Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H16O4.2C6H12N4 |
| Molecular Weight | 480.6042 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1N2CN3CN1CN(C2)C3.C4N5CN6CN4CN(C5)C6.CC7(C)[C@H](CC[C@@]7(C)C(O)=O)C(O)=O
InChI
InChIKey=SPPRWKXUYGFXJY-YJGIZBEXSA-N
InChI=1S/C10H16O4.2C6H12N4/c1-9(2)6(7(11)12)4-5-10(9,3)8(13)14;2*1-7-2-9-4-8(1)5-10(3-7)6-9/h6H,4-5H2,1-3H3,(H,11,12)(H,13,14);2*1-6H2/t6-,10+;;/m1../s1
| 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 | C10H16O4 |
| Molecular Weight | 200.2316 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 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 |
|---|---|---|
| Simulated cometary matter as a test for enantiomer separating chromatography for use on comet 46P/Wirtanen. | 2001 |
|
| 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 |
|
| Antimicrobial activity of four root canal sealers against endodontic pathogens. | 2001 Dec |
|
| Septum formation in Aspergillus nidulans. | 2001 Dec |
|
| Wnt/Frizzled activation of Rho regulates vertebrate gastrulation and requires a novel Formin homology protein Daam1. | 2001 Dec 28 |
|
| The formin/diaphanous-related protein, FHOS, interacts with Rac1 and activates transcription from the serum response element. | 2001 Dec 7 |
|
| Effect of ultrasonic vibration and various sealer and cement combinations on titanium post removal. | 2001 Jan |
|
| 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 |
|
| Application of fluorescent in situ hybridization for specific diagnosis of Pneumocystis carinii pneumonia in foals and pigs. | 2001 May |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Delphilin: a novel PDZ and formin homology domain-containing protein that synaptically colocalizes and interacts with glutamate receptor delta 2 subunit. | 2002 Feb 1 |
|
| Ground-glass hepatocytes in fibrinogen storage disease in Japanese Black calves. | 2002 Feb-Apr |
|
| A 1:1 adduct of hexamethylenetetramine and 4-hydroxy-3-methoxybenzaldehyde. | 2002 Jan |
|
| 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 |
|
| Cell polarity: following formin function. | 2002 Jan 8 |
|
| 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 |
|
| 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 |
|
| Hexamethylenetetramine-4-nitrocatechol-water (1/2/1). | 2002 Nov |
|
| 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 |
|
| 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 |
|
| 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 16 19:05:10 GMT 2023
by
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on
Sat Dec 16 19:05:10 GMT 2023
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| Record UNII |
024EIE5BUQ
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| Record Status |
Validated (UNII)
|
| Record Version |
|
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024EIE5BUQ
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630-55-7
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101806
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258-503-8
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DTXSID00968015
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53370-47-1
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211-137-2
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