PIPOBROMAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H16Br2N2O2
Molecular Weight	356.054
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

BrCCC(=O)N1CCN(CC1)C(=O)CCBr

InChI

InChIKey=NJBFOOCLYDNZJN-UHFFFAOYSA-N

InChI=1S/C10H16Br2N2O2/c11-3-1-9(15)13-5-7-14(8-6-13)10(16)2-4-12/h1-8H2

HIDE SMILES / InChI

Molecular Formula	C10H16Br2N2O2
Molecular Weight	356.054
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://activebiochem.com/drug/Pipobroman.html
Curator's Comment: description was created based on several sources, including: http://www.drugbank.ca/drugs/DB00236

Pipobroman (trade names Vercite, Vercyte) is an anti-cancer drug that probably acts as an alkylating agent. It is marketed by Abbott Laboratories. Pipobroman (PB) has well documented clinical activity in polycythemia vera (PV) and essential thrombocythemia (ET). The mechanism of action is uncertain but pipobroman is thought to alkylate DNA leading to disruption of DNA synthesis and eventual cell death

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: http://www.drugbank.ca/drugs/DB00236	Crosslinking Agent 83

Conditions

Condition	Modality	Targets	Highest Phase	Product
Polycythemia vera 18 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14565648	Primary		Approved 8583	VERCYTE Approved Use Pipobroman Launch Date 1966
Refractory chronic myeloid leukaemia 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14565648	Primary		Approved 8583	VERCYTE Approved Use Pipobroman Launch Date 1966

Doses

Dose	Population	Adverse events
75 mg 1 times / day multiple, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/	unhealthy, 61.8 Health Status: unhealthy Age Group: 61.8 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/	Disc. AE: Pancytopenia, Gastric pain... AEs leading to discontinuation/dose reduction: Pancytopenia Gastric pain Diarrhea Aplasia bone marrow Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/

AEs

AE	Significance	Dose	Population
Aplasia bone marrow	Disc. AE	75 mg 1 times / day multiple, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/	unhealthy, 61.8 Health Status: unhealthy Age Group: 61.8 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/
Diarrhea	Disc. AE	75 mg 1 times / day multiple, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/	unhealthy, 61.8 Health Status: unhealthy Age Group: 61.8 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/
Gastric pain	Disc. AE	75 mg 1 times / day multiple, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/	unhealthy, 61.8 Health Status: unhealthy Age Group: 61.8 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/
Pancytopenia	Disc. AE	75 mg 1 times / day multiple, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/	unhealthy, 61.8 Health Status: unhealthy Age Group: 61.8 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14617017/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8242	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8242
MolPort	MolPort-003-665-507	https://www.molport.com/shop/molecule-link/MolPort-003-665-507
ZINC	ZINC000001530753	http://zinc15.docking.org/substances/ZINC000001530753

PubMed

Title	Date	PubMed
Polycythemia vera.	2010-10	20237866
Inhibition of allogeneic inflammatory responses by the Ribonucleotide Reductase Inhibitors, Didox and Trimidox.	2010-08-18	20718971
Essential thrombocythemia: past and present.	2009-10	19636672
[Confluent indurated facial nodules and pustules in a 55-year-old man].	2008-09	18615248
A case of bromoderma and bromism.	2008-02	18047506
Pipobroman gets regulatory approval outside Germany.	2008-01	19633773
Practical approach to treating essential thrombocythaemia: case studies.	2007-10	17727566
[Multiples squamous cell carcinomas during treatment with pipobroman].	2007-07-28	17657187
A review of the therapeutic agents used in the management of polycythaemia vera.	2007-06	17352450
The treatment of polycythaemia vera: an update in the JAK2 era.	2007-03	17551678
Essential thrombocythemia.	2007-01-08	17210076
Long-term incidence of hematological evolution in three French prospective studies of hydroxyurea and pipobroman in polycythemia vera and essential thrombocythemia.	2006-06	16810617
Del(5q) and MLL amplification in homogeneously staining region in acute myeloblastic leukemia: a recurrent cytogenetic association.	2006-04	16425025
Acute leukemia in polycythemia vera: an analysis of 1638 patients enrolled in a prospective observational study.	2005-04-01	15585653
Cytogenetic response to pipobroman in Philadelphia-positive chronic myeloid leukemia with thrombocythemic onset.	2005-02	15378276
Cytoreductive therapy for patients with essential thrombocythemia at high risk of thromboembolic complications. The difficult choice of the optimal drug.	2004-11	15531447
Long-term follow-up of young patients with essential thrombocythemia treated with pipobroman.	2004-08	15175894
Long-term evaluation of 164 patients with essential thrombocythaemia treated with pipobroman: occurrence of leukaemic evolution.	2003-11	14617017
Polycythemia vera.	2003-10	14560782
Treatment of polycythemia vera and essential thrombocythemia: the role of pipobroman.	2003-09	14565648
Pharmacotherapy of essential thrombocythaemia: economic considerations.	2003-09	12943479
Treatment indications and choice of a platelet-lowering agent in essential thrombocythemia.	2003-05	12901347
Polycythemia vera in young patients: a study on the long-term risk of thrombosis, myelofibrosis and leukemia.	2003-01	12551821
Long-term outcomes of polycythemia vera patients treated with pipobroman as initial therapy.	2003	12764352
Transition of essential thrombocythemia to megakaryoblastic leukemia after long-term therapy with sequential busulfan, pipobroman and hydroxyurea.	2003	12714827
[Polycythemia vera].	2002-10-15	12564173
Acute myeloid leukemia (AML) having evolved from essential thrombocythemia (ET): distinctive chromosome abnormalities in patients treated with pipobroman or hydroxyurea.	2002-10	12357360
What is the standard treatment in essential thrombocythemia.	2002-08	12430943
Pipobroman is safe and effective treatment for patients with essential thrombocythaemia at high risk of thrombosis.	2002-03	11886392
Bone marrow aplasia after pipobroman: an immune-mediated mechanism?	2001-12	11736962
[Multiple skin and mouth squamous cell carcinomas related to long-term treatment with hydroxyurea].	2001-09	11590345
[Synthesis and anti-tumor activities of 1,4-bis[3-(amino-dithiocarboxy)propionyl] piperazine derivatives].	2001-03	12580084
Current treatment practice for essential thrombocythaemia in adults.	2001-03	11336593
Management of patients with essential thrombocythemia: current concepts and perspectives.	2001-03	11317966
[Hydroxyurea--is it a harmless drug in Vaquez disease?]].	2001-03	11317962
Aplastic anemia responsive to cyclosporine complicating the evolution of polycythemia vera.	1999-05	10342591

Patents

Sample Use Guides

In Vivo Use Guide

Polycythemia vera: 1 mg/kg/day Chronic granulocytic leukemia: 1.5-2.5 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:25:46 GMT 2025` Edited by `admin` on `Mon Mar 31 21:25:46 GMT 2025`
Record UNII	6Q99RDT97R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VERCYTE

Preferred Name

English

PIPOBROMAN

Official Name

English

PIPOBROMAN [JAN]

Common Name

English

PIPOBROMAN [HSDB]

Common Name

English

Pipobroman [WHO-DD]

Common Name

English

A-8103

Code

English

1,4-Bis(3-bromopropionyl)piperazine

Systematic Name

English

PIPERAZINE, 1,4-BIS(3-BROMO-1-OXOPROPYL)-

Systematic Name

English

PIPOBROMAN [USAN]

Common Name

English

PIPOBROMAN [ORANGE BOOK]

Common Name

English

pipobroman [INN]

Common Name

English

PIPOBROMAN [VANDF]

Common Name

English

NSC-25154

Code

English

PIPOBROMAN [MART.]

Common Name

English

PIPOBROMAN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1590