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Showing drug card for Pipobroman (DB00236)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:41
Primary Accession Number DB00236
Secondary Accession Number
  • APRD00693
Name Pipobroman
Drug Type
  • Approved
  • Small Molecule
Description An antineoplastic agent that acts by alkylation. [PubChem]
Synonyms Not Available
Brand Names
  1. Amedel
  2. Vercyte
Brand Mixtures Not Available
Chemical IUPAC Name 3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-one
Chemical Formula C10H16Br2N2O2
Chemical Structure Structure
CAS Registry Number 54-91-1
InChI Identifier InChI=1/C10H16Br2N2O2/c11-3-1-9(15)13-5-7-14(8-6-13)10(16)2-4-12/h1-8H2
InChI Key NJBFOOCLYDNZJN-UHFFFAOYAD
KEGG Drug D00467 Link Image
KEGG Compound C07362 Link Image
PubChem Compound 4842 Link Image
PubChem Substance 148729 Link Image
ChEBI ID Not Available
PharmGKB ID PA450982 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Pipobroman Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 356.0540
Monoisotopic Molecular Weight 353.9579
State Solid
Melting Point > 300 oC
Experimental Water Solubility 2490 mg/L Source: PhysProp
Predicted Water Solubility 2.24e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.1 Source: PhysProp
Predicted LogP 1.09 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.20 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 BrCCC(=O)N1CCN(CC1)C(=O)CCBr
Canonical SMILES BrCCC(=O)N1CCN(CC1)C(=O)CCBr
Drug Category
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
ATC Codes
AHFS Codes Not Available
Indication For the treatment of polycythaemia vera and refractory chronic myeloid leukaemia.
Pharmacology Pipobroman is an antineoplastic agent. Specifically it is a piperazine derivative with a chemical structure close to that of many DNA alkylating agents. Pipobroman has well documented clinical activity against polycythemia vera and essential thrombocythemia.
Mechanism of Action The mechanism of action is uncertain but pipobroman is thought to alkylate DNA leading to disruption of DNA synthesis and eventual cell death.
Absorption Well absorbed from the GI tract.
Toxicity Symptoms of overdose include hematologic toxicity, especially with chronic overdosage.
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Show Link Image
Interactions Not Available
Drug Interactions
Drug Interaction
Acebutolol Antagonism
Atenolol Antagonism
Betaxolol Antagonism
Bevantolol Antagonism
Bisoprolol Antagonism
Carteolol Antagonism
Carvedilol Antagonism
Esmolol Antagonism
Labetalol Antagonism
Metoprolol Antagonism
Nadolol Antagonism
Oxprenolol Antagonism
Penbutolol Antagonism
Pindolol Antagonism
Practolol Antagonism
Propranolol Antagonism
Sotalol Antagonism
Timolol Antagonism
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia 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]

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.