Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H12N4.H2O4S |
| Molecular Weight | 238.265 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.C1N2CN3CN1CN(C2)C3
InChI
InChIKey=CCCDIBJJOMJPQI-UHFFFAOYSA-N
InChI=1S/C6H12N4.H2O4S/c1-7-2-9-4-8(1)5-10(3-7)6-9;1-5(2,3)4/h1-6H2;(H2,1,2,3,4)
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| 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 Date1967 |
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 |
|
1 g single, oral Recommended |
healthy, 24-65 |
|
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 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 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 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 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 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 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Activation of the Rac-binding partner FHOD1 induces actin stress fibers via a ROCK-dependent mechanism. | 2003-10-03 |
|
| Formins: signaling effectors for assembly and polarization of actin filaments. | 2003-07-01 |
|
| Adducts of hexamethylenetetramine with ferrocenecarboxylic acid and ferrocene-1,1'-dicarboxylic acid: multiple disorder in space groups Fmm2 and Cmcm. | 2003-07 |
|
| Gremlin is the BMP antagonist required for maintenance of Shh and Fgf signals during limb patterning. | 2003-07 |
|
| The Formin family protein, formin homolog overexpressed in spleen, interacts with the insulin-responsive aminopeptidase and profilin IIa. | 2003-07 |
|
| Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody. | 2003-06-20 |
|
| Prognostic significance of microvascular thrombosis in donor kidney allograft biopsies. | 2003-06-15 |
|
| A locus for asphyxiating thoracic dystrophy, ATD, maps to chromosome 15q13. | 2003-06 |
|
| Two bis(ammonium) 1,5-naphthalenedisulfonate salts. | 2003-06 |
|
| Structural changes of hexamethylenetetramine and undecanedioic acid co-crystal (HMT-C11) as a function of the temperature. | 2003-06 |
|
| [Quantitative assessment of the biological activity of chemicals by soil microbial associations]. | 2003-05-21 |
|
| Glomerular lesions in dogs infected with Leishmania organisms. | 2003-05 |
|
| Measuring gluconeogenesis using a low dose of 2H2O: advantage of isotope fractionation during gas chromatography. | 2003-05 |
|
| AgC(CN)3-based coordination polymers. | 2003-04-21 |
|
| Syntheses of two new 1D and 3D networks of Cu(II) and Co(II) using malonate and urotropine as bridging ligands: crystal structures and magnetic studies. | 2003-04-21 |
|
| Detection of sugar syrups in apple juice by delta(2)H per thousand and delta(13)C per thousand analysis of hexamethylenetetramine prepared from fructose. | 2003-03-26 |
|
| ForC, a novel type of formin family protein lacking an FH1 domain, is involved in multicellular development in Dictyostelium discoideum. | 2003-02-15 |
|
| Crystallographic analysis of the thermal motion of the inclusion complex of cyclomaltoheptaose (beta-cyclodextrin) with hexamethylenetetramine. | 2003-02-07 |
|
| Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine. | 2003-02 |
|
| (1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines. | 2003-02 |
|
| Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry. | 2003-02 |
|
| Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms. | 2003-01-30 |
|
| Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water. | 2002-12-26 |
|
| A Formin Homology protein and a profilin are required for cytokinesis and Arp2/3-independent assembly of cortical microfilaments in C. elegans. | 2002-12-23 |
|
| Invasive Aspergillosis in Italian AIDS patients. | 2002-12 |
|
| Formin-2, polyploidy, hypofertility and positioning of the meiotic spindle in mouse oocytes. | 2002-12 |
|
| A simple method for the specific detection of Ren-1 renin. | 2002-12 |
|
| Syntheses and characterizations of copper(II) polymeric complexes constructed from 1,2,4,5-benzenetetracarboxylic acid. | 2002-11-18 |
|
| A comparative evaluation of sealing ability of rootcanal sealers. | 2002-11-08 |
|
| Hexamethylenetetramine-4-nitrocatechol-water (1/2/1). | 2002-11 |
|
| Degeneration of Pick bodies visualized by methenamine-silver staining and immunohistochemistry. | 2002-09 |
|
| Dipole-dipole coupling constant for a directly bonded CH pair--a carbon-13 relaxation study. | 2002-08 |
|
| Value of urinary prophylaxis with methenamine in gynecologic surgery. | 2002-08 |
|
| Formins initiate new actin filaments. | 2002-08 |
|
| An actin nucleation mechanism mediated by Bni1 and profilin. | 2002-08 |
|
| Role of formins in actin assembly: nucleation and barbed-end association. | 2002-07-26 |
|
| Monolithic scavenger resins by amine functionalizations of poly(4-vinylbenzyl chloride-co-divinylbenzene) PolyHIPE materials. | 2002-07-25 |
|
| Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid. | 2002-06 |
|
| Primary evaluation of methenamine as a NPN compound with probable effects on increasing ruminal escaped protein. | 2002-06 |
|
| Mutational analysis of human profilin I reveals a second PI(4,5)-P2 binding site neighbouring the poly(L-proline) binding site. | 2002-05-28 |
|
| Identification of interaction partners of the cytosolic polyproline region of CD95 ligand (CD178). | 2002-05-22 |
|
| Vibrational frequencies and structural determinations of hexamethylenetetraamine. | 2002-05 |
|
| Ground-glass hepatocytes in fibrinogen storage disease in Japanese Black calves. | 2002-04-12 |
|
| Comparison of staining methods and a nested PCR assay to detect Histoplasma capsulatum in tissue sections. | 2002-04 |
|
| Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast. | 2002-03 |
|
| Effects of instrumentation, irrigation and dressing with calcium hydroxide on infection in pulpless teeth with periapical bone lesions. | 2002-01 |
|
| Biodegradation of formaldehyde and its derivatives in industrial wastewater with methylotrophic yeast Hansenula polymorpha and with the yeast-bioaugmented activated sludge. | 2002 |
|
| Genes and proteins in renal development. | 2002 |
|
| Methenamine hippurate for preventing urinary tract infections. | 2002 |
|
| The evolutionary history of effectors downstream of Cdc42 and Rac. | 2002 |
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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| Record UNII |
0373WW6GZQ
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| Record Status |
Validated (UNII)
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| Record Version |
|
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Preferred Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
| Code System | Code | Type | Description | ||
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DBSALT002246
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19267-18-6
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NON-SPECIFIC STOICHIOMETRY | |||
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0373WW6GZQ
Created by
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22165885
Created by
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |