Phthaloyl Amlodipine

Product Description

Phthaloyl Amlodipine is a derivative of Amlodipine which is a calcium channel blocker commonly used in the treatment of hypertension and angina The modification of Amlodipine through phthaloylation attachment of a phthaloyl group can potentially alter its pharmacokinetic properties or enhance its therapeutic effectiveness Below are the key details about this compound

 Chemical Details

 IUPAC Name 22Aminoethoxymethyl42ethoxyethoxyphthaloyl 14dihydro26dimethyl35pyridinecarboxylate

 Molecular Formula C21H26N2O4

 Molecular Weight 37045 gmol

 Structure

   Amlodipine a calcium channel blocker is modified by attaching a phthaloyl group derived from phthalic acid at one position

 Physical Properties

 Appearance Typically white to offwhite crystalline powder

 Melting Point Likely higher than Amlodipine due to the presence of the phthaloyl group

 Solubility Likely soluble in organic solvents like ethanol and methanol but less soluble in water

 Applications

1 Pharmacological Use

    Calcium Channel Blocker Like Amlodipine Phthaloyl Amlodipine would be expected to function as a calcium channel blocker affecting the smooth muscles in blood vessels leading to vasodilation and thus a reduction in blood pressure It may also be used to treat angina chest pain due to reduced blood flow to the heart

    The phthaloyl group may enhance the lipophilicity allowing for improved membrane penetration or alter the drugs bioavailability or duration of action

2 Drug Development

    Modifying Amlodipine with a phthaloyl group can be part of drug design efforts to optimize pharmacokinetics such as increasing solubility stability or the drugs affinity for specific receptors

    Prodrugs In some cases introducing a phthaloyl group can be used to create a prodrug which would undergo enzymatic cleavage in the body to release the active Amlodipine molecule

3 Research

    Preclinical Studies This compound could be of interest for preclinical pharmacological studies focused on understanding the role of phthaloylation in drug bioavailability receptor interactions or metabolism

    Investigating the lipophilicity and membrane permeability changes imparted by the phthaloyl group could be key in optimizing its therapeutic profile

 Chemical Reactivity

1 Phthaloyl Group C6H4CO2

    The phthaloyl group is an aromatic ester and its attachment to Amlodipine can modify the compounds lipophilicity as phthaloyl groups are known to be less polar compared to the parent molecule

    This modification could enhance the cell membrane permeability or biological halflife of the compound

2 Amlodipine Backbone

    The Amlodipine structure consists of a dihydropyridine ring which is responsible for blocking calcium channels The phthaloyl modification could potentially influence the binding affinity to the calcium channel receptor or alter its pharmacokinetic profile

 Synthesis of Phthaloyl Amlodipine

 Step 1 Phthaloylation of Amlodipine  React Amlodipine with phthalic anhydride or a phthaloyl chloride derivative in the presence of a suitable base eg pyridine triethylamine to form the phthaloyl derivative

 Step 2 Purification and crystallization may follow to obtain the pure phthaloylated Amlodipine

 Safety and Handling

 Toxicity  

    The toxicity of Phthaloyl Amlodipine would be expected to follow that of Amlodipine but the phthaloyl group could potentially alter its safety profile Like other calcium channel blockers it may cause hypotension dizziness or peripheral edema

 Precautions  

    Standard precautions for handling pharmaceutical intermediates should be followed including using gloves protective eyewear and working in a wellventilated area

 Storage  

    Store in a tightly sealed container in a cool dry place away from light and sources of moisture  

 Potential Side Effects

 Amlodipine Side Effects Since Phthaloyl Amlodipine is based on Amlodipine common side effects may include

    Swelling in the lower legs or feet edema

    Headaches

    Dizziness or lightheadedness

    Flushing

    Nausea or abdominal pain

 Conclusion

Phthaloyl Amlodipine may represent an interesting modification of Amlodipine aimed at optimizing its therapeutic properties The addition of a phthaloyl group could improve drug stability bioavailability or receptor interaction making it a potential candidate for further drug development or preclinical research Further studies would be needed to fully understand the pharmacokinetics and pharmacodynamics of this modified compound

Would you like more specific details on its synthesis potential applications or other derivatives of Amlodipine