CHEBI:28830 - chlorambucil

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ChEBI Name chlorambucil
ChEBI ID CHEBI:28830
Definition A monocarboxylic acid that is butanoic acid substituted at position 4 by a 4-[bis(2-chloroethyl)amino]phenyl group. A chemotherapy drug that can be used in combination with the antibody obinutuzumab for the treatment of chronic lymphocytic leukemia.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:48770, CHEBI:3601, CHEBI:25817
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Formula C14H19Cl2NO2
Net Charge 0
Average Mass 304.21160
Monoisotopic Mass 303.079
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
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
alkylating agent
Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
(via nitrogen mustard )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
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ChEBI Ontology
Outgoing chlorambucil (CHEBI:28830) has role alkylating agent (CHEBI:22333)
chlorambucil (CHEBI:28830) has role antineoplastic agent (CHEBI:35610)
chlorambucil (CHEBI:28830) has role carcinogenic agent (CHEBI:50903)
chlorambucil (CHEBI:28830) has role immunosuppressive agent (CHEBI:35705)
chlorambucil (CHEBI:28830) is a aromatic amine (CHEBI:33860)
chlorambucil (CHEBI:28830) is a monocarboxylic acid (CHEBI:25384)
chlorambucil (CHEBI:28830) is a nitrogen mustard (CHEBI:37598)
chlorambucil (CHEBI:28830) is a organochlorine compound (CHEBI:36683)
chlorambucil (CHEBI:28830) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid
Synonyms Sources
4-(p-bis(β-chloroethyl)aminophenyl)butyric acid NIST Chemistry WebBook
4-[p-[bis(2-chloroethyl)amino]phenyl]butyric acid NIST Chemistry WebBook
Ambochlorin NIST Chemistry WebBook
CHLORAMBUCIL PDBeChem
Chlorambucil KEGG DRUG
chloraminophen ChemIDplus
γ-[p-di(2-chloroethyl)aminophenyl]butyric acid NIST Chemistry WebBook
Leukeran NIST Chemistry WebBook
N,N-di-2-chloroethyl-γ-p-aminophenylbutyric acid NIST Chemistry WebBook
phenylbutyric acid nitrogen mustard ChemIDplus
Manual Xrefs Databases
588 DrugCentral
CBL PDBeChem
Chlorambucil Wikipedia
D00266 KEGG DRUG
DB00291 DrugBank
LSM-2645 LINCS
View more database links
Registry Numbers Types Sources
305-03-3 CAS Registry Number NIST Chemistry WebBook
305-03-3 CAS Registry Number ChemIDplus
999011 Reaxys Registry Number Reaxys
999011 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
22025197 PubMed citation Europe PMC
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Last Modified
22 February 2017