Methenamine

Identification

Name

Methenamine

Accession Number

DB06799

Description

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Methenamine (DB06799)

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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

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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.

Associated Conditions

• Urinary Tract Infection

Contraindications & Blackbox Warnings

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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

• Methenamine
  • Formaldehyde
  • ammonium

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

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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.

Affected organisms

• Staphylococcus saprophyticus
• Escherichia coli
• Enterococcus faecalis
• Enterococcus faecium

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acenocoumarol	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.
Aluminium phosphate	The therapeutic efficacy of Methenamine can be decreased when used in combination with Aluminium phosphate.
Aluminum hydroxide	The therapeutic efficacy of Methenamine can be decreased when used in combination with Aluminum hydroxide.
Amphetamine	The serum concentration of Amphetamine can be decreased when it is combined with Methenamine.
BCG vaccine	The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Methenamine.
Bendroflumethiazide	The therapeutic efficacy of Methenamine can be decreased when used in combination with Bendroflumethiazide.

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Food Interactions

• Drink plenty of fluids.
• Take with food.

Products

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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

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International/Other Brands

Hexamine

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Hip Rex Tab 1gm	Tablet		Oral	Graceway Pharmaceuticals	1993-12-31	2008-07-16
Hiprex	Tablet	1 g/1	Oral	Validus Pharmaceuticals LLC	1976-09-09	Not applicable
Hiprex	Tablet	1 g/1	Oral	sanofi-aventis U.S. LLC	1976-09-09	2016-05-09
Mandelamine	Tablet		Oral	Erfa Canada 2012 Inc	1951-12-31	Not applicable
Methenamine Hippurate	Tablet	1 g/1	Oral	Alvogen Inc.	2010-05-03	Not applicable
Methenamine Hippurate	Tablet	1 g/1	Oral	Winthrop U.S.	2012-01-23	2019-05-30
Methenamine Hippurate	Tablet	1 g/1	Oral	County Line Pharmaceuticals, LLC	2010-05-03	2022-07-01
Methenamine Mandelate	Tablet, film coated	500 mg/1	Oral	bryant ranch prepack	2018-07-19	Not applicable
Methenamine Mandelate	Tablet, film coated	1000 mg/1	Oral	Physicians Total Care, Inc.	2010-02-01	2013-06-30
Methenamine Mandelate	Tablet	1000 mg/1	Oral	Edenbridge Pharmaceuticals LLC.	2009-12-15	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Methenamine Hippurate	Tablet	1 g/1	Oral	Amneal Pharmaceuticals of New York Llc	2003-07-01	Not applicable
Methenamine Hippurate	Tablet	1 g/1	Oral	Carilion Materials Management	2003-07-01	Not applicable
Methenamine Hippurate	Tablet	1000 mg/1	Oral	AvPAK	2020-12-02	Not applicable
Methenamine Hippurate	Tablet	1 g/1	Oral	Aurobindo Pharma Limited	2016-07-05	Not applicable
Methenamine Hippurate	Tablet	1 g/1	Oral	Golden State Medical Supply	2003-07-01	2017-01-02
Methenamine Hippurate	Tablet	1 g/1	Oral	Leading Pharma, Llc	2016-06-03	Not applicable
Methenamine Hippurate	Tablet	1000 mg/1	Oral	Micro Labs Limited	2019-08-15	Not applicable
Methenamine Hippurate	Tablet	1 g/1	Oral	Rising Pharmaceuticals	2003-07-01	2009-09-14
Methenamine Hippurate	Tablet	1 g/1	Oral	Ingenus Pharmaceuticals, LLC	2020-12-18	Not applicable
Methenamine Hippurate	Tablet	1 g/1	Oral	CorePharma, LLC	2003-07-01	2020-02-01

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

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
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
Cleaning Disinfectant	Methenamine (250 g/2500g) + Benzalkonium bromide (125 g/2500g)	Liquid	Extracorporeal	Wuxi Youjie Technology Co. LTD	2020-04-28	Not applicable
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
Cystex Plus	Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)	Tablet	Oral	DSE Healthcare Solutions, LLC	2012-04-01	2018-11-30
Cystex Plus	Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)	Tablet	Oral	Clarion Brands, Llc	2015-11-01	Not applicable
Disinfectant(Model III)Sanitizer Hand And Surface	Methenamine (0.15 g/60g) + Benzalkonium bromide (0.054 g/60g)	Liquid	Extracorporeal	Wuxi Youjie Technology Co. LTD	2020-04-28	Not applicable
Disinfectant(Model III)Sanitizer Hand And Surface	Methenamine (1.25 g/500g) + Benzalkonium bromide (0.45 g/500g)	Liquid	Extracorporeal	Wuxi Youjie Technology Co. LTD	2020-04-28	Not applicable
Good Neighbor Antibacterial Plus Urinary Pain Relief	Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)	Tablet	Oral	AmerisourceBergen Drug Corp	2019-09-25	Not applicable
Meijer Antibacterial Plus Urinary Pain Relief	Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)	Tablet	Oral	Meijer Distribution Inc.	2017-02-22	Not applicable

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
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
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
Cleaning Disinfectant	Methenamine (250 g/2500g) + Benzalkonium bromide (125 g/2500g)	Liquid	Extracorporeal	Wuxi Youjie Technology Co. LTD	2020-04-28	Not applicable
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
Cystex Plus	Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)	Tablet	Oral	Clarion Brands, Llc	2015-11-01	Not applicable
Cystex Plus	Methenamine (162 mg/1) + Sodium salicylate (162.5 mg/1)	Tablet	Oral	DSE Healthcare Solutions, LLC	2012-04-01	2018-11-30
Darcalma	Methenamine (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)	Tablet	Oral	River's Edge Pharmaceuticals, LLC	2008-12-22	2011-07-31
Darcalma	Methenamine (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)	Tablet	Oral	Kylemore Pharmaceuticals, LLC	2009-12-01	2009-12-02
Darpaz	Methenamine (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)	Tablet	Oral	River's Edge Pharmaceuticals, LLC	2008-12-01	2011-05-31

Categories

ATC Codes

J01XX05 — Methenamine

• J01XX — Other antibacterials
• J01X — OTHER ANTIBACTERIALS
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Acids, Carbocyclic
• Amides
• Amines
• Anti-Bacterial Agents
• Anti-Infective Agents
• Anti-Infective Agents, Urinary
• Antibacterials for Systemic Use
• Antiinfectives for Systemic Use
• Benzene Derivatives
• Benzoates
• Cycloparaffins
• Hydroxy Acids
• Keto Acids
• Polyamines
• Renal Agents
• Urinary Acidifying Agents

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)

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. [PubMed:24689705]

External Links

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

AHFS Codes

• 08:36.00 — Urinary Anti-infectives

FDA label

Download (1.62 MB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Urinary Tract Infection	1
4	Completed	Prevention	Urinary Tract Infections, Recurrent	1
4	Enrolling by Invitation	Treatment	Urinary Tract Infections, Recurrent	1
4	Not Yet Recruiting	Prevention	Female Urogenital Diseases / Urinary Tract Infection / UTI - Lower Urinary Tract Infection	1
4	Recruiting	Treatment	Urinary Tract Infection	1
3	Completed	Treatment	Dysuria	1
2	Recruiting	Prevention	Pelvic Organ Prolapse (POP) / Postoperative Urinary Retention / Urinary Tract Infection	1
0	Terminated	Treatment	Osteomyelitis	1
Not Available	Completed	Prevention	Catheter Related Infections / Urinary Tract Infection	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral
Liquid	Extracorporeal
Tablet, film coated	Oral
Granule, for solution	Oral
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
Capsule	Oral
Granule, effervescent	Oral
Liquid	Topical
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

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-0006-9300000000-e762ea01823717c4bda9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0006-0900000000-05c8e159897335060443
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-01ox-2900000000-86fe33e31cc8f7108c14
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-01ti-9300000000-7eb44254c8cc65c09acd
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-004i-9000000000-fd4edf8f48f9c42bca0c
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-004l-9000000000-371b89c99afba4931848
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable

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Drug created on September 14, 2010 16:21 / Updated on April 16, 2021 12:23