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Details

Stereochemistry ACHIRAL
Molecular Formula C6H12N4.H2O4S
Molecular Weight 238.265
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHENAMINE SULFATE

SMILES

OS(O)(=O)=O.C1N2CN3CN1CN(C2)C3

InChI

InChIKey=CCCDIBJJOMJPQI-UHFFFAOYSA-N
InChI=1S/C6H12N4.H2O4S/c1-7-2-9-4-8(1)5-10(3-7)6-9;1-5(2,3)4/h1-6H2;(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Description
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
UREX

Approved Use

FOR 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

Cmax

ValueDoseCo-administeredAnalytePopulation
34 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
177 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
4.8 h
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

Doses

DosePopulationAdverse 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
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
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
Micturition painful
Micturition frequency
Albuminuria
Hematuria
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Disseminated histoplasmosis presenting as pyoderma gangrenosum-like lesions in a patient with acquired immunodeficiency syndrome.
2001 Aug
The lock-in phase in the urotropine-sebacic acid system.
2001 Aug
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
Plaque-like structures and arteriosclerotic changes in "diffuse neurofibrillary tangles with calcification" (DNTC).
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
Wnt/Frizzled activation of Rho regulates vertebrate gastrulation and requires a novel Formin homology protein Daam1.
2001 Dec 28
Effect of ultrasonic vibration and various sealer and cement combinations on titanium post removal.
2001 Jan
New temperature modification makes the Bielschowsky silver stain reproducible.
2001 Jan
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
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
Perspectives of a long-time observer.
2001 Mar 1
mDia-interacting protein acts downstream of Rho-mDia and modifies Src activation and stress fiber formation.
2001 Oct 19
Genes and proteins in renal development.
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
Dipole-dipole coupling constant for a directly bonded CH pair--a carbon-13 relaxation study.
2002 Aug
An actin nucleation mechanism mediated by Bni1 and profilin.
2002 Aug
Invasive Aspergillosis in Italian AIDS patients.
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
Delphilin: a novel PDZ and formin homology domain-containing protein that synaptically colocalizes and interacts with glutamate receptor delta 2 subunit.
2002 Feb 1
Effects of instrumentation, irrigation and dressing with calcium hydroxide on infection in pulpless teeth with periapical bone lesions.
2002 Jan
Evaluation of lectin staining in the diagnosis of fungal keratitis in an experimental rabbit model.
2002 Jan 25
Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid.
2002 Jun
Primary evaluation of methenamine as a NPN compound with probable effects on increasing ruminal escaped protein.
2002 Jun
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
Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms.
2002 Nov-Dec
Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine.
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
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
Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody.
2003 Jun 20
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
[Quantitative assessment of the biological activity of chemicals by soil microbial associations].
2003 May-Jun
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
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 Wed Jul 05 22:40:48 UTC 2023
Edited
by admin
on Wed Jul 05 22:40:48 UTC 2023
Record UNII
0373WW6GZQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHENAMINE SULFATE
Common Name English
HEXAMETHYLENETETRAMINE SULFATE
Common Name English
1,3,5,7-TETRAAZATRICYCLO(3.3.1.13,7)DECANE, SULFATE
Systematic Name English
Code System Code Type Description
DRUG BANK
DBSALT002246
Created by admin on Wed Jul 05 22:40:48 UTC 2023 , Edited by admin on Wed Jul 05 22:40:48 UTC 2023
PRIMARY
CAS
19267-18-6
Created by admin on Wed Jul 05 22:40:48 UTC 2023 , Edited by admin on Wed Jul 05 22:40:48 UTC 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
0373WW6GZQ
Created by admin on Wed Jul 05 22:40:48 UTC 2023 , Edited by admin on Wed Jul 05 22:40:48 UTC 2023
PRIMARY
PUBCHEM
22165885
Created by admin on Wed Jul 05 22:40:48 UTC 2023 , Edited by admin on Wed Jul 05 22:40:48 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY