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
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 |
|---|---|---|
| The unpredictability of seal after post space preparation: a fluid transport study. | 2001 Apr |
|
| Disseminated histoplasmosis presenting as pyoderma gangrenosum-like lesions in a patient with acquired immunodeficiency syndrome. | 2001 Aug |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Methenamine hippurate for preventing urinary tract infections. | 2002 |
|
| The evolutionary history of effectors downstream of Cdc42 and Rac. | 2002 |
|
| Value of urinary prophylaxis with methenamine in gynecologic surgery. | 2002 Aug |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine. | 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 |
|
| 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 |
|
| 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 |
|
| 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.
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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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ACTIVE MOIETY
SUBSTANCE RECORD
