Identification
- Generic Name
- Pipobroman
- DrugBank Accession Number
- DB00236
- Background
An antineoplastic agent that acts by alkylation.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pipobroman (DB00236)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Polycythemia •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include hematologic toxicity, especially with chronic overdosage.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Pipobroman is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Pipobroman is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Pipobroman is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Pipobroman is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Pipobroman is combined with Bupivacaine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
- 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
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Abbott laboratories pharmaceutical products div
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet 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) -1.3 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 splash10-056r-3980000000-8bd279e69119d9648d5b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0039000000-5495758f44269c540c74 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0469000000-b8556274514eddb577ac Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0ufr-3539000000-00e1e55397f71183b699 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0931000000-2a3abf9a0ad7717c36aa Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000f-9500000000-3b368173ebebb3c40105 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0gz0-6931000000-2658536fdbcb5fe52c15 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 159.0425686 predictedDarkChem Lite v0.1.0 [M-H]- 151.90329 predictedDeepCCS 1.0 (2019) [M+H]+ 159.8195686 predictedDarkChem Lite v0.1.0 [M+H]+ 154.26129 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.1994686 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.8328 predictedDeepCCS 1.0 (2019)
Targets
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Yes
Cross-linking/alkylation
References
- 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]
- 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 January 02, 2024 23:43