Details
Stereochemistry | RACEMIC |
Molecular Formula | C8H8O3.C6H12N4 |
Molecular Weight | 292.3336 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1N2CN3CN1CN(C2)C3.OC(C(O)=O)C4=CC=CC=C4
InChI
InChIKey=UXNFIJPHRQEWRQ-UHFFFAOYSA-N
InChI=1S/C8H8O3.C6H12N4/c9-7(8(10)11)6-4-2-1-3-5-6;1-7-2-9-4-8(1)5-10(3-7)6-9/h1-5,7,9H,(H,10,11);1-6H2
Molecular Formula | C8H8O3 |
Molecular Weight | 152.1473 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
|
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 |
---|---|---|
Comparative effects of aging in men and women on the properties of the arterial tree. | 2001 Apr |
|
Developmental changes in the fine structure and histochemical properties of mucous cells in the parotid gland of the infant Japanese macaque. | 2001 Dec |
|
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 |
|
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 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 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 |
|
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 |
|
Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast. | 2002 Jan |
|
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 |
|
Vibrational frequencies and structural determinations of hexamethylenetetraamine. | 2002 May |
|
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 |
|
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 |
|
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 |
|
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 |
|
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
Mon Mar 31 18:02:00 GMT 2025
by
admin
on
Mon Mar 31 18:02:00 GMT 2025
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Record UNII |
695N30CINR
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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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NCI_THESAURUS |
C255
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m7308
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11478
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SUB03216MIG
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Methenamine Mandelate
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DBSALT001271
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587-23-5
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695N30CINR
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209-597-4
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161623
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100000088516
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C77070
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1409604
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |