Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H6O6S.C6H12N4 |
| Molecular Weight | 358.37 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1N2CN3CN1CN(C2)C3.OC(=O)C4=C(O)C=CC(=C4)S(O)(=O)=O
InChI
InChIKey=AFOTXNKRSJVXBS-UHFFFAOYSA-N
InChI=1S/C7H6O6S.C6H12N4/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
| 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 |
| 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 |
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 |
|---|---|---|
| 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 |
|
| 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 |
|
| Formins initiate new actin filaments. | 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 |
|
| Ground-glass hepatocytes in fibrinogen storage disease in Japanese Black calves. | 2002 Feb-Apr |
|
| Effects of instrumentation, irrigation and dressing with calcium hydroxide on infection in pulpless teeth with periapical bone lesions. | 2002 Jan |
|
| A comparative evaluation of sealing ability of rootcanal sealers. | 2002 Jan-Mar |
|
| Monolithic scavenger resins by amine functionalizations of poly(4-vinylbenzyl chloride-co-divinylbenzene) PolyHIPE materials. | 2002 Jul 25 |
|
| Role of formins in actin assembly: nucleation and barbed-end association. | 2002 Jul 26 |
|
| Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid. | 2002 Jun |
|
| Primary evaluation of methenamine as a NPN compound with probable effects on increasing ruminal escaped protein. | 2002 Jun |
|
| Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast. | 2002 Mar |
|
| Vibrational frequencies and structural determinations of hexamethylenetetraamine. | 2002 May |
|
| Identification of interaction partners of the cytosolic polyproline region of CD95 ligand (CD178). | 2002 May 22 |
|
| Mutational analysis of human profilin I reveals a second PI(4,5)-P2 binding site neighbouring the poly(L-proline) binding site. | 2002 May 28 |
|
| Hexamethylenetetramine-4-nitrocatechol-water (1/2/1). | 2002 Nov |
|
| Syntheses and characterizations of copper(II) polymeric complexes constructed from 1,2,4,5-benzenetetracarboxylic acid. | 2002 Nov 18 |
|
| Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms. | 2002 Nov-Dec |
|
| Degeneration of Pick bodies visualized by methenamine-silver staining and immunohistochemistry. | 2002 Sep |
|
| AgC(CN)3-based coordination polymers. | 2003 Apr 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 Apr 21 |
|
| Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine. | 2003 Feb |
|
| (1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines. | 2003 Feb |
|
| Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry. | 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 |
|
| 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 |
|
| Gremlin is the BMP antagonist required for maintenance of Shh and Fgf signals during limb patterning. | 2003 Jul |
|
| The Formin family protein, formin homolog overexpressed in spleen, interacts with the insulin-responsive aminopeptidase and profilin IIa. | 2003 Jul |
|
| Formins: signaling effectors for assembly and polarization of actin filaments. | 2003 Jul 1 |
|
| A locus for asphyxiating thoracic dystrophy, ATD, maps to chromosome 15q13. | 2003 Jun |
|
| Two bis(ammonium) 1,5-naphthalenedisulfonate salts. | 2003 Jun |
|
| Structural changes of hexamethylenetetramine and undecanedioic acid co-crystal (HMT-C11) as a function of the temperature. | 2003 Jun |
|
| Prognostic significance of microvascular thrombosis in donor kidney allograft biopsies. | 2003 Jun 15 |
|
| Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody. | 2003 Jun 20 |
|
| 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 Mar 26 |
|
| Glomerular lesions in dogs infected with Leishmania organisms. | 2003 May |
|
| Measuring gluconeogenesis using a low dose of 2H2O: advantage of isotope fractionation during gas chromatography. | 2003 May |
|
| [Quantitative assessment of the biological activity of chemicals by soil microbial associations]. | 2003 May-Jun |
|
| 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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Edited
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| Record UNII |
FIA8FFW7DP
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| Record Status |
Validated (UNII)
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| Record Version |
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |