Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H12N4 |
Molecular Weight | 140.1863 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1N2CN3CN1CN(C2)C3
InChI
InChIKey=VKYKSIONXSXAKP-UHFFFAOYSA-N
InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
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 |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/24689705Curator's Comment: description was created based on several sources, including, http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/016151s025lbl.pdf
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24689705
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 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 |
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Simulated cometary matter as a test for enantiomer separating chromatography for use on comet 46P/Wirtanen. | 2001 |
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The unpredictability of seal after post space preparation: a fluid transport study. | 2001 Apr |
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Disseminated histoplasmosis presenting as pyoderma gangrenosum-like lesions in a patient with acquired immunodeficiency syndrome. | 2001 Aug |
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The lock-in phase in the urotropine-sebacic acid system. | 2001 Aug |
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Developmental changes in the fine structure and histochemical properties of mucous cells in the parotid gland of the infant Japanese macaque. | 2001 Dec |
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Antimicrobial activity of four root canal sealers against endodontic pathogens. | 2001 Dec |
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Effects of chlorhexidine gluconate as an endodontic irrigant on the apical seal: short-term results. | 2001 Dec |
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Post retention: the effect of sequence of post-space preparation, cementation time, and different sealers. | 2001 Dec |
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Evaluation of the genotoxicity of zinc oxide eugenol-based, calcium hydroxide-based, and epoxy resin-based root canal sealers by comet assay. | 2001 Dec |
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Plaque-like structures and arteriosclerotic changes in "diffuse neurofibrillary tangles with calcification" (DNTC). | 2001 Dec |
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The 143 and 300 K polymorphs of hexamethylenetetraminium 2,4-dinitrophenolate monohydrate. | 2001 Dec |
|
Wnt/Frizzled activation of Rho regulates vertebrate gastrulation and requires a novel Formin homology protein Daam1. | 2001 Dec 28 |
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The formin/diaphanous-related protein, FHOS, interacts with Rac1 and activates transcription from the serum response element. | 2001 Dec 7 |
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Effect of ultrasonic vibration and various sealer and cement combinations on titanium post removal. | 2001 Jan |
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Setting times for endodontic sealers under clinical usage and in vitro conditions. | 2001 Jun |
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Formaldehyde release from ground root canal sealer in vitro. | 2001 Jun |
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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 |
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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 |
|
Genes and proteins in renal development. | 2002 |
|
The evolutionary history of effectors downstream of Cdc42 and Rac. | 2002 |
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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 |
|
Formin' actin filament bundles. | 2002 Feb |
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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 |
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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 |
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Cell polarity: following formin function. | 2002 Jan 8 |
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Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid. | 2002 Jun |
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Primary evaluation of methenamine as a NPN compound with probable effects on increasing ruminal escaped protein. | 2002 Jun |
|
Vibrational frequencies and structural determinations of hexamethylenetetraamine. | 2002 May |
|
Hexamethylenetetramine-4-nitrocatechol-water (1/2/1). | 2002 Nov |
|
Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms. | 2002 Nov-Dec |
|
(1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines. | 2003 Feb |
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Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry. | 2003 Feb |
|
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 |
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Formins: signaling effectors for assembly and polarization of actin filaments. | 2003 Jul 1 |
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Structural changes of hexamethylenetetramine and undecanedioic acid co-crystal (HMT-C11) as a function of the temperature. | 2003 Jun |
|
Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody. | 2003 Jun 20 |
|
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
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7028634
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
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Record UNII |
J50OIX95QV
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 520.2280
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WHO-VATC |
QJ01XX55
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EPA PESTICIDE CODE |
45501
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WHO-VATC |
QJ01XX05
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CFR |
21 CFR 176.170
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WHO-VATC |
QR01AX01
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WHO-ATC |
J01XX05
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NCI_THESAURUS |
C255
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WHO-ATC |
R01AX01
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JECFA EVALUATION |
INS-239
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CODEX ALIMENTARIUS (GSFA) |
INS-239
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LIVERTOX |
NBK567340
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C61841
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DB06799
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Methenamine
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m7308
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HEXAMETHYLENETETRAMINE
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SUB08845MIG
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100-97-0
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CHEMBL1201270
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26346
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4101
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202-905-8
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1409003
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DTXSID6020692
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100000092106
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403347
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |