| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| Other Sizes |
| Targets |
Not applicable (inactive metabolite/internal standard). Lansoprazole Sulfide does not have a therapeutic target; it is the reduced, non-antibacterial metabolite of lansoprazole. However, interestingly, Lansoprazole Sulfide (unlabeled) has been reported to have anti-TB (Mycobacterium tuberculosis) activity in vitro, inhibiting intracellular and extracellular M. tuberculosis with IC50 values of 0.59 microM and 0.46 microM, respectively, indicating it retains some antimicrobial properties distinct from its parent PPI activity. Its mechanism against TB may involve inhibition of the bacterial ATP synthase or other targets.
|
|---|---|
| ln Vitro |
Lansoprazole Sulfide (unlabeled) is an orally active anti-TB agent. It exhibits an IC50 of 0.59 microM against intracellular Mycobacterium tuberculosis (within infected macrophages) and 0.46 microM against the bacterium in broth culture. It demonstrates a high selectivity index, with significantly lower cytotoxicity against mammalian cells (IC50 > 20 microM). The D4-labeled version is used as an internal standard and is not tested for activity in binding or functional assays. In the context of PPIs, lansoprazole sulfide is not responsible for acid suppression.
|
| ln Vivo |
Not applicable for internal standard. For the unlabeled metabolite in an M. tuberculosis model: the compound has been evaluated in vitro for its bactericidal activity against replicating M. tuberculosis H37Rv in broth and within THP-1-derived human macrophages. It shows a minimum inhibitory concentration (MIC) in the range of 0.5-2 microM against a panel of drug-sensitive and multi-drug resistant (MDR) clinical isolates. It also demonstrates synergy with the first-line anti-TB drug rifampin. However, as a deuterated internal standard, it is not used in these assays.
|
| Enzyme Assay |
Not applicable (Lansoprazole Sulfide D4 is an analytical internal standard, not an enzyme assay tool). The parent drug lansoprazole is a prodrug that converts to its active sulfenic acid form in the acidic environment of the parietal cell. It then forms a covalent disulfide bond with cysteine residues on the H+/K+-ATPase. Lansoprazole sulfide is formed by reduction of the sulfoxide group, likely via non-enzymatic or enzymatic (e.g., thiol-dependent) reduction. It is not a target of specific receptor-binding assays.
|
| Cell Assay |
Not applicable (internal standard for bioanalysis, not for cell-based efficacy studies). For the unlabeled metabolite, its anti-TB activity is tested using THP-1 human macrophages infected with M. tuberculosis. THP-1 cells are differentiated into adherent macrophages with PMA (phorbol 12-myristate 13-acetate, 50 ng/mL) for 48-72 hours. Macrophages (1 × 10⁵ cells/well) are infected with M. tuberculosis H37Rv at an MOI of 1-10 for 4 hours. Extracellular bacteria are washed off, and infected cells are treated with varying concentrations of lansoprazole sulfide (0.1-10 microM) for 5-7 days. Cells are then lysed, and serial dilutions are plated on 7H11 agar. Colony-forming units (CFU) are counted after 21 days of incubation. The IC50 for intracellular killing is calculated.
|
| Animal Protocol |
Not applicable for efficacy studies. Lansoprazole Sulfide D4 is used as an internal standard in bioanalytical studies. Male Sprague-Dawley rats (200-250 g, n=6) are dosed orally with lansoprazole (10-30 mg/kg). Blood samples are collected from the jugular vein at 0, 0.5, 1, 2, 4, 8, and 12 hours post-dose. Plasma is separated and protein precipitated with acetonitrile containing Lansoprazole Sulfide D4 as the internal standard. The supernatant is analyzed by LC-MS/MS. The concentration of lansoprazole sulfide (the metabolite) is quantified by the peak area ratio to the D4 internal standard. Pharmacokinetic parameters (Cmax, Tmax, AUC, t½) for the metabolite are calculated.
|
| ADME/Pharmacokinetics |
Lansoprazole Sulfide D4 is a stable isotope-labeled internal standard with a mass shift of +4 Da. The metabolite lansoprazole sulfide is formed from lansoprazole via reduction, primarily in the liver by reductases (e.g., sulfoxide reductases). The sulfide metabolite is biologically inactive as a PPI (does not inhibit acid secretion). In humans, the exposure (AUC) of the sulfide metabolite is approximately 10-30% of the parent drug. It is further metabolized and conjugated before excretion (via urine and bile).
|
| Toxicity/Toxicokinetics |
The D4-labeled version is for research use only and not for human consumption. As an inactive metabolite, lansoprazole sulfide does not contribute to the acute toxicity profile of lansoprazole (which includes headache, GI upset, and risk of Clostridium difficile infection). The unlabeled lansoprazole sulfide has been shown to have low mammalian cell cytotoxicity (IC50 > 20 microM) in THP-1 and Vero cells. It is not considered genotoxic in standard in vitro assays.
|
| References | |
| Additional Infomation |
Lansoprazole (Prevacid®) is a widely prescribed PPI. Its metabolism is heavily influenced by CYP2C19 genetic polymorphisms (poor metabolizers vs. extensive metabolizers). Lansoprazole Sulfide D4 is a research internal standard used in LC-MS/MS for the accurate quantification of the lansoprazole sulfide metabolite in plasma, urine, and tissue samples. This is critical for understanding the complete ADME (absorption, distribution, metabolism, excretion) profile of lansoprazole, for bioequivalence studies, and for assessing the impact of drug-drug interactions (e.g., with CYP2C19 inhibitors) on the metabolism of lansoprazole. Interestingly, the parent lansoprazole sulfide is also a promising anti-TB scaffold.
|
| Molecular Formula |
C16H10D4F3N3OS
|
|---|---|
| Molecular Weight |
357.386716712
|
| Exact Mass |
357.106
|
| CAS # |
1216682-38-0
|
| PubChem CID |
45039649
|
| Appearance |
White to off-white solid powder
|
| LogP |
4.499
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
24
|
| Complexity |
413
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
[2H]C1=C(C(=C2C(=C1[2H])NC(=N2)SCC3=NC=CC(=C3C)OCC(F)(F)F)[2H])[2H]
|
| InChi Key |
CCHLMSUZHFPSFC-QFFDRWTDSA-N
|
| InChi Code |
InChI=1S/C16H14F3N3OS/c1-10-13(20-7-6-14(10)23-9-16(17,18)19)8-24-15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)/i2D,3D,4D,5D
|
| Chemical Name |
4,5,6,7-tetradeuterio-2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfanyl]-1H-benzimidazole
|
| 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 (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| 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 | 2.7981 mL | 13.9903 mL | 27.9806 mL | |
| 5 mM | 0.5596 mL | 2.7981 mL | 5.5961 mL | |
| 10 mM | 0.2798 mL | 1.3990 mL | 2.7981 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
