chlorambucil (CHEBI:28830)

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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

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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38 38 0 0 0 0 999 V2000

0.2645 0.5821 -1.2768 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0931 1.3449 -0.1443 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4194 -0.5457 0.6762 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2118 -0.7252 -1.4353 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9387 0.7678 0.8321 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0609 -1.2971 -0.4652 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4799 2.7013 0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8630 2.6086 0.7101 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5771 3.9749 0.8494 C 0 0 0 0 0 0 0 0 0 0 0 0

4.8957 4.1896 0.9752 O 0 0 0 0 0 0 0 0 0 0 0 0

3.8515 3.8797 1.5296 C 0 0 0 0 0 0 0 0 0 0 0 0

3.9096 3.4792 2.6871 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.5074 -2.5371 -0.6747 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.6587 -3.6260 -0.3334 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2188 -3.5602 0.9508 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4507 -4.8186 1.0051 Cl 0 0 0 0 0 0 0 0 0 0 0 0

-2.6305 -2.6975 -1.5337 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.7964 -1.6658 -1.4983 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.8948 -1.8210 -2.8668 Cl 0 0 0 0 0 0 0 0 0 0 0 0

0.8836 0.9616 -1.9970 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0274 -0.9485 1.3949 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0667 -1.2559 -2.2645 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2025 1.2943 1.6694 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5846 3.1855 -0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1907 3.3413 0.5971 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5131 1.9353 0.1408 H 0 0 0 0 0 0 0 0 0 0 0 0

1.7227 2.1670 1.7023 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7105 4.3975 -0.1513 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9384 4.6647 1.4066 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6805 3.4057 3.1046 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0195 -3.7546 -1.1828 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2279 -4.5569 -0.2604 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4028 -3.6596 1.8417 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7632 -2.6169 1.0204 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2293 -2.6964 -2.5522 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0927 -3.6785 -1.3945 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4304 -0.6383 -1.5385 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3786 -1.7814 -0.5830 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 4 0 0 0 0

2 7 1 0 0 0 0

1 4 4 0 0 0 0

5 3 4 0 0 0 0

5 2 4 0 0 0 0

6 3 4 0 0 0 0

4 6 4 0 0 0 0

6 13 1 0 0 0 0

7 8 1 0 0 0 0

8 9 1 0 0 0 0

9 11 1 0 0 0 0

11 10 2 0 0 0 0

11 12 1 0 0 0 0

13 17 1 0 0 0 0

13 14 1 0 0 0 0

14 15 1 0 0 0 0

15 16 1 0 0 0 0

17 18 1 0 0 0 0

18 19 1 0 0 0 0

1 20 1 0 0 0 0

3 21 1 0 0 0 0

4 22 1 0 0 0 0

5 23 1 0 0 0 0

7 24 1 0 0 0 0

7 25 1 0 0 0 0

8 26 1 0 0 0 0

8 27 1 0 0 0 0

9 28 1 0 0 0 0

9 29 1 0 0 0 0

12 30 1 0 0 0 0

14 31 1 0 0 0 0

14 32 1 0 0 0 0

15 33 1 0 0 0 0

15 34 1 0 0 0 0

17 35 1 0 0 0 0

17 36 1 0 0 0 0

18 37 1 0 0 0 0

18 38 1 0 0 0 0

M END): 15 ms

reading 38 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

38 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Wikipedia	License
Chlorambucil, sold under the brand name Leukeran among others, is a chemotherapy medication used to treat chronic lymphocytic leukemia (CLL), Hodgkin lymphoma, and non-Hodgkin lymphoma. For CLL it is a preferred treatment. It is given by mouth. Common side effects include bone marrow suppression. Other serious side effects include an increased long term risk of further cancer, infertility, and allergic reactions. Use during pregnancy often results in harm to the baby. Chlorambucil is in the alkylating agent family of medications. It works by blocking the formation of DNA and RNA. Chlorambucil was approved for medical use in the United States in 1957. It is on the World Health Organization's List of Essential Medicines. It was originally made from nitrogen mustard.
Read full article at Wikipedia

Formula

C14H19Cl2NO2

Net Charge

Average Mass

304.21160

Monoisotopic Mass

303.07928

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):	drug allergen Any drug which causes the onset of an allergic reaction. 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):	drug allergen Any drug which causes the onset of an allergic reaction. 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.

View more via ChEBI Ontology

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 drug allergen (CHEBI:88188) 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

Citations

Last Modified

07 March 2019

CHEBI:28830 - chlorambucil

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