U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of METHENAMINE

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
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
34 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
177 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.8 h
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

Doses

DosePopulationAdverse 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:
healthy, 24-65
n = 10
Health Status: healthy
Age Group: 24-65
Sex: M+F
Population Size: 10
Sources:
1 g single, oral
Recommended
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
healthy, 24-65
n = 10
Health Status: healthy
Age Group: 24-65
Sex: M+F
Population Size: 10
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Urinary tract infections
Sources:
Other AEs: Bladder irritation, Micturition painful...
Other AEs:
Bladder irritation
Micturition painful
Micturition frequency
Albuminuria
Hematuria
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
Health Status: unhealthy
Condition: Urinary tract infections
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Urinary tract infections
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Urinary tract infections
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Urinary tract infections
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Urinary tract infections
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Evaluation of Er:YAG laser and EDTAC on dentin adhesion of six endodontic sealers.
2001
Disseminated histoplasmosis presenting as pyoderma gangrenosum-like lesions in a patient with acquired immunodeficiency syndrome.
2001 Aug
Developmental changes in the fine structure and histochemical properties of mucous cells in the parotid gland of the infant Japanese macaque.
2001 Dec
Antimicrobial activity of four root canal sealers against endodontic pathogens.
2001 Dec
Plaque-like structures and arteriosclerotic changes in "diffuse neurofibrillary tangles with calcification" (DNTC).
2001 Dec
The 143 and 300 K polymorphs of hexamethylenetetraminium 2,4-dinitrophenolate monohydrate.
2001 Dec
Septum formation in Aspergillus nidulans.
2001 Dec
The formin/diaphanous-related protein, FHOS, interacts with Rac1 and activates transcription from the serum response element.
2001 Dec 7
New temperature modification makes the Bielschowsky silver stain reproducible.
2001 Jan
Evidence for the binding of a human sperm component with diaphanous protein.
2001 Jan-Feb
Formaldehyde release from ground root canal sealer in vitro.
2001 Jun
Application of fluorescent in situ hybridization for specific diagnosis of Pneumocystis carinii pneumonia in foals and pigs.
2001 May
Oral exfoliative cytology in the diagnosis of paracoccidioidomycosis.
2001 May-Jun
Determination of the enrichment of the hydrogen bound to carbon 5 of glucose on 2H2O administration.
2001 Oct 15
mDia-interacting protein acts downstream of Rho-mDia and modifies Src activation and stress fiber formation.
2001 Oct 19
Methenamine hippurate for preventing urinary tract infections.
2002
The evolutionary history of effectors downstream of Cdc42 and Rac.
2002
Formins initiate new actin filaments.
2002 Aug
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
Hexamethylenetetraminium 2,4,6-trinitrophenolate.
2002 Jan
Comparison of methods for identification of Pneumocystis carinii in bronchoalveolar lavage fluid.
2002 Jun
Formins direct Arp2/3-independent actin filament assembly to polarize cell growth in yeast.
2002 Mar
Identification of interaction partners of the cytosolic polyproline region of CD95 ligand (CD178).
2002 May 22
Dimethylsilane polyamines: cytostatic compounds with potentials as anticancer drugs. II. Uptake and potential cytotoxic mechanisms.
2002 Nov-Dec
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
Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine.
2003 Feb
(1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines.
2003 Feb
Crystallographic analysis of the thermal motion of the inclusion complex of cyclomaltoheptaose (beta-cyclodextrin) with hexamethylenetetramine.
2003 Feb 7
Gremlin is the BMP antagonist required for maintenance of Shh and Fgf signals during limb patterning.
2003 Jul
Structural changes of hexamethylenetetramine and undecanedioic acid co-crystal (HMT-C11) as a function of the temperature.
2003 Jun
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
Glomerular lesions in dogs infected with Leishmania organisms.
2003 May
Patents

Sample Use Guides

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 Thu Jul 06 21:38:25 UTC 2023
Edited
by admin
on Thu Jul 06 21:38:25 UTC 2023
Record UNII
J50OIX95QV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHENAMINE
EP   HSDB   INCI   INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INN   INCI  
Official Name English
METHENAMINE [MI]
Common Name English
HEXAMETHYLENAMINE
Common Name English
INS NO.239
Code English
HEXAMETHYLENE TETRAMINE
Common Name English
HEXAMINE
JAN  
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
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
WHO-VATC QJ01XX55
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
EPA PESTICIDE CODE 45501
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
WHO-VATC QJ01XX05
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
CFR 21 CFR 176.170
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
WHO-VATC QR01AX01
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
WHO-ATC J01XX05
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
NCI_THESAURUS C255
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
WHO-ATC R01AX01
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
JECFA EVALUATION INS-239
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
CODEX ALIMENTARIUS (GSFA) INS-239
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
LIVERTOX NBK567340
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C61841
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
DRUG BANK
DB06799
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
LACTMED
Methenamine
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
MERCK INDEX
M7308
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
HEXAMETHYLENETETRAMINE
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
JECFA MONOGRAPH
INS-239
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
EVMPD
SUB08845MIG
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
FDA UNII
J50OIX95QV
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
CAS
100-97-0
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201270
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
NSC
26346
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
INN
119
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
DAILYMED
J50OIX95QV
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
CHEBI
6824
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
HSDB
563
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
RXCUI
6832
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY RxNorm
PUBCHEM
4101
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-905-8
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
DRUG CENTRAL
3344
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
MESH
D008709
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
RS_ITEM_NUM
1409003
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID6020692
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
SMS_ID
100000092106
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
NSC
403347
Created by admin on Thu Jul 06 21:38:27 UTC 2023 , Edited by admin on Thu Jul 06 21:38:27 UTC 2023
PRIMARY
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