CHLORAMBUCIL

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC L01AA02
UNII 18D0SL7309
EPA CompTox DTXSID7020263

Structure

InChI Key JCKYGMPEJWAADB-UHFFFAOYSA-N
Smiles O=C(O)CCCc1ccc(N(CCCl)CCCl)cc1
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H19Cl2NO2
Molecular Weight 304.22
AlogP 3.38
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 9.0
Polar Surface Area 40.54
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 19.0

Pharmacology

Mechanism of Action Action Reference
DNA inhibitor INHIBITOR ISBN
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 65100 - - -
Enzyme Oxidoreductase
- - - - 44
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- - - - 23
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 80700 - 37400 66-103
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibitory activity of compound for AA8 cells to reduce cell density by 50% (exposed to compound for 4 hours) Cricetulus griseus 36.0 nM
Inhibition of chymotrypsin at 250 uM unidentified 23.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM None 44.0 %
In vitro cytotoxicity against transformed chinese hamster fibroblast line UV4. Cricetulus griseus 600.0 nM
In vivo antitumor activity against murine S-180 sarcoma at a dose of 1.3 mg/kg administered intraperitoneally 7qd in mice expressed as percent inhibition Mus musculus 37.1 %
In vivo antitumor activity against murine S-180 sarcoma at a dose of 2.5 mg/kg administered intraperitoneally 7qd in mice expressed as percent inhibition Mus musculus 52.94 %
In vivo antitumor activity against murine S-180 sarcoma at a dose of 5 mg/kg administered intraperitoneally 7qd in mice expressed as percent inhibition Mus musculus 73.3 %
In vivo antitumor activity against murine S-180 sarcoma at a dose of 6.8 mg/kg administered intraperitoneally 7qd in mice expressed as percent inhibition Mus musculus 77.38 %
Growth inhibition in mouse L929 cells after 48 hrs Mus musculus 30.0 %
Cytotoxicity against human MDA-MB-468 cells expressing estrogen receptor after 5 days by MTT assay Homo sapiens 650.0 nM
Cytotoxicity against human MDA-MB-468 cells transfected with NAD(P)H: quinone oxidoreductase NQO1 after 5 days by MTT assay Homo sapiens 790.0 nM
Cytotoxicity against human IMR32 cells after 72 hrs by MTT assay Homo sapiens 20.09 ug.mL-1
Cytotoxicity against human U87 cells after 72 hrs by MTT assay Homo sapiens 18.82 ug.mL-1
Cytotoxicity against human A549 cells after 72 hrs by MTT assay Homo sapiens 21.09 ug.mL-1
Cytotoxicity against human COLO205 cells after 72 hrs by MTT assay Homo sapiens 26.67 ug.mL-1
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 123.94 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 102.73 %
Induction of DNA damage in human A549 cells assessed as inhibition of EGFP translation at 50 uM after 1 hr by fluorescence assay Homo sapiens 45.0 %
Inhibition of human OATP1B3-mediated [3H]CCK-8 at 100 uM after 5 mins relative to control Homo sapiens 66.0 %
Cytotoxicity against human MDA-MB-231 cells assessed as cell viability after 5 days by cell viability analyzer Homo sapiens 520.0 nM
Cytotoxicity against human HeLa cells assessed as cell viability after 5 days by cell viability analyzer Homo sapiens 943.0 nM
Cytotoxicity against human MCF7 cells assessed as cell viability after 5 days by cell viability analyzer Homo sapiens 26.4 nM
Cytotoxicity against human A549 cells assessed as cell viability after 5 days by cell viability analyzer Homo sapiens 85.7 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 7.69 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 8.33 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 9.18 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 5.1 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 17.67 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.65 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 0.85 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 5.43 %
Antiangiogenic activity in chicken fertilized egg chorioallantoic membrane assessed as avascular zone by measuring reduction in number of branching points at 20 ug/kg/day, iv administered as bolus dose on embryo development day 11 for 3 days by epifluorescence microscopic analysis relative to control Gallus gallus 33.0 %
Antiproliferative activity against embryonic stem cells in intact mouse embryoid bodies Mus musculus 1.25 ug.mL-1
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 10.4 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.09 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.09 %

Related Entries

Cross References

Resources Reference
ChEBI 28830
ChEMBL CHEMBL515
DrugBank DB00291
DrugCentral 588
FDA SRS 18D0SL7309
Human Metabolome Database HMDB0014436
Guide to Pharmacology 7143
KEGG C06900
PDB CBL
PharmGKB PA448926
PubChem 2708
SureChEMBL SCHEMBL4308
ZINC ZINC000000001115
CONTENTS