Chlorambucil

Base Information

• Chemical Name: Chlorambucil
• CAS No.: 305-03-3
• Molecular Formula: C14H19Cl2NO2
• Molecular Weight: 304.216
• Hs Code.: 2922499990
• European Community (EC) Number: 206-162-0
• NSC Number: 756674,3088
• UN Number: 2811
• UNII: 18D0SL7309
• DSSTox Substance ID: DTXSID7020263
• Nikkaji Number: J1.521K
• Wikipedia: Chlorambucil
• Wikidata: Q415939
• NCI Thesaurus Code: C362
• RXCUI: 2346
• Metabolomics Workbench ID: 42680
• ChEMBL ID: CHEMBL515

Synonyms:4-(Bis(2-chloroethyl)amino)benzenebutanoic Acid;Amboclorin;CB 1348;CB-1348;CB1348;Chlorambucil;Chloraminophene;Chlorbutin;Leukeran;Lympholysin;N,N-Di-(2-chloroethyl)-p-aminophenylbutyric Acid;NSC 3088;NSC-3088;NSC3088

Chemical Property of Chlorambucil

Chemical Property:

• Appearance/Colour: beige powder
• Vapor Pressure: 2.98E-09mmHg at 25°C
• Melting Point: 65-70 °C
• Refractive Index: 1.536
• Boiling Point: 460.09 °C at 760 mmHg
• Flash Point: 232.054 °C
• PSA: 40.54000
• Density: 1.248 g/cm³
• LogP: 3.37790
• Water Solubility.: <0.01 g/100 mL at 22℃
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 303.0792842
• Heavy Atom Count: 19
• Complexity: 250
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T:Toxic
• Statements: R45:; R25:; R36/37/38:
• Safety Statements: S53:; S26:; S45:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antineoplastic Agents, Alkylating
• Canonical SMILES: C1=CC(=CC=C1CCCC(=O)O)N(CCCl)CCCl
• Recent ClinicalTrials: Phase II Study of Chlorambucil and Subcutaneous Rituximab in Patients With Extranodal MALT Lymphoma
• Recent EU Clinical Trials: A pilot study of chlorambucil in pre-treated metastatic pancreatic adenocarcinoma patients bearing a germ line BRCA or other DNA Defects Repair (DDR) mutations.
• General Description: Chlorambucil (305-03-3) is an alkylating anticancer agent that was studied as part of a "switch off/switch on" drug delivery system, where its cytotoxicity was modulated by conjugation to a bi-nuclear amino acid platform (MAAP) and subsequent release via a cell-targeting peptide. This approach demonstrated controlled activation of its therapeutic effects, enhancing specificity for cancer cells while minimizing off-target toxicity. The study highlighted its potential as part of a versatile drug-carrier system for targeted chemotherapy.

Technology Process of Chlorambucil

There total 63 articles about Chlorambucil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.9%

cycl-isopropylidene malonate (2033-24-1) + 2-(4-(N,N-bis(2-chloroethyl)amino)phenyl)acetaldehyde (500590-36-3) → chlorambucil (305-03-3)

Guidance literature:

With formic acid; triethylamine; at 50 - 95 ℃; for 5h; Temperature;

Reference yield: 54.0%

4-(4-(bis(2-chloroethyl)amino)phenyl)-4-oxobutanoic acid → chlorambucil (305-03-3)

Guidance literature:

With formic acid; 1,1,1,3',3',3'-hexafluoro-propanol; water; at 80 ℃; for 2h; chemoselective reaction; Sealed tube;

DOI:10.1002/adsc.202000821

Reference yield: 53.1%

methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate (79481-83-7) → chlorambucil (305-03-3)

Guidance literature:

With hydrogenchloride; In water; at 60 ℃; for 1h;

upstream raw materials:

oxirane

methyl 4-(4-aminophenyl)butanoate

methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

methyl 3-<4-phenyl>butyrate

Downstream raw materials:

4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid anilide

N-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyryl)-glycine methyl ester

4-{4-[bis-(2-iodo-ethyl)-amino]-phenyl}-butyric acid

4-(N,N-bis-chloroethylamino-phenyl)butyl(N-hydroxysuccinimide)ester

Refernces

Switch off/switch on regulation of drug cytotoxicity by conjugation to a cell targeting peptide

10.1016/j.ejmech.2014.07.073

This research aimed to develop a "switch off/switch on" regulation of drug cytotoxicity for targeted cancer therapy by conjugating anticancer drugs to bi-nuclear amino acid platforms (MAAPs) through solid-phase organic synthesis (SPOS). The purpose was to enhance the therapeutic efficacy of multiple drugs linked to a single carrier molecule, potentially improving target cell specificity and reducing side effects. The researchers synthesized MAAPs loaded with various anticancer agents, including Azatoxin (AZA), Camptothecin (CAMP), Prednisone (PRED), Chlorambucil (CLB), and the 9-aminoacridine anticancer compound YG-42. They demonstrated that the cytotoxic activity of these drugs could be controlled by chemical modification and delivery, effectively "switching off" the activity when conjugated to the MAAP and "switching on" when delivered to target cancer cells via a cell-targeting peptide. The conclusions supported the versatility of this approach for constructing MAAPs with various drugs and linkages, showing high variability in bio-stability and drug release kinetics. This research paves the way for more sophisticated MAAPs bearing diverse chemotherapeutic "cocktails" for preclinical cancer therapy assessment.

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