Identification

Generic Name
Pipobroman
DrugBank Accession Number
DB00236
Background

An antineoplastic agent that acts by alkylation.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 356.054
Monoisotopic: 353.95785306
Chemical Formula
C10H16Br2N2O2
Synonyms
  • 1,4-bis(3-bromopropionyl)piperazine
  • N,N-bis-(3-bromopropionyl)-piperazine
  • Pipobroman
  • Pipobromanum
External IDs
  • A-8103
  • NSC-25154

Pharmacology

Indication

For the treatment of polycythaemia vera and refractory chronic myeloid leukaemia.

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Associated Conditions
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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 due to the structural similarity with other DNA alkylating agents, pipobroman is thought to alkylate DNA leading to disruption of DNA synthesis and eventual cell death.1

TargetActionsOrganism
ADNA
cross-linking/alkylation
Humans
Absorption

Well absorbed from the GI tract.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include hematologic toxicity, especially with chronic overdosage.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Pipobroman.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Pipobroman.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Pipobroman.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Pipobroman.
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Food Interactions
Not Available

Products

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International/Other Brands
Vercite (Abbott Laboratories) / Vercyte (Abbott Laboratories)

Categories

ATC Codes
L01AX02 — Pipobroman
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
Piperazines
Alternative Parents
Tertiary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organobromides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Alkyl bromides
Substituents
Aliphatic heteromonocyclic compound / Alkyl bromide / Alkyl halide / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
phytanoyl-CoAs (CHEBI:8242)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6Q99RDT97R
CAS number
54-91-1
InChI Key
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

References

General References
  1. Passamonti F, Lazzarino M: Treatment of polycythemia vera and essential thrombocythemia: the role of pipobroman. Leuk Lymphoma. 2003 Sep;44(9):1483-8. [Article]
  2. AIFA Approved Drug Proucts: vercite (pipobroman) tablet for oral use [Link]
Human Metabolome Database
HMDB0014381
KEGG Drug
D00467
KEGG Compound
C07362
PubChem Compound
4842
PubChem Substance
46506548
ChemSpider
4676
RxNav
8347
ChEBI
8242
ChEMBL
CHEMBL1585
ZINC
ZINC000001530753
Therapeutic Targets Database
DAP000988
PharmGKB
PA164747673
Wikipedia
Pipobroman

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Abbott laboratories pharmaceutical products div
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)> 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)-1.3ChemAxon
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Nucleotide
Organism
Humans
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.
References
  1. 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. [Article]
  2. Passamonti F, Lazzarino M: Treatment of polycythemia vera and essential thrombocythemia: the role of pipobroman. Leuk Lymphoma. 2003 Sep;44(9):1483-8. [Article]

Drug created at June 13, 2005 13:24 / Updated at April 28, 2022 23:24