METHENAMINE HIPPURATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H9NO3.C6H12N4
Molecular Weight	319.3589
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ROAIXOJGRFKICW-UHFFFAOYSA-N

InChI=1S/C9H9NO3.C6H12N4/c11-8(12)6-10-9(13)7-4-2-1-3-5-7;1-7-2-9-4-8(1)5-10(3-7)6-9/h1-5H,6H2,(H,10,13)(H,11,12);1-6H2

HIDE SMILES / InChI

Molecular Formula	C9H9NO3
Molecular Weight	179.1727
Charge	0
Count

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

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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24689705
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.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/016151s025lbl.pdf	Preventing		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
34 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7076604/	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

Value	Dose	Co-administered	Analyte	Population
177 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7076604/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7076604/	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/7076604	healthy, 24-65 Health Status: healthy Age Group: 24-65 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7076604	Sources: https://pubmed.ncbi.nlm.nih.gov/7076604
1 g single, oral Recommended Dose: 1 g Route: oral Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/7076604	healthy, 24-65 Health Status: healthy Age Group: 24-65 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7076604	Sources: https://pubmed.ncbi.nlm.nih.gov/7076604
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf	Other AEs: Bladder irritation, Micturition painful... Other AEs: Bladder irritation Micturition painful Micturition frequency Albuminuria Hematuria Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf

AEs

AE	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017681s018lbl.pdf

Sourcing

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
AA Blocks	AA00H913	http://www.aablocks.com/goods/Goods/detail?id=AA00H913
abcr GmbH	AB117019	http://www.abcr.com/shop/en/AB117019
abcr GmbH	AB208085	http://www.abcr.com/shop/en/AB208085
Acadechem	ACDS-033175	http://www.acadechemical.com/product/107874
Aceschem	ACS015590	https://www.aceschem.com/catalog/100-97-0.html
Achemica	ACMC-20ahs9	http://www.achemica.com/prodinfo/?id=137609
Achemtek	0104-006318	http://www.achemtek.com/100-97-0
Acros Organics	AC120610010	https://www.fishersci.com/shop/products/hexamethylenetetramine-99-acros-organics/AC120610010
Acros Organics	AC120610025	https://www.fishersci.com/shop/products/hexamethylenetetramine-99-acros-organics/AC120610025
Acros Organics	AC120610100	https://www.fishersci.com/shop/products/hexamethylenetetramine-99-acros-organics-3/AC120610100
Acros Organics	AC232890010	https://www.fishersci.com/shop/products/hexamethylenetetramine-98-5-contains-anticaking-agent-acros-organics/AC232890010
Acros Organics	AC232890025	https://www.fishersci.com/shop/products/hexamethylenetetramine-98-5-contains-anticaking-agent-acros-organics/AC232890025
AK Scientific, Inc. (AKSCI)	H722	http://www.aksci.com/item_detail.php?cat=H722
Alfa Aesar	36462	https://www.alfa.com/en/catalog/036462/
Alfa Aesar	A17213	https://www.alfa.com/en/catalog/A17213/
Alfa Chemistry	100-97-0	https://www.alfachemic.com/catalysts/hexamethylenetetramine-cas-100-97-0-item-322016.htm
Anward	ANW-73975	http://www.anward.com/pro_result/60426
ApexBio Technology	B1972	http://www.apexbt.com/methenamine.html
Aurora Fine Chemicals LLC	K02.100.666	http://online.aurorafinechemicals.com/info?ID=K02.100.666
Aurum Pharmatech LLC	NE10461	http://www.Aurumpharmatech.com/Product/ProductDetails/NE10461
Avantor Inc	101226-032	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101226-032
Avantor Inc	200012-662	https://us.vwr.com/store/product/7514440/methenamine
Avantor Inc	BT224480-1KG	https://us.vwr.com/store/product/16902719/hexamethylenetetramine-99
Avantor Inc	BT224480-250G	https://us.vwr.com/store/product/16902719/hexamethylenetetramine-99
Avantor Inc	BT224480-5KG	https://us.vwr.com/store/product/16902719/hexamethylenetetramine-99
BioSynth	J-000293	https://www.biosynth.com/en/products/all-products/products/J-000293.html
BioSynth	J-521456	https://www.biosynth.com/en/products/all-products/products/J-521456.html
BOC Sciences	23304-08-7	https://www.bocsci.com/methenamine-d12-cas-23304-08-7-item-212445.html
Boerchem	BC222881	http://www.boerchem.com/?product_37656.html
Capot Chemical	20918	http://www.capotchem.com/en/20918.htm
Capot Chemical	PubChem20918	http://www.capotchem.com/en/20918.htm
Chem Scene	CS-2724	http://www.chemscene.com/100-97-0.html
ChemMol	44006954	http://www.chemmol.com/chemmol/44006954.html
Chemspace	CSSB00000182268	https://chem-space.com/CSSB00000182268
Clearsynth	CS-EB-01320	https://www.clearsynth.com/en/CSEB01320.html
Clearsynth	CS-ER-01312	https://www.clearsynth.com/en/CSER01312.html
Clearsynth	CS-T-79160	https://www.clearsynth.com/en/CST79160.html
DC Chemicals	DC36056	http://www.dcchemicals.com//product_show-Aminoform.html
Enamine	Z362014242	https://www.enaminestore.com/catalog/Z362014242
eNovation Chemicals	D382735	http://www.enovationchem.com/productDetails.asp?productID=D382735
Finetech	FT-0627024	http://www.finetechnology-ind.com/prod/detail/pub/100-97-0.html
Finetech	FT-0669190	http://www.finetechnology-ind.com/prod/detail/pub/23304-08-7.html
Fisher Chemical	H288500	https://www.fishersci.com/shop/products/hexamethylenetetramine-certified-acs-fisher-chemical/H288500
Fisher Chemical	H290500	https://www.fishersci.com/shop/products/hexamethylenetetramine-crystalline-usp-fisher-chemical/H290500
iChemical	EBD2203367	http://www.ichemical.com/products/100-97-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
LGC Standards	DRE-A17897500ME-100	https://www.lgcstandards.com/US/en/p/DRE-A17897500ME-100
LGC Standards	DRE-C17897500	https://www.lgcstandards.com/US/en/p/DRE-C17897500
LGC Standards	LGCFOR1998.00	https://www.lgcstandards.com/US/en/p/LGCFOR1998.00
LGC Standards	MM1998.00	https://www.lgcstandards.com/US/en/p/MM1998.00
Matrix Scientific	134489	https://www.matrixscientific.com/134489.html
mcule	MCULE-8414341610	https://mcule.com/MCULE-8414341610/
MedChem Express	HY-B0514	http://www.medchemexpress.com/hexamethylenetetramine.html
Molcore	MC41827	https://www.molcore.com/product/100-97-0
MuseChem	A001044	https://www.musechem.com/product/A001044.html
Oakwood	237165	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=118164&ExtHyperLink=1
Otava	2827497	https://search.otavachemicals.com/#!/search?query=2827497&type=code&base=dbb
Parchem	22238	http://www.parchem.com/chemical-supplier-distributor/Hexamethylenetetramine-012238.aspx
Parchem	24998	http://www.parchem.com/chemical-supplier-distributor/Hexamethylene-Tetramine-014998.aspx
Renno Tech	RP20622	http://www.rennotech.com/product_show.asp?id=26356
Selleck Chemicals	S3139	http://www.selleckchem.com/products/methenamine-mandelamine.html
Sigma-Aldrich	13-0750_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/130750?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	13-0760_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/130760?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1409003_USP	https://www.sigmaaldrich.com/catalog/product/usp/1409003?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	15614_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/15614?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	33233_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/33233?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017518	http://www.sinfoobiotech.com/product/1020916
Smolecule	S535108	http://www.smolecule.com/products/s535108
TCI (Tokyo Chemical Industry)	H0093	http://www.tcichemicals.com/eshop/en/us/commodity/H0093/index.html
THE BioTek	bt-275136	https://www.thebiotek.com/product/inhibitors/bt-275136
VladaChem	VL142620	https://www.vladachem.com/product.php?products=100-97-0
VladaChem	VL163235	https://www.vladachem.com/product.php?products=100-97-0
Yuhao Chemical	LQ0300	http://www.chemyuhao.com/100-97-0.html

PubMed

Title	Date	PubMed
Activation of the Rac-binding partner FHOD1 induces actin stress fibers via a ROCK-dependent mechanism.	2003-10-03	12857739
Formins: signaling effectors for assembly and polarization of actin filaments.	2003-07-01	12775772
Adducts of hexamethylenetetramine with ferrocenecarboxylic acid and ferrocene-1,1'-dicarboxylic acid: multiple disorder in space groups Fmm2 and Cmcm.	2003-07	12855846
Gremlin is the BMP antagonist required for maintenance of Shh and Fgf signals during limb patterning.	2003-07	12808456
The Formin family protein, formin homolog overexpressed in spleen, interacts with the insulin-responsive aminopeptidase and profilin IIa.	2003-07	12677009
Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody.	2003-06-20	12887259
Prognostic significance of microvascular thrombosis in donor kidney allograft biopsies.	2003-06-15	12811244
A locus for asphyxiating thoracic dystrophy, ATD, maps to chromosome 15q13.	2003-06	12807964
Two bis(ammonium) 1,5-naphthalenedisulfonate salts.	2003-06	12794355
Structural changes of hexamethylenetetramine and undecanedioic acid co-crystal (HMT-C11) as a function of the temperature.	2003-06	12761411
[Quantitative assessment of the biological activity of chemicals by soil microbial associations].	2003-05-21	12754832
Glomerular lesions in dogs infected with Leishmania organisms.	2003-05	12755294
Measuring gluconeogenesis using a low dose of 2H2O: advantage of isotope fractionation during gas chromatography.	2003-05	12582010
AgC(CN)3-based coordination polymers.	2003-04-21	12691573
Syntheses of two new 1D and 3D networks of Cu(II) and Co(II) using malonate and urotropine as bridging ligands: crystal structures and magnetic studies.	2003-04-21	12691560
Detection of sugar syrups in apple juice by delta(2)H per thousand and delta(13)C per thousand analysis of hexamethylenetetramine prepared from fructose.	2003-03-26	12643633
ForC, a novel type of formin family protein lacking an FH1 domain, is involved in multicellular development in Dictyostelium discoideum.	2003-02-15	12538772
Crystallographic analysis of the thermal motion of the inclusion complex of cyclomaltoheptaose (beta-cyclodextrin) with hexamethylenetetramine.	2003-02-07	12559733
Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine.	2003-02	12589036
(1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines.	2003-02	12554977
Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry.	2003-02	12554976
Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms.	2003-01-30	12552990
Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water.	2002-12-26	12489971
A Formin Homology protein and a profilin are required for cytokinesis and Arp2/3-independent assembly of cortical microfilaments in C. elegans.	2002-12-23	12498681
Invasive Aspergillosis in Italian AIDS patients.	2002-12	12478322
Formin-2, polyploidy, hypofertility and positioning of the meiotic spindle in mouse oocytes.	2002-12	12447394
A simple method for the specific detection of Ren-1 renin.	2002-12	12427159
Syntheses and characterizations of copper(II) polymeric complexes constructed from 1,2,4,5-benzenetetracarboxylic acid.	2002-11-18	12425647
A comparative evaluation of sealing ability of rootcanal sealers.	2002-11-08	12420566
Hexamethylenetetramine-4-nitrocatechol-water (1/2/1).	2002-11	12415179
Degeneration of Pick bodies visualized by methenamine-silver staining and immunohistochemistry.	2002-09	12416557
Dipole-dipole coupling constant for a directly bonded CH pair--a carbon-13 relaxation study.	2002-08	12323134
Value of urinary prophylaxis with methenamine in gynecologic surgery.	2002-08	12174159
Formins initiate new actin filaments.	2002-08	12149629
An actin nucleation mechanism mediated by Bni1 and profilin.	2002-08	12134165
Role of formins in actin assembly: nucleation and barbed-end association.	2002-07-26	12052901
Monolithic scavenger resins by amine functionalizations of poly(4-vinylbenzyl chloride-co-divinylbenzene) PolyHIPE materials.	2002-07-25	12123360
Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid.	2002-06	12188444
Primary evaluation of methenamine as a NPN compound with probable effects on increasing ruminal escaped protein.	2002-06	12126137
Mutational analysis of human profilin I reveals a second PI(4,5)-P2 binding site neighbouring the poly(L-proline) binding site.	2002-05-28	12052260
Identification of interaction partners of the cytosolic polyproline region of CD95 ligand (CD178).	2002-05-22	12023017
Vibrational frequencies and structural determinations of hexamethylenetetraamine.	2002-05	12083657
Ground-glass hepatocytes in fibrinogen storage disease in Japanese Black calves.	2002-04-12	11944997
Comparison of staining methods and a nested PCR assay to detect Histoplasma capsulatum in tissue sections.	2002-04	11939735
Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast.	2002-03	11875440
Effects of instrumentation, irrigation and dressing with calcium hydroxide on infection in pulpless teeth with periapical bone lesions.	2002-01	11858203
Biodegradation of formaldehyde and its derivatives in industrial wastewater with methylotrophic yeast Hansenula polymorpha and with the yeast-bioaugmented activated sludge.	2002	12449312
Genes and proteins in renal development.	2002	11937757
Methenamine hippurate for preventing urinary tract infections.	2002	11869659
The evolutionary history of effectors downstream of Cdc42 and Rac.	2002	11864373

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:39 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:39 GMT 2025`
Record UNII	M329791L57
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HIPREX

Preferred Name

English

METHENAMINE HIPPURATE

Official Name

English

METHENAMINE HIPPURATE [ORANGE BOOK]

Common Name

English

GLYCINE, N-BENZOYL, COMPD. WITH 1,3,5,7-TETRAAZATRICYCLO(3.3.1.1(SUP 3,7))DECANE (1:1)

Common Name

English

Methenamine hippurate [WHO-DD]

Common Name

English

METHENAMINE HIPPURATE [USP MONOGRAPH]

Common Name

English

METHENAMINE HIPPURATE [USAN]

Common Name

English

METHENAMINE HIPPURATE [USP IMPURITY]

Common Name

English

METHENAMINE HIPPURATE [USP-RS]

Common Name

English

HEXAMINE HIPPURATE

Common Name

English

METHENAMINE HIPPURATE [MART.]

Common Name

English

Hexamethylenetetramine monohippurate

Common Name

English

METHENAMINE HIPPURATE [VANDF]

Common Name

English

UREX

Brand Name

English

METHENAMINE HIPPURATE [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C255