METHENAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H12N4
Molecular Weight	140.1863
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

C1N2CN3CN1CN(C2)C3

InChI

InChIKey=VKYKSIONXSXAKP-UHFFFAOYSA-N

InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2

HIDE SMILES / InChI

Molecular Formula	C6H12N4
Molecular Weight	140.1863
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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.

Originator

Approval Year

Conditions

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205	Preventing		Approved 8,429	UREX

C_max

Value	Dose	Co-administered	Analyte	Population
34 μg/mL	1 g 2 times / day multiple, oral		METHENAMINE serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
177 μg × h/mL	1 g 2 times / day multiple, oral		METHENAMINE serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.8 h	1 g 2 times / day multiple, oral		METHENAMINE serum	Homo sapiens

Doses

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Dose	Population	Adverse events
1 g 2 times / day multiple, oral Recommended	healthy, 24-65
1 g single, oral Recommended	healthy, 24-65
8 g 1 times / day multiple, oral Overdose	unhealthy	Other AEs: Bladder irritation, Micturition painful...

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AEs

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AE	Dose	Population
Albuminuria	8 g 1 times / day multiple, oral Overdose	unhealthy
Bladder irritation	8 g 1 times / day multiple, oral Overdose	unhealthy
Hematuria	8 g 1 times / day multiple, oral Overdose	unhealthy
Micturition frequency	8 g 1 times / day multiple, oral Overdose	unhealthy
Micturition painful	8 g 1 times / day multiple, oral Overdose	unhealthy

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY41827	https://www.001chemical.com/chem/100-97-0
3B Scientific (Wuhan) Corp	3B4-0592	http://www.3bsc.com/index/pro_info.php?id=18440
3B Scientific (Wuhan) Corp	3B4-0593	http://www.3bsc.com/index/pro_info.php?id=18441
3B Scientific (Wuhan) Corp	3B4-0594	http://www.3bsc.com/index/pro_info.php?id=18442
3B Scientific (Wuhan) Corp	3B4-3002	http://www.3bsc.com/index/pro_info.php?id=77635

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PubMed

Show entries

Title	Date	PubMed
Simulated cometary matter as a test for enantiomer separating chromatography for use on comet 46P/Wirtanen.	2001	11642294
Developmental changes in the fine structure and histochemical properties of mucous cells in the parotid gland of the infant Japanese macaque.	2001 Dec	11838714
Effects of chlorhexidine gluconate as an endodontic irrigant on the apical seal: short-term results.	2001 Dec	11771589
Post retention: the effect of sequence of post-space preparation, cementation time, and different sealers.	2001 Dec	11771587
Evaluation of the genotoxicity of zinc oxide eugenol-based, calcium hydroxide-based, and epoxy resin-based root canal sealers by comet assay.	2001 Dec	11771581

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Patents

Sample Use Guides

In Vivo Use Guide

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.