| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
|
||
| 500mg |
|
||
| Other Sizes |
| Targets |
Methenamine hippurate targets urinary tract pathogens through the release of formaldehyde in acidic urine. Formaldehyde is a broad-spectrum antimicrobial agent that denatures bacterial proteins and nucleic acids. The hippurate component improves the compound's solubility and effectiveness. The compound is effective against most common urinary tract pathogens, including Escherichia coli, Proteus species, and Enterococcus species. It does not have a specific molecular target but acts through a general antimicrobial mechanism.
|
|---|---|
| ln Vitro |
Formaldehyde is released by the urinary antibacterial agent hexamine hippurate, which is eliminated in the urine. At pH 5 to 6, urotropine hippurate exhibits strong in vitro action against Escherichia coli, Staphylococcus aureus, Aerobacter, Pseudomonas aeruginosa, and Proteus vulgaris. It also exhibits activity against Klebsiella pneumoniae. The consequences of Lebsiella and Proteus species are diverse. Staphylococcus aureus, Escherichia coli, and pseudomonas aeruginosa. Hemolytic Streptococcus and Staphylococcus aureus at pH 7.4. Compared to methenamine, hippuric acid, or sulfadiazine alone, this impact is more potent [1].
In vitro, Methenamine hippurate demonstrates antibacterial activity against a wide range of urinary tract pathogens. The compound is tested in vitro using broth microdilution or agar diffusion methods to determine MIC values against clinical isolates. The antimicrobial activity is dependent on the acidic pH of the urine, as formaldehyde release requires acidic conditions. These in vitro studies confirm the compound's efficacy against common urinary pathogens and support its clinical use. |
| ln Vivo |
In vivo, Methenamine hippurate is administered orally for the treatment and prophylaxis of lower urinary tract infections. Following oral administration, the compound is absorbed and excreted in the urine, where it hydrolyzes to release formaldehyde in acidic urine. The formaldehyde exerts a local antiseptic effect in the urinary tract. The compound is effective for long-term prophylactic use in patients with recurrent urinary tract infections. It is not effective in patients with alkaline urine.
|
| Enzyme Assay |
In vitro antimicrobial susceptibility testing for Methenamine hippurate is conducted using standard methods such as broth microdilution or agar diffusion. The compound is tested at concentrations ranging from 0.1-1000 µg/ml against urinary tract pathogens. MIC values are determined after 18-24 hours of incubation. The effect of urine pH on antimicrobial activity is assessed by testing at different pH values (typically pH 5.0-7.0). Quality control strains (e.g., E. coli ATCC 25922) are included. All assays include appropriate growth controls and reference antibiotics.
|
| Cell Assay |
In vitro cell-based assays for Methenamine hippurate are not typically conducted, as the compound acts through the release of formaldehyde, a general antimicrobial agent, rather than through a specific cellular target. However, cytotoxicity studies may be performed in mammalian cell lines to assess safety. Cells are treated with compound concentrations ranging from 0.1-1000 µg/ml for 24-72 hours, and cell viability is assessed using MTT assays. These studies help to establish the safety margin of the compound.
|
| Animal Protocol |
In vivo animal studies with Methenamine hippurate are conducted in animal models of urinary tract infection. The compound is administered orally at doses ranging from 10-100 mg/kg. Efficacy is assessed by measuring bacterial counts in urine and bladder tissue. The effect of urine pH on efficacy is evaluated by manipulating urine pH. Pharmacokinetic studies assess urinary excretion and formaldehyde release. Each group consists of 6-10 animals with appropriate controls (e.g., untreated infected animals).
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of Methenamine hippurate include good oral absorption from the gastrointestinal tract. Following absorption, the compound is rapidly excreted in the urine, where it achieves high concentrations. The hippurate component improves solubility and may affect the compound's pharmacokinetic profile. The compound hydrolyzes to formaldehyde in acidic urine (pH < 6), with the rate of hydrolysis increasing as pH decreases. The plasma half-life is relatively short. The compound does not achieve significant systemic concentrations of formaldehyde.
|
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Overview of Use During Lactation Methylamine can pass into breast milk in small amounts, and its use appears to be safe even during the nursing period for newborns. ◉ Effects on Breastfed Infants In one study, four newborns were allowed to breastfeed after their mothers took 1 gram of hippuric methylamine. No adverse reactions were reported. ◉ Effects on Lactation and Breast Milk As of the revision date, no relevant published information was found. Toxicological data for Methenamine hippurate indicate that it is generally well-tolerated at therapeutic doses. Common adverse effects include gastrointestinal upset, nausea, and rash. The compound is contraindicated in patients with renal insufficiency, severe dehydration, or gout. Formaldehyde release in the urine may cause bladder irritation at high doses. The compound is not recommended for long-term use in patients with hepatic impairment. Comprehensive safety data are available from clinical use. |
| References |
[1]. Forbes R, et al. ALternatives To prophylactic Antibiotics for the treatment of Recurrent urinary tract infection in women (ALTAR): study protocol for a multicentre, pragmatic, patient-randomised, non-inferiority trial. Trials. 2018;19(1):616. Published 20
[2]. Gibson GR. A clinical appraisal of methenamine hippurate in urinary tract infections. Med J Aust. 1970;1(4):167‐170. |
| Additional Infomation |
Methylhamine hippurate is an N-acylglycine that functions similarly to N-benzoylglycine. It is the hippurate salt form of methylamine, a prodrug and an inactive weak base that slowly hydrolyzes in acidic urine to ammonia and formaldehyde, a potent urinary tract disinfectant. Formaldehyde may exert its antibacterial effect through protein denaturation. Depending on the urine concentration, formaldehyde can exhibit bactericidal or bacteriostatic activity. The concentration of formaldehyde in urine depends on the pH, volume, and flow rate. Formaldehyde is antibacterial against both Gram-positive and Gram-negative bacteria. See also: Methylamine (containing the active moiety).
Methenamine hippurate is an approved therapeutic agent for the treatment and prophylaxis of lower urinary tract infections. It is an orally active urinary antiseptic that releases formaldehyde in acidic urine. The compound is effective against most common urinary tract pathogens and is used as an alternative to antibiotics for long-term prophylaxis. It is available as a generic medication. The hippurate salt form improves solubility and effectiveness compared to other methenamine salts. |
| Molecular Formula |
C₁₅H₂₁N₅O₃
|
|---|---|
| Molecular Weight |
319.36
|
| Exact Mass |
319.164
|
| CAS # |
5714-73-8
|
| PubChem CID |
21945
|
| Appearance |
Typically exists as solid at room temperature
|
| Boiling Point |
464.1ºC at 760mmHg
|
| Melting Point |
89-95ºC
|
| Flash Point |
234.5ºC
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
23
|
| Complexity |
282
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C(C1C([H])=C([H])C([H])=C([H])C=1[H])N([H])C([H])([H])C(=O)O[H].N12C([H])([H])N3C([H])([H])N(C([H])([H])N(C3([H])[H])C1([H])[H])C2([H])[H]
|
| Synonyms |
Methenamine hippurate; Methenamine hippurate
|
| 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 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)
|
| Solubility (In Vitro) |
H2O : ~100 mg/mL (~313.13 mM)
DMSO : ~25 mg/mL (~78.28 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (313.13 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1313 mL | 15.6563 mL | 31.3126 mL | |
| 5 mM | 0.6263 mL | 3.1313 mL | 6.2625 mL | |
| 10 mM | 0.3131 mL | 1.5656 mL | 3.1313 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
