 oC | PhysProp | |
| State | ||
| Solid | BioSpider | |
| MSDS Link | ||
| 1260312287.pdf | www.sciencelab.com | |
| FDA Label | ||
| 1260312289.html | FDA | |
| Experimental Water Solubility | ||
| Not Available | Not Applicable | |
| Predicted Water Solubility | ||
| 0.00227 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] | PhysProp | |
| 0.03 mg/mL [Predicted by ALOGPS] | Alogps | |
| Experimental LogP | ||
| 2.82 [HANSCH,C ET AL. (1995)] | PhysProp | |
| Predicted LogP | ||
| 3.36 [Predicted by ALOGPS] | Alogps | |
| pKa | ||
| 5 | DrugBank | |
| SDF File | ||
| 1260312235.sdf | Pubchem | |
| Mol File | ||
| 1260312223.mol | Molconvert | |
| Pdb File | ||
| 1260312293.pdb | Molconvert | |
| Mass Spec File | ||
| Not Available | Not Applicable | |
| Associated Disorder | ||
| Not Available | Not Applicable | |
| Pathway | ||
| map07042 - Antineoplastics - agents from natural products | Kegg Drug | |
| Category | ||
| Not Available | Not Applicable | |
| ATC Code | ||
| L01CA02 | DPD | |
| AHFS Code | ||
| 10:00.00 | DPD | |
| Schedule | ||
| SCHEDULE F (Canada) | DPD | |
| Indication | ||
| For treatment of acute leukaemia, malignant lymphoma, Hodgkin's disease, acute erythraemia, acute panmyelosis | DrugBank | |
| Pharmacology | ||
| Vincristine is a vinca alkaloid antineoplastic agent used as a treatment for various cancers including breast cancer, Hodgkin's disease, Kaposi's sarcoma, and testicular cancer. The vinca alkaloids are structurally similar compounds comprised of 2 multiringed units, vindoline and catharanthine. The vinca alkaloids have become clinically useful since the discovery of their antitumour properties in 1959. Initially, extracts of the periwinkle plant (Catharanthus roseus) were investigated because of putative hypoglycemic properties, but were noted to cause marrow suppression in rats and antileukemic effects in vitro. Vincristine binds to the microtubular proteins of the mitotic spindle, leading to crystallization of the microtubule and mitotic arrest or cell death. Vincristine has some immunosuppressant effect. The vinca alkaloids are considered to be cell cycle phase-specific. | DrugBank | |
| Mechanism Of Action | ||
| The antitumor activity of Vincristine is thought to be due primarily to inhibition of mitosis at metaphase through its interaction with tubulin. Like other vinca alkaloids, Vincristine may also interfere with: 1) amino acid, cyclic AMP, and glutathione metabolism, 2) calmodulin-dependent Ca2+-transport ATPase activity, 3) cellular respiration, and 4) nucleic acid and lipid biosynthesis. | DrugBank | |
| Tubulin is a structural protein which polymerizes to form microtubules. The cell cytoskeleton and mitotic spindle, amongst other things, are made of microtubules. Vincristine binds to tubulin dimers, inhibiting assembly of microtubule structures. Disruption of the microtubules arrests mitosis in metaphase. The vinca alkaloids therefore affect all rapidly dividing cell types including cancer cells, but also intestinal epithelium and bone marrow. Uses | Wikipedia | |
| Vincristine (brand name, Oncovin), also known as leurocristine, is a vinca alkaloid from the Catharanthus roseus (Madagascar periwinkle), formerly Vinca rosea and hence its name. It is a mitotic inhibitor, and is used in cancer chemotherapy. // Mode of action | Wikipedia | |
| Absorption | ||
| Not Available | Not Applicable | |
| Protein Binding | ||
| ~75% | DrugBank | |
| Half Life | ||
| 19 to 155 hours | Wikipedia | |
| 19-155 hours | DrugBank | |
| Biotransformation | ||
| Hepatic | DrugBank | |
| Toxicity | ||
| IVN-RAT LD50 1300 mg/kg | DrugBank | |
| The medical literature documents cases of ascending paralysis due to massive encephalopathy and spinal nerve demyelination, accompanied by intractable pain, almost uniformly leading to death; a handful of survivors were left with devastating neurological damage with no hope of recovery | Wikipedia | |
| Dosage | ||
| Liquid (Intravenous) | DPD | |
| Solution (Intravenous) | DPD | |
| Patient Information | ||
| 1260312324.html | RxList | |
| Interactions | ||
| Not Available | Not Applicable | |
| Contraindications | ||
| Not Available | Not Applicable | |
| Targets | ||
P07437[ UniProt | Analyze ] |
DrugBank |