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Desmopressin acetate, is a compound that plays an important role in living organisms. It usually exists in a solid form and is a white or slightly yellowish crystalline powder. Its appearance may vary slightly due to production methods and purity. The CAS number is 62288-83-9, which is a unique identifier used to accurately identify and track the compound in chemical databases. Its molecular formula is C48H68N14O14S2, with a molecular weight of 1129.269, indicating that it is composed of elements such as carbon, hydrogen, nitrogen, oxygen, and sulfur. It is a structural analogue of natural arginine vasopressin and also a derivative of vasopressin. The solubility in different solvents is crucial for its application. Generally speaking, its solubility in water is high, which makes it convenient for preparing drug solutions. However, in some organic solvents, their solubility may be low, which needs to be adjusted according to specific application scenarios. It has a strong antidiuretic effect and a long-lasting effect, but has not shown vasoconstriction, so its drug side effects are relatively small. In the medical field, it has attracted much attention due to its unique biological activity and has shown potential application value in multiple fields.
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Customized Bottle Caps And Corks:
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Chemical Formula |
C50H72N14O16S2 |
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Exact Mass |
1188 |
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Molecular Weight |
1189 |
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m/z |
1188 (100.0%), 1189 (54.1%), 1190(14.3%), 1070 (9.0%), 1069 (5.2%), 1071 (4.5%), 1070 (2.6%), 1070 (2.5%), 1069 (1.6%), 1071 (1.2%), 1071 (1.1%), 1072 (1.1%) |
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Elemental Analysis |
C, 51.67; H, 6.03; N, 18.34; O, 17.96; S, 6.00 |
1. Treatment of diabetes insipidus
Desmopressin Acetate is the preferred medication for the treatment of Central Diabetes Insipidus (CDI). Diabetes insipidus is a disease caused by insufficient secretion of antidiuretic hormone (AVP) or insensitivity of the kidneys to it, characterized by polyuria, thirst, and low specific gravity urine. Its structure is similar to natural AVP and can stimulate the reabsorption of water by the renal collecting duct, thereby reducing urine output.
2. Treatment of nocturnal polyuria
It is also used to treat nocturnal polyuria, a common symptom that affects sleep quality. FDA has approved the use of Noctiva for adult patients who get up at least twice a night to urinate. By reducing nocturnal urine output, this medication helps improve the patient's sleep quality.
3. Control bleeding
It has the effect of enhancing the activity of plasma procoagulant factor VIII and can be used to control and treat hemorrhagic diseases. For example, it is used to treat bleeding caused by hemophilia A (a hereditary coagulation factor deficiency) and cirrhosis. In addition, it can also be used to control and prevent bleeding during small surgeries.
4. Other uses
In addition to the main uses mentioned above, vasopressin acetate also has other applications in certain special circumstances. For example:
(1) In the field of cardiovascular disease, it can be used to treat diseases such as heart failure and acute myocardial infarction. By reducing urine output, it helps to reduce cardiac load and improve heart function.
(2) In the field of neurology, it may have potential neuroprotective effects and can be used to treat certain neurological diseases, such as Parkinson's disease and Alzheimer's disease.
(3) In the field of kidneys, it can be used to treat certain kidney diseases, such as acute kidney injury and chronic kidney disease. By regulating water salt balance and improving renal function, it helps to reduce renal burden and delay disease progression.
Desmopressin acetate is a synthetic drug commonly used to treat diseases such as diabetes insipidus and hemophilia.
Step 1: Firstly, react benzyl chloride with methanol to produce benzyl methyl ester.
C6H5CH2COCl+CH3OH → C6H5CH2COOCH3+HCl
Step 2: React methyl benzoate with dimethyl sulfoxide under alkaline conditions to produce phenylacetyl imine.
C6H5CH2COOCH3+(CH3)2SO+NaOH → C6H5CH=CH2+CH3O-Na++(CH3)2SO2
Step 3: React phenylacetyl imine with butyryl chloride under alkaline conditions to produce phenylacetyl butyryl imine.
C6H5CH=CH2+CH3(CH2)2COCl+NaOH → C6H5CH=C (CH2)2CH3+CH3O-Na++HCl
Step 4: React phenylacetylsuccinimide with dimethylformamide under alkaline conditions to produce Desmopressin butyryl imine.
C6H5CH=C(CH2)2CH3+DMF+NaOH → C6H5CH=N(CH3)C(CH2)2CH3+H2O+NaOH
Step 5: React succinimide with acetic anhydride under alkaline conditions to produce Desmopressin acetylamide.
C6H5CH=N(CH3)C(CH2)2CH3+(CH3CO) 2O+NaOH → C6H5CH=N(CH3)COCH3+CH3COONa+H2O
Step 6: React desmopressin acetamide with ethanolamine to produce desmopressin acetamide.
C6H5CH=N(CH3)COCH3+NH2CH2CH2OH → C6H5CH(NHCOCH3)N(CH3)CH2CH2OH
Step 7: Finally, react demethyl acetate with acetic anhydride under alkaline conditions to produce ethyl demethyl acetate.
C6H5CH(NHCOCH3)N(CH3)CH2CH2OH+(CH3CO) 2O+NaOH → C6H5CH(NHCOCH3)N(CH3)CH2CH2OCH3+CH3COONa+H2O
The above are the detailed steps and chemical equations of a common synthesis method for ethyl Vicenate in Bundesliga. Please note that this is only one of the synthesis methods, and there may be other different methods in the laboratory. In addition, synthetic drugs need to be carried out in a compliant environment and under the guidance of professionals, and do not attempt to synthesize drugs at home.
Desmopressin Acetate is an artificially synthesized vasopressin analogue. It is obtained through chemical modification of natural arginine vasopressin (1- cysteine deamination, 8-L-arginine replaced by D-arginine). Its antidiuretic effect is 10-100 times stronger than that of the natural hormone, and it has no vasoconstrictive side effects. It is widely used in clinical settings for conditions such as central diabetes insipidus, nocturnal enuresis, hemophilia, and control of surgical bleeding. The following analysis is conducted from four dimensions: chemical structure, pharmacological mechanism, analytical methods, and clinical application.
Chemical Structure and Physical and Chemical Properties
The molecular formula of Desmopressin Acetate is C₄₈H₆₈N₁₄O₁₄S₂, with a molecular weight of 1129.27. Its structural characteristics are:
Cysteine deamination: Eliminate the amino group of cysteine in natural hormones, reducing the metabolic rate;
D-arginine replaces L-arginine: Enhance receptor binding specificity, prolong the duration of action (half-life 3-4 hours).
This drug is a white powder, soluble in water, DMSO and ethanol. Its stability is affected by temperature and it needs to be stored refrigerated (2-8℃). Its density is 1.56 g/cm³, the melting point is not specified, but it is prone to decomposition at high temperatures and needs to be protected from light and humid environments.
Pharmacological Mechanism and Analytical Methods
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Antidiuretic mechanism
Desmopressin activates the V2 receptor in the renal tubules, promoting the transport of water channel protein-2 (AQP2) to the cell membrane, increasing the reabsorption of water in the renal tubules, thereby reducing urine output. The analysis should pay attention to:
Receptor binding experiment: Using radiolabeled ligands (such as ³H-Descosine) to determine the affinity with V2 receptors and verify the drug's activity;
Detection of AQP2 expression: Through Western blot or immunofluorescence analysis, the expression level of AQP2 in renal tissue is measured to evaluate the drug's effect on water reabsorption;
Urine osmotic pressure measurement: In clinical practice, the osmotic pressure of the patient's urine is measured using an ice point osmometer, directly reflecting the drug's antidiuretic effect.
Mechanism of hemostasis
Desmopressin can stimulate endothelial cells to release von Willebrand factor (vWF) and coagulation factor VIII (FⅧ), enhancing platelet adhesion function. The analysis methods include:
ELISA for vWF/FⅧ level determination: Quantitative analysis of the promoting effect of the drug on the release of coagulation factors;
Platelet function test: Determine the effect of the drug on platelet aggregation rate using a platelet aggregation instrument;
Bleeding time measurement: Clinically, the Simplate II method is used to measure the bleeding time of patients to verify the hemostatic effect of the drug.
Pharmacokinetic analysis
Plasma concentration determination: Use HPLC-MS/MS to detect the concentration of Desmopressin in plasma after administration, plot the time-concentration curve, and calculate the half-life (3-4 hours) and bioavailability (about 85% for subcutaneous injection);
Tissue distribution study: Observe the distribution of the drug in organs such as the kidney and liver using radioactive autoradiography, and determine the concentration in target organs.
Quality control analysis methods
Purity and impurity detection
HPLC method: Use a C18 column as the stationary phase, acetonitrile-water (containing 0.1% TFA) as the mobile phase, and detect the purity of the main peak (≥98% is required);
Mass spectrometry analysis: Confirm the molecular weight and possible degradation products (such as deacetylated impurities) through ESI-MS.
Content determination
Non-aqueous titration method: Use acetic acid as the solvent and perchloric acid as the titrant to determine the drug content;
Ultraviolet spectrophotometry: Measure the absorbance at 280 nm and calculate the concentration.
Residual solvent detection
Use GC-MS to detect residual organic solvents (such as DMSO, ethanol) in the production process, ensuring compliance with ICH guidelines (such as DMSO residue ≤ 0.5%).
Clinical Application and Monitoring
Indications and Dose
Central diabetes insipidus: Adults 0.1-0.2 mg per dose, three times a day; Children 0.05-0.1 mg per dose;
Nocturnal enuresis: 0.2-0.4 mg before bedtime;
Surgical hemostasis: Intravenous infusion at 0.3 μg/kg.
Monitoring of Adverse Reactions
Hyponatremia: Regularly monitor serum sodium concentration (<130 mmol/L requires discontinuation of the medication);
Water retention: Observe signs such as weight gain and headache, and limit water intake when necessary.
Analysis of Drug Interactions
Antidepressants/Chlorpromazine: May enhance antidiuretic effect, increasing the risk of hyponatremia;
Indomethacin: Can enhance urine concentration effect, but does not affect the duration of drug efficacy.
Research Frontiers and Challenges
Antitumor Potential: Recent studies have shown that Desmopressin can inhibit tumor cell proliferation (such as CT-26 colon cancer cells) by activating V2 receptors, but the mechanism remains to be clarified;
Resistance Issues: Long-term use may lead to receptor desensitization, and the need to explore combined medication regimens;
New Formulation Development: Nanoparticles, microspheres, etc. as sustained-release formulations can prolong the duration of action and reduce the frequency of administration.
Conclusion
The analysis of Desmopressin Acetate requires integration of chemical structure analysis, pharmacological mechanism verification, quality control, and clinical monitoring to ensure its efficacy and safety. Future research should focus on the elucidation of resistance mechanisms and the development of new delivery systems to expand its clinical application scope.
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