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 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
Bone marrow aplasia after pipobroman: an immune-mediated mechanism?	2001 Dec	11736962
[Multiple skin and mouth squamous cell carcinomas related to long-term treatment with hydroxyurea].	2001 Sep	11590345
[Polycythemia vera].	2002 Oct 15	12564173
Polycythemia vera in young patients: a study on the long-term risk of thrombosis, myelofibrosis and leukemia.	2003 Jan	12551821
Treatment of polycythemia vera and essential thrombocythemia: the role of pipobroman.	2003 Sep	14565648
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
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

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 `Sat Dec 16 05:00:55 GMT 2023` Edited by `admin` on `Sat Dec 16 05:00:55 GMT 2023`
Record UNII	6Q99RDT97R
Record Status	`Validated (UNII)`
Record Version

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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