U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry RACEMIC
Molecular Formula C8H8O3.C6H12N4
Molecular Weight 292.3336
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHENAMINE MANDELATE

SMILES

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

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 C8H8O3
Molecular Weight 152.1473
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

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

1967
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
Health Status: healthy
Age Group: 24-65
Sex: M+F
Sources:
1 g single, oral
Recommended
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
healthy, 24-65
Health Status: healthy
Age Group: 24-65
Sex: M+F
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
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
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
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
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
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Comparative effects of aging in men and women on the properties of the arterial tree.
2001 Apr
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
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 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
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
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
Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast.
2002 Jan
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
Vibrational frequencies and structural determinations of hexamethylenetetraamine.
2002 May
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
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
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
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
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 Mon Mar 31 18:02:00 GMT 2025
Edited
by admin
on Mon Mar 31 18:02:00 GMT 2025
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
HEXAMINE MANDELATE
JAN  
Preferred 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
Methenamine mandelate [WHO-DD]
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
Classification Tree Code System Code
NCI_THESAURUS C255
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
Code System Code Type Description
MERCK INDEX
m7308
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY Merck Index
PUBCHEM
11478
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
EVMPD
SUB03216MIG
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
LACTMED
Methenamine Mandelate
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
DRUG BANK
DBSALT001271
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
CAS
587-23-5
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
DAILYMED
695N30CINR
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
ECHA (EC/EINECS)
209-597-4
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
FDA UNII
695N30CINR
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
RXCUI
161623
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY RxNorm
SMS_ID
100000088516
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
NCI_THESAURUS
C77070
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
RS_ITEM_NUM
1409604
Created by admin on Mon Mar 31 18:02:00 GMT 2025 , Edited by admin on Mon Mar 31 18:02:00 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY