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| Other Sizes |
| Targets |
Oxolamine citrate acts as a histamine H1 receptor antagonist, contributing to its antitussive and antihistamine properties. It is also an inhibitor of CYP2B1/2, a cytochrome P450 enzyme involved in drug metabolism. The compound's mechanism involves shifting energy metabolism from mitochondrial respiration to glycolysis, and it has been shown to affect warfarin anticoagulant properties. Additionally, oxolamine citrate inhibits the conversion of podophyllotoxin to epipodophyllotoxin. Its primary pharmacological targets are the histamine H1 receptor and the drug-metabolizing enzyme CYP2B1/2.
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| ln Vitro |
In vitro, oxolamine citrate exhibits anti-inflammatory activity. As a CYP2B1/2 inhibitor, it can modulate the metabolism of other drugs that are substrates of this enzyme. The compound's antitussive effects are mediated through its action as a histamine H1 receptor antagonist. It has been studied for its ability to shift energy metabolism from mitochondrial respiration to glycolysis. Specific IC₅₀ values for its in vitro activities have not been widely reported in the available literature, but its pharmacological profile as a cough suppressant and anti-inflammatory agent is well established.
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| ln Vivo |
In vivo, oxolamine citrate functions as an effective cough suppressant, used in the treatment of respiratory tract diseases. It has been demonstrated to have anti-inflammatory activity in preclinical models. The compound's antitussive effects are clinically relevant for managing cough associated with colds and other respiratory conditions. Detailed in vivo efficacy data, including specific animal model studies, are limited in the publicly available literature, but its clinical use as a cough suppressant supports its in vivo activity.
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| Enzyme Assay |
Non-cellular assays for oxolamine citrate would typically involve enzyme inhibition studies, particularly focusing on its activity as a CYP2B1/2 inhibitor. These assays measure the compound's ability to inhibit the enzymatic activity of CYP2B1/2 using specific substrates and detecting metabolite formation via HPLC or mass spectrometry. Histamine H1 receptor binding affinity can be assessed using radioligand binding assays with membrane preparations expressing the receptor, measuring the displacement of a labeled antagonist to determine binding affinity (Ki) and receptor occupancy.
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| Cell Assay |
Cell-based assays for oxolamine citrate may include studies evaluating its anti-inflammatory effects in immune cells, such as measuring cytokine production in stimulated macrophages or evaluating its impact on glycolysis versus mitochondrial respiration in cancer cell lines. The compound's effect on warfarin anticoagulant properties could be studied in hepatocyte cultures to assess its impact on drug metabolism pathways. Cytotoxicity and cell viability assays may also be performed to evaluate its safety profile in various cell types, though specific protocols are not widely documented in the available literature.
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| Animal Protocol |
In vivo animal models for oxolamine citrate would typically involve cough models in guinea pigs or other species to evaluate its antitussive efficacy. Anti-inflammatory activity could be assessed in standard models such as carrageenan-induced paw edema in rats or other inflammation models. Pharmacokinetic and toxicity studies in rodents would be conducted to evaluate absorption, distribution, metabolism, excretion, and safety profile. However, specific detailed protocols for these studies are not extensively documented in publicly available sources, as oxolamine citrate is a known pharmaceutical compound rather than a novel research chemical.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for oxolamine citrate are limited in the available literature. As a small molecule with a molecular weight of 437.44 g/mol, it is expected to be well absorbed following oral administration. The compound is soluble in water and ethanol, which would facilitate gastrointestinal absorption. It is metabolized in part by cytochrome P450 enzymes, particularly CYP2B1/2, which it also inhibits. The compound's distribution, half-life, and elimination pathways have not been extensively characterized in publicly available sources.
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| Toxicity/Toxicokinetics |
Oxolamine citrate is generally well-tolerated at therapeutic doses. As a medication used for coughs and colds, its safety profile has been established through clinical use. Specific toxicity data, including LD₅₀ values and detailed toxicological studies, are not widely reported in the available literature. Like many pharmaceuticals, it may cause side effects in some individuals, though these are not extensively documented in the search results. For research use, standard laboratory safety precautions should be followed when handling the compound.
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| References | |
| Additional Infomation |
See also: Oxolamine (notes moved to).
Oxolamine citrate is a pharmaceutical compound that has been used clinically as a cough suppressant. It is also known by the synonyms SKF-9976 and AF-438. The compound has been studied for its anti-inflammatory effects and its ability to shift energy metabolism from mitochondrial respiration to glycolysis. It is an inhibitor of CYP2B1/2 and has been shown to affect warfarin anticoagulant properties. Oxolamine citrate is available as a research chemical for pharmacological studies. It has not been reported to have undergone significant clinical trials as a novel therapeutic agent, as it is an established compound rather than an investigational new drug. The compound is for research use only and not for human therapeutic use. |
| Molecular Formula |
C20H27N3O8
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|---|---|
| Molecular Weight |
437.44
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| Exact Mass |
437.18
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| CAS # |
1949-20-8
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| PubChem CID |
264891
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.066g/cm3
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| Boiling Point |
364.8ºC at 760 mmHg
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| Melting Point |
153-154ºC
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| Flash Point |
174.4ºC
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| Vapour Pressure |
1.64E-05mmHg at 25°C
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| LogP |
1.372
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
31
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| Complexity |
454
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C(C(=O)O[H])(C([H])([H])C(=O)O[H])C([H])([H])C(=O)O[H].O1C(C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])[H])=NC(C2C([H])=C([H])C([H])=C([H])C=2[H])=N1
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| InChi Key |
RBZIGQJSMCOHSS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H19N3O.C6H8O7/c1-3-17(4-2)11-10-13-15-14(16-18-13)12-8-6-5-7-9-12;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-9H,3-4,10-11H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
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| Chemical Name |
N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine;2-hydroxypropane-1,2,3-tricarboxylic 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: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
DMSO: ≥ 100 mg/mL (228.60 mM)
H2O: 14.29 mg/mL (32.67 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.72 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 (5.72 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.72 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 28 mg/mL (64.01 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2860 mL | 11.4301 mL | 22.8603 mL | |
| 5 mM | 0.4572 mL | 2.2860 mL | 4.5721 mL | |
| 10 mM | 0.2286 mL | 1.1430 mL | 2.2860 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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