Methenamine

Identification

Summary

Methenamine is a urinary tract antiseptic and antibacterial drug used for the prophylaxis and treatment of frequently recurring urinary tract infections requiring a long-term therapy.

Brand Names
Hyophen, Mandelamine, Phosphasal, Urelle, Uribel, Urimar Reformulated Oct 2013, Urin DS, Urogesic Blue Reformulated Apr 2012, Ustell, Utira
Generic Name
Methenamine
DrugBank Accession Number
DB06799
Background

Methenamine is a heterocyclic organic compound with a cage-like structure similar to adamantane. In salt form it is used for the treatment of urinary tract infection (Example: methenamine hippurate which is the hippuric acid salt of methenamine).

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 140.1863
Monoisotopic: 140.106196404
Chemical Formula
C6H12N4
Synonyms
  • 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane
  • Hexamethylenamine
  • Hexamethylene tetramine
  • Hexamethylenetetramine
  • Hexamethylentetramin
  • Hexamethylentetraminum
  • Hexamine
  • Hexaminum
  • HMT
  • HMTA
  • metenamina
  • méthénamine
  • Methenamine
  • methenaminum
External IDs
  • E-239
  • E239
  • INS NO.239
  • INS-239

Pharmacology

Indication

For prophylactic or suppressive treatment of frequently recurring urinary tract infections when long-term therapy is considered necessary. This drug is not used to treat infection and should only be used after appropriate eradication of infection with antimicrobial agents.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Ingestion of a 1-gram dose of methenamine hippurate produces antibacterial activity in the urine within 1/2 hour. Administration of 1 g twice daily produces continuous antibacterial activity in the urine.

Mechanism of action

Methenamine does not have antibacterial properties in an alkaline environment (pH≥6); however, in a more acidic environment (pH<6), methenamine is hydrolyzed to formaldehyde. (1) Formaldehyde is considered to be highly bactericidal. (1) Formaldehyde has nonspecific antibacterial activity and works by denaturing proteins and nucleic acid of bacteria. (1) Certain bacteria such as Proteus sp. can alkalize urine, inhibiting the beneficial activity of formaldehyde. (1) The key role of the salt component of the drug, for example hippuric acid, is to maintain the acidic state of the urine. (1)

Absorption

After oral administration, rapid absorption of methenamine occurs. (1)

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

When in acidic urine (pH<6), methenamine is hydrolyzed to formaldehyde which acts as an antiseptic. (1)

Hover over products below to view reaction partners

Route of elimination

Methenamine is primarily eliminated via the kidneys. (1)

Half-life

Elimination half-life = 3-4 hours assuming normal renal function. (1)

Clearance

70-90% of a single oral dose of methenamine is excreted unchanged in the urine within 24 hours. (1)

Adverse Effects
Adverseeffects
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Toxicity

Less than 3.5% of patients treated with this drug will experience minor adverse events such as upset stomach, dysuria, nausea, and rash.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Methenamine is combined with Acenocoumarol.
AcetazolamideThe serum concentration of the active metabolites of Methenamine can be reduced when Methenamine is used in combination with Acetazolamide resulting in a loss in efficacy.
Acetyl sulfisoxazoleMethenamine can cause a decrease in the absorption of Acetyl sulfisoxazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
AlmasilateThe therapeutic efficacy of Methenamine can be decreased when used in combination with Almasilate.
AluminiumThe therapeutic efficacy of Methenamine can be decreased when used in combination with Aluminium.
Aluminium phosphateThe therapeutic efficacy of Methenamine can be decreased when used in combination with Aluminium phosphate.
Aluminum hydroxideThe therapeutic efficacy of Methenamine can be decreased when used in combination with Aluminum hydroxide.
AmphetamineThe serum concentration of Amphetamine can be decreased when it is combined with Methenamine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Methenamine.
BendroflumethiazideThe therapeutic efficacy of Methenamine can be decreased when used in combination with Bendroflumethiazide.
Interactions
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Food Interactions
  • Drink plenty of fluids.
  • Take with food.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Methenamine citrateQ4U8R7741634317-08-3UAMIYHCXAONPMG-UHFFFAOYSA-N
Methenamine diphosphateIZP83XSR3072962-49-3BGAZSPYPJDSHIT-UHFFFAOYSA-N
Methenamine hippurateM329791L575714-73-8ROAIXOJGRFKICW-UHFFFAOYSA-N
Methenamine hydrochlorideA3F8KN5WMU24360-05-2NGDSBQHTMKGUQU-UHFFFAOYSA-N
Methenamine mandelate695N30CINR587-23-5UXNFIJPHRQEWRQ-UHFFFAOYSA-N
Methenamine phosphate11G6DJX54Q72962-48-2GJJQWIOYOCDCJA-UHFFFAOYSA-N
Methenamine sulfate0373WW6GZQ19267-18-6CCCDIBJJOMJPQI-UHFFFAOYSA-N
Product Images
International/Other Brands
Hexamine
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Hip Rex Tab 1gmTablet1 gOralGraceway Pharmaceuticals1993-12-312008-07-16Canada flag
HiprexTablet1 g/1OralValidus Pharmaceuticals LLC1976-09-09Not applicableUS flag
HiprexTablet1 g/1Oralsanofi-aventis U.S. LLC1976-09-092016-05-09US flag
MandelamineTablet500 mgOralErfa Canada 2012 Inc1951-12-31Not applicableCanada flag
Methenamine HippurateTablet1 g/1OralWinthrop U.S.2012-01-232019-05-30US flag00955 1037 10 nlmimage10 be44df06
Methenamine HippurateTablet1 g/1OralCounty Line Pharmaceuticals, LLC2010-05-032022-07-01US flag43199 0020 01 nlmimage10 bc3c5e42
Methenamine HippurateTablet1 g/1OralAlvogen Inc.2010-05-03Not applicableUS flag
Methenamine MandelateTablet, film coated1000 mg/1OralSeton Pharmaceuticals2010-02-01Not applicableUS flag
Methenamine MandelateTablet, film coated500 mg/1OralChartwell Rx, Llc2021-10-01Not applicableUS flag
Methenamine MandelateTablet, film coated500 mg/1OralMethod Pharmaceuticals, LLC2018-07-19Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Methenamine HippurateTablet1 g/1OralGolden State Medical Supply2003-07-012017-01-02US flag64720 0139 10 nlmimage10 473c23c1
Methenamine HippurateTablet1 g/1OralLeading Pharma, Llc2016-06-03Not applicableUS flag
Methenamine HippurateTablet1000 mg/1OralMicro Labs Limited2019-08-15Not applicableUS flag
Methenamine HippurateTablet1 g/1OralIngenus Pharmaceuticals, LLC2020-12-18Not applicableUS flag
Methenamine HippurateTablet1 g/1OralRising Pharmaceuticals2003-07-012009-09-14US flag
Methenamine HippurateTablet1 g/1OralCorePharma, LLC2003-07-012020-02-01US flag
Methenamine HippurateTablet1 g/1OralAmneal Pharmaceuticals of New York Llc2003-07-01Not applicableUS flag
Methenamine HippurateTablet1000 mg/1OralAvPAK2020-12-02Not applicableUS flag
Methenamine HippurateTablet1 g/1OralCarilion Materials Management2003-07-01Not applicableUS flag68151 098420180907 15195 k7dszx
Methenamine HippurateTablet1 g/1OralAurobindo Pharma Limited2016-07-05Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Hiprex 1g TabletTabletOraliNova Pharmaceuticals (Singapore) Pte Ltd (incorporated In Singapore) Malaysia Branch2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Air DisinfectantMethenamine (387.5 g/2500g) + Benzalkonium chloride (150 g/2500g)LiquidExtracorporealWuxi Youjie Technology Co. LTD2020-04-28Not applicableUS flag
Azo Urinary Tract Defense Antibacterial ProtectionMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOrali-Health, Inc.2015-11-06Not applicableUS flag
Cleaning DisinfectantMethenamine (250 g/2500g) + Benzalkonium bromide (125 g/2500g)LiquidExtracorporealWuxi Youjie Technology Co. LTD2020-04-28Not applicableUS flag
CVS Antibacterial Plus Urinary Pain ReliefMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOralCVS Pharmacy, Inc2017-02-22Not applicableUS flag
Cystex PlusMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOralClarion Brands, Llc2015-11-01Not applicableUS flag
Cystex PlusMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOralDSE Healthcare Solutions, LLC2012-04-012018-11-30US flag
Disinfectant(Model III)Sanitizer Hand And SurfaceMethenamine (0.15 g/60g) + Benzalkonium bromide (0.054 g/60g)LiquidExtracorporealWuxi Youjie Technology Co. LTD2020-04-28Not applicableUS flag
Disinfectant(Model III)Sanitizer Hand And SurfaceMethenamine (1.25 g/500g) + Benzalkonium bromide (0.45 g/500g)LiquidExtracorporealWuxi Youjie Technology Co. LTD2020-04-28Not applicableUS flag
Good Neighbor Antibacterial Plus Urinary Pain ReliefMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOralAmerisourceBergen Drug Corp2019-09-25Not applicableUS flag
Meijer Antibacterial Plus Urinary Pain ReliefMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOralMeijer Distribution Inc.2017-02-22Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Air DisinfectantMethenamine (387.5 g/2500g) + Benzalkonium chloride (150 g/2500g)LiquidExtracorporealWuxi Youjie Technology Co. LTD2020-04-28Not applicableUS flag
Azo Urinary Tract Defense Antibacterial ProtectionMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOrali-Health, Inc.2015-11-06Not applicableUS flag
Azuphen MbMethenamine (120 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methylene blue trihydrate (10 mg/1) + Phenyl salicylate (36 mg/1) + Sodium phosphate, monobasic, monohydrate (40.8 mg/1)CapsuleOralBurel Pharmaceuticals, Llc2015-09-282016-11-01US flag
Cleaning DisinfectantMethenamine (250 g/2500g) + Benzalkonium bromide (125 g/2500g)LiquidExtracorporealWuxi Youjie Technology Co. LTD2020-04-28Not applicableUS flag
CVS Antibacterial Plus Urinary Pain ReliefMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOralCVS Pharmacy, Inc2017-02-22Not applicableUS flag
Cystex PlusMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOralClarion Brands, Llc2015-11-01Not applicableUS flag
Cystex PlusMethenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)TabletOralDSE Healthcare Solutions, LLC2012-04-012018-11-30US flag
DarcalmaMethenamine (81.6 mg/1) + Hyoscyamine sulfate dihydrate (.12 mg/1) + Methylene blue trihydrate (10.8 mg/1) + Phenyl salicylate (36.2 mg/1) + Sodium phosphate, monobasic, unspecified form (40.8 mg/1)TabletOralKylemore Pharmaceuticals, LLC2009-12-012009-12-02US flag
DarcalmaMethenamine (81.6 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methylene blue trihydrate (10.8 mg/1) + Phenyl salicylate (36.2 mg/1) + Sodium phosphate, monobasic, unspecified form (40.8 mg/1)TabletOralRiver's Edge Pharmaceuticals, LLC2008-12-222011-07-31US flag
DarpazMethenamine (81 mg/1) + Hyoscyamine sulfate dihydrate (.12 mg/1) + Methylene blue trihydrate (10.8 mg/1) + Phenyl salicylate (32.4 mg/1) + Sodium phosphate, monobasic (40.8 mg/1)TabletOralRiver's Edge Pharmaceuticals, LLC2008-12-012011-05-31US flag

Categories

ATC Codes
J01XX05 — Methenamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1,3,5-triazinanes. These are triazinanes having three nitrogen ring atoms at the 1-, 3-, and 5- positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Triazinanes
Sub Class
1,3,5-triazinanes
Direct Parent
1,3,5-triazinanes
Alternative Parents
Azacyclic compounds / Aminals / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1,3,5-triazinane / Aliphatic heteropolycyclic compound / Aminal / Azacycle / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
polycyclic cage (CHEBI:6824)
Affected organisms
  • Staphylococcus saprophyticus
  • Escherichia coli
  • Enterococcus faecalis
  • Enterococcus faecium

Chemical Identifiers

UNII
J50OIX95QV
CAS number
100-97-0
InChI Key
VKYKSIONXSXAKP-UHFFFAOYSA-N
InChI
InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
IUPAC Name
1,3,5,7-tetraazatricyclo[3.3.1.1³,⁷]decane
SMILES
C1N2CN3CN1CN(C2)C3

References

General References
  1. Lo TS, Hammer KD, Zegarra M, Cho WC: Methenamine: a forgotten drug for preventing recurrent urinary tract infection in a multidrug resistance era. Expert Rev Anti Infect Ther. 2014 May;12(5):549-54. doi: 10.1586/14787210.2014.904202. Epub 2014 Apr 1. [Article]
Human Metabolome Database
HMDB0029598
KEGG Drug
D00393
PubChem Compound
4101
PubChem Substance
310264893
ChemSpider
3959
RxNav
6832
ChEBI
6824
ChEMBL
CHEMBL1201270
ZINC
ZINC000086040406
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Hexamethylenetetramine
FDA label
Download (1.62 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentUrinary Tract Infection1
4CompletedPreventionUrinary Tract Infections, Recurrent1
4Enrolling by InvitationTreatmentUrinary Tract Infections, Recurrent1
4Not Yet RecruitingPreventionFemale Urogenital Diseases / Urinary Tract Infection / UTI - Lower Urinary Tract Infection1
4RecruitingTreatmentUrinary Tract Infection1
3CompletedTreatmentDysuria1
2RecruitingPreventionPelvic Organ Prolapse (POP) / Postoperative Urinary Retention (POUR) / Urinary Tract Infection1
0TerminatedTreatmentOsteomyelitis1
Not AvailableCompletedPreventionCatheter Related Infections / Urinary Tract Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
LiquidExtracorporeal
TabletOral1 g
Tablet, film coatedOral
TabletOral500 mg
Granule, for solutionOral
TabletOral
TabletOral1 g/1
TabletOral1000 mg/1
TabletOral500 mg/1
Tablet, film coatedOral1000 mg/1
Tablet, film coatedOral500 mg/1
Granule
CapsuleOral
Granule, effervescentOral
LiquidTopical
Tablet, coatedOral
Tablet, film coatedOral
Tablet, sugar coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility766.0 mg/mLALOGPS
logP-1.4ALOGPS
logP0.39ChemAxon
logS0.74ALOGPS
pKa (Strongest Basic)5.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.96 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37 m3·mol-1ChemAxon
Polarizability14.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0006-9300000000-e762ea01823717c4bda9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0900000000-05c8e159897335060443
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01ox-2900000000-86fe33e31cc8f7108c14
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01ti-9300000000-7eb44254c8cc65c09acd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9000000000-fd4edf8f48f9c42bca0c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004l-9000000000-371b89c99afba4931848
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Drug created on September 14, 2010 16:21 / Updated on October 22, 2021 23:18