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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
Structure of METHENAMINE HYDROCHLORIDE

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

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 ClH
Molecular Weight 36.461
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
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
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 17:35:55 UTC 2022
Edited
by admin
on Fri Dec 16 17:35:55 UTC 2022
Record UNII
A3F8KN5WMU
Record Status Validated (UNII)
Record Version
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Name Type Language
METHENAMINE HYDROCHLORIDE
Common Name English
HEXAMETHYLENETETRAMINE HYDROCHLORIDE
Common Name English
METHENAMINE MONOHYDROCHLORIDE
WHO-DD  
Common Name English
UROTROPINE HYDROCHLORIDE
Common Name English
PELLURIN
Common Name English
1,3,5,7-TETRAAZATRICYCLO(3.3.1.13,7)DECANE, HYDROCHLORIDE (1:1)
Systematic Name English
UROBENYL
Common Name English
Methenamine monohydrochloride [WHO-DD]
Common Name English
HEXAMETHYLENETETRAMINE, MONOHYDROCHLORIDE
Common Name English
UROTROPINE MONOHYDROCHLORIDE
Common Name English
Code System Code Type Description
PUBCHEM
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
CAS
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
CAS
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
DRUG BANK
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
ECHA (EC/EINECS)
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
EPA CompTox
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
FDA UNII
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