Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H6O6S.C6H12N4.H2O |
| Molecular Weight | 376.386 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.C1N2CN3CN1CN(C2)C3.OC(=O)C4=C(O)C=CC(=C4)S(O)(=O)=O
InChI
InChIKey=LSLQJEMTDYAWAR-UHFFFAOYSA-N
InChI=1S/C7H6O6S.C6H12N4.H2O/c8-6-2-1-4(14(11,12)13)3-5(6)7(9)10;1-7-2-9-4-8(1)5-10(3-7)6-9;/h1-3,8H,(H,9,10)(H,11,12,13);1-6H2;1H2
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C7H6O6S |
| Molecular Weight | 218.184 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C6H12N4 |
| Molecular Weight | 140.1863 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| Comparative effects of aging in men and women on the properties of the arterial tree. | 2001 Apr |
|
| 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 |
|
| Wnt/Frizzled activation of Rho regulates vertebrate gastrulation and requires a novel Formin homology protein Daam1. | 2001 Dec 28 |
|
| 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 |
|
| Identification of a carboxyl-terminal diaphanous-related formin homology protein autoregulatory domain. | 2001 Jan 26 |
|
| 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 |
|
| 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 |
|
| mDia-interacting protein acts downstream of Rho-mDia and modifies Src activation and stress fiber formation. | 2001 Oct 19 |
|
| 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 |
|
| Value of urinary prophylaxis with methenamine in gynecologic surgery. | 2002 Aug |
|
| An actin nucleation mechanism mediated by Bni1 and profilin. | 2002 Aug |
|
| Invasive Aspergillosis in Italian AIDS patients. | 2002 Dec |
|
| Formin-2, polyploidy, hypofertility and positioning of the meiotic spindle in mouse oocytes. | 2002 Dec |
|
| A simple method for the specific detection of Ren-1 renin. | 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 |
|
| Formin' actin filament bundles. | 2002 Feb |
|
| Influence of calcium hydroxide dressing on the obturation of simulated lateral canals. | 2002 Feb |
|
| Delphilin: a novel PDZ and formin homology domain-containing protein that synaptically colocalizes and interacts with glutamate receptor delta 2 subunit. | 2002 Feb 1 |
|
| A 1:1 adduct of hexamethylenetetramine and 4-hydroxy-3-methoxybenzaldehyde. | 2002 Jan |
|
| Hexamethylenetetraminium 2,4,6-trinitrophenolate. | 2002 Jan |
|
| Evaluation of lectin staining in the diagnosis of fungal keratitis in an experimental rabbit model. | 2002 Jan 25 |
|
| Cell polarity: following formin function. | 2002 Jan 8 |
|
| Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid. | 2002 Jun |
|
| Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast. | 2002 Mar |
|
| Degeneration of Pick bodies visualized by methenamine-silver staining and immunohistochemistry. | 2002 Sep |
|
| Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine. | 2003 Feb |
|
| ForC, a novel type of formin family protein lacking an FH1 domain, is involved in multicellular development in Dictyostelium discoideum. | 2003 Feb 15 |
|
| A locus for asphyxiating thoracic dystrophy, ATD, maps to chromosome 15q13. | 2003 Jun |
|
| Two bis(ammonium) 1,5-naphthalenedisulfonate salts. | 2003 Jun |
|
| Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody. | 2003 Jun 20 |
|
| Measuring gluconeogenesis using a low dose of 2H2O: advantage of isotope fractionation during gas chromatography. | 2003 May |
|
| Activation of the Rac-binding partner FHOD1 induces actin stress fibers via a ROCK-dependent mechanism. | 2003 Oct 3 |
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
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admin
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Edited
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| Record UNII |
61CU4T79WM
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| Record Status |
Validated (UNII)
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| Record Version |
|
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DTXSID00209096
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56841785
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61CU4T79WM
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6033-39-2
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |