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 247 Target ID: CHEMBL2311221 Sources: http://www.drugbank.ca/drugs/DB00236	Crosslinking Agent 80

Conditions

Condition	Modality	Targets	Highest Phase	Product
Polycythemia vera 14 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14565648	Primary		Approved 8360	VERCYTE Approved Use Pipobroman Launch Date -1.25711999E11
Refractory chronic myeloid leukaemia 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14565648	Primary		Approved 8360	VERCYTE Approved Use Pipobroman Launch Date -1.25711999E11

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
Management of patients with essential thrombocythemia: current concepts and perspectives.	2001 Mar	11317966
Long-term outcomes of polycythemia vera patients treated with pipobroman as initial therapy.	2003	12764352
Polycythemia vera.	2003 Oct	14560782
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
Pipobroman gets regulatory approval outside Germany.	2008 Jan	19633773
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