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Details

Stereochemistry ACHIRAL
Molecular Formula C9H9NO3.C6H12N4
Molecular Weight 319.3589
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHENAMINE HIPPURATE

SMILES

C1N2CN3CN1CN(C2)C3.OC(=O)CNC(=O)C4=CC=CC=C4

InChI

InChIKey=ROAIXOJGRFKICW-UHFFFAOYSA-N
InChI=1S/C9H9NO3.C6H12N4/c11-8(12)6-10-9(13)7-4-2-1-3-5-7;1-7-2-9-4-8(1)5-10(3-7)6-9/h1-5H,6H2,(H,10,13)(H,11,12);1-6H2

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 C9H9NO3
Molecular Weight 179.1727
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
Developmental changes in the fine structure and histochemical properties of mucous cells in the parotid gland of the infant Japanese macaque.
2001 Dec
Antimicrobial activity of four root canal sealers against endodontic pathogens.
2001 Dec
Effects of chlorhexidine gluconate as an endodontic irrigant on the apical seal: short-term results.
2001 Dec
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
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
In vitro longitudinal assessment of coronal discoloration from endodontic sealers.
2001 Nov
Modification of the levels of polyphenols in wort and beer by addition of hexamethylenetetramine or sulfite during mashing.
2001 Nov
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
Comparison of staining methods and a nested PCR assay to detect Histoplasma capsulatum in tissue sections.
2002 Apr
Value of urinary prophylaxis with methenamine in gynecologic surgery.
2002 Aug
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
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
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
Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast.
2002 Jan
Evaluation of lectin staining in the diagnosis of fungal keratitis in an experimental rabbit model.
2002 Jan 25
Cell polarity: following formin function.
2002 Jan 8
A comparative evaluation of sealing ability of rootcanal sealers.
2002 Jan-Mar
Role of formins in actin assembly: nucleation and barbed-end association.
2002 Jul 26
Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast.
2002 Mar
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
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
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:11:36 UTC 2023
Edited
by admin
on Fri Dec 15 15:11:36 UTC 2023
Record UNII
M329791L57
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHENAMINE HIPPURATE
JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
HIPREX
Brand Name English
METHENAMINE HIPPURATE [ORANGE BOOK]
Common Name English
GLYCINE, N-BENZOYL, COMPD. WITH 1,3,5,7-TETRAAZATRICYCLO(3.3.1.1(SUP 3,7))DECANE (1:1)
Common Name English
Methenamine hippurate [WHO-DD]
Common Name English
METHENAMINE HIPPURATE [USP MONOGRAPH]
Common Name English
METHENAMINE HIPPURATE [USAN]
Common Name English
METHENAMINE HIPPURATE [USP IMPURITY]
Common Name English
METHENAMINE HIPPURATE [USP-RS]
Common Name English
HEXAMINE HIPPURATE
Common Name English
METHENAMINE HIPPURATE [MART.]
Common Name English
Hexamethylenetetramine monohippurate
Common Name English
METHENAMINE HIPPURATE [VANDF]
Common Name English
UREX
Brand Name English
METHENAMINE HIPPURATE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C255
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
Code System Code Type Description
EVMPD
SUB14537MIG
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
CAS
5714-73-8
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
PUBCHEM
21945
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
DRUG BANK
DBSALT001270
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
FDA UNII
M329791L57
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
EPA CompTox
DTXSID10972603
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201270
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
SMS_ID
100000091093
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
RXCUI
29652
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY RxNorm
DAILYMED
M329791L57
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
MESH
C011481
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
NCI_THESAURUS
C47610
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
RS_ITEM_NUM
1409502
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
MERCK INDEX
m7308
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY Merck Index
LACTMED
Methenamine Hippurate
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
ECHA (EC/EINECS)
227-206-5
Created by admin on Fri Dec 15 15:11:36 UTC 2023 , Edited by admin on Fri Dec 15 15:11:36 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY