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

Structure Search

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

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 202 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/016151s025lbl.pdf	Preventing		Approved 8307	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 -7.8710399E10

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 n = 10 Health Status: healthy Age Group: 24-65 Sex: M+F Population Size: 10 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 n = 10 Health Status: healthy Age Group: 24-65 Sex: M+F Population Size: 10 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 Condition: Urinary tract infections 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 Condition: Urinary tract infections 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 Condition: Urinary tract infections 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 Condition: Urinary tract infections 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 Condition: Urinary tract infections 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 Condition: Urinary tract infections 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
AK Scientific, Inc. (AKSCI)	H722	http://www.aksci.com/item_detail.php?cat=H722
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	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
Acros Organics	AC120610100	https://www.fishersci.com/shop/products/hexamethylenetetramine-99-acros-organics-3/AC120610100
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
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	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
Avantor Inc	200012-662	https://us.vwr.com/store/product/7514440/methenamine
BOC Sciences	23304-08-7	https://www.bocsci.com/methenamine-d12-cas-23304-08-7-item-212445.html
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
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
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
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
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	24998	http://www.parchem.com/chemical-supplier-distributor/Hexamethylene-Tetramine-014998.aspx
Parchem	22238	http://www.parchem.com/chemical-supplier-distributor/Hexamethylenetetramine-012238.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	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
Sigma-Aldrich	1409003_USP	https://www.sigmaaldrich.com/catalog/product/usp/1409003?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
abcr GmbH	AB117019	http://www.abcr.com/shop/en/AB117019
abcr GmbH	AB208085	http://www.abcr.com/shop/en/AB208085
eNovation Chemicals	D382735	http://www.enovationchem.com/productDetails.asp?productID=D382735
iChemical	EBD2203367	http://www.ichemical.com/products/100-97-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-8414341610	https://mcule.com/MCULE-8414341610/

PubMed

Title	Date	PubMed
Antimicrobial activity of four root canal sealers against endodontic pathogens.	2001 Dec	11800436
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
Plaque-like structures and arteriosclerotic changes in "diffuse neurofibrillary tangles with calcification" (DNTC).	2001 Dec	11761720
Wnt/Frizzled activation of Rho regulates vertebrate gastrulation and requires a novel Formin homology protein Daam1.	2001 Dec 28	11779461
Localization of a mammalian homolog of diaphanous, mDia1, to the mitotic spindle in HeLa cells.	2001 Feb	11171383
Effect of ultrasonic vibration and various sealer and cement combinations on titanium post removal.	2001 Jan	11487157
Identification of a carboxyl-terminal diaphanous-related formin homology protein autoregulatory domain.	2001 Jan 26	11035012
Toward designed assembly of microporous coordination networks constructed from silver(I)-hexamethylenetetramine layers.	2001 Jul 2	11421706
Setting times for endodontic sealers under clinical usage and in vitro conditions.	2001 Jun	11487139
Modification of the levels of polyphenols in wort and beer by addition of hexamethylenetetramine or sulfite during mashing.	2001 Nov	11714309
Determination of the enrichment of the hydrogen bound to carbon 5 of glucose on 2H2O administration.	2001 Oct 15	11673889
Genes and proteins in renal development.	2002	11937757
Formins initiate new actin filaments.	2002 Aug	12149629
Invasive Aspergillosis in Italian AIDS patients.	2002 Dec	12478322
A Formin Homology protein and a profilin are required for cytokinesis and Arp2/3-independent assembly of cortical microfilaments in C. elegans.	2002 Dec 23	12498681
Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water.	2002 Dec 26	12489971
Delphilin: a novel PDZ and formin homology domain-containing protein that synaptically colocalizes and interacts with glutamate receptor delta 2 subunit.	2002 Feb 1	11826110
Ground-glass hepatocytes in fibrinogen storage disease in Japanese Black calves.	2002 Feb-Apr	11944997
A 1:1 adduct of hexamethylenetetramine and 4-hydroxy-3-methoxybenzaldehyde.	2002 Jan	11781494
Hexamethylenetetraminium 2,4,6-trinitrophenolate.	2002 Jan	11781493
Evaluation of lectin staining in the diagnosis of fungal keratitis in an experimental rabbit model.	2002 Jan 25	11815751
Cell polarity: following formin function.	2002 Jan 8	11790314
Monolithic scavenger resins by amine functionalizations of poly(4-vinylbenzyl chloride-co-divinylbenzene) PolyHIPE materials.	2002 Jul 25	12123360
Primary evaluation of methenamine as a NPN compound with probable effects on increasing ruminal escaped protein.	2002 Jun	12126137
Vibrational frequencies and structural determinations of hexamethylenetetraamine.	2002 May	12083657
Identification of interaction partners of the cytosolic polyproline region of CD95 ligand (CD178).	2002 May 22	12023017
Hexamethylenetetramine-4-nitrocatechol-water (1/2/1).	2002 Nov	12415179
Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms.	2002 Nov-Dec	12552990
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 Apr 21	12691560
Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine.	2003 Feb	12589036
ForC, a novel type of formin family protein lacking an FH1 domain, is involved in multicellular development in Dictyostelium discoideum.	2003 Feb 15	12538772
Adducts of hexamethylenetetramine with ferrocenecarboxylic acid and ferrocene-1,1'-dicarboxylic acid: multiple disorder in space groups Fmm2 and Cmcm.	2003 Jul	12855846
The Formin family protein, formin homolog overexpressed in spleen, interacts with the insulin-responsive aminopeptidase and profilin IIa.	2003 Jul	12677009
Two bis(ammonium) 1,5-naphthalenedisulfonate salts.	2003 Jun	12794355
Prognostic significance of microvascular thrombosis in donor kidney allograft biopsies.	2003 Jun 15	12811244
Immunofluorescence of the epizootic ulcerative syndrome pathogen, Aphanomyces invadans, using a monoclonal antibody.	2003 Jun 20	12887259
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 Mar 26	12643633
[Quantitative assessment of the biological activity of chemicals by soil microbial associations].	2003 May-Jun	12754832
Activation of the Rac-binding partner FHOD1 induces actin stress fibers via a ROCK-dependent mechanism.	2003 Oct 3	12857739

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 `Sun Dec 18 18:01:39 UTC 2022` Edited by `admin` on `Sun Dec 18 18:01:39 UTC 2022`
Record UNII	J50OIX95QV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHENAMINE

Official Name

English

METHENAMINE [MI]

Common Name

English

HEXAMETHYLENAMINE

Common Name

English

INS NO.239

Code

English

HEXAMETHYLENE TETRAMINE

Common Name

English

HEXAMINE

Common Name

English

URITONE

Brand Name

English

E-239

Code

English

Hexamethylenetetramine

Common Name

English

Methenamine [WHO-DD]

Common Name

English

HMT

Common Name

English

1,3,5,7-TETRAAZAADAMANTANE

Systematic Name

English

methenamine [INN]

Common Name

English

1,3,5,7-TETRAAZATRICYCLO(3.3.1.1 SUP(3,7))DECANE

Common Name

English

METHENAMINE [EP MONOGRAPH]

Common Name

English

INS-239

Code

English

METHENAMINE [USP MONOGRAPH]

Common Name

English

METHENAMINE [MART.]

Common Name

English

METHENAMINE [USP-RS]

Common Name

English

METHENAMINE [HSDB]

Common Name

English

1,3,5,7-TETRAAZATRICYCLO(3.3.1.13,7)DECANE

Systematic Name

English

METHENAMINE [VANDF]

Common Name

English

NSC-26346

Code

English

METHENAMINE [INCI]

Common Name

English

NSC-403347

Code

English

HMTA

Common Name

English

HEXAMINE [JAN]

Common Name

English

UROTROPIN

Brand Name

English

AMINOFORM

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.2280