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Showing drug card for Cisplatin (DB00515)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:08:13
Primary Accession Number DB00515
Secondary Accession Number
  • APRD00359
Name Cisplatin
Drug Type
  • Approved
  • Small Molecule
Description Cisplatin, cisplatinum or cis-diamminedichloroplatinum(II) (CDDP) is a platinum-based chemotherapy drug used to treat various types of cancers, including sarcomas, some carcinomas (e.g. small cell lung cancer, and ovarian cancer), lymphomas and germ cell tumors. It was the first member of its class, which now also includes carboplatin and oxaliplatin.
Synonyms
  1. CACP
  2. CPDC
  3. CPDD
  4. Cis-DDP
  5. Cis-Diaminedichloroplatinum
  6. Cis-Diamminedichloroplatinum
  7. DDP
  8. DDPT
  9. Diamminedichloroplatinum
  10. Platinum Ammine Chloride
  11. Platinum Ammonium Chloride
  12. Platinum Diamine Dichloride
  13. Trans-DDP
  14. Trans-Diaminedichloroplatinum
  15. Trans-Diamminedichloroplatinum
  16. Trans-Dichlorodiammine Platinum
  17. Trans-Platinumdiammine Dichloride
Brand Names
  1. Abiplatin
  2. Biocisplatinum
  3. Briplatin
  4. Carboquone
  5. Cis Pt II
  6. Cismaplat
  7. Cisplatine
  8. Cisplatyl
  9. Citoplationo
  10. Lederplatin
  11. Neoplatin
  12. Plastin
  13. Platamine
  14. Platiblastin
  15. Platidiam
  16. Platinex
  17. Platinol
  18. Platinol-AQ
  19. Platinoxan
  20. Randa
Brand Mixtures Not Available
Chemical IUPAC Name azane; dichloroplatinum
Chemical Formula Cl2H6N2Pt
Chemical Structure Structure
CAS Registry Number 15663-27-1
InChI Identifier InChI=1/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+4/p-2/f2Cl.2H3N.Pt/h2*1h;;;/q2*-1;;;m/rCl2Pt.2H3N/c1-3-2;;/h;2*1H3/q+2;;
InChI Key BSJGASKRWFKGMV-PAACDROBCM
KEGG Drug D00275 Link Image
KEGG Compound C06911 Link Image
PubChem Compound 441203 Link Image
PubChem Substance 7847341 Link Image
ChEBI ID 27899 Link Image
PharmGKB ID PA449014 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02126613 Link Image
RxList Link http://www.rxlist.com/cgi/generic3/cisplatin.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Cisplatin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 300.0510
Monoisotopic Molecular Weight 298.9556
State Solid
Melting Point 270 oC
Experimental Water Solubility 2530 mg/L Source: PhysProp
Predicted Water Solubility Not Available Calculated using ALOGPS
Experimental LogP/Hydrophobicity -2.19 Source: PhysProp
Predicted LogP Not Available Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS Not Available Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES N.N.Cl[Pt++]Cl
Canonical SMILES N.N.Cl[Pt++]Cl
Drug Category
  • Antineoplastic Agents
  • Cross-Linking Reagents
  • Radiation-Sensitizing Agents
ATC Codes
AHFS Codes
  • 10:00.00
Indication For the treatment of metastatic testicular tumors, metastatic ovarian tumors and advanced bladder cancer.
Pharmacology Cisplatin is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.
Mechanism of Action Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations.
Absorption Not Available
Toxicity Not Available
Protein Binding Greater than 90%.
Biotransformation Not Available
Half Life 20-30 minutes
Dosage Forms
Form Route
Solution Intravenous
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. DNA
Drug Target 1 [top]
Target 1 ID 874
Target 1 Name DNA
Target 1 Synonyms
  1. Deoxyribonucleic acid
Target 1 Gene Name Not Available
Target 1 Protein Sequence Not Available
Target 1 Number of Residues 0
Target 1 Molecular Weight 7656 (double strand)
Target 1 Theoretical pI Not Available
Target 1 GO Classification
Function
information storage
information transfer
Process
DNA replication and chromosomal cycle
DNA replication
DNA-dependent DNA replication
DNA replication, synthesis of RNA primer
transcription
transcription, DNA dependent
Component
cell
intracellular
nucleus
mitochondria
Target 1 General Function Biological information storage and information transfer
Target 1 Specific Function DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
RNA polymerase map03020 Link Image
Target 1 Reactions
  • DNA + DNA polymerase + nNTP = 2 DNA + nNDP; DNA + RNA polymerase + NTP = mRNA + nNDP
Target 1 Pfam Domain Function Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Not Available
Target 1 UniProtKB/Swiss-Prot Entry Name Not Available
Target 1 PDB ID 1BNA Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus and mitochondria
Target 1 Gene Sequence >Example: Dickerson dodecamer 
CGCGAATTCGCG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus All loci
Target 1 SNPs Not Available
Target 1 General References
  1. Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  3. Sharma S, Gong P, Temple B, Bhattacharyya D, Dokholyan NV, Chaney SG: Molecular Dynamic Simulations of Cisplatin- and Oxaliplatin-d(GG) Intrastand Cross-links Reveal Differences in their Conformational Dynamics. J Mol Biol. 2007 Aug 23;. [PubMed Link Image]
  4. Moriyama-Gonda N, Shiina H, Terashima M, Satoh K, Igawa M: Rationale and clinical implication of combined chemotherapy with cisplatin and oestrogen in prostate cancer: primary evidence based on methylation analysis of oestrogen receptor-alpha. BJU Int. 2007 Oct 8;. [PubMed Link Image]
  5. Garcia Sar D, Montes-Bayon M, Aguado Ortiz L, Blanco-Gonzalez E, Sierra LM, Sanz-Medel A: In vivo detection of DNA adducts induced by cisplatin using capillary HPLC-ICP-MS and their correlation with genotoxic damage in Drosophila melanogaster. Anal Bioanal Chem. 2007 Oct 12;. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.