| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
| Targets |
Nuclear factor erythroid 2-related factor 2 (Nrf2) and glutathione (GSH) biosynthesis pathway. Bucillamine induces the nuclear translocation of Nrf2, increasing expression of γ-GCS and GSS, leading to increased intracellular GSH levels and GSH activity. The compound also inhibits VEGF production and modulates immune responses.
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| ln Vitro |
Bucillamine induces the nuclear translocation of Nrf2, increasing the expression of γ-glutamylcysteine synthetase (γ-GCS) and glutathione synthetase (GSS), which further induces the production of intracellular antioxidant glutathione (GSH), HO-1, and SOD2. It protects sensory hair cells from cisplatin damage through its scavenging effects and induction of intracellular GSH. Bucillamine (25 and 100 µM) inhibits JNK activation and caspase-3 cleavage in HaCaT cells.
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| ln Vivo |
When rats undergo liver transplantation, bucillamine dramatically increases their chances of survival and guards against liver damage [1]. Rat experimental CNV size and leakage are considerably reduced by bucillamine (subconjunctival injection) [2].
In vivo, bucillamine protects against ischemia-reperfusion (I/R) injury in high-risk organ transplants. It inhibits VEGF production and can be used for the research of choroidal neovascularization (CNV) and rheumatoid arthritis (RA). Bucillamine protects sensory hair cells from cisplatin damage and prevents hearing loss in adult mice. It also protects mouse skin from UVB-induced p53 activation and inflammatory responses. |
| Enzyme Assay |
In vitro enzyme assays for bucillamine involve measuring its effects on Nrf2 nuclear translocation and GSH biosynthesis. Cells are treated with bucillamine, and Nrf2 translocation is assessed by immunofluorescence or Western blot. GSH levels are measured using colorimetric or fluorometric assays. The compound's ability to induce antioxidant gene expression is evaluated by qPCR.
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| Cell Assay |
In vitro cellular assays for bucillamine involve treating cells (such as HaCaT keratinocytes or auditory cells) with the compound and measuring cell viability, oxidative stress, and apoptosis. Cells are treated with bucillamine and exposed to stressors such as cisplatin or UVB radiation. Cell viability is assessed by MTT or other metabolic assays. Apoptosis is measured by caspase activity or flow cytometry.
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| Animal Protocol |
In vivo animal studies for bucillamine typically involve administration to rodent models of rheumatoid arthritis, ischemia-reperfusion injury, or cisplatin-induced hearing loss. Efficacy is assessed by measuring inflammatory markers, tissue damage, or functional outcomes. Bucillamine protects against cisplatin-induced hearing loss in mice and protects skin from UVB-induced damage in SKH-1 hairless mice.
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| ADME/Pharmacokinetics |
Bucillamine is orally bioavailable and enters cells rapidly via the same pathway as cysteine, replenishing thiol groups in glutathione (GSH) and increasing intracellular GSH levels and GSH activity. It has a molecular weight of 223.31 g/mol. The compound's pharmacokinetic profile supports oral administration for the treatment of rheumatoid arthritis and other inflammatory conditions.
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| Toxicity/Toxicokinetics |
Preclinical toxicity studies of bucillamine have established its safety profile for the treatment of rheumatoid arthritis. The compound has been shown to protect against oxidative damage and inflammation. Knockdown studies of HO-1 and SOD2 suggest that the protective effect of bucillamine against cisplatin is independent of the enzymatic activity of HO-1 and SOD.
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| References | |
| Additional Infomation |
Bucillamine is an organic molecular entity. It has been used in research on the treatment and prevention of gout and rheumatoid arthritis. Bucillamine is a highly bioavailable oral derivative of the endogenous amino acid cysteine, containing two sulfhydryl groups as donors, and possesses potential antioxidant and anti-inflammatory activities. After oral administration, Bucillamine rapidly enters cells via the same pathway as cysteine, replenishing the sulfhydryl groups in glutathione (GSH), thereby increasing intracellular GSH levels and activity. GSH is an antioxidant that plays an important protective role against oxidative stress and damage. Bucillamine may also have other anti-inflammatory effects, but its mechanism of action is not fully elucidated.
Bucillamine (SA96, Thiobutarit) is an orally bioavailable synthetic cysteine derivative with antioxidant and anti-inflammatory activity. It induces Nrf2 nuclear translocation, increasing GSH biosynthesis and protecting against oxidative damage. Bucillamine has been widely used in the treatment of rheumatoid arthritis and has shown protective effects against ischemia-reperfusion injury, cisplatin-induced hearing loss, and UVB-induced skin damage. |
| Molecular Formula |
C7H13NO3S2
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|---|---|
| Molecular Weight |
223.31
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| Exact Mass |
223.033
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| CAS # |
65002-17-7
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| Related CAS # |
82017-48-9 (disuflide);
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| PubChem CID |
656604
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
438.0±45.0 °C at 760 mmHg
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| Melting Point |
119-123ºC
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| Flash Point |
218.7±28.7 °C
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| Vapour Pressure |
0.0±2.3 mmHg at 25°C
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| Index of Refraction |
1.553
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| LogP |
1.28
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
13
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| Complexity |
218
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(C)(C(=O)N[C@@H](CS)C(=O)O)S
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| InChi Key |
VUAFHZCUKUDDBC-BYPYZUCNSA-N
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| InChi Code |
InChI=1S/C7H13NO3S2/c1-7(2,13)6(11)8-4(3-12)5(9)10/h4,12-13H,3H2,1-2H3,(H,8,11)(H,9,10)/t4-/m0/s1
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| Chemical Name |
(2R)-2-[(2-methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 Vitro) |
H2O : ~5 mg/mL (~22.39 mM)
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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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4781 mL | 22.3904 mL | 44.7808 mL | |
| 5 mM | 0.8956 mL | 4.4781 mL | 8.9562 mL | |
| 10 mM | 0.4478 mL | 2.2390 mL | 4.4781 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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