Pipobroman
Identification
- Name
- Pipobroman
- Accession Number
- DB00236
- Description
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
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- Indication
For the treatment of polycythaemia vera and refractory chronic myeloid leukaemia.
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
- 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.
Target Actions Organism ADNA cross-linking/alkylationHumans - 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
- Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data
- Toxicity
Symptoms of overdose include hematologic toxicity, especially with chronic overdosage.
- Affected organisms
- Humans and other mammals
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareDarbepoetin alfa The risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Pipobroman. Erythropoietin The risk or severity of Thrombosis can be increased when Erythropoietin is combined with Pipobroman. Methoxy polyethylene glycol-epoetin beta The risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Pipobroman. Peginesatide The risk or severity of Thrombosis can be increased when Peginesatide is combined with Pipobroman. Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Not Available
Products
- Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets
- 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)
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
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014381
- KEGG Drug
- D00467
- KEGG Compound
- C07362
- PubChem Compound
- 4842
- PubChem Substance
- 46506548
- ChemSpider
- 4676
- 8347
- ChEBI
- 8242
- ChEMBL
- CHEMBL1585
- ZINC
- ZINC000001530753
- Therapeutic Targets Database
- DAP000988
- PharmGKB
- PA164747673
- Wikipedia
- Pipobroman
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Abbott laboratories pharmaceutical products div
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet 10 MG Tablet 25 MG - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) > 300 °C PhysProp water solubility 2490 mg/L Not Available logP 0.42 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 2.24 mg/mL ALOGPS logP 1.09 ALOGPS logP 0.41 ChemAxon logS -2.2 ALOGPS pKa (Strongest Basic) -0.72 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 40.62 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 69.45 m3·mol-1 ChemAxon Polarizability 28.44 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9197 Blood Brain Barrier + 0.9859 Caco-2 permeable - 0.5115 P-glycoprotein substrate Non-substrate 0.5493 P-glycoprotein inhibitor I Inhibitor 0.52 P-glycoprotein inhibitor II Non-inhibitor 0.9347 Renal organic cation transporter Non-inhibitor 0.5366 CYP450 2C9 substrate Non-substrate 0.9097 CYP450 2D6 substrate Non-substrate 0.5765 CYP450 3A4 substrate Non-substrate 0.6178 CYP450 1A2 substrate Non-inhibitor 0.892 CYP450 2C9 inhibitor Non-inhibitor 0.8645 CYP450 2D6 inhibitor Non-inhibitor 0.9468 CYP450 2C19 inhibitor Non-inhibitor 0.6421 CYP450 3A4 inhibitor Non-inhibitor 0.8322 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8849 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.9059 Biodegradation Not ready biodegradable 0.9427 Rat acute toxicity 3.1778 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.829 hERG inhibition (predictor II) Non-inhibitor 0.8346
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Accelerate your drug discovery research with our ADMET & drug target dataset
Yes
Cross-linking/alkylation
References
- 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]
- 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]
- 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]
- 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]
Drug created on June 13, 2005 13:24 / Updated on February 21, 2021 18:50