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Substance Name: Chlorambucil [USP:INN:BAN]
RN: 305-03-3
UNII: 18D0SL7309
InChIKey: JCKYGMPEJWAADB-UHFFFAOYSA-N

Note

  • A nitrogen mustard alkylating agent used as antineoplastic for chronic lymphocytic leukemia, Hodgkin's disease, and others. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed).

Molecular Formula

  • C14-H19-Cl2-N-O2

Molecular Weight

  • 304.2151
 

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

  • Known to be a Carcinogen
  • Overall Carcinogenic Evaluation: Group 1
  • Reportable Quantity (RQ) = 10 lb

Names and Synonyms

Name of Substance

  • Chlorambucil
  • Chlorambucil [USP:INN:BAN]

MeSH Heading

  • Chlorambucil

Synonyms

  • 4-(Bis(2-chloroethyl)amino)benzenebutanoic acid
  • 4-(Bis(2-chloroethyl)amino)phenylbutyric acid
  • 4-(p-(Bis(2-chloroethyl)amino)phenyl)butyric acid
  • 4-14-00-01715 (Beilstein Handbook Reference)
  • AI3-26083
  • Ambochlorin
  • Amboclorin
  • Benzenebutanoic acid, 4-(bis(2-chloroethyl)amino)-
  • BRN 0999011
  • Butanoic acid, 4-(bis(2-chloroethyl)amino) benzene
  • Butyric acid, 4-(p-(bis(2-chloroethyl)amino)phenyl)
  • CB 1348
  • Cb l348
  • CCRIS 126
  • Chloorambucol
  • Chlorambucil
  • Chlorambucilum
  • Chlorambucilum [INN-Latin]
  • Chloraminophen
  • Chloraminophene
  • Chlorbutin
  • Chlorbutine
  • Chlorbutinum
  • Chloroambucil
  • Chlorobutin
  • Chlorobutine
  • Clorambucile
  • Clorambucile [DCIT]
  • Clorambucilo
  • Clorambucilo [INN-Spanish]
  • Ecloril
  • EINECS 206-162-0
  • Elcoril
  • Elcorin
  • gamma-(p-Bis(2-chloroethyl)aminophenyl)butyric acid
  • gamma-(p-bis(2-chloroethyl)aminophenyl)butyricacid
  • gamma-(p-Di(2-chloroethyl)aminophenyl)butyric acid
  • HSDB 3026
  • Kyselina 4-(N,N-bis-(2-chlorethyl)-p-aminofenyl)maselna
  • Kyselina 4-(N,N-bis-(2-chlorethyl)-p-aminofenyl)maselna [Czech]
  • Leukeran
  • Linfolizin
  • Linfolysin
  • Lympholysin
  • N,N-Di-2-chloroethyl-gamma-p-aminophenylbutyric acid
  • N,N-Di-2-chloroethyl-gamma-para-aminophenyl butyric acid
  • NCI-C03485
  • NSC 3088
  • NSC-3088
  • p-(N,N-Di-2-chlorethylaminophenyl)butyric acid
  • p-(N,N-Di-2-chloroethyl)aminophenyl butyric acid
  • p-N,N-Di-(beta-chloroethyl)aminophenyl butyric acid
  • para-(Di(2-chloroethyl)aminophenyl)butyric acid
  • para-N,N-Di(beta-chloroethyl)aminophenyl butyric acid
  • Phenylbuttersaeure-lost
  • Phenylbuttersaeure-lost [German]
  • Phenylbutyric acid nitrogen mustard
  • RCRA waste number U035
  • UNII-18D0SL7309

Systematic Names

  • Benzenebutanoic acid, 4-(bis(2-chloroethyl)amino)-
  • Butyric acid, 4-(p-bis(2-chloroethyl)aminophenyl)-
  • Chlorambucil

Superlist Names

  • Benzenebutanoic acid, 4-(bis(2-chloroethyl)amino)-
  • Chlorambucil
  • RCRA waste no. U035

Registry Numbers

CAS Registry Number

  • 305-03-3

FDA UNII

  • 18D0SL7309

System Generated Number

  • 0000305033

Structure Descriptors

InChI

InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)

InChIKey

JCKYGMPEJWAADB-UHFFFAOYSA-N

Smiles

OC(=O)CCCc1ccc(cc1)N(CCCl)CCCl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 3mg/kg (3mg/kg) BLOOD: OTHER CHANGES

GASTROINTESTINAL: OTHER CHANGES		 Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 201, 1965.
man TDLo oral 3571ug/kg (3.571mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 361, 1983.
monkey LDLo intravenous 3mg/kg (3mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: OTHER CHANGES		 Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 201, 1965.
mouse LD50 intraperitoneal 20mg/kg (20mg/kg)   British UK Patent Application. Vol. #2028335,
mouse LD50 oral 80mg/kg (80mg/kg)   British UK Patent Application. Vol. #2028335,
mouse LD50 subcutaneous 26mg/kg (26mg/kg)   British UK Patent Application. Vol. #2028335,
rat LD50 intracrebral > 400ug/kg (0.4mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 18, Pg. 760, 1966.
rat LD50 intraperitoneal 14mg/kg (14mg/kg)   Biochemical Pharmacology. Vol. 13, Pg. 969, 1964.
rat LD50 oral 76mg/kg (76mg/kg)   Food and Chemical Toxicology. Vol. 22, Pg. 665, 1984.
rat LDLo subcutaneous 32mg/kg (32mg/kg)   European Journal of Cancer. Vol. 13, Pg. 873, 1977.
women TDLo oral 82600ug/kg (82.6mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: COUGH

LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL)		 Cancer Vol. 41, Pg. 455, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 65 deg C   EXP
pKa Dissociation Constant 5.75 (none)   EXP
log P (octanol-water) 1.7 (none)   EXP
Water Solubility 1.24E+04 mg/L 25 EST
Vapor Pressure 9.30E-07 mm Hg 25 EST
Henry's Law Constant 2.71E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.90E-10 cm3/molecule-sec 25 EST

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