molecular formula C17H19N3O3S B000731 Omeprazole CAS No. 73590-58-6

Omeprazole

Cat. No.: B000731
CAS No.: 73590-58-6
M. Wt: 345.4 g/mol
InChI Key: SUBDBMMJDZJVOS-UHFFFAOYSA-N
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Mechanism of Action

Target of Action

Omeprazole is a proton pump inhibitor (PPI) . Its primary target is the H+/K+ ATPase pump on gastric secretory cells . This pump is responsible for the final step in the production of gastric acid in the stomach .

Mode of Action

This compound works by inhibiting the H+/K+ ATPase pump , thereby reducing the secretion of gastric acid . It forms a covalent bond with the sulfhydryl group of the cysteine residues on the pump, leading to the inhibition of acid secretion . This results in an increase in gastric pH, providing relief from acid-related disorders .

Biochemical Pathways

This compound affects several biochemical pathways. It inhibits gastric acid secretion, which is part of the larger digestive function of the stomach . This compound has also been found to modulate autophagy in pancreatic cancer cells . Furthermore, it has been shown to bind to a wide range of proteins, forming highly stable complexes .

Pharmacokinetics

This compound shows concentration-dependent elimination kinetics and its oral bioavailability increases with the dose and during repeated administration . It is completely metabolized in the liver, primarily by CYP2C19 and CYP3A4 . The two major plasma metabolites are the sulphone and hydroxythis compound, neither of which contributes to the antisecretory activity . About 80% of a given dose is excreted in the urine, and the remainder via the bile .

Result of Action

The inhibition of gastric acid secretion by this compound leads to a decrease in gastric acidity. This provides relief from conditions such as gastroesophageal reflux disease (GERD), peptic ulcer disease, and other diseases characterized by the oversecretion of gastric acid . In addition, this compound promotes the healing of tissue damage and ulcers caused by gastric acid and H. pylori infection .

Action Environment

The action of this compound can be influenced by environmental factors. For instance, a study on fish showed that inhibition of gastric acid secretion with this compound affected the fish’s specific dynamic action and growth rate . This suggests that the environment and the physiological state of the organism can influence the action and efficacy of this compound .

Biochemical Analysis

Biochemical Properties

Omeprazole’s therapeutic mechanism of action involves the formation of a disulfide linkage to cysteine residues in the H+/K+ ATPase pump on gastric secretory cells . This covalent linkage between the sole sulfur group of this compound and selected cysteine residues of the pump protein results in inhibition of acid secretion in the stomach .

Cellular Effects

This compound has been shown to have a wide range of effects on various types of cells. It has been found to bind to multiple proteins and is capable of forming highly stable complexes that are not dependent on disulfide linkages between the drug and protein targets .

Molecular Mechanism

The molecular mechanism of this compound involves the formation of a covalent bond with cysteine residues in the H+/K+ ATPase pump, resulting in the inhibition of acid secretion . This binding is not fully inhibited by cysteine alkylation and occurs at neutral pH .

Temporal Effects in Laboratory Settings

In a study where this compound and its stable isotope D3–this compound were administered to mice, several new metabolites of this compound were identified in both brain and plasma samples . A total of seventeen metabolites were observed, and the observed metabolites were different from each administration route or each matrix (brain or plasma) .

Dosage Effects in Animal Models

The study mentioned above administered this compound and its stable isotope D3–this compound concomitantly in a dose level of 50 mg/kg (1:1 ratio of this compound and D3–this compound mixture) to mice . The metabolite production varied according to the route of administration in the mouse plasma and brain .

Metabolic Pathways

This compound is involved in various metabolic pathways. In the study mentioned above, several new metabolites of this compound were identified in both brain and plasma samples .

Transport and Distribution

The study mentioned above found that the observed metabolites of this compound were different from each administration route or each matrix (brain or plasma) .

Subcellular Localization

The study mentioned above found that several new metabolites of this compound were identified in both brain and plasma samples .

Comparison with Similar Compounds

While all these compounds share a similar mechanism of action, omeprazole is unique in its specific chemical structure and pharmacokinetic properties . For instance, esthis compound is the S-isomer of this compound and is considered to have a more consistent pharmacokinetic profile . Pantoprazole and lansoprazole differ in their chemical structures and are used for slightly different clinical indications .

Conclusion

This compound is a widely used proton pump inhibitor with significant therapeutic benefits for acid-related disorders. Its synthesis involves complex chemical reactions, and it undergoes various transformations to form active metabolites. This compound’s mechanism of action and its applications in scientific research make it a valuable compound in both medicine and industry. Compared to other proton pump inhibitors, this compound stands out due to its unique chemical properties and clinical efficacy.

Properties

IUPAC Name

6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI

InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

SUBDBMMJDZJVOS-UHFFFAOYSA-N
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Canonical SMILES

CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C17H19N3O3S
Record name omeprazole
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DSSTOX Substance ID

DTXSID6021080
Record name Omeprazole
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Molecular Weight

345.4 g/mol
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Physical Description

Solid
Record name Omeprazole
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Solubility

35.4 [ug/mL] (The mean of the results at pH 7.4), Freely soluble in ethanol and methanol, and slightly soluble in acetone and isopropanol and very slightly soluble in water., In water, 82.3 mg/L at 25 °C /Estimated/, 0.5 mg/mL
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Description Aqueous solubility in buffer at pH 7.4
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Vapor Pressure

9.2X10-13 mm Hg at 25 °C /Estimated/
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Mechanism of Action

Hydrochloric acid (HCl) secretion into the gastric lumen is a process regulated mainly by the H(+)/K(+)-ATPase of the proton pump, expressed in high quantities by the parietal cells of the stomach. ATPase is an enzyme on the parietal cell membrane that facilitates hydrogen and potassium exchange through the cell, which normally results in the extrusion of potassium and formation of HCl (gastric acid). Omeprazole is a member of a class of antisecretory compounds, the substituted _benzimidazoles_, that stop gastric acid secretion by selective inhibition of the _H+/K+ ATPase_ enzyme system. Proton-pump inhibitors such as omeprazole bind covalently to cysteine residues via disulfide bridges on the alpha subunit of the _H+/K+ ATPase_ pump, inhibiting gastric acid secretion for up to 36 hours. This antisecretory effect is dose-related and leads to the inhibition of both basal and stimulated acid secretion, regardless of the stimulus. **Mechanism of H. pylori eradication** Peptic ulcer disease (PUD) is frequently associated with _Helicobacter pylori_ bacterial infection (NSAIDs). The treatment of H. pylori infection may include the addition of omeprazole or other proton pump inhibitors as part of the treatment regimen,. _H. pylori_ replicates most effectively at a neutral pH. Acid inhibition in H. pylori eradication therapy, including proton-pump inhibitors such as omeprazole, raises gastric pH, discouraging the growth of H.pylori. It is generally believed that proton pump inhibitors inhibit the _urease_ enzyme, which increases the pathogenesis of H. pylori in gastric-acid related conditions., Omeprazole is a selective and irreversible proton pump inhibitor. Omeprazole suppresses gastric acid secretion by specific inhibition of the hydrogen-potassium adenosinetriphosphatase (H+, K+-ATPase) enzyme system found at the secretory surface of parietal cells. It inhibits the final transport of hydrogen ions (via exchange with potassium ions) into the gastric lumen. Since the H+/K+ ATPase enzyme system is regarded as the acid (proton) pump of the gastric mucosa, omeprazole is known as a gastric acid pump inhibitor. Omeprazole inhibits both basal and stimulated acid secretion irrespective of the stimulus., After oral administration, the onset of the antisecretory effect of omeprazole occurs within one hour, with the maximum effect occurring within two hours. Inhibition of secretion is about 50% of maximum at 24 hours and the duration of inhibition lasts up to 72 hours. The antisecretory effect thus lasts far longer than would be expected from the very short (less than one hour) plasma half-life, apparently due to prolonged binding to the parietal H + /K + ATPase enzyme. When the drug is discontinued, secretory activity returns gradually, over 3 to 5 days. The inhibitory effect of omeprazole on acid secretion increases with repeated once-daily dosing, reaching a plateau after four days.
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Color/Form

Crystals from acetonitrile, White to off-white crystalline powder

CAS No.

73590-58-6
Record name Omeprazole
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Record name 6-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole
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Melting Point

156 °C
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Synthesis routes and methods I

Procedure details

To a 50 mL beaker was added about 1 g of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole to 30 mL of dimethylformamide (DMF). Additional (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole was added to the resulting solution until a suspension of the material was formed. The solution was stirred for approximately 10 minutes, and then filtered through a 0.45 μm Poly(tetrafluoroethylene) (PTFE) or Nylon filter. The resulting saturated solution was placed in a shallow petri dish, covered and stored under refrigerated conditions (approximately 5° C.) with a humidity range of about 0 to 50 percent until crystals formed (between 4-6 days). The identity of the title compound is confirmed by single crystal x-ray diffraction and Raman spectroscopy, and shown to contain between about 96 and 98 percent (w/w) of the 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole and between about 2 and 4 percent (w/w) of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole.
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
30 mL
Type
solvent
Reaction Step One
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Synthesis routes and methods II

Procedure details

Approximately 850 mL of methanol was placed in a 1 liter glass bottle with a screw cap. The solution was saturated by dissolving approximately 10.5 g of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole, and the resulting solution was stirred. Once the solution was saturated, an additional 17 g of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl-methyl]sulfinyl]-1H-benzimidazole was added to the saturated solution to create a suspension. The cap was sealed and the saturated suspension was allowed to stir and equilibrate for about four days.
[Compound]
Name
glass
Quantity
1 L
Type
reactant
Reaction Step One
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
10.5 g
Type
reactant
Reaction Step Two
[Compound]
Name
(5)6-methoxy
Quantity
17 g
Type
reactant
Reaction Step Three

Synthesis routes and methods III

Procedure details

To a 50 mL beaker was added about 1 g of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole to 30 mL of dimethylformamide (DMF) containing 1 mL of ammonium hydroxide. Additional (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole was added to the resulting solution until a suspension of the material was formed. The solution was stirred for approximately 10 minutes, and then filtered through a 0.45 μm Poly(tetrafluoroethylene) (PTFE) or Nylon filter. The resulting saturated solution was placed in a shallow petri dish, covered and stored under ambient conditions (approximately 25° C.) and a humidity range of 0 to 50 percent until crystals formed (between 1-4 days). The identity of the title compound is confirmed by single crystal x-ray diffraction and/or Raman spectroscopy. The resulting material was shown to contain between about 96 and 98 percent (w/w) of the 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole and between about 2 and 4 percent (w/w) of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole.
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
30 mL
Type
solvent
Reaction Step One
Quantity
1 mL
Type
reactant
Reaction Step Two
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Synthesis routes and methods IV

Procedure details

The procedure set forth in Example 2 is repeated except that ethanol is employed as a solvent in place of DMF and the resulting structure is shown by various X-ray crystal diffraction and/or Raman spectroscopy to contain between about 82 and 85 percent (w/w) of 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole and between about 15 and 18 percent (w/w) of 5-methoxy 2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Strategy Settings

Precursor scoring Relevance Heuristic
Min. plausibility 0.01
Model Template_relevance
Template Set Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph 6

Feasible Synthetic Routes

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Omeprazole
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Customer
Q & A

Q1: How does omeprazole inhibit gastric acid secretion?

A1: this compound is a prodrug that requires activation in the acidic environment of the parietal cell canaliculi. [] Once activated, it binds to cysteine residues on the H+/K+ ATPase pump, irreversibly inhibiting its function. [] This inhibition effectively blocks the final step of acid secretion in the stomach. []

Q2: What are the downstream effects of this compound's acid suppression?

A2: this compound's potent and prolonged acid suppression leads to various physiological changes, including increased serum gastrin levels. [] Studies have shown that there is no direct correlation between fasting serum gastrin levels and the degree of gastric acid suppression in patients receiving this compound. []

Q3: What is the molecular formula and weight of this compound?

A3: While the provided texts do not explicitly state the molecular formula and weight of this compound, they highlight its single sulfur group, significant in its mechanism of action. []

Q4: How do the enantiomers of this compound differ in their pharmacokinetic properties?

A4: Research indicates that artemisinin, an antimalarial drug, induces CYP2C19, an enzyme involved in the metabolism of this compound. [] This induction significantly affects the pharmacokinetics of both this compound enantiomers. []

Q5: What is the stability of this compound in oral suspensions?

A5: this compound-sodium bicarbonate oral suspensions, stored at 4°C in darkness, retain over 96% of their initial this compound concentration for up to 28 days. [] The viscosity of these refrigerated suspensions remains stable over 7 days. []

Q6: Does this compound interact with other drugs?

A6: Yes, this compound can interact with various drugs. It has been shown to reduce the formation of the active metabolite of clopidogrel, potentially impacting its efficacy. [] Further research suggests that esthis compound, the S-enantiomer of this compound, may have a more favorable drug interaction profile compared to this compound. []

Q7: Does this compound act as a catalyst in any biological reactions?

A7: While this compound itself is not a catalyst, its mechanism of action involves irreversible binding to the H+/K+ ATPase, ultimately inhibiting the catalytic activity of this enzyme. []

A7: The provided research papers do not delve into the computational chemistry and modeling of this compound.

Q8: How does the structure of this compound contribute to its target specificity?

A9: While specific SAR studies are not discussed in the provided texts, this compound's structure, particularly its sulfur group, is essential for its activation and subsequent binding to the H+/K+ ATPase. [, ]

Q9: What are the formulation strategies to improve the stability or bioavailability of this compound?

A10: The use of enteric coating in this compound formulations protects the drug from degradation in the acidic environment of the stomach, ensuring its release and absorption in the small intestine. [, ]

Q10: How is this compound metabolized in the body?

A11: this compound is primarily metabolized by the cytochrome P450 (CYP) system in the liver, specifically by the CYP2C19 isoenzyme. [, , ] Genetic polymorphisms in CYP2C19 can significantly influence this compound's pharmacokinetics and therapeutic efficacy. [, , ]

Q11: What is the duration of action of a single dose of this compound?

A12: A single dose of 20 mg of this compound can significantly suppress maximal acid output (MAO) for over 24 hours. [] The duration of acid suppression can vary depending on the dose and individual patient factors. []

Q12: Does this compound exhibit gender-specific pharmacokinetic differences?

A13: Research suggests that there are gender-based pharmacokinetic differences in this compound metabolism. Studies have observed a significant increase in the Cmax, AUC, and elimination half-life of this compound in females compared to males. []

Q13: What is the efficacy of this compound in treating duodenal ulcers?

A14: this compound has been shown to be effective in healing duodenal ulcers, often demonstrating superior healing rates compared to H2 receptor antagonists like ranitidine and cimetidine. [, , ] The optimal dosage and duration of this compound treatment for duodenal ulcers may vary depending on individual patient factors. []

Q14: What is the role of this compound in Helicobacter pylori eradication?

A15: While this compound alone is not sufficient to eradicate Helicobacter pylori infection, it plays a crucial role in combination therapies. [, ] Studies suggest that higher doses of this compound (80 mg b.d.) combined with amoxicillin are more effective in achieving H. pylori eradication than lower doses. []

Q15: Is this compound effective in preventing stress ulcers?

A16: Studies suggest that both this compound and cimetidine can be effective in preventing stress ulcers, with this compound potentially demonstrating superior efficacy compared to cimetidine. []

Q16: Are there any known resistance mechanisms to this compound?

A16: The provided research does not focus on specific resistance mechanisms to this compound.

Q17: What is the safety profile of long-term this compound treatment?

A18: While this compound is generally well-tolerated, long-term treatment, especially at high doses, has been associated with potential adverse effects. [, ]

Q18: Are there any specific safety concerns regarding this compound use in children?

A19: Research indicates that high doses of this compound can be used to treat eosinophilic esophagitis (EoE) in children, but close monitoring for potential adverse effects is necessary. []

Q19: Are there any specific drug delivery systems designed for this compound?

A20: The provided texts do not discuss specific drug delivery systems for this compound beyond the use of enteric coatings in oral formulations. [, ]

Q20: What analytical methods are used to quantify this compound and its metabolites in biological samples?

A22: High-performance liquid chromatography (HPLC) with UV detection is a commonly used method for quantifying this compound and its metabolites in biological samples. [, , ]

A20: The provided research papers do not address the environmental impact and degradation of this compound.

Q21: How does the dissolution rate of this compound formulations impact its bioavailability?

A24: While the provided texts do not extensively cover dissolution rate, they emphasize the significance of enteric coatings in protecting this compound from degradation in the stomach, thereby ensuring its optimal dissolution and absorption in the intestine. [, ]

A21: Specific details about the validation of analytical methods for this compound are not provided in the research papers.

A21: The provided texts do not delve into the immunogenicity and immunological responses associated with this compound.

Q22: Does this compound interact with any drug transporters?

A28: Research indicates that this compound may interact with P-glycoprotein, a drug transporter, potentially impacting the absorption and bioavailability of co-administered drugs. []

Q23: Can this compound affect the activity of drug-metabolizing enzymes?

A29: Yes, this compound has been shown to inhibit the activity of CYP2C19, a key enzyme involved in the metabolism of various drugs. [, , , ] This inhibition can lead to increased plasma concentrations of co-administered drugs metabolized by CYP2C19, potentially increasing the risk of adverse effects. [, , , ]

A23: The provided texts do not specifically address the biocompatibility and biodegradability of this compound.

Q24: Are there alternative treatments to this compound for acid-related disorders?

A31: Yes, alternative treatments to this compound include other PPIs such as lansoprazole, esthis compound, pantoprazole, and rabeprazole, as well as H2 receptor antagonists like ranitidine and famotidine. [, , , , , ]

Q25: How does the efficacy of esthis compound compare to this compound?

A32: Esthis compound, the S-enantiomer of this compound, has demonstrated comparable or superior efficacy to this compound in some studies, particularly at higher doses. [, ]

A25: The provided texts do not cover aspects of recycling and waste management related to this compound.

A25: Specific research infrastructure and resources dedicated to this compound research are not mentioned in the provided papers.

Q26: What is the historical context of this compound's development and use?

A35: this compound represents a significant milestone in the treatment of acid-related disorders. It was the first PPI introduced into clinical practice and revolutionized the management of conditions like peptic ulcer disease and GERD. []

A36: The research presented highlights the interdisciplinary nature of this compound research, encompassing fields like pharmacology, gastroenterology, biochemistry, and pharmaceutics. [, , , , , ]

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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.