EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

carmustine
BCNU

Supplier Sponsors

Name:1,3-bis(2-chloroethyl)-1-nitrosourea
CAS Number: 154-93-8Picture of molecule3D/inchi
Other(deleted CASRN):1159711-15-5
ECHA EINECS - REACH Pre-Reg:205-838-2
FDA UNII: U68WG3173Y
Nikkaji Web:J2.968H
Beilstein Number:2049744
MDL:MFCD00057706
XlogP3:1.50 (est)
Molecular Weight:214.05013000
Formula:C5 H9 Cl2 N3 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:orange-yellow solid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 4000 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Carmustine >98%
Odor: characteristic
Use: Carmustine is antineoplastic nitrosourea. Carmustine alkylates and cross-links DNA during all phases of the cell cycle, resulting in disruption of DNA function, cell cycle arrest, and apoptosis. This agent also carbamoylates proteins, including DNA
Sigma-Aldrich: Sigma
For experimental / research use only.
Carmustine ≥98%
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-child LDLo 78 mg/kg/52W-I
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Cancer Vol. 42, Pg. 74, 1978.

intravenous-dog LDLo 2 mg/kg
Cancer Chemotherapy Reports, Part 1. Vol. 57, Pg. 33, 1973.

oral-dog LDLo 5 mg/kg
Advances in Cancer Research. Vol. 16, Pg. 273, 1972.

parenteral-hamster LD10 18 mg/kg
Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.

intravenous-human TDLo 6 mg/kg
BLOOD: THROMBOCYTOPENIA GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: LEUKOPENIA
Cancer Treatment Reports. Vol. 60, Pg. 709, 1976.

intravenous-human TDLo 125 mg/kg
BLOOD: LEUKOPENIA BLOOD: THROMBOCYTOPENIA GASTROINTESTINAL: NAUSEA OR VOMITING
Advances in Cancer Research. Vol. 16, Pg. 273, 1972.

intramuscular-mouse LD50 86300 ug/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: ATAXIA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 766, 1978.

intraperitoneal-mouse LD50 21260 ug/kg
National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986

intravenous-mouse LD50 45 mg/kg
Proceedings of the Society for Experimental Biology and Medicine. Vol. 118, Pg. 756, 1965.

oral-mouse LD50 19 mg/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Toxicology and Applied Pharmacology. Vol. 21, Pg. 405, 1972.

unreported-mouse LD50 42 mg/kg
Cancer Research. Vol. 46, Pg. 2703, 1986.

intramuscular-rat LD50 79600 ug/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: ATAXIA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 766, 1978.

intraperitoneal-rat LD50 17420 ug/kg
National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986

intravenous-rat LD50 13800 ug/kg
LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Oncology. Vol. 37, Pg. 177, 1980.

oral-rat LD50 20 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 166, Pg. 104, 1969.

Dermal Toxicity:
subcutaneous-mouse LD50 24 mg/kg
KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Toxicology and Applied Pharmacology. Vol. 21, Pg. 405, 1972.

subcutaneous-rat LD50 83200 ug/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: ATAXIA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 766, 1978.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for carmustine usage levels up to:
 not for fragrance use.
 
Recommendation for carmustine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :2578
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1,3-bis(2-chloroethyl)-1-nitrosourea
Chemidplus:0000154938
EPA/NOAA CAMEO:hazardous materials
RTECS:YS2625000 for cas# 154-93-8
 
References:
 1,3-bis(2-chloroethyl)-1-nitrosourea
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:154-93-8
Pubchem (cid):2578
Pubchem (cas):154-93-8
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C06873
HMDB (The Human Metabolome Database):HMDB14407
FooDB:FDB012974
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 clam
Search PMC Picture
 
Synonyms:
 BCNU
 carmubris
bischloroethyl nitrosourea
1,3-bis(2-chloroethyl)-1-nitrosourea
N,N'-bis(2-chloroethyl)-N-nitrosourea
bis-N,N'-(chloroethyl)nitrosourea
 

Articles:

PubMed:Developing Therapies for Brain Tumors: The Impact of the Johns Hopkins Hunterian Neurosurgical Research Laboratory.
PubMed:Gliadel wafer implantation combined with standard radiotherapy and concurrent followed by adjuvant temozolomide for treatment of newly diagnosed high-grade glioma: a systematic literature review.
PubMed:Mechlorethamine gel for the topical treatment of stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma.
PubMed:Modeling mass transfer from carmustine-loaded polymeric implants for malignant gliomas.
PubMed:Impact of United States Food and Drug Administration's boxed warnings on adverse drug reactions reporting rates and risk mitigation for multiple myeloma drugs.
PubMed:Growth pattern of tumor recurrence following bis-chloroethylnitrosourea (BCNU) wafer implantation in malignant glioma.
PubMed:Establishing the standard of care for patients with newly diagnosed and recurrent glioblastoma.
PubMed:The chemopreventive effect of dimethylthiourea against carmustine-induced myelotoxicity in rats.
PubMed:Controversies in the adjuvant therapy of high-grade gliomas.
PubMed:Space-occupying cyst development in the resection cavity of malignant gliomas following Gliadel® implantation--incidence, therapeutic strategies, and outcome.
PubMed:Protective effect of N-acetylcysteine against carmustine-induced myelotoxicity in rats.
PubMed:Extended O6-methylguanine methyltransferase promoter hypermethylation following n-butylidenephthalide combined with 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) on inhibition of human hepatocellular carcinoma cell growth.
PubMed:Protective mechanism of quercetin and rutin using glutathione metabolism on HO-induced oxidative stress in HepG2 cells.
PubMed:Interstitial chemotherapy with biodegradable BCNU (Gliadel) wafers in the treatment of malignant gliomas.
PubMed:Myeloid clonogenic assays for comparison of the in vitro toxicity of alkylating agents.
PubMed:Recurrent malignant glioma in adults.
PubMed:Dacarbazine-based chemotherapy for metastatic melanoma: thirty-year experience overview.
PubMed:Cardiotoxicity of chemotherapeutic agents: incidence, treatment and prevention.
PubMed:In vivo enhanced antitumor activity of carmustine [N,N'-bis(2-chloroethyl)-N-nitrosourea] by simvastatin.
PubMed:Comparative study on the influence of two 2-chloroethylnitrosoureas with different carbamoylating potential towards glutathione and glutathione-related enzymes in different organs of the rat.
PubMed:Influence of glutathione on the mutagenicity of 2-chloroethylnitrosoureas. Mutagenic potential of glutathione derivatives formed from 2-chloroethylnitrosoureas and glutathione.
PubMed:A method to determine the carbamoylating potential of 1-(2-chloroethyl)-1-nitrosoureas.
PubMed:Carcinogenic N-nitroso compounds and their environmental significance.
PubMed:Solid tumor chemotherapy: new drugs and horizons.
 
Notes:
Isol. from the common clam Mercenaria mercenaria and from Mercenaria campechiensis Carmustine is one of the nitrosoureas indicated as palliative therapy as a single agent or in established combination therapy with other approved chemotherapeutic agents in treatment of brain tumors, multiple myeloma, Hodgkin's disease, and non-Hodgkin's lymphomas. Although it is generally agreed that carmustine alkylates DNA and RNA, it is not cross resistant with other alkylators. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins.
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