Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H12N4.ClH |
| Molecular Weight | 176.647 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C1N2CN3CN1CN(C2)C3
InChI
InChIKey=NGDSBQHTMKGUQU-UHFFFAOYSA-N
InChI=1S/C6H12N4.ClH/c1-7-2-9-4-8(1)5-10(3-7)6-9;/h1-6H2;1H
| 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 | ClH |
| Molecular Weight | 36.461 |
| 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 |
|---|---|---|
| Simulated cometary matter as a test for enantiomer separating chromatography for use on comet 46P/Wirtanen. | 2001 |
|
| Post retention: the effect of sequence of post-space preparation, cementation time, and different sealers. | 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 143 and 300 K polymorphs of hexamethylenetetraminium 2,4-dinitrophenolate monohydrate. | 2001 Dec |
|
| Failure of ureteric bud invasion: a new model of renal agenesis in mice. | 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 |
|
| Occupational allergic contact dermatitis from quaternium-15 in an electroencephalography skin preparation gel. | 2001 Jan |
|
| Coordination of microtubules and the actin cytoskeleton by the Rho effector mDia1. | 2001 Jan |
|
| Identification of a carboxyl-terminal diaphanous-related formin homology protein autoregulatory domain. | 2001 Jan 26 |
|
| Toward designed assembly of microporous coordination networks constructed from silver(I)-hexamethylenetetramine layers. | 2001 Jul 2 |
|
| Formaldehyde release from ground root canal sealer in vitro. | 2001 Jun |
|
| A primary observation on the preparation and obturation of oval canals. | 2001 Mar |
|
| Cenani-Lenz syndrome with renal hypoplasia is not linked to FORMIN or GREMLIN. | 2001 Mar |
|
| Amyloid beta protein deposition in patients with frontotemporal lobar degeneration: relationship to age and apolipoprotein E genotype. | 2001 May 25 |
|
| In vitro longitudinal assessment of coronal discoloration from endodontic sealers. | 2001 Nov |
|
| Methenamine hippurate for preventing urinary tract infections. | 2002 |
|
| The evolutionary history of effectors downstream of Cdc42 and Rac. | 2002 |
|
| Dipole-dipole coupling constant for a directly bonded CH pair--a carbon-13 relaxation study. | 2002 Aug |
|
| Value of urinary prophylaxis with methenamine in gynecologic surgery. | 2002 Aug |
|
| Formins initiate new actin filaments. | 2002 Aug |
|
| An actin nucleation mechanism mediated by Bni1 and profilin. | 2002 Aug |
|
| 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 |
|
| Role of formins in actin assembly: nucleation and barbed-end association. | 2002 Jul 26 |
|
| Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid. | 2002 Jun |
|
| Vibrational frequencies and structural determinations of hexamethylenetetraamine. | 2002 May |
|
| Identification of interaction partners of the cytosolic polyproline region of CD95 ligand (CD178). | 2002 May 22 |
|
| 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 |
|
| 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 |
|
| AgC(CN)3-based coordination polymers. | 2003 Apr 21 |
|
| Crystallographic analysis of the thermal motion of the inclusion complex of cyclomaltoheptaose (beta-cyclodextrin) with hexamethylenetetramine. | 2003 Feb 7 |
|
| 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 |
|
| 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 |
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
Fri Dec 16 17:35:55 UTC 2022
by
admin
on
Fri Dec 16 17:35:55 UTC 2022
|
| Record UNII |
A3F8KN5WMU
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
20339725
Created by
admin on Fri Dec 16 17:35:55 UTC 2022 , Edited by admin on Fri Dec 16 17:35:55 UTC 2022
|
PRIMARY | |||
|
58713-21-6
Created by
admin on Fri Dec 16 17:35:55 UTC 2022 , Edited by admin on Fri Dec 16 17:35:55 UTC 2022
|
NON-SPECIFIC STOICHIOMETRY | |||
|
24360-05-2
Created by
admin on Fri Dec 16 17:35:55 UTC 2022 , Edited by admin on Fri Dec 16 17:35:55 UTC 2022
|
PRIMARY | |||
|
DBSALT002248
Created by
admin on Fri Dec 16 17:35:55 UTC 2022 , Edited by admin on Fri Dec 16 17:35:55 UTC 2022
|
PRIMARY | |||
|
246-206-6
Created by
admin on Fri Dec 16 17:35:55 UTC 2022 , Edited by admin on Fri Dec 16 17:35:55 UTC 2022
|
PRIMARY | |||
|
DTXSID4051902
Created by
admin on Fri Dec 16 17:35:55 UTC 2022 , Edited by admin on Fri Dec 16 17:35:55 UTC 2022
|
PRIMARY | |||
|
A3F8KN5WMU
Created by
admin on Fri Dec 16 17:35:55 UTC 2022 , Edited by admin on Fri Dec 16 17:35:55 UTC 2022
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
