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Identification
Name Pipobroman
Accession Number DB00236 (APRD00693)
Type small molecule
Groups approved
Description

An antineoplastic agent that acts by alkylation. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Amedel
  • Vercyte
Brand name mixtures Not Available
Categories
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
CAS number 54-91-1
Weight Average: 356.054
Monoisotopic: 353.957853060
Chemical Formula C10H16Br2N2O2
InChI Key InChIKey=NJBFOOCLYDNZJN-UHFFFAOYSA-N
InChI
InChI=1S/C10H16Br2N2O2/c11-3-1-9(15)13-5-7-14(8-6-13)10(16)2-4-12/h1-8H2
Plain Text
IUPAC Name
3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-one
SMILES
BrCCC(=O)N1CCN(CC1)C(=O)CCBr
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Piperazines
Substructures
  • Amino Ketones
  • Piperazines
  • Aliphatic and Aryl Amines
  • Alkyl Halides
  • Heterocyclic compounds
  • Carboxamides and Derivatives
Pharmacology
Indication For the treatment of polycythaemia vera and refractory chronic myeloid leukaemia.
Pharmacodynamics 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.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms of overdose include hematologic toxicity, especially with chronic overdosage.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point > 300 oC
Experimental Properties
Property Value Source
water solubility 2490 mg/L PhysProp
logP 1.1 PhysProp
Predicted Properties
Property Value Source
water solubility 2.24e+00 g/l ALOGPS
logP 1.09 ALOGPS
logP 0.41 ChemAxon Molconvert
logS -2.20 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 40.62 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 69.45 ChemAxon Molconvert
polarizability 28.35 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00467 Link_out
KEGG Compound C07362 Link_out
PubChem Compound 4842 Link_out
PubChem Substance 46506548 Link_out
ChemSpider 4676 Link_out
Therapeutic Targets Database DAP000988 Link_out
PharmGKB PA450982 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Pipobroman Link_out
ATC Codes
  • L01AX02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. DNA

Pharmacological action: yes
Actions: cross-linking/alkylation

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.

Gene Sequence: FASTA

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Yellin TO: Effects of piposulfan (Ancyte) on protein and DNA synthesis in Ehrlich ascites carcinoma. Life Sci II. 1971 Jun 8;10(11):605-12. Pubmed
  4. Passamonti F, Lazzarino M: Treatment of polycythemia vera and essential thrombocythemia: the role of pipobroman. Leuk Lymphoma. 2003 Sep;44(9):1483-8. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:37

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.