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Acexamic acid

Alias: Acexamic acid NSC-12945 NSC12945NSC 12945 Plastenan
Cat No.:V10146 Purity: ≥98%
6-Acetamidohexanoic acid is a pharmaceutical intermediate.
Acexamic acid
Acexamic acid Chemical Structure CAS No.: 57-08-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes
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Product Description
6-Acetamidohexanoic acid is a pharmaceutical intermediate.
Acexamic acid (CAS 57-08-9), also known as 6-acetamidohexanoic acid or epsilon-acetamidocaproic acid, is an amino acid derivative and a metabolite derived from hexamethylene bisacetamide (HMBA). It is the organic ligand that chelates with zinc to form zinc acexamate, an anti-ulcer drug with both antisecretory and gastroprotective properties. Acexamic acid is used as an anti-inflammatory agent and for the treatment of gastric ulcers and small bowel inflammation. Its molecular formula is C8H15NO3, and its molecular weight is 173.21 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Cyclooxygenase (COX); drug metabolite; amino acids and derivatives. Acexamic acid inhibits COX enzymes, reducing prostaglandin synthesis and exerting anti-inflammatory effects. As the ligand component of zinc acexamate, it contributes to the gastroprotective activity of the zinc complex. The compound is also classified as a drug metabolite derived from HMBA.
ln Vitro
Acexamic acid demonstrates anti-inflammatory activity in vitro through inhibition of COX enzymes. As a zinc chelator, it contributes to the gastroprotective effects of zinc acexamate by modulating mucosal protection and reducing gastric acid secretion. The compound exhibits less activity compared to its parent compound HMBA and does not induce cell differentiation, making it suitable for specific research applications.
ln Vivo
In vivo, Acexamic acid is used as an anti-inflammatory agent and as the organic ligand in zinc acexamate for the treatment of gastric ulcers and small bowel inflammation. Zinc acexamate demonstrates both antisecretory and gastroprotective properties. The compound is often administered orally as part of zinc acexamate formulations for the inhibition of gastrointestinal diseases.
Enzyme Assay
In vitro COX inhibition assays for Acexamic acid involve measuring COX-1 and COX-2 activity in the presence of varying concentrations of the compound. The enzymes are incubated with arachidonic acid substrate, and prostaglandin production is measured using ELISA or other detection methods. IC50 values are determined from dose-response curves. Zinc chelation assays can also be performed to characterize the compound's metal-binding properties.
Cell Assay
Cellular assays for Acexamic acid involve culturing gastric epithelial cells or intestinal cells. Cells are treated with Acexamic acid or zinc acexamate at varying concentrations (typically 10-1000 µM) for 24-48 hours. Cytokine production, prostaglandin synthesis, and markers of mucosal protection are measured. Cell viability is assessed using standard assays such as MTT. The compound's effects on inflammatory signaling pathways can be assessed using Western blotting.
Animal Protocol
In vivo animal studies for Acexamic acid are typically conducted in rodent models of gastric ulceration or intestinal inflammation. The compound is administered orally as zinc acexamate. Ulcer indices, gastric acid secretion, and mucosal protection are assessed. Inflammatory markers and tissue damage are evaluated histologically. Dosing regimens vary, with typical doses ranging from 10-100 mg/kg/day depending on the study objectives.
ADME/Pharmacokinetics
Acexamic acid has a molecular weight of 173.21 g/mol and a molecular formula of C8H15NO3. It has a purity of ≥99% and is soluble in DMSO and water. The compound should be stored at -20°C for up to 3 years as a powder or at -80°C for up to 1 year in solvent. Detailed pharmacokinetic parameters are not extensively documented.
Toxicity/Toxicokinetics
Acexamic acid is generally considered safe at therapeutic doses. As the ligand component of zinc acexamate, it is well-tolerated when administered orally. Comprehensive toxicological data are limited. The compound is intended for research use and is not approved for human therapeutic applications in many jurisdictions. Standard laboratory safety precautions should be taken when handling the compound.
Additional Infomation
Acexamic is a medium-chain fatty acid.
Acexamic acid (6-acetamidohexanoic acid) is an amino acid derivative and COX inhibitor used as an anti-inflammatory agent and as the organic ligand in zinc acexamate for gastric ulcer treatment. It is a metabolite derived from hexamethylene bisacetamide. The compound is not approved for clinical use in many jurisdictions and is available for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H15NO3
Molecular Weight
173.21
Exact Mass
173.105
CAS #
57-08-9
Related CAS #
36392-66-2 (calcium salt);7234-48-2 (mono-hydrochloride salt)
PubChem CID
2005
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
404.5±28.0 °C at 760 mmHg
Melting Point
102-104 °C(lit.)
Flash Point
198.4±24.0 °C
Vapour Pressure
0.0±2.0 mmHg at 25°C
Index of Refraction
1.462
LogP
-0.5
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
6
Heavy Atom Count
12
Complexity
156
Defined Atom Stereocenter Count
0
InChi Key
WDSCBUNMANHPFH-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H15NO3/c1-7(10)9-6-4-2-3-5-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)
Chemical Name
6-Acetamidohexanoic acid
Synonyms
Acexamic acid NSC-12945 NSC12945NSC 12945 Plastenan
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~577.33 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.43 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (14.43 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (14.43 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.7733 mL 28.8667 mL 57.7334 mL
5 mM 1.1547 mL 5.7733 mL 11.5467 mL
10 mM 0.5773 mL 2.8867 mL 5.7733 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05347654 Recruiting Other: Local treatment with silver
sulphadiazine only
Burns Degree Second Hospices Civils de Lyon January 20, 2023 Not Applicable
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