U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H12N4
Molecular Weight 140.1865
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHENAMINE

SMILES

C1N2CN3CN1CN(C2)C3

InChI

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

HIDE SMILES / InChI

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
Biodegradation of formaldehyde and its derivatives in industrial wastewater with methylotrophic yeast Hansenula polymorpha and with the yeast-bioaugmented activated sludge.
2002
Genes and proteins in renal development.
2002
Methenamine hippurate for preventing urinary tract infections.
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
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
Invasive Aspergillosis in Italian AIDS patients.
2002 Dec
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
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 comparative evaluation of sealing ability of rootcanal sealers.
2002 Jan-Mar
Monolithic scavenger resins by amine functionalizations of poly(4-vinylbenzyl chloride-co-divinylbenzene) PolyHIPE materials.
2002 Jul 25
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
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
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
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
AgC(CN)3-based coordination polymers.
2003 Apr 21
Syntheses of two new 1D and 3D networks of Cu(II) and Co(II) using malonate and urotropine as bridging ligands: crystal structures and magnetic studies.
2003 Apr 21
Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine.
2003 Feb
(1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines.
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
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
The Formin family protein, formin homolog overexpressed in spleen, interacts with the insulin-responsive aminopeptidase and profilin IIa.
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
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
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
Measuring gluconeogenesis using a low dose of 2H2O: advantage of isotope fractionation during gas chromatography.
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.
Name Type Language
METHENAMINE
EP   HSDB   INCI   INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INN   INCI  
Official Name English
METHENAMINE [MI]
Common Name English
HEXAMETHYLENAMINE
Common Name English
INS NO.239
Code English
HEXAMETHYLENE TETRAMINE
Common Name English
HEXAMINE
JAN  
Common Name English
URITONE
Brand Name English
E-239
Code English
HEXAMETHYLENETETRAMINE
Common Name English
HMT
Common Name English
1,3,5,7-TETRAAZAADAMANTANE
Systematic Name English
METHENAMINE [INN]
Common Name English
1,3,5,7-TETRAAZATRICYCLO(3.3.1.1 SUP(3,7))DECANE
Common Name English
METHENAMINE [EP MONOGRAPH]
Common Name English
INS-239
Code English
METHENAMINE [MART.]
Common Name English
METHENAMINE [USP-RS]
Common Name English
METHENAMINE [HSDB]
Common Name English
1,3,5,7-TETRAAZATRICYCLO(3.3.1.13,7)DECANE
Systematic Name English
METHENAMINE [VANDF]
Common Name English
NSC-26346
Code English
METHENAMINE [INCI]
Common Name English
NSC-403347
Code English
METHENAMINE [USP]
Common Name English
HMTA
Common Name English
METHENAMINE [WHO-DD]
Common Name English
HEXAMINE [JAN]
Common Name English
UROTROPIN
Brand Name English
AMINOFORM
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.2280
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
WHO-VATC QJ01XX55
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
EPA PESTICIDE CODE 45501
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
WHO-VATC QJ01XX05
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
CFR 21 CFR 176.170
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
WHO-VATC QR01AX01
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
WHO-ATC J01XX05
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
NCI_THESAURUS C255
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
WHO-ATC R01AX01
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
JECFA EVALUATION INS-239
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-239
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
LIVERTOX 615
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C61841
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
DRUG BANK
DB06799
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
LACTMED
Methenamine
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
USP_CATALOG
1409003
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M7308
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
HEXAMETHYLENETETRAMINE
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
JECFA MONOGRAPH
INS-239
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
EVMPD
SUB08845MIG
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
FDA UNII
J50OIX95QV
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
CAS
100-97-0
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201270
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
INN
119
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
HSDB
563
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
RXCUI
6832
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY RxNorm
PUBCHEM
4101
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-905-8
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
DRUG CENTRAL
3344
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
MESH
D008709
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY
EPA CompTox
100-97-0
Created by admin on Fri Jun 25 21:19:50 UTC 2021 , Edited by admin on Fri Jun 25 21:19:50 UTC 2021
PRIMARY