Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C8H8O3.C6H12N4 |
| Molecular Weight | 292.3341 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc(cc1)C(C(=O)O)O.C1N2CN3CN1CN(C2)C3
InChI
InChIKey=UXNFIJPHRQEWRQ-UHFFFAOYSA-N
InChI=1S/C8H8O3.C6H12N4/c9-7(8(10)11)6-4-2-1-3-5-6;1-7-2-9-4-8(1)5-10(3-7)6-9/h1-5,7,9H,(H,10,11);1-6H2
| Molecular Formula | C6H12N4 |
| Molecular Weight | 140.1865 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C8H8O3 |
| Molecular Weight | 152.1476 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionCurator's Comment:: description was created based on several sources, including, http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/016151s025lbl.pdf
Curator's Comment:: description was created based on several sources, including, http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/016151s025lbl.pdf
Methenamine is an antibacterial agent for preventing recurrent urinary tract infection. It can be used as methenamine hippurate or methenamine mandelate preparations and is United States Food and Drug Administration-approved. Methenamine exerts its activity because it is hydrolyzed to formaldehyde in acid urine.
Originator
Approval Year
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | UREX Approved UseFOR URAMIT MB™: URAMIT MB™ is indicated for the treatment of symptoms of irritative voiding. Indicated for the relief of local symptoms, such as inflammation, hypermotility, and pain, which accompany lower urinary tract infections. Indicated for the relief of urinary tract symptoms caused by diagnostic procedures. Launch Date-7.8710399E10 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
34 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7076604/ |
1 g 2 times / day multiple, oral dose: 1 g route of administration: Oral experiment type: MULTIPLE co-administered: |
METHENAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
177 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7076604/ |
1 g 2 times / day multiple, oral dose: 1 g route of administration: Oral experiment type: MULTIPLE co-administered: |
METHENAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7076604/ |
1 g 2 times / day multiple, oral dose: 1 g route of administration: Oral experiment type: MULTIPLE co-administered: |
METHENAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 g 2 times / day multiple, oral Recommended Dose: 1 g, 2 times / day Route: oral Route: multiple Dose: 1 g, 2 times / day Sources: |
healthy, 24-65 n = 10 Health Status: healthy Age Group: 24-65 Sex: M+F Population Size: 10 Sources: |
|
1 g single, oral Recommended |
healthy, 24-65 n = 10 Health Status: healthy Age Group: 24-65 Sex: M+F Population Size: 10 Sources: |
|
8 g 1 times / day multiple, oral Overdose Dose: 8 g, 1 times / day Route: oral Route: multiple Dose: 8 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Urinary tract infections Sources: |
Other AEs: Bladder irritation, Micturition painful... Other AEs: Bladder irritation Sources: Micturition painful Micturition frequency Albuminuria Hematuria |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Albuminuria | 8 g 1 times / day multiple, oral Overdose Dose: 8 g, 1 times / day Route: oral Route: multiple Dose: 8 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Urinary tract infections Sources: |
|
| Bladder irritation | 8 g 1 times / day multiple, oral Overdose Dose: 8 g, 1 times / day Route: oral Route: multiple Dose: 8 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Urinary tract infections Sources: |
|
| Hematuria | 8 g 1 times / day multiple, oral Overdose Dose: 8 g, 1 times / day Route: oral Route: multiple Dose: 8 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Urinary tract infections Sources: |
|
| Micturition frequency | 8 g 1 times / day multiple, oral Overdose Dose: 8 g, 1 times / day Route: oral Route: multiple Dose: 8 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Urinary tract infections Sources: |
|
| Micturition painful | 8 g 1 times / day multiple, oral Overdose Dose: 8 g, 1 times / day Route: oral Route: multiple Dose: 8 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Urinary tract infections Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Simulated cometary matter as a test for enantiomer separating chromatography for use on comet 46P/Wirtanen. | 2001 |
|
| The unpredictability of seal after post space preparation: a fluid transport study. | 2001 Apr |
|
| Comparative effects of aging in men and women on the properties of the arterial tree. | 2001 Apr |
|
| Disseminated histoplasmosis presenting as pyoderma gangrenosum-like lesions in a patient with acquired immunodeficiency syndrome. | 2001 Aug |
|
| The lock-in phase in the urotropine-sebacic acid system. | 2001 Aug |
|
| Antimicrobial activity of four root canal sealers against endodontic pathogens. | 2001 Dec |
|
| Effects of chlorhexidine gluconate as an endodontic irrigant on the apical seal: short-term results. | 2001 Dec |
|
| Post retention: the effect of sequence of post-space preparation, cementation time, and different sealers. | 2001 Dec |
|
| Evaluation of the genotoxicity of zinc oxide eugenol-based, calcium hydroxide-based, and epoxy resin-based root canal sealers by comet assay. | 2001 Dec |
|
| Plaque-like structures and arteriosclerotic changes in "diffuse neurofibrillary tangles with calcification" (DNTC). | 2001 Dec |
|
| The 143 and 300 K polymorphs of hexamethylenetetraminium 2,4-dinitrophenolate monohydrate. | 2001 Dec |
|
| Failure of ureteric bud invasion: a new model of renal agenesis in mice. | 2001 Dec |
|
| Septum formation in Aspergillus nidulans. | 2001 Dec |
|
| The formin/diaphanous-related protein, FHOS, interacts with Rac1 and activates transcription from the serum response element. | 2001 Dec 7 |
|
| [An 84-year-old woman with progressive mental deterioration and abnormal behavior]. | 2001 Feb |
|
| Effect of ultrasonic vibration and various sealer and cement combinations on titanium post removal. | 2001 Jan |
|
| The histological effects of four endodontic sealers implanted in the oral mucosa: submucous injection versus implant in polyethylene tubes. | 2001 Jul |
|
| Toward designed assembly of microporous coordination networks constructed from silver(I)-hexamethylenetetramine layers. | 2001 Jul 2 |
|
| Setting times for endodontic sealers under clinical usage and in vitro conditions. | 2001 Jun |
|
| Formaldehyde release from ground root canal sealer in vitro. | 2001 Jun |
|
| A distinctive pediatric renal neoplasm characterized by epithelioid morphology, basement membrane production, focal HMB45 immunoreactivity, and t(6;11)(p21.1;q12) chromosome translocation. | 2001 Jun |
|
| A primary observation on the preparation and obturation of oval canals. | 2001 Mar |
|
| Application of fluorescent in situ hybridization for specific diagnosis of Pneumocystis carinii pneumonia in foals and pigs. | 2001 May |
|
| Amyloid beta protein deposition in patients with frontotemporal lobar degeneration: relationship to age and apolipoprotein E genotype. | 2001 May 25 |
|
| Oral exfoliative cytology in the diagnosis of paracoccidioidomycosis. | 2001 May-Jun |
|
| In vitro longitudinal assessment of coronal discoloration from endodontic sealers. | 2001 Nov |
|
| Modification of the levels of polyphenols in wort and beer by addition of hexamethylenetetramine or sulfite during mashing. | 2001 Nov |
|
| Determination of the enrichment of the hydrogen bound to carbon 5 of glucose on 2H2O administration. | 2001 Oct 15 |
|
| mDia-interacting protein acts downstream of Rho-mDia and modifies Src activation and stress fiber formation. | 2001 Oct 19 |
|
| A comparison of the effect of three endodontic sealers on adherence of mouse peritoneal macrophages. | 2001 Sep |
|
| Biodegradation of formaldehyde and its derivatives in industrial wastewater with methylotrophic yeast Hansenula polymorpha and with the yeast-bioaugmented activated sludge. | 2002 |
|
| The evolutionary history of effectors downstream of Cdc42 and Rac. | 2002 |
|
| Comparison of staining methods and a nested PCR assay to detect Histoplasma capsulatum in tissue sections. | 2002 Apr |
|
| Dipole-dipole coupling constant for a directly bonded CH pair--a carbon-13 relaxation study. | 2002 Aug |
|
| An actin nucleation mechanism mediated by Bni1 and profilin. | 2002 Aug |
|
| Invasive Aspergillosis in Italian AIDS patients. | 2002 Dec |
|
| A Formin Homology protein and a profilin are required for cytokinesis and Arp2/3-independent assembly of cortical microfilaments in C. elegans. | 2002 Dec 23 |
|
| Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water. | 2002 Dec 26 |
|
| Influence of calcium hydroxide dressing on the obturation of simulated lateral canals. | 2002 Feb |
|
| Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast. | 2002 Jan |
|
| Evaluation of lectin staining in the diagnosis of fungal keratitis in an experimental rabbit model. | 2002 Jan 25 |
|
| A comparative evaluation of sealing ability of rootcanal sealers. | 2002 Jan-Mar |
|
| Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid. | 2002 Jun |
|
| Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms. | 2002 Nov-Dec |
|
| AgC(CN)3-based coordination polymers. | 2003 Apr 21 |
|
| ForC, a novel type of formin family protein lacking an FH1 domain, is involved in multicellular development in Dictyostelium discoideum. | 2003 Feb 15 |
|
| Crystallographic analysis of the thermal motion of the inclusion complex of cyclomaltoheptaose (beta-cyclodextrin) with hexamethylenetetramine. | 2003 Feb 7 |
|
| Adducts of hexamethylenetetramine with ferrocenecarboxylic acid and ferrocene-1,1'-dicarboxylic acid: multiple disorder in space groups Fmm2 and Cmcm. | 2003 Jul |
|
| Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody. | 2003 Jun 20 |
|
| Glomerular lesions in dogs infected with Leishmania organisms. | 2003 May |
Patents
Sample Use Guides
One tablet (1 g) twice daily for adults and children over 12 years of age. One-half tablet or one tablet (0.5 or 1 g) twice daily for children 6 to 12 years of age.
Route of Administration:
Oral
The antibacterial activity of methenamine and two of its organic acid salts was compared by continuous turbidimetric monitoring of static cultures exposed to the drugs and in an in vitro model of the treatment of bacterial cystitis. At pH 5.5, concentrations of 32 to 125 mg methenamine per 1 caused some inhibition of bacterial growth (Klebsiella aerogenes), but 250 to 500 mg/l were needed to suppress growth overnight. Methenamine hippurate was found to be less active than methenamine itself, whereas methenamine mandelate was as active as the parent compound.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 20:58:34 UTC 2021
by
admin
on
Fri Jun 25 20:58:34 UTC 2021
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| Record UNII |
695N30CINR
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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NCI_THESAURUS |
C255
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| Code System | Code | Type | Description | ||
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M7308
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PRIMARY | Merck Index | ||
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11478
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SUB03216MIG
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1409604
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PRIMARY | USP-RS | ||
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Methenamine Mandelate
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DBSALT001271
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587-23-5
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209-597-4
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695N30CINR
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161623
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C77070
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
