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HomeProduct name listPipobroman

Pipobroman

  • CAS NO.:54-91-1
  • Empirical Formula: C10H16Br2N2O2
  • Molecular Weight: 356.05
  • MDL number: MFCD00866372
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-04 20:04:50
Pipobroman Structural

What is Pipobroman?

Absorption

Well absorbed from the GI tract.

Toxicity

Symptoms of overdose include hematologic toxicity, especially with chronic overdosage.

Originator

Vercyte ,Abbott ,US ,1966

The Uses of Pipobroman

diuretic, antihypertensive

Background

An antineoplastic agent that acts by alkylation.

Indications

For the treatment of polycythaemia vera and refractory chronic myeloid leukaemia.

Definition

ChEBI: Pipobroman is an N-acylpiperazine that is piperazine in which each of the nitrogens has been acylated by a 3-bromopropionoyl group. An anti-cancer drug. It has a role as an antineoplastic agent and an alkylating agent. It is a N-acylpiperazine, a tertiary carboxamide and an organobromine compound.

Manufacturing Process

To a solution of 17.2 g (0.10 mol) of 3-bromopropionyl chloride in 100 ml of anhydrous benzene was added dropwise with stirring a solution of 8.6 g (0.10 mol) of anhydrous piperazine in 20 ml of dry chloroform over a period of 30 minutes. The temperature rose spontaneously to 45°C during the addition. After the temperature ceased to rise, stirring was continued for another hour. The reaction mixture was then filtered to remove the piperazine hydrochloride by-product. The filtrate was evaporated to dryness and the residue recrystallized from ethanol to obtain the desired N,N'-bis-(3bromopropionyl)piperazine as a white crystalline solid melting at 103°C to 104°C. The identity of the product was further established by elemental analysis.

brand name

Vercyte (Abbott).

Therapeutic Function

Antineoplastic

Pharmacokinetics

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.

Safety Profile

Poison by ingestion,subcutaneous and intraperitoneal routes. An experimentalteratogen. Other experimental reproductive effects.Human mutation data reported. When heated todecomposition it emits very toxic fumes of Br- and NOx.

Metabolism

Not Available

Properties of Pipobroman

Melting point: 106-107℃
Boiling point: 487℃
Density  1.691
refractive index  1.6220 (estimate)
Flash point: 248℃
storage temp.  under inert gas (nitrogen or Argon) at 2-8°C
solubility  Chloroform (Slightly), Methanol (Slightly, Heated)
form  Solid
pka -0.56±0.70(Predicted)
color  Crystals from H2O
EPA Substance Registry System Pipobroman (54-91-1)

Safety information for Pipobroman

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H351:Carcinogenicity
H361:Reproductive toxicity
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Pipobroman

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