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Substance Name: Carmustine [USAN:USP:INN:BAN]
RN: 154-93-8
UNII: U68WG3173Y
InChIKey: DLGOEMSEDOSKAD-UHFFFAOYSA-N

Note

  • A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed)

Molecular Formula

  • C5-H9-Cl2-N3-O2

Molecular Weight

  • 214.0511
 

Classification Codes

Classification Codes

  • Alkylating Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2A
  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Name of Substance

  • Carmustine
  • Carmustine [USAN:USP:INN:BAN]

MeSH Heading

  • Carmustine

Synonyms

  • 1,3-Bis(2-chloroethyl)-1-nitrosourea
  • 1,3-Bis(2-chloroethyl)nitrosourea
  • 1,3-Bis(beta-chloroethyl)-1-nitrosourea
  • AI3-52216
  • BCNU
  • Becenum
  • Bi CNU
  • BiCNU
  • Bis(2-chloroethyl)1-nitrosourea
  • Bis(2-chloroethyl)nitrosourea
  • Bis-N,N'-(chloroethyl)nitrosourea
  • Bischlorethylnitrosourea
  • Bischlorethylnitrosurea
  • Bischloroethyl nitrosourea
  • Bischloroethylnitrosourea
  • BRN 2049744
  • Carmubris
  • Carmustin
  • Carmustina
  • Carmustina [INN-Spanish]
  • Carmustine
  • Carmustinum
  • Carmustinum [INN-Latin]
  • CCRIS 810
  • DTI 015
  • EINECS 205-838-2
  • FDA 0345
  • Gliadel
  • gliadel wafer
  • HSDB 7761
  • N,N'-Bis(2-chloroethyl)-N-nitrosourea
  • NCI-C04773
  • Nitrumon
  • NSC 409962
  • NSC-409962
  • SK 27702
  • SRI 1720
  • UNII-U68WG3173Y

Systematic Names

  • Carmustine
  • N,N'-Bis(2-chloroethyl)-N-nitrosourea
  • Urea, 1,3-bis(2-chloroethyl)-1-nitroso-
  • Urea, N,N'-bis(2-chloroethyl)-N-nitroso-

Superlist Names

  • BCNU
  • BCNU [Chloroethyl nitrosoureas]
  • Bischloroethyl nitrosourea
  • Bischloroethyl nitrosourea [Chloroethyl nitrosoureas]
  • Carmustine

Registry Numbers

CAS Registry Number

  • 154-93-8

FDA UNII

  • U68WG3173Y

Other Registry Numbers

  • 1159711-15-5
  • 1191292-23-5

System Generated Number

  • 0000154938

Structure Descriptors

InChI

1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)

InChIKey

DLGOEMSEDOSKAD-UHFFFAOYSA-N

Smiles

C(CCl)NC(=O)N(CCCl)N=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo intravenous 78mg/kg/52W-I (78mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Cancer Vol. 42, Pg. 74, 1978.
dog LDLo intravenous 2mg/kg (2mg/kg)   Cancer Chemotherapy Reports, Part 1. Vol. 57, Pg. 33, 1973.
dog LDLo oral 5mg/kg (5mg/kg)   Advances in Cancer Research. Vol. 16, Pg. 273, 1972.
hamster LD10 parenteral 18mg/kg (18mg/kg)   Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
human TDLo intravenous 6mg/kg (6mg/kg) BLOOD: THROMBOCYTOPENIA

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: LEUKOPENIA
Cancer Treatment Reports. Vol. 60, Pg. 709, 1976.
human TDLo intravenous 125mg/kg (125mg/kg) BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Advances in Cancer Research. Vol. 16, Pg. 273, 1972.
monkey LDLo intravenous 10mg/kg (10mg/kg) BLOOD: LEUKOPENIA

BLOOD: OTHER CHANGES

GASTROINTESTINAL: OTHER CHANGES
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 202, 1965.
mouse LD50 intramuscular 86300ug/kg (86.3mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 766, 1978.
mouse LD50 intramuscular 86300ug/kg (86.3mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: ATAXIA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 766, 1978.
mouse LD50 intraperitoneal 21260ug/kg (21.26mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 45mg/kg (45mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 118, Pg. 756, 1965.
mouse LD50 oral 19mg/kg (19mg/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.
mouse LD50 subcutaneous 24mg/kg (24mg/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.
mouse LD50 unreported 42mg/kg (42mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
rat LD50 intramuscular 79600ug/kg (79.6mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: ATAXIA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 766, 1978.
rat LD50 intraperitoneal 17420ug/kg (17.42mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat LD50 intravenous 13800ug/kg (13.8mg/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.
rat LD50 oral 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 166, Pg. 104, 1969.
rat LD50 subcutaneous 83200ug/kg (83.2mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 766, 1978.
rat LD50 subcutaneous 83200ug/kg (83.2mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: ATAXIA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 766, 1978.
women LDLo parenteral 1566mg/kg (1566mg/kg) LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
JAMA, Journal of the American Medical Association. Vol. 244, Pg. 687, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 31 deg C   EXP
log P (octanol-water) 1.53 (none)   EXP
Water Solubility 4000 mg/L 25 EXP
Vapor Pressure 3.69E-05 mm Hg 25 EST
Henry's Law Constant 4.76E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.63E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.