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

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 278 Target ID: CHEMBL2311221 Sources: http://www.drugbank.ca/drugs/DB00236	Crosslinking Agent 81

Conditions

Condition	Modality	Targets	Highest Phase	Product
Polycythemia vera 15 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14565648	Primary		Approved 8429	VERCYTE Approved Use Pipobroman Launch Date 1966
Refractory chronic myeloid leukaemia 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14565648	Primary		Approved 8429	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 n = 140 Health Status: unhealthy Condition: polycythemia vera Age Group: 61.8 Sex: M+F Population Size: 140 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 n = 140 Health Status: unhealthy Condition: polycythemia vera Age Group: 61.8 Sex: M+F Population Size: 140 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 n = 140 Health Status: unhealthy Condition: polycythemia vera Age Group: 61.8 Sex: M+F Population Size: 140 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 n = 140 Health Status: unhealthy Condition: polycythemia vera Age Group: 61.8 Sex: M+F Population Size: 140 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 n = 140 Health Status: unhealthy Condition: polycythemia vera Age Group: 61.8 Sex: M+F Population Size: 140 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
Aplastic anemia responsive to cyclosporine complicating the evolution of polycythemia vera.	1999 May	10342591
Bone marrow aplasia after pipobroman: an immune-mediated mechanism?	2001 Dec	11736962
[Synthesis and anti-tumor activities of 1,4-bis[3-(amino-dithiocarboxy)propionyl] piperazine derivatives].	2001 Mar	12580084
Current treatment practice for essential thrombocythaemia in adults.	2001 Mar	11336593
Management of patients with essential thrombocythemia: current concepts and perspectives.	2001 Mar	11317966
[Hydroxyurea--is it a harmless drug in Vaquez disease?]].	2001 Mar	11317962
[Multiple skin and mouth squamous cell carcinomas related to long-term treatment with hydroxyurea].	2001 Sep	11590345
What is the standard treatment in essential thrombocythemia.	2002 Aug	12430943
Pipobroman is safe and effective treatment for patients with essential thrombocythaemia at high risk of thrombosis.	2002 Mar	11886392
Acute myeloid leukemia (AML) having evolved from essential thrombocythemia (ET): distinctive chromosome abnormalities in patients treated with pipobroman or hydroxyurea.	2002 Oct	12357360
[Polycythemia vera].	2002 Oct 15	12564173
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 in young patients: a study on the long-term risk of thrombosis, myelofibrosis and leukemia.	2003 Jan	12551821
Treatment indications and choice of a platelet-lowering agent in essential thrombocythemia.	2003 May	12901347
Long-term evaluation of 164 patients with essential thrombocythaemia treated with pipobroman: occurrence of leukaemic evolution.	2003 Nov	14617017
Polycythemia vera.	2003 Oct	14560782
Treatment of polycythemia vera and essential thrombocythemia: the role of pipobroman.	2003 Sep	14565648
Pharmacotherapy of essential thrombocythaemia: economic considerations.	2003 Sep	12943479
Long-term follow-up of young patients with essential thrombocythemia treated with pipobroman.	2004 Aug	15175894
Cytoreductive therapy for patients with essential thrombocythemia at high risk of thromboembolic complications. The difficult choice of the optimal drug.	2004 Nov	15531447
Acute leukemia in polycythemia vera: an analysis of 1638 patients enrolled in a prospective observational study.	2005 Apr 1	15585653
Cytogenetic response to pipobroman in Philadelphia-positive chronic myeloid leukemia with thrombocythemic onset.	2005 Feb	15378276
Del(5q) and MLL amplification in homogeneously staining region in acute myeloblastic leukemia: a recurrent cytogenetic association.	2006 Apr	16425025
Long-term incidence of hematological evolution in three French prospective studies of hydroxyurea and pipobroman in polycythemia vera and essential thrombocythemia.	2006 Jun	16810617
Essential thrombocythemia.	2007 Jan 8	17210076
A review of the therapeutic agents used in the management of polycythaemia vera.	2007 Jun	17352450
[Multiples squamous cell carcinomas during treatment with pipobroman].	2007 Jun-Jul	17657187
The treatment of polycythaemia vera: an update in the JAK2 era.	2007 Mar	17551678
Practical approach to treating essential thrombocythaemia: case studies.	2007 Oct	17727566
A case of bromoderma and bromism.	2008 Feb	18047506
Pipobroman gets regulatory approval outside Germany.	2008 Jan	19633773
[Confluent indurated facial nodules and pustules in a 55-year-old man].	2008 Sep	18615248
Essential thrombocythemia: past and present.	2009 Oct	19636672
Inhibition of allogeneic inflammatory responses by the Ribonucleotide Reductase Inhibitors, Didox and Trimidox.	2010 Aug 18	20718971
Polycythemia vera.	2010 Oct	20237866

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

Name

Type

Language

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

VERCYTE

Brand 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