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Pipobroman

HCID 4842
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
54-91-1
Standard-SMILES
O=C(CCBr)N1CCN(C(=O)CCBr)CC1
InChIKey
NJBFOOCLYDNZJN-UHFFFAOYSA-N
Summenformel
C10H16Br2N2O2
Durchschnittliche Molmasse
356,05 g/mol
Monoisotopische Masse
353,95785

Überblick

Pipobroman can cause developmental toxicity according to state or federal government labeling requirements.

Namen und Bezeichner

Bevorzugter Name
Pipobroman
IUPAC
3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-one
Englischer Name
Pipobroman
Summenformel
C10H16Br2N2O2
Molmasse
356.05

Namen und Synonyme

pipobroman54-91-1VercyteAmedel1,4-Bis(3-bromopropionyl)piperazinePipobromanumA-8103NSC-25154Piperazine, 1,4-bis(3-bromo-1-oxopropyl)-3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-oneN,N-Bis-(3-bromopropionyl)-piperazineNSC25154
Weitere Namen anzeigen
Pipobroman, 10 mM in DMSO1,4-Bis(3-bromo-1-oxopropyl)piperadine1,4-Bis(3-bromo-1-oxopropyl)piperazine1,1'-(1,4-Piperazinediyl)bis[3-bromo]-1-propanone
A 1803DTXSID7023485Piperazine, 1,4-bis(3-bromopropionyl)-6Q99RDT97RCHEBI:8242DTXCID5034853-bromo-1-(4-(3-bromopropanoyl)piperazin-1-yl)propan-1-oneRefChem:57594

Datenbank-Bezeichner

CAS
54-91-1
PubChem CID
4842
DTXSID
DTXSID7023485
ChEMBL
CHEMBL1585
ChEBI
CHEBI:8242

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,4
Polarare Oberfläche (TPSA)
40,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
16
Formalladung
0
Komplexität
227

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 Einträge

1.1

0.42

OdorSLIGHTLY SHARP, FRUITY ODOR
TasteSLIGHT BITTER TASTE
Color/Form · 2 Einträge

CRYSTALS

WHITE OR PRACTICALLY WHITE, CRYSTALLINE POWDER

Solubility · 2 Einträge

FREELY SOL IN CHLOROFORM; SOL IN METHANOL & ACETONE; SPARINGLY SOL IN ALC & BENZENE; SLIGHTLY SOL IN WATER; VERY SLIGHTLY SOL IN ETHER

2.24e+00 g/L

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 3 Einträge

> 300 °C

106-107 °C

> 300 °C

Physical DescriptionSolid

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationHazard Traits - Developmental Toxicity

Sicherheit und Schutzausrüstung

Cleanup Methods · 2 Einträge

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Spill kits containing all materials needed to clean up spills of hazardous drugs should be assembled or purchased. These kits should be readily available in all areas where hazardous drugs are routinely handled. If hazardous drugs are being prepared or administered in a nonroutine area (home setting or unusual patient-care area), a spill kit should be obtained by the drug handler. The kit should include two pairs of disposable gloves (one outer pair of utility gloves and one inner latex pair); low-permeability, disposable protective garments (coveralls or gown and shoe covers); safety glasses or splash goggles; respirator; absorbent, plastic-backed sheets or spill pads; disposable toweling; at least 2 sealable thick plastic hazardous waste disposal bags (prelabeled with an appropriate warning label); a disposable scoop for collecting glass fragments; and a puncture-resistant container for glass fragments. All individuals who routinely handle hazardous drugs must be trained in proper spill management and cleanup procedures. Spills and breakages must be cleaned up immediately according to the following procedures. If the spill is not located in a confined space, the spill area should be identified and other people should be prevented from approaching and spreading the contamination. Wearing protective apparel from the spill kit, workers should remove any broken glass fragments and place them in the puncture-resistant container. Liquids should be absorbed with a spill pad; powder should be removed with damp disposable gauze pads or soft toweling. The hazardous material should be completely removed and the area rinsed with water and then cleaned with detergent. The spill cleanup should proceed progressively from areas of lesser to greater contamination. The detergent should be thoroughly rinsed and removed. All contaminated materials should be placed in the disposal bags provided and sealed and transported to a designated containment receptacle. Spills occurring in the biohazard cabinet should be cleaned up immediately; a spill kit should be used if the volume exceeds 150 ml or the contents of one drug vial or ampule. If there is broken glass, utility gloves should be worn to remove it and place it in the puncture-resistant container located in the biohazard cabinet. The biological safety cabinet, including the drain spillage trough, should be thoroughly cleaned. If the spill is not easily and thoroughly contained, the biological safety cabinet should be decontaminated after cleanup. If the spill contaminates the high efficiency particulate air filter, use of the biological safety cabinet should be suspended until the cabinet has been decontaminated and the high efficiency particulate air filter replaced. /Antineoplastic agents/

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Pharmacodynamics · 1 Eintrag

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.

Mechanism of Action · 2 Einträge

The mechanism of action is uncertain, but due to the structural similarity with other DNA alkylating agents, pipobroman is thought to alkylate DNA leading to disruption of DNA synthesis and eventual cell death.

Pipobroman has been classified as a polyfunctional alkylating agent, but its precise mechanism of action is not known.

MeSH Pharmacological Classification · 1 Eintrag

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026)

Absorption, Distribution and Excretion · 2 Einträge

Well absorbed from the GI tract.

The drug is well absorbed following oral administration. Studies of its distribution and fate in man have not been reported.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses

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Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
UNII
6Q99RDT97R
EC Number
620-535-9
Nikkaji
J4.157B
Stability/Shelf Life
STABLE IN LIGHT & AIR
Collision Cross Section160.25 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
106 · 106-107℃
Siedepunkt
487 ℃ · 487℃
Dichte
1.691 · 1.691
Brechungsindex
1.622 · 1.6220 (estimate)
Flammpunkt
248 ℃ · 248℃
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly, Heated)
Aggregatzustand
Solid
pka
-0.56 · -0.56±0.70(Predicted)
Farbe
2 O · Crystals from H2O
InChI
1S/C10H16Br2N2O2/c11-3-1-9(15)13-5-7-14(8-6-13)10(16)2-4-12/h1-8H2
InChIKey
NJBFOOCLYDNZJN-UHFFFAOYSA-N
SMILES
BrCCC(=O)N1CCN(CC1)C(=O)CCBr
EPA chemische Informationen
Pipobroman (54-91-1)

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ If hazardous drugs are routinely prepared or administered in carpeted areas, special equipment is necessary to remove the spill. Absorbent powder should be substituted for pads or sheets and left in place on the spill for the time recommended by the manufacturer. The powder should then be picked up with a small vacuum unit reserved for hazardous drug cleanup. The carpet should then be cleaned according to usual procedures. The vacuum bag should be removed and discarded or cleaned, and the exterior of the vacuum cleaner should be washed with detergent and rinsed before being covered and stored. The contaminated powder should be discarded into a sealable plastic bag and segregated with other contaminated waste materials. Alternatively, inexpensive wet or dry vacuum units may be purchased for this express use and used with appropriate cleaners. All such units are contaminated, once used, and must be cleaned, stored, and ultimately discarded /properly/ ... The circumstances and handling of spills should be documented. Health-care personnel exposed during spill management should also complete an incident report or exposure form. /Antineoplastic agents/

Disposal Methods · 5 Einträge

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ All contaminated disposables should be contained in sealable bags for transfer to larger waste containers. /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ All bottles must be discarded as contaminated waste after decontamination of the biohazard cabinet. All protective apparel (gown, gloves, goggles, and respirator) should be discarded as contaminated waste. /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The contaminated filters must be removed, bagged in thick plastic and prepared for disposal in a hazardous waste dump site or incinerator licensed by the Environmental Protection Agency (EPA). /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The gown should be removed and placed in a sealable container before removal of the inner gloves. The inner gloves should be removed last and placed in the container with the gown. /Antineoplastic agents/

For more Disposal Methods (Complete) data for PIPOBROMAN (7 total), please visit the HSDB record page.

Preventive Measures · 5 Einträge

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Accidental contamination of the health-care environment, resulting in exposure of personnel, patients, visitors, and family members to hazardous substances, is prevented by maintaining the physical integrity and security of packages of hazardous drugs. 1. Access to all areas where hazardous drugs are stored is limited to specified authorized staff. 2. A method should be present for identifying to personnel those drugs that require special precautions (eg, cytotoxics). One way to accomplish this is to apply appropriate warning labels to all hazardous drug containers, shelves, and bins where the drug products are stored. ... 3. A method of identifying, for patients and family members, those drugs that require special precautions in the home should be in place. This may be accomplished in the health-care setting, by providing specific labeling for discharge medications, along with written instructions. 4. Methods for identifying shipping cartons of hazardous drugs should be required from manufacturers and distributors of these drugs. 5. Written procedures for handling damaged packages of hazardous drugs should be maintained. Personnel involved in shipping and receiving hazardous drugs should be trained in these procedures, including the proper use of protective garments and equipment. Damaged shipping cartons of hazardous drugs should be received and opened in an isolated area (eg, in a laboratory fume hood, if available, not in a vertical laminar airflow biological safety cabinet used for preparing sterile products). /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Facilities (eg, shelves, carts, counters, and trays) for storing hazardous drugs are designed to prevent breakage and to limit contamination in the event of leakage. Bins, shelves with barriers at the front, or other design features that reduce the chance of drug containers falling to the floor should be used. Hazardous drugs requiring refrigeration should be stored separately from nonhazardous drugs in individual bins designed to prevent breakage and to contain leakage. /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Until the reproductive risks (or lack thereof) associated with handling hazardous drugs within a safety program have been substantiated, staff who are pregnant or breast-feeding should be allowed to avoid contact with these drugs. Policies should be in effect that provide these individuals with alternative tasks or responsibilities if they so desire. /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The pharmacy should provide access to information on toxicity, treatment of acute exposure (if available), chemical inactivators, solubility and stability of hazardous drugs (including investigational agents) used in the workplace. /Antineoplastic agents/

For more Preventive Measures (Complete) data for PIPOBROMAN (19 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 5 Einträge

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Protective apparel: Disposable closed-front gown or coveralls, disposable utility gloves over disposable latex gloves, NIOSH-approved air-purifying half-mask respirator equipped with a high efficiency filter, and eye protection should be worn. /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Class 100 clean-air work stations, both horizontal and vertical airflow (with no containment characteristics), are inappropriate engineering controls for handling hazardous drugs because they provide no personnel protection and permit environmental contamination. Although there are no engineering controls designed specifically for the safe handling of hazardous chemicals as sterile products, Class II contained vertical-flow biological safety cabinets (biohazard cabinets) have been adopted for this use. Biohazard cabinetry is, however, designed for the handling of infectious agents, not hazardous chemicals. ... Based on design, ease of use, and cost considerations, Class II contained-vertical-flow biohazard cabinetry is currently recommended for use in preparing sterile doses of hazardous drugs. Class II cabinetry design and performance specifications are defined in NSF Standard 49. Biological safety cabinets selected for use with hazardous drugs should meet NSF Standard 49 specifications to ensure the maximum protection from these engineering controls. /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Workers should wear powder free, disposable surgical latex gloves of good quality when preparing hazardous drugs. Selection criteria for gloves should include thickness (especially at the fingertips where stress is the greatest), fit, length, and tactile sensation. ... The practice of double gloving is supported by research that indicates that many glove materials vary in drug permeability even within lots; therefore, double gloving is recommended. ... In general, surgical latex gloves fit better, have appropriate elasticity for double gloving and maintaining the integrity of the glove-gown interface, and have sufficient tactile sensation (even during double gloving) for stringent aseptic procedures. ... Powdered gloves should be avoided. /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Workers who are not protected by the containment environment of a biohazard cabinet should use respiratory protection when handling hazardous drugs. Respiratory protection should be an adjunct to and not a substitute for engineering controls. Surgical masks of all types provide no respiratory protection against powdered or liquid aerosols of hazardous drugs. In situations where workers may be exposed to potential eye contact with hazardous drugs, an appropriate plastic face shield or splash goggles should be worn. /Antineoplastic agents/

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ During compounding of hazardous drugs (eg, crushing, dissolving, and preparing an ointment), workers should wear low permeability gowns and double gloves. Compounding should take place in a protective area such as a disposable glove box. If compounding must be done in the open, an area away from drafts and traffic must be selected, and the worker should use appropriate respiratory protection. /Antineoplastic agents/

Toxikologische Informationen

Medical Surveillance · 1 Eintrag

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ There is no method available for routine monitoring of personnel for evidence of hazardous drug exposure. Tests for the presence of mutagens or chromosomal damage are not drug specific and are of value only in controlled studies. Chemical analysis of urine for the presence of hazardous drugs at the sensitivity level needed to detect occupational exposure is limited to a few drugs and is not yet commercially available. /Antineoplastic agents/

Human Toxicity Excerpts · 4 Einträge

ADVERSE EFFECTS INCL SEVERE ANEMIA, IN PART OF HEMOLYTIC NATURE, & RETICULOCYTOSIS. LEUKOPENIA & THROMBOCYTOPENIA, OF COURSE, ARE RESULT OF INTENDED ACTION OF DRUG, BUT LEUKOCYTE COUNT SHOULD BE KEPT ABOVE 3000/CU MM & PLATELET COUNT ABOVE 100,000/CU MM.

ADVERSE GI REACTIONS (TRANSIENT NAUSEA, VOMITING, ABDOMINAL CRAMPS, & DIARRHEA) HAVE BEEN REPORTED INFREQUENTLY. RASH HAS BEEN OBSERVED IN A FEW PATIENTS.

Pipobroman is a highly toxic drug with a low therapeutic index, and a therapeutic response is not likely to occur without some evidence of toxicity. The drug must be used only under constant supervision by physicians experienced in therapy with cytotoxic agents.

Pipobroman's principal toxic effect is bone marrow depression resulting in leukopenia, thrombocytopenia, and anemia manifested by a reduction in hemoglobin of at least 2 g/dl. Depression of the bone marrow may not occur for 4 weeks or more after treatment is initiated. Usually, the temporary discontinuance of therapy with the drug has been effective in controlling toxicity; however, persistent cytopenia has been reported. Anemia may occur with total pipobroman dosage as low as 30 mg/kg and may be more severe at higher dosage. In most instances, leukopenia accompanies the anemia. Anemia usually has responded to dosage reduction and to blood transfusions in amounts sufficient to produce a hemoglobin level of at least 10 g/dl. A hemolytic process suggested by a rapid drop in hemoglobin, increased bilirubin concentrations, and reticulocytosis has been observed in several patients. If evidence of this hemolytic process develops, pipobroman therapy should be discontinued.

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Pipobroman

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity ExcerptsAnti-neoplastic agent was injected into pregnant mice. At doses of 30 mg/kg given on days 11 through 14 of gestation brachygnathia and small noses occurred.
Probable Routes of Human Exposure · 1 Eintrag

/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The danger to health-care personnel from handling a hazardous drug stems from a combination of its inherent toxicity and the extent to which workers are exposed to the drug in the course of carrying out their duties. This exposure may be through inadvertent ingestion of the drug on foodstuffs (eg, workers' lunches), inhalation of drug dusts or droplets or direct skin contact. /Antineoplastic agents/

Sicherheitsdaten

wgk
WGK 3
Toxizität
LD50 orl-rat: 220 mg/kg IYKEDH 4,467,73
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
54-91-1(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 Oral
MEDICATION
Methods of Manufacturing · 2 Einträge

STRUCTURE-CYTOSTATIC EFFECT STUDIES.

PIPERAZINE, IN DRY CHLOROFORM SOLN, IS DOUBLY CONDENSED WITH 3-BROMOPROPIONYL CHLORIDE USING EXCESS OF PIPERAZINE TO ENCOURAGE DEHYDROCHLORINATION. CRUDE PRODUCT IS CRYSTALLIZED FROM ISOPROPYL ALCOHOL.

Formulations/PreparationsDOSAGE FORMS--TABLETS NF: 10 & 25 MG.

Anwendungen

Verwendendiuretic, antihypertensive

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Piperazin3-Brompropionylchlorid

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