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
- 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
Structure for Methenamine (DB06799)
- 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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in treatment of Urinary tract infections •••••••••••• Prophylaxis of Urinary tract infections •••••••••••• - Contraindications & Blackbox Warnings
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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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Methenamine is combined with Acenocoumarol. Acetazolamide The 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 sulfisoxazole Methenamine can cause a decrease in the absorption of Acetyl sulfisoxazole resulting in a reduced serum concentration and potentially a decrease in efficacy. Almasilate The therapeutic efficacy of Methenamine can be decreased when used in combination with Almasilate. Aluminium The therapeutic efficacy of Methenamine can be decreased when used in combination with Aluminium. - Food Interactions
- Drink plenty of fluids.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Methenamine citrate Q4U8R77416 34317-08-3 UAMIYHCXAONPMG-UHFFFAOYSA-N Methenamine diphosphate IZP83XSR30 72962-49-3 BGAZSPYPJDSHIT-UHFFFAOYSA-N Methenamine hippurate M329791L57 5714-73-8 ROAIXOJGRFKICW-UHFFFAOYSA-N Methenamine hydrochloride A3F8KN5WMU 24360-05-2 NGDSBQHTMKGUQU-UHFFFAOYSA-N Methenamine mandelate 695N30CINR 587-23-5 UXNFIJPHRQEWRQ-UHFFFAOYSA-N Methenamine phosphate 11G6DJX54Q 72962-48-2 GJJQWIOYOCDCJA-UHFFFAOYSA-N Methenamine sulfate 0373WW6GZQ 19267-18-6 CCCDIBJJOMJPQI-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Hexamine
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Hip Rex Tab 1gm Tablet 1 g Oral Graceway Pharmaceuticals 1993-12-31 2008-07-16 Canada 
Hiprex Tablet 1 g/1 Oral sanofi-aventis U.S. LLC 1976-09-09 2016-05-09 US 
Hiprex Tablet 1 g/1 Oral Validus Pharmaceuticals LLC 1976-09-09 Not applicable US Hiprex Tablet 1 g/1 Oral Validus Pharmaceuticals LLC 1976-09-09 Not applicable US Mandelamine Tablet 500 mg Oral Searchlight Pharma Inc 1951-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Methenamine Hippurate Tablet 1000 mg/1 Oral American Health Packaging 2022-07-20 Not applicable US Methenamine Hippurate Tablet 1 g/1 Oral Leading Pharma, Llc 2016-06-03 Not applicable US Methenamine Hippurate Tablet 1000 mg/1 Oral Micro Labs Limited 2019-08-15 Not applicable US Methenamine Hippurate Tablet 1 g/1 Oral Golden State Medical Supply 2003-07-01 2017-01-02 US 
Methenamine Hippurate Tablet 1 g/1 Oral Ingenus Pharmaceuticals, LLC 2020-12-18 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Hiprex 1g Tablet Tablet Oral iNova Pharmaceuticals (Singapore) Pte Ltd (incorporated In Singapore) Malaysia Branch 2020-09-08 Not applicable Malaysia 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Air Disinfectant Methenamine (387.5 g/2500g) + Benzalkonium chloride (150 g/2500g) Liquid Extracorporeal Wuxi Youjie Technology Co. LTD 2020-04-28 Not applicable US All-In-One UTI Emergency Kit Methenamine (162 mg/1) + Phenazopyridine hydrochloride (99.5 mg/1) + Sodium salicylate (162.5 mg/1) Kit; Tablet Oral Uqora Inc 2022-10-17 Not applicable US Azo Urinary Tract Defense Antibacterial Protection Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1) Tablet Oral i-Health, Inc. 2015-11-06 Not applicable US Cleaning Disinfectant Methenamine (250 g/2500g) + Benzalkonium bromide (125 g/2500g) Liquid Extracorporeal Wuxi Youjie Technology Co. LTD 2020-04-28 Not applicable US CVS Antibacterial Plus Urinary Pain Relief Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1) Tablet Oral CVS Pharmacy, Inc 2017-02-22 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Air Disinfectant Methenamine (387.5 g/2500g) + Benzalkonium chloride (150 g/2500g) Liquid Extracorporeal Wuxi Youjie Technology Co. LTD 2020-04-28 Not applicable US All-In-One UTI Emergency Kit Methenamine (162 mg/1) + Phenazopyridine hydrochloride (99.5 mg/1) + Sodium salicylate (162.5 mg/1) Kit; Tablet Oral Uqora Inc 2022-10-17 Not applicable US Azo Urinary Tract Defense Antibacterial Protection Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1) Tablet Oral i-Health, Inc. 2015-11-06 Not applicable US Azuphen Mb Methenamine (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) Capsule Oral Burel Pharmaceuticals, Llc 2015-09-28 2016-11-01 US Cleaning Disinfectant Methenamine (250 g/2500g) + Benzalkonium bromide (125 g/2500g) Liquid Extracorporeal Wuxi Youjie Technology Co. LTD 2020-04-28 Not applicable US
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[3.3.1.1^{3,7}]decane
- SMILES
- C1N2CN3CN1CN(C2)C3
References
- General References
- 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]
- External Links
- Human Metabolome Database
- HMDB0029598
- KEGG Drug
- D00393
- PubChem Compound
- 4101
- PubChem Substance
- 310264893
- ChemSpider
- 3959
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Urinary Tract Infections, Recurrent 1 4 Completed Treatment Urinary Tract Infection 1 4 Enrolling by Invitation Treatment Urinary Tract Infections, Recurrent 1 4 Recruiting Treatment Urinary Tract Infection 1 4 Withdrawn Prevention Female Urogenital Diseases / Urinary Tract Infection / UTI - Lower Urinary Tract Infection 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit; tablet Oral Tablet Oral Liquid Extracorporeal Tablet Oral 1 g Tablet, film coated Oral 1 gr Tablet, film coated Oral Tablet Oral 500 mg Granule, for solution Oral 500 mg Tablet Oral Tablet Oral 1 g/1 Tablet Oral 1000 mg/1 Tablet Oral 500 mg/1 Tablet, film coated Oral 1000 mg/1 Tablet, film coated Oral 500 mg/1 Granule 105 g Granule Capsule Oral Liquid Topical Granule, effervescent Oral Tablet, coated Oral Tablet, film coated Oral Tablet, sugar coated Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 766.0 mg/mL ALOGPS logP -1.4 ALOGPS logP 0.39 Chemaxon logS 0.74 ALOGPS pKa (Strongest Basic) 5.88 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.96 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 37 m3·mol-1 Chemaxon Polarizability 14.25 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 120.2082623 predictedDarkChem Lite v0.1.0 [M-H]- 120.3669623 predictedDarkChem Lite v0.1.0 [M-H]- 120.3453623 predictedDarkChem Lite v0.1.0 [M-H]- 127.49708 predictedDeepCCS 1.0 (2019) [M+H]+ 121.1643623 predictedDarkChem Lite v0.1.0 [M+H]+ 121.1508623 predictedDarkChem Lite v0.1.0 [M+H]+ 121.2149623 predictedDarkChem Lite v0.1.0 [M+H]+ 129.77257 predictedDeepCCS 1.0 (2019) [M+Na]+ 120.6050623 predictedDarkChem Lite v0.1.0 [M+Na]+ 120.6549623 predictedDarkChem Lite v0.1.0 [M+Na]+ 120.6170623 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.0518 predictedDeepCCS 1.0 (2019)
Drug created at September 14, 2010 16:21 / Updated at February 20, 2024 23:54