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Details

Stereochemistry RACEMIC
Molecular Formula C8H8O3.C6H12N4
Molecular Weight 292.3341
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHENAMINE MANDELATE

SMILES

c1ccc(cc1)C(C(=O)O)O.C1N2CN3CN1CN(C2)C3

InChI

InChIKey=UXNFIJPHRQEWRQ-UHFFFAOYSA-N
InChI=1S/C8H8O3.C6H12N4/c9-7(8(10)11)6-4-2-1-3-5-6;1-7-2-9-4-8(1)5-10(3-7)6-9/h1-5,7,9H,(H,10,11);1-6H2

HIDE SMILES / InChI

Molecular Formula C6H12N4
Molecular Weight 140.1865
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H8O3
Molecular Weight 152.1476
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
The unpredictability of seal after post space preparation: a fluid transport study.
2001 Apr
Comparative effects of aging in men and women on the properties of the arterial tree.
2001 Apr
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
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
The formin/diaphanous-related protein, FHOS, interacts with Rac1 and activates transcription from the serum response element.
2001 Dec 7
[An 84-year-old woman with progressive mental deterioration and abnormal behavior].
2001 Feb
Effect of ultrasonic vibration and various sealer and cement combinations on titanium post removal.
2001 Jan
The histological effects of four endodontic sealers implanted in the oral mucosa: submucous injection versus implant in polyethylene tubes.
2001 Jul
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
A primary observation on the preparation and obturation of oval canals.
2001 Mar
Application of fluorescent in situ hybridization for specific diagnosis of Pneumocystis carinii pneumonia in foals and pigs.
2001 May
Amyloid beta protein deposition in patients with frontotemporal lobar degeneration: relationship to age and apolipoprotein E genotype.
2001 May 25
Oral exfoliative cytology in the diagnosis of paracoccidioidomycosis.
2001 May-Jun
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
Determination of the enrichment of the hydrogen bound to carbon 5 of glucose on 2H2O administration.
2001 Oct 15
mDia-interacting protein acts downstream of Rho-mDia and modifies Src activation and stress fiber formation.
2001 Oct 19
A comparison of the effect of three endodontic sealers on adherence of mouse peritoneal macrophages.
2001 Sep
Biodegradation of formaldehyde and its derivatives in industrial wastewater with methylotrophic yeast Hansenula polymorpha and with the yeast-bioaugmented activated sludge.
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 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
Influence of calcium hydroxide dressing on the obturation of simulated lateral canals.
2002 Feb
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
A comparative evaluation of sealing ability of rootcanal sealers.
2002 Jan-Mar
Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid.
2002 Jun
Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms.
2002 Nov-Dec
AgC(CN)3-based coordination polymers.
2003 Apr 21
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
Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody.
2003 Jun 20
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 Jun 25 20:58:34 UTC 2021
Edited
by admin
on Fri Jun 25 20:58:34 UTC 2021
Record UNII
695N30CINR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHENAMINE MANDELATE
GREEN BOOK   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
Common Name English
METHENAMINE MANDELATE [MI]
Common Name English
HEXAMINE MANDELATE [JAN]
Common Name English
HEXYDALINE
Common Name English
METHENAMINE MANDELATE [GREEN BOOK]
Common Name English
METHENAMINE MANDELATE [USP-RS]
Common Name English
METHENAMINE MANDELATE [MART.]
Common Name English
METHENAMINE MANDELATE [USP MONOGRAPH]
Common Name English
BENZENEACETIC ACID, .ALPHA.-HYDROXY-, (+/-)-, COMPD. WITH 1,3,5,7-TETRAAZATRICYCLO((3.3.1.1(SUP 3,7))DECANE (1:1)
Common Name English
HEXAMETHYLENAMINE MANDELATE
Common Name English
MANDELAMINE
Brand Name English
HEXAMETHYLENETETRAMINE MONO-(+/-)-MANDELATE
Common Name English
METHENAMINE MANDELATE [VANDF]
Common Name English
HEXAMINE MANDELATE
JAN  
Common Name English
METHENAMINE MANDELATE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C255
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
Code System Code Type Description
MERCK INDEX
M7308
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY Merck Index
PUBCHEM
11478
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY
EVMPD
SUB03216MIG
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY
USP_CATALOG
1409604
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY USP-RS
LACTMED
Methenamine Mandelate
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY
DRUG BANK
DBSALT001271
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY
CAS
587-23-5
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY
ECHA (EC/EINECS)
209-597-4
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY
FDA UNII
695N30CINR
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY
RXCUI
161623
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C77070
Created by admin on Fri Jun 25 20:58:34 UTC 2021 , Edited by admin on Fri Jun 25 20:58:34 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY