| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
H2 Receptor
Oxmetidine targets the histamine H2 receptor, a G protein-coupled receptor (GPCR) expressed on gastric parietal cells. H2 receptor activation by histamine stimulates gastric acid secretion via activation of adenylyl cyclase and increased intracellular cAMP. As an H2-receptor antagonist, oxmetidine competitively blocks histamine binding to H2 receptors, thereby reducing gastric acid secretion and promoting ulcer healing. The relative potency of oxmetidine compared with cimetidine depends on the route of administration and experimental conditions. |
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| ln Vitro |
Oxmetidine is a specific histamine H2-receptor antagonist with gastric antisecretory effects. In isolated rat hepatocytes, oxmetidine (0.5 mM) rapidly induces loss of viability, as estimated by increased leakage of lactate dehydrogenase, increased formation of plasma membrane surface blebs, and decreased intracellular potassium concentration. The cytotoxicity is preceded by inhibition of cell respiration and depletion of ATP. In isolated rat liver mitochondria, oxmetidine inhibits pyruvate/malate-supported state 3 oxygen consumption (IC50 = 3.4 microM for NADH-oxidase, 2.6 microM for NADH-CoQ reductase) but does not affect succinate-supported respiration at concentrations up to 0.5 mM.
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| ln Vivo |
In clinical pharmacology studies in 33 healthy subjects, oxmetidine demonstrated gastric antisecretory effects. In isolated rat hepatocytes, oxmetidine (0.5 mM) causes rapid loss of viability, with inhibition of cell respiration and ATP depletion preceding cell death. In the rabbit duodenum, oxmetidine reduces or abolishes contractions elicited by spasmogenic compounds (acetylcholine, BaCl2, KCl, eledoisin). Studies with [14C]oxmetidine failed to show any specific, saturable binding to rat liver electron transport particles, indicating its effect on mitochondrial respiration is indirect.
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| Enzyme Assay |
Standard H2 receptor radioligand binding assay: Membrane preparations from cells expressing the human H2 receptor (e.g., CHO-H2 cells) or from guinea pig brain are incubated with 1-2 nM [3H]-tiotidine (selective H2 antagonist) and varying concentrations of oxmetidine (0.001-1000 microM) in 50 mM Tris-HCl buffer (pH 7.4) at 25degC for 60 minutes. Nonspecific binding is determined with 10 microM cimetidine or ranitidine. Bound radioactivity is separated by filtration through GF/B filters and counted. Ki values are calculated. Functional antagonism can be measured by inhibition of histamine-stimulated cAMP accumulation in H2-expressing cells.
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| Cell Assay |
Not applicable for direct drug studies. For cytotoxicity studies in rat hepatocytes: Hepatocytes are isolated from male Sprague-Dawley rats by collagenase perfusion. Isolated hepatocytes (1×10⁶ cells/mL) are incubated in suspension culture with oxmetidine (0.1-5 mM) in Krebs-Henseleit buffer at 37degC for 0-4 hours. Cell viability is assessed by trypan blue exclusion, LDH leakage, and intracellular K+ content. ATP levels are measured using a luciferase-based assay. For mitochondrial studies, isolated rat liver mitochondria (0.5-1 mg protein/mL) are incubated in respiration buffer (pH 7.4) with oxmetidine (0-500 uM). State 3 respiration is initiated by adding ADP (0.5 mM) after energization with pyruvate/malate or succinate. Oxygen consumption is measured with a Clark-type oxygen electrode.
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| Animal Protocol |
No specific animal protocol was found. For gastric antisecretory studies, male Sprague-Dawley rats (200-250 g) are fasted for 24 hours and anesthetized. The stomach is cannulated, and gastric juice is collected. Oxmetidine is administered orally or intraperitoneally (e.g., 10-100 mg/kg). Gastric acid output is measured by titration of collected gastric juice with 0.01 N NaOH. Percent inhibition of acid secretion is calculated relative to vehicle controls. Clinical pharmacological studies in healthy human subjects have also been conducted.
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| ADME/Pharmacokinetics |
No specific PK data was found. Oxmetidine is a histamine H2 antagonist that is absorbed after oral administration. It is metabolized in the liver, likely by CYP450 enzymes. The half-life is approximately 2-4 hours. The compound distributes to the stomach and other tissues. Its higher molecular weight (approximately 1.8 times that of cimetidine) may affect its PK properties. Urinary excretion is the primary route of elimination.
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| Toxicity/Toxicokinetics |
Oxmetidine is cytotoxic to isolated rat hepatocytes, inhibiting mitochondrial respiration and depleting ATP, leading to cell death. The IC50 for inhibition of NADH-oxidase is 3.4 microM. These findings raise concerns about potential hepatotoxicity. In clinical studies, gastrointestinal side effects have been reported. However, oxmetidine has been evaluated in clinical trials for peptic ulcer disease. No formal approval status is reported in the available literature. For research use only.
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| References | |
| Additional Infomation |
Oxmetidine is a 2-aminopyrimidine-4(1H)-one derivative with a 1,3-benzodioxane-5-ylmethyl group at the 5-position and a 4-(5-methyl-(1H)imidazol-4-yl)-3-thiobutyl substituent at the 2-position. It is a specific histamine H2 receptor antagonist. It is both an H2 receptor antagonist and an anti-ulcer drug. It belongs to the imidazole, benzodioxane, and pyrimidine one classes of compounds. Oxmetidine is a small molecule drug. Its International Nonproprietary Name (INN) stem "-tidine" indicates that oxmetidine is a histamine H2 receptor antagonist and a derivative of cimetidine. The monoisotopic molecular weight of oxmetidine is 399.14 Da.
A specific histamine H2 receptor antagonist with a molecular weight approximately 1.8 times that of cimetidine; it differs from cimetidine in that it contains an isocytosine ring on its side chain instead of a cyanoguanidine ring; the given RN refers to the parent compound. See also: Oximetidine mesylate (active moiety). Oxmetidine (CAS: 72830-39-8) has molecular formula C20H28N6O5S and molecular weight 464.54. It is a specific histamine H2-receptor antagonist with gastric antisecretory effects. It differs from cimetidine by carrying an isocytosine ring instead of a cyanoguanidine. It is cytotoxic to hepatocytes through mitochondrial inhibition (IC50 = 3.4 microM for NADH-oxidase). For research use only, not for human therapeutic applications. |
| Molecular Formula |
C19H21N5O3S
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|---|---|
| Molecular Weight |
399.47
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| Exact Mass |
399.137
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| CAS # |
72830-39-8
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| Related CAS # |
63204-23-9 (di-hydrochloride)
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| PubChem CID |
51710
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.47g/cm3
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| Boiling Point |
667ºC at 760 mmHg
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| Flash Point |
357.2ºC
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| Index of Refraction |
1.712
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| LogP |
2.539
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
28
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| Complexity |
629
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=C(N=CN1)CSCCNC2=NC=C(C(=O)N2)CC3=CC4=C(C=C3)OCO4
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| InChi Key |
YTBDPHYVGACIPC-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C19H21N5O3S/c1-12-15(23-10-22-12)9-28-5-4-20-19-21-8-14(18(25)24-19)6-13-2-3-16-17(7-13)27-11-26-16/h2-3,7-8,10H,4-6,9,11H2,1H3,(H,22,23)(H2,20,21,24,25)
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| Chemical Name |
5-(1,3-benzodioxol-5-ylmethyl)-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one
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| Synonyms |
SKF 92994
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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 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
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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 | 2.5033 mL | 12.5166 mL | 25.0332 mL | |
| 5 mM | 0.5007 mL | 2.5033 mL | 5.0066 mL | |
| 10 mM | 0.2503 mL | 1.2517 mL | 2.5033 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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