methenamine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
3344 100-97-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • hexamethylenetetramine
  • methenamine
  • hexamethylenamine
  • hexamine
  • methenamin
  • methenamine hippurate
  • hexamethylenetetramine hippurate
  • hexamethylenetetramine hippuric acid complex
  • methenamine mandelate
An anti-infective agent most commonly used in the treatment of urinary tract infections. Its anti-infective action derives from the slow release of formaldehyde by hydrolysis at acidic pH. (From Martindale, The Extra Pharmacopoeia, 30th ed, p173)
  • Molecular weight: 140.19
  • Formula: C6H12N4
  • CLOGP: 2.44
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 12.96
  • ALOGS: 0.74
  • ROTB: 0
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 g O
3 g O

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,MAP2K6,MAP3K21,MAP3K7,MAPK7,MET,NTRK2,PDK2,PDK4,PIK3CD,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,TGFBR1,TTK,ULK1 37
kinase-selectivity-class AAK1,AXL,CAMK2D,CDK4,CDK7,CSK,EPHB4,FLT3,GAK,INSR,IRAK1,IRAK3,IRAK4,LRRK2,MAP3K7,MAP4K1,MAP4K3,MAP4K5,NUAK1,PIK3CD,PTK2,SIK2,TEK 23
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
July 5, 1967 FDA CNTY LINE PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Urinary tract infection 143.03 21.56 101 2895 305531 90319920
Endocarditis enterococcal 74.98 21.56 12 2984 247 90625204
Respiratory syncytial virus test positive 69.96 21.56 14 2982 1044 90624407
Mitral valve replacement 66.74 21.56 12 2984 503 90624948
Aortic valve replacement 53.51 21.56 11 2985 938 90624513
Fall 39.93 21.56 63 2933 481747 90143704
Drug monitoring procedure not performed 26.68 21.56 6 2990 781 90624670
Hyperammonaemia 24.88 21.56 9 2987 6466 90618985
Cystitis 24.17 21.56 19 2977 66699 90558752
Emotional distress 23.98 21.56 15 2981 36647 90588804
Hypothermia 23.21 21.56 11 2985 15564 90609887
Urine analysis abnormal 22.87 21.56 8 2988 5213 90620238
Thyroid cancer metastatic 22.78 21.56 4 2992 146 90625305

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Urinary tract infection 64.04 37.08 32 703 99252 42521348
Pathogen resistance 37.58 37.08 12 723 11438 42609162

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Urinary tract infection 135.59 20.84 96 3166 326186 110259851
Endocarditis enterococcal 71.84 20.84 12 3250 365 110585672
Respiratory syncytial virus test positive 66.73 20.84 14 3248 1480 110584557
Mitral valve replacement 65.76 20.84 12 3250 614 110585423
Aortic valve replacement 48.85 20.84 11 3251 1615 110584422
Fall 41.33 20.84 68 3194 603414 109982623
Drug monitoring procedure not performed 24.23 20.84 6 3256 1324 110584713
Pathogen resistance 23.08 20.84 11 3251 17661 110568376
Thyroid cancer metastatic 22.44 20.84 4 3258 179 110585858

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC G04BX17 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Other urologicals
ATC J01XX05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER ANTIBACTERIALS
Other antibacterials
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000892 Anti-Infective Agents, Urinary
MeSH PA D000900 Anti-Bacterial Agents
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:35441 antiinfective agent

Related Drugs by ATC class:

G04BX Other urologicals 10 drugs
acetohydroxamic aciddapoxetinedimethyl sulfoxidemagnesium hydroxidepentosan polysulfatephenazopyridinephenyl salicylatesalicylic acidsuccinimidetiopronin
J01XX Other antibacterials 12 drugs
bacitracinclofoctoldaptomycinfosfomycingepotidacinlefamulinlinezolidmandelic acidnitroxolinespectinomycintedizolid phosphatexibornol

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Urinary tract infectious disease indication 68566005
Prevention of Bacterial Urinary Tract Infection indication
Gastritis contraindication 4556007 DOID:4029
Hypocalcemia contraindication 5291005
Severe chronic ulcerative colitis contraindication 14311001
Disorder of autonomic nervous system contraindication 15241006
Cirrhosis of liver contraindication 19943007 DOID:5082
Hyperphosphatemia contraindication 20165001 DOID:0050459
Glaucoma contraindication 23986001 DOID:1686
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Hyperthyroidism contraindication 34486009 DOID:7998
Glomerulonephritis contraindication 36171008 DOID:2921
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Hypernatremia contraindication 39355002
Hypovolemic shock contraindication 39419009
Gastrointestinal ulcer contraindication 40845000
Body fluid retention contraindication 43498006
Uremia contraindication 44730006 DOID:4676
Conduction disorder of the heart contraindication 44808001
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Paralytic ileus contraindication 55525008 DOID:8442
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Blood coagulation disorder contraindication 64779008 DOID:1247
Diabetes mellitus contraindication 73211009 DOID:9351
Factor II deficiency contraindication 73975000
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Hiatal hernia contraindication 84089009 DOID:12642
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Hemophilia contraindication 90935002
Myasthenia gravis contraindication 91637004 DOID:437
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Liver function tests abnormal contraindication 166603001
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Pyloric obstruction contraindication 244815007
Benign prostatic hyperplasia contraindication 266569009
Edema contraindication 267038008
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Fever greater than 100.4 Fahrenheit contraindication 426000000
Severe dehydration contraindication 450316000




🐶 Veterinary Drug Use

SpeciesUseRelation
Cats Urinary tract infections Indication
Cats Management of complications resulting from surgical manipulations of the urinary tract Indication
Dogs Urinary tract infections Indication
Dogs Management of complications resulting from surgical manipulations of the urinary tract Indication

🐶 Veterinary products

ProductApplicantIngredients
Mesulfin Tablets Zoetis Inc. 2

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.59 Basic
pKa2 5.59 Basic
pKa3 1.09 Basic
pKa4 1.0 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

IDSource
4018578 VUID
N0000146894 NUI
D00393 KEGG_DRUG
5714-73-8 SECONDARY_CAS_RN
587-23-5 SECONDARY_CAS_RN
4017868 VANDF
4017869 VANDF
4018578 VANDF
C0025638 UMLSCUI
CHEBI:6824 CHEBI
CHEMBL1201270 ChEMBL_ID
DB06799 DRUGBANK_ID
CHEMBL1201104 ChEMBL_ID
CHEMBL3833312 ChEMBL_ID
D008709 MESH_DESCRIPTOR_UI
4101 PUBCHEM_CID
119 INN_ID
10913 IUPHAR_LIGAND_ID
C011481 MESH_SUPPLEMENTAL_RECORD_UI
C023055 MESH_SUPPLEMENTAL_RECORD_UI
J50OIX95QV UNII
161623 RXNORM
5069 MMSL
5070 MMSL
5071 MMSL
72179 MMSL
941 MMSL
945 MMSL
d00106 MMSL
002861 NDDF
002862 NDDF
002863 NDDF
372773008 SNOMEDCT_US
55741006 SNOMEDCT_US
56123002 SNOMEDCT_US
68293009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
URELLE HUMAN PRESCRIPTION DRUG LABEL 5 0037-6321 TABLET 81 mg ORAL Unapproved drug other 12 sections
URIBEL HUMAN PRESCRIPTION DRUG LABEL 5 0076-0111 CAPSULE 120 mg ORAL unapproved drug other 20 sections
Hyophen HUMAN PRESCRIPTION DRUG LABEL 5 0076-0901 TABLET 81.60 mg ORAL unapproved drug other 19 sections
Phosphasal HUMAN PRESCRIPTION DRUG LABEL 5 0076-0902 TABLET 81.60 mg ORAL unapproved drug other 20 sections
Ustell HUMAN PRESCRIPTION DRUG LABEL 5 0076-0903 CAPSULE 120 mg ORAL unapproved drug other 20 sections
Methenamine Hippurate HUMAN PRESCRIPTION DRUG LABEL 1 0115-1754 TABLET 1 g ORAL ANDA 12 sections
URIBEL TABS HUMAN PRESCRIPTION DRUG LABEL 5 0178-0745 TABLET, COATED 81.60 mg ORAL unapproved drug other 13 sections
Walgreens Pain Relief plus UTI Bacteria Control HUMAN OTC DRUG LABEL 2 0363-1277 TABLET 162 mg ORAL unapproved drug other 10 sections
Walgreens Antibacterial Plus Urinary Pain Relief HUMAN OTC DRUG LABEL 2 0363-4404 TABLET 162 mg ORAL unapproved drug other 10 sections
UROGESIC BLUE HUMAN PRESCRIPTION DRUG LABEL 4 0485-0151 TABLET, COATED 81.60 mg ORAL unapproved drug other 18 sections
UROGESIC BLUE HUMAN PRESCRIPTION DRUG LABEL 4 0485-0151 TABLET, COATED 81.60 mg ORAL unapproved drug other 18 sections
Preferred Antibacterial Plus Urinary Pain Relief HUMAN OTC DRUG LABEL 2 10956-763 TABLET 162 mg ORAL unapproved drug other 10 sections
Rite Aid Antibacterial Plus Urinary Pain Relief HUMAN OTC DRUG LABEL 2 11822-4892 TABLET 162 mg ORAL unapproved drug other 10 sections
Uretron D/S HUMAN PRESCRIPTION DRUG LABEL 5 12539-144 TABLET 81.60 mg ORAL unapproved drug other 20 sections
UroAv-81 HUMAN PRESCRIPTION DRUG LABEL 5 15338-502 TABLET 81 mg ORAL unapproved drug other 18 sections
UroAv-B HUMAN PRESCRIPTION DRUG LABEL 5 15338-503 CAPSULE 118 mg ORAL unapproved drug other 18 sections
URIMAR-T CAPS HUMAN PRESCRIPTION DRUG LABEL 5 28595-224 CAPSULE 120 mg ORAL unapproved drug other 19 sections
MB CAPS HUMAN PRESCRIPTION DRUG LABEL 5 28595-299 CAPSULE 120 mg ORAL unapproved drug other 18 sections
HIPREX HUMAN PRESCRIPTION DRUG LABEL 1 30698-477 TABLET 1 g ORAL NDA 13 sections
TopCare Antibacterial Plus Urinary Pain Relief HUMAN OTC DRUG LABEL 2 36800-314 TABLET 162 mg ORAL unapproved drug other 10 sections
Meijer Antibacterial Plus Urinary Pain Relief HUMAN OTC DRUG LABEL 2 41250-557 TABLET 162 mg ORAL unapproved drug other 10 sections
Methenamine Hippurate HUMAN PRESCRIPTION DRUG LABEL 1 42571-332 TABLET 1000 mg ORAL ANDA 11 sections
Methenamine Mandelate Human Prescription Drug Label 1 42799-105 TABLET 500 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Methenamine Mandelate Human Prescription Drug Label 1 42799-106 TABLET 1000 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Good Neighbor Antibacterial Plus Urinary Pain Relief HUMAN OTC DRUG LABEL 2 46122-622 TABLET 162 mg ORAL unapproved drug other 10 sections
Methenamine Hippurate HUMAN PRESCRIPTION DRUG LABEL 1 47781-577 TABLET 1 g ORAL NDA 22 sections
Azo Urinary Tract DefenseAntibacterial Protection HUMAN OTC DRUG LABEL 2 49973-011 TABLET 162 mg ORAL unapproved drug other 16 sections
Methenamine Hippurate HUMAN PRESCRIPTION DRUG LABEL 1 50268-549 TABLET 1000 mg ORAL ANDA 11 sections
METHENAMINE HIPPURATE HUMAN PRESCRIPTION DRUG LABEL 1 50742-142 TABLET 1 g ORAL ANDA 14 sections
CVS DUAL ACTION PAIN RELIEF HUMAN OTC DRUG LABEL 2 51316-777 TABLET 162 mg ORAL unapproved drug other 10 sections