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Identification
NamePipobroman
Accession NumberDB00236  (APRD00693)
TypeSmall Molecule
GroupsApproved
Description

An antineoplastic agent that acts by alkylation. [PubChem]

Structure
Thumb
Synonyms
Vercyte
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
VerciteAbbott Laboratories
VercyteAbbott Laboratories
Brand mixturesNot Available
SaltsNot Available
Categories
UNII6Q99RDT97R
CAS number54-91-1
WeightAverage: 356.054
Monoisotopic: 353.95785306
Chemical FormulaC10H16Br2N2O2
InChI KeyInChIKey=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
IUPAC Name
3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-one
SMILES
BrCCC(=O)N1CCN(CC1)C(=O)CCBr
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as piperazines. These are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPiperazines
Alternative Parents
Substituents
  • Piperazine
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alkyl halide
  • Alkyl bromide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of polycythaemia vera and refractory chronic myeloid leukaemia.
PharmacodynamicsPipobroman 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 actionThe mechanism of action is uncertain but pipobroman is thought to alkylate DNA leading to disruption of DNA synthesis and eventual cell death.
Related Articles
AbsorptionWell absorbed from the GI tract.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include hematologic toxicity, especially with chronic overdosage.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9197
Blood Brain Barrier+0.9859
Caco-2 permeable-0.5115
P-glycoprotein substrateNon-substrate0.5493
P-glycoprotein inhibitor IInhibitor0.52
P-glycoprotein inhibitor IINon-inhibitor0.9347
Renal organic cation transporterNon-inhibitor0.5366
CYP450 2C9 substrateNon-substrate0.9097
CYP450 2D6 substrateNon-substrate0.5765
CYP450 3A4 substrateNon-substrate0.6178
CYP450 1A2 substrateNon-inhibitor0.892
CYP450 2C9 inhibitorNon-inhibitor0.8645
CYP450 2D6 inhibitorNon-inhibitor0.9468
CYP450 2C19 inhibitorNon-inhibitor0.6421
CYP450 3A4 inhibitorNon-inhibitor0.8322
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8849
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.9059
BiodegradationNot ready biodegradable0.9427
Rat acute toxicity3.1778 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.829
hERG inhibition (predictor II)Non-inhibitor0.8346
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point> 300 °CPhysProp
water solubility2490 mg/LNot Available
logP0.42HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.24 mg/mLALOGPS
logP1.09ALOGPS
logP0.41ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-0.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.45 m3·mol-1ChemAxon
Polarizability28.44 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesL01AX02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
cross-linking/alkylation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
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:17139284 ]
  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:17016423 ]
  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:5556760 ]
  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:14565648 ]
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Drug created on June 13, 2005 07:24 / Updated on September 25, 2013 16:16