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| Targets |
The primary targets of N-Acetylpenicillamine relate to its thiol chemistry and metal chelation properties. As a derivative of penicillamine, it can chelate heavy metals through its sulfhydryl group, making it useful in heavy metal poisoning treatment. The compound also functions as a nitric oxide donor in certain experimental contexts. It has been used as a form of immunosuppression to treat rheumatoid arthritis. As a protected form of penicillamine, it serves as a chiral reagent for amino acid derivatization, targeting the stereochemical analysis of amino compounds.
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| ln Vitro |
In vitro activities of N-Acetylpenicillamine are primarily related to its chemical properties rather than specific biological potency. The compound is used as a control molecule in studies involving nitric oxide donors, where it serves as a reference for comparing the effects of other thiol-containing compounds. Its metal-chelating properties have been demonstrated in vitro through various analytical methods. As a chiral derivatization reagent, it reacts with amino acids and amino alcohols to form diastereomeric derivatives that can be separated and analyzed by chromatography. The compound's thiol group may also exhibit antioxidant properties through free radical scavenging.
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| ln Vivo |
In vivo, N-Acetylpenicillamine has been used therapeutically for heavy metal poisoning, where it chelates metal ions and promotes their excretion. It has also been employed as an immunosuppressive agent in the treatment of rheumatoid arthritis. As a penicillamine derivative, it shares similar pharmacological properties including immunomodulatory effects. The compound's ability to form stable complexes with metal ions enables its use in conditions involving metal accumulation or toxicity. However, detailed pharmacokinetic and pharmacodynamic data from controlled animal studies are limited in the public domain.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for N-Acetylpenicillamine are not typically conducted as the compound is used primarily as a chemical tool rather than a receptor-targeting drug. However, metal chelation assays can be performed using spectrophotometric methods to measure the compound's ability to bind metal ions such as copper, mercury, or lead. For nitric oxide studies, the compound serves as a control in assays measuring nitrite/nitrate production or cGMP accumulation. Chiral derivatization assays involve reacting the compound with amino acid mixtures followed by HPLC or GC analysis of the resulting derivatives.
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| Cell Assay |
In vitro cellular assays for N-Acetylpenicillamine typically focus on its metal chelation and antioxidant properties. Cell-based models of metal toxicity are used to evaluate the compound's protective effects against heavy metal-induced cytotoxicity. The compound may be tested in cell culture systems for its ability to reduce oxidative stress through its thiol group. As a control molecule in nitric oxide studies, it is used in cellular assays measuring NO production or signaling. Immunosuppressive effects have been evaluated in lymphocyte proliferation assays.
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| Animal Protocol |
In vivo animal experiments for N-Acetylpenicillamine have historically involved models of heavy metal poisoning, where the compound is administered to animals following metal exposure to evaluate its chelation efficacy. Rodent models of rheumatoid arthritis have been used to assess immunosuppressive effects. Dosing typically involves oral or intraperitoneal administration, with endpoints including metal tissue levels, urinary metal excretion, inflammatory markers, and clinical signs of toxicity or disease. The compound's thiol chemistry makes it useful for studying oxidative stress in vivo.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of N-Acetylpenicillamine are similar to those of penicillamine. The compound has a molecular weight of 191.25 g/mol and molecular formula C₇H₁₃NO₃S. As a small thiol-containing amino acid derivative, it is expected to be absorbed orally and distributed throughout the body. The compound undergoes renal excretion, consistent with its use in chelation therapy where metal complexes are eliminated via urine. Storage: powder at -20°C for 3 years or 4°C for 2 years; in solvent at -80°C for 6 months or -20°C for 1 month.
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| Toxicity/Toxicokinetics |
N-Acetylpenicillamine is considered to have a manageable toxicity profile when used as a therapeutic agent. As a penicillamine derivative, potential adverse effects may include those associated with thiol compounds, such as gastrointestinal disturbances, hypersensitivity reactions, and effects on renal function. However, the compound is primarily used in research settings as a chemical tool. Standard toxicological evaluations would be required for therapeutic development. The compound is generally handled with standard laboratory safety precautions for thiol-containing chemicals.
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| Additional Infomation |
N-acetyl-D-penicillamine is an N-acetyl-D-amino acid, wherein the amino acid is D-penicillamine.
N-Acetylpenicillamine (CAS# 15537-71-0, molecular formula C₇H₁₃NO₃S, molecular weight 191.25) is a compound derived from the amino acid penicillamine. It is primarily recognized for its role in chelation therapy, particularly in treating heavy metal poisoning, and as a nitric oxide donor control molecule. The compound is used as a chiral reagent for the precolumn derivatization of amino acids and has immunosuppressive applications in rheumatoid arthritis. No clinical trials or regulatory approvals have been identified. Storage: powder at -20°C for 3 years or 4°C for 2 years. |
| Molecular Formula |
C7H13NO3S
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|---|---|
| Molecular Weight |
191.2480
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| Exact Mass |
191.062
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| CAS # |
15537-71-0
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| PubChem CID |
65532
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| Appearance |
White to off-white solid powder
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| Density |
1.201g/cm3
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| Boiling Point |
392.7ºC at 760mmHg
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| Melting Point |
185-190ºC (dec.)
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| Flash Point |
191.3ºC
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| Vapour Pressure |
2.92E-07mmHg at 25°C
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| Index of Refraction |
1.508
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| LogP |
0.675
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
12
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| Complexity |
203
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| Defined Atom Stereocenter Count |
1
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| SMILES |
S([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C(=O)O[H])N([H])C(C([H])([H])[H])=O
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| InChi Key |
MNNBCKASUFBXCO-YFKPBYRVSA-N
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| InChi Code |
InChI=1S/C7H13NO3S/c1-4(9)8-5(6(10)11)7(2,3)12/h5,12H,1-3H3,(H,8,9)(H,10,11)/t5-/m0/s1
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| Chemical Name |
(2S)-2-acetamido-3-methyl-3-sulfanylbutanoic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
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| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2288 mL | 26.1438 mL | 52.2876 mL | |
| 5 mM | 1.0458 mL | 5.2288 mL | 10.4575 mL | |
| 10 mM | 0.5229 mL | 2.6144 mL | 5.2288 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.
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.
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