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305-03-3 molecular structure
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4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid

ChemBase ID: 176
Molecular Formular: C14H19Cl2NO2
Molecular Mass: 304.21216
Monoisotopic Mass: 303.07928421
SMILES and InChIs

SMILES:
ClCCN(c1ccc(CCCC(=O)O)cc1)CCCl
Canonical SMILES:
ClCCN(c1ccc(cc1)CCCC(=O)O)CCCl
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

Cite this record

CBID:176 http://www.chembase.cn/molecule-176.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid
IUPAC Traditional name
chlorambucil
Brand Name
Ambochlorin
Amboclorin
Ecloril
Elcoril
Leukeran
Leukeran Tablets
Leukersan
Leukoran
Linfolizin
Linfolysin
Pepstatin
Synonyms
Chloraminophen
Chloraminophene
Phenylbutyric Acid Nitrogen Mustard
Chlorobutine
Chlorobutin
Chloroambucil
Chlorbutine
Chlorbutin
Chlocambucil
4-(p-[bis-(2-Chloroethyl)-amino]-phenyl)-butyric acid
4-[Bis(2-chloroethyl)amino]benzenebutyric acid
4-(4-[Bis(2-chloroethyl)amino]phenyl)butyric acid
Chlorambucil
Chlorambucil
CAS Number
305-03-3
EC Number
206-162-0
MDL Number
MFCD00021783
Beilstein Number
999011
PubChem SID
46506842
160963639
24278287
24853850
PubChem CID
2708
CHEBI ID
28830
ATC CODE
L01AA02
CHEMBL
515
Chemspider ID
2607
DrugBank ID
DB00291
KEGG ID
D00266
Unique Ingredient Identifier
18D0SL7309
Wikipedia Title
Chlorambucil
Medline Plus
a682899

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.4555492  H Acceptors
H Donor LogD (pH = 5.5) 2.8512278 
LogD (pH = 7.4) 1.0883248  Log P 3.937155 
Molar Refractivity 79.6828 cm3 Polarizability 30.39351 Å3
Polar Surface Area 40.54 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.81  LOG S -3.59 
Solubility (Water) 7.73e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1.24E+004 mg/L expand Show data source
Melting Point
64-66°C expand Show data source
65-70 °C expand Show data source
Vapor Pressure
5.7 x 10-8 mm Hg at 25 °C expand Show data source
Hydrophobicity(logP)
3.9 expand Show data source
Storage Condition
2-8°C expand Show data source
RTECS
ES7525000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
45-25-36/37/38 expand Show data source
R:25-45 expand Show data source
Safety Statements
53-26-45 expand Show data source
S:28-36/37/39-45-53 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H315-H319-H335-H350 expand Show data source
GHS Precautionary statements
P201-P261-P301 + P310-P305 + P351 + P338-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Oral expand Show data source
Excretion
N/A expand Show data source
Half Life
1.5 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
D (US) expand Show data source
Gene Information
human ... CYP2D6(1565) expand Show data source
Purity
≥98.0% (T) expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C14H19Cl2NO2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals Wikipedia Wikipedia
DrugBank - DB00291 external link
Item Information
Drug Groups approved
Description A nitrogen mustard alkylating agent used as antineoplastic agent for the treatment of various malignant and nonmalignant diseases. 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)
Indication For treatment of chronic lymphatic (lymphocytic) leukemia, childhood minimal-change nephrotic syndrome, and malignant lymphomas including lymphosarcoma, giant follicular lymphoma, Hodgkin's disease, non-Hodgkin's lymphomas, and Waldenstr?m’s Macroglobulinemia.
Pharmacology Chlorambucil is an antineoplastic in the class of alkylating agents that is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.
Affected Organisms
Humans and other mammals
Half Life 1.5 hours
Protein Binding 99%
Elimination Chlorambucil is extensively metabolized in the liver primarily to phenylacetic acid mustard. The pharmacokinetic data suggests that oral chlorambucil undergoes rapid gastrointestinal absorption and plasma clearance and that it is almost completely metabolized, having extremely low urinary excretion.
References
Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7. [Pubmed]
Yang K, Tan J, Wu T: Alkylating agents for Waldenstrom's macroglobulinaemia. Cochrane Database Syst Rev. 2009 Jan 21;(1):CD006719. [Pubmed]
Foon KA, Hallek MJ: Changing paradigms in the treatment of chronic lymphocytic leukemia. Leukemia. 2010 Mar;24(3):500-11. Epub 2009 Dec 24. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - C0253 external link
Biochem/physiol Actions
Chlorambucil is an anti-cancer drug that alkylates DNA and induces apoptosis. Death of chronic lymphocytic leukemia cells occurs via a p53-dependent mechanism.
Sigma Aldrich - 23125 external link
Other Notes
Alkylating antitumor agent, can be covalently coupled to monoclonal anticarcinoembryonic antigen1
MP Biomedicals - 02101346 external link
Alkylating antitumor agent.
Can be covalently coupled to monoclonal anticarcinombryonic antigen.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7. Pubmed
  • • Yang K, Tan J, Wu T: Alkylating agents for Waldenstrom's macroglobulinaemia. Cochrane Database Syst Rev. 2009 Jan 21;(1):CD006719. Pubmed
  • • Foon KA, Hallek MJ: Changing paradigms in the treatment of chronic lymphocytic leukemia. Leukemia. 2010 Mar;24(3):500-11. Epub 2009 Dec 24. Pubmed
  • • Bernier, L.G., et al., Protides Biol. Fluids , 31 : 787 (1983).
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PATENTS

PATENTS

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