Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H12N4.C6H8O7 |
| Molecular Weight | 332.3098 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1N2CN3CN1CN(C2)C3.OC(=O)CC(O)(CC(O)=O)C(O)=O
InChI
InChIKey=UAMIYHCXAONPMG-UHFFFAOYSA-N
InChI=1S/C6H12N4.C6H8O7/c1-7-2-9-4-8(1)5-10(3-7)6-9;7-3(8)1-6(13,5(11)12)2-4(9)10/h1-6H2;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
| 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 | C6H8O7 |
| Molecular Weight | 192.1235 |
| 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 |
|---|---|---|
| The unpredictability of seal after post space preparation: a fluid transport study. | 2001 Apr |
|
| The lock-in phase in the urotropine-sebacic acid system. | 2001 Aug |
|
| Evaluation of the genotoxicity of zinc oxide eugenol-based, calcium hydroxide-based, and epoxy resin-based root canal sealers by comet assay. | 2001 Dec |
|
| The formin/diaphanous-related protein, FHOS, interacts with Rac1 and activates transcription from the serum response element. | 2001 Dec 7 |
|
| Localization of a mammalian homolog of diaphanous, mDia1, to the mitotic spindle in HeLa cells. | 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 |
|
| 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 |
|
| Perspectives of a long-time observer. | 2001 Mar 1 |
|
| In vitro longitudinal assessment of coronal discoloration from endodontic sealers. | 2001 Nov |
|
| 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 |
|
| 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 |
|
| Cytotoxicity of resin-, zinc oxide-eugenol-, and calcium hydroxide-based root canal sealers on human periodontal ligament cells and permanent V79 cells. | 2002 Feb |
|
| Formin' actin filament bundles. | 2002 Feb |
|
| 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 |
|
| 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 |
|
| Syntheses and characterizations of copper(II) polymeric complexes constructed from 1,2,4,5-benzenetetracarboxylic acid. | 2002 Nov 18 |
|
| Degeneration of Pick bodies visualized by methenamine-silver staining and immunohistochemistry. | 2002 Sep |
|
| 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 |
|
| A locus for asphyxiating thoracic dystrophy, ATD, maps to chromosome 15q13. | 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 |
|
| [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
by
admin
on
Edited
Sat Dec 17 22:21:47 UTC 2022
by
admin
on
Sat Dec 17 22:21:47 UTC 2022
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| Record UNII |
Q4U8R77416
|
| Record Status |
Validated (UNII)
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| Record Version |
|
-
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251-933-7
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34317-08-3
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DBSALT002250
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118640
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DTXSID60187881
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