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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 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 H2O4S
Molecular Weight 98.078
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
Simulated cometary matter as a test for enantiomer separating chromatography for use on comet 46P/Wirtanen.
2001
Comparative effects of aging in men and women on the properties of the arterial tree.
2001 Apr
The lock-in phase in the urotropine-sebacic acid system.
2001 Aug
The formin/diaphanous-related protein, FHOS, interacts with Rac1 and activates transcription from the serum response element.
2001 Dec 7
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
A primary observation on the preparation and obturation of oval canals.
2001 Mar
mDia-interacting protein acts downstream of Rho-mDia and modifies Src activation and stress fiber formation.
2001 Oct 19
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
Invasive Aspergillosis in Italian AIDS patients.
2002 Dec
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
Hexamethylenetetraminium 2,4,6-trinitrophenolate.
2002 Jan
Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid.
2002 Jun
A locus for asphyxiating thoracic dystrophy, ATD, maps to chromosome 15q13.
2003 Jun
Two bis(ammonium) 1,5-naphthalenedisulfonate salts.
2003 Jun
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
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 Fri Dec 16 16:19:13 UTC 2022
Edited
by admin
on Fri Dec 16 16:19:13 UTC 2022
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 Fri Dec 16 16:19:13 UTC 2022 , Edited by admin on Fri Dec 16 16:19:13 UTC 2022
PRIMARY
CAS
19267-18-6
Created by admin on Fri Dec 16 16:19:13 UTC 2022 , Edited by admin on Fri Dec 16 16:19:13 UTC 2022
NON-SPECIFIC STOICHIOMETRY
FDA UNII
0373WW6GZQ
Created by admin on Fri Dec 16 16:19:13 UTC 2022 , Edited by admin on Fri Dec 16 16:19:13 UTC 2022
PRIMARY
PUBCHEM
22165885
Created by admin on Fri Dec 16 16:19:13 UTC 2022 , Edited by admin on Fri Dec 16 16:19:13 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY