Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00409)
Name
Methenamine
Synonyms    Click to Show/Hide the Synonyms of This API
methenamine; Hexamethylenetetramine; 100-97-0; Hexamine; Urotropine; Aminoform; Urotropin; Hexamethylenamine; Hexamethylene tetramine; 1,3,5,7-Tetraazaadamantane; Methenamin; Hexamethylenetetraamine; Formamine; Uritone; Aminoformaldehyde; Ammonioformaldehyde; Ammoform; Antihydral; Cystamin; Cystogen; Duirexol; Hexaform; Hexaloids; Metramine; Resotropin; Uratrine; Urodeine; Xametrin; Formin; Heterin; Hexasan; Uramin; Preparation AF; Hexamethyleneamine; Hexilmethylenamine; Hexa-Flo-Pulver; Ekagom H; methenaminum; Aceto HMT; Herax UTS; Hexamethylentetramin; Metenamina; Hexaminum; Formin (heterocycle); Nocceler H; Sanceler H; 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane; Hexamine (heterocycle); Vulkacit H 30; Hexamethylentetraminum; Hexamethylentetramine; Hexasan (VAN); Mandelamine; S 4 (heterocycle); Hexamethylenetetraminum; Uro-phosphate; 1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane; Esametilentetramina; Metenamine; Methamin; Vesaloin; Hexa (vulcanization accelerator); UNII-J50OIX95QV; 1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decane; Hexamine (JAN); Hexamine (TN); Hexamethylenetetramine (aliphatic); Methenamine (USP/INN); MFCD00006895; 1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane; J50OIX95QV; 1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 37))decane; CHEBI:6824; H.M.T.; Formin (the heterocyclic compound); NSC26346; 1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane; NSC-26346; 1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 3,7))decane; NCGC00094719-04; Hexamine Silver; DSSTox_CID_692; Hexamethylenetetramine-palladium chloride adduct; Methenamine Silver; Silver Methenamine; DSSTox_RID_75739; Hexamethylenetetramine, 99%; 1,3,5,7-tetraazatricyclo[3.3.1.1?,?]decane; DSSTox_GSID_20692; 1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane; Caswell No. 482; Methenamine [USAN:INN]; Sanceler HT; Metenamina [INN-Spanish]; Methenaminum [INN-Latin]; Heksa K; Hexamine Superfine; Nocceler H-PO; Sanceler HT-PO; Hexa B; 1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane hydroiodide; CAS-100-97-0; Esametilentetramina [Italian]; Hexamethylentetramin [German]; SMR000857139; Cohedur H 30; CCRIS 2297; HSDB 563; hexamethylene-tetramine; NSC403347; Rhenogran HEXA 80; Thixon 715B; Methenamine, >26% in a non hazardous diluent; NSC-403347; 1,3,5,7-Tetraazotricyclo[3.3.1.13,7]decane; SR-05000002024; Methenamine [USP:INN]; 1,3,5,7-tetraazatricyclo[3.3.1.1<3,7>]decane; 1,3,5,7-Tetraazatricyclo[3.3.1.1{3,7}]decane; EINECS 202-905-8; NSC 26346; UN1328; 1,3,5,7-Tetraazatricyclo[3.3.1.1(sup 3,7)]decane; EPA Pesticide Chemical Code 045501; NSC 403347; Hexamethylenetetramine, 98.5%, contains an anticaking agent; Hexamethylamine; Naphthamine; Vesalvine; Urisol; EL 10 (corrosion inhibitor); Hexamethylenetetramine solutions; AI3-09611; HEXAMETHYLENETETRAMINE, ACS; Prestwick_79; Vulkacit H30; 1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decane; Grasselerator 102; Cystex (Salt/Mix); hexam-ethylenetetraamine; hexamethylene tetraamine; PubChem20918; Spectrum_000991; ACMC-20ahs9; Spectrum2_000827; Spectrum3_001730; Spectrum4_000872; Spectrum5_001603; Methenamine (Mandelamine); Formaldehyde-ammonia 6:4; [16]-Adamazane, INN; component of Uro-Phosphate; Uro-phosphate (Salt/Mix); 1,5,7-Tetraazaadamantane; EC 202-905-8; Hexamethylentetramin(german); Hexamethylenetetramine, 8CI; 1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane; SCHEMBL33785; BSPBio_003380; Hexamethylenetetramine, tech.; KBioGR_001563; KBioSS_001471; Hexamethylenetetramine [UN1328] [Flammable solid]; MLS001332361; MLS001332362; MLS002207085; DivK1c_000322; SPECTRUM1500394; SPBio_000753; Hexamethylenetetramine, BioXtra; INS NO.239; CHEMBL1201270; DTXSID6020692; GTPL10913; HMS501A04; KBio1_000322; KBio2_001471; KBio2_004039; KBio2_006607; KBio3_002600; INS-239; NINDS_000322; HMS1920L13; HMS2091D08; HMS2233B09; HMS3371O15; HMS3652A05; HMS3715D17; Pharmakon1600-01500394; HY-B0514; STR00289; Tox21_113455; Tox21_201606; Tox21_300502; ANW-73975; CCG-40289; Hexamethylenetetramine, LR, >=99%; NSC757101; SBB008794; STL197471; ZINC86040406; AKOS000120003; AKOS005169648; Tox21_113455_1; Urotropine 100 microg/mL in Methanol; DB06799; MCULE-8414341610; NE10461; NSC-757101; IDI1_000322; NCGC00094719-01; NCGC00094719-02; NCGC00094719-03; NCGC00094719-05; NCGC00094719-06; NCGC00094719-08; NCGC00254463-01; NCGC00259155-01; SBI-0051439.P003; FT-0627024; FT-0669190; Hexamethylenetetramine, ReagentPlus(R), 99%; ST50823696; SW199604-2; 1,5,7-Tetraazatricyclo[3.3.1.13,7]decane; 3070-EP2269990A1; 3070-EP2295550A2; 3070-EP2298734A2; 3070-EP2371811A2; 3070-EP2377849A2; D00393; Hexamethylenetetramine, ACS reagent, >=99.0%; Q71969; 22128-EP2272817A1; 22128-EP2275404A1; 22128-EP2280000A1; 22128-EP2305652A2; 22128-EP2308848A1; 22128-EP2314593A1; 34431-EP2301536A1; 34431-EP2301538A1; 34431-EP2311455A1; 34543-EP2301536A1; 34543-EP2301538A1; 34543-EP2311455A1; AB00052038_08; AB00052038_09; 1,3,5,7-tetraaza-tricyclo[3.3.1.13,7]decane; 1,3,5,7-tetraazatricyclo-[3.3.1.13,7]decane; 1,3,5,7-tetraazatricyclo[3,3,1,13,7]decane; 1,5:3,7-Dimethano-1,3,5,7-tetraazacyclooctane; AE-641/00560026; WLN: T66 B6 A B-C 1B I BN DN FN HNTJ; Hexamethylenetetramine [UN1328] [Flammable solid]; Hexamethylenetetramine, analytical reference material; Hexamethylenetetramine, p.a., ACS reagent, 99.0%; Hexamethylenetetramine, SAJ first grade, >=98.5%; J-000293; J-521456; SR-05000002024-1; SR-05000002024-3; 1,3,5,7-tetraaza-tricyclo[3.3.1.1*3,7*]decane; 1,3,5,7-Tetraazatricyclo-[3.3.1.1(3,7)]decane; BRD-K30114692-001-10-0; Hexamethylenetetramine, JIS special grade, >=99.0%; F2173-0429; Z362014242; Methenamine, European Pharmacopoeia (EP) Reference Standard; Methenamine, United States Pharmacopeia (USP) Reference Standard; 67931-01-5
Clinical Status
Approved
Disease Indication Urinary tract infection ICD-11: GC08 [1]
PubChem CID
4101
Formula
C6H12N4
Canonical SMILES
C1N2CN3CN1CN(C2)C3
InChI
1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
InChIKey
VKYKSIONXSXAKP-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=4101"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 140.19 Topological Polar Surface Area 13
XlogP 0.3 Complexity 84.8
Heavy Atom Count 10 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Methenamine 1000 mg tablet Click to Show/Hide the Full List of Formulation(s):          9 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c red no. 40; Fd&c yellow no. 6; Magnesium stearate; Anhydrous dibasic calcium phosphate; Magnesium aluminum silicate; Titanium dioxide; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Edenbridge Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c blue no. 2; Magnesium stearate; Talc; Titanium dioxide; Croscarmellose sodium; Polyvinyl alcohol; Silicon dioxide; Cellulose, microcrystalline; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Bryant Ranch Prepack; Seton Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c yellow no. 6; Magnesium stearate; Povidone; Silicon dioxide; Saccharin sodium
                   Dosage Form Oral Tablet
                   Company CorePharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Saccharin sodium dihydrate; Fd&c yellow no. 5; Magnesium stearate; Povidone
                   Dosage Form Oral Tablet
                   Company Winthrop
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Saccharin sodium dihydrate DIG Info Carbonic anhydrase XII (Ki = 633 nM) [6]
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c yellow no. 5; Magnesium stearate; Povidone; Saccharin sodium
                   Dosage Form Oral Tablet
                   Company Validus Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 6 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c yellow no. 6; Magnesium stearate; Silicon dioxide; Povidone k29/32; Saccharin sodium
                   Dosage Form Oral Tablet
                   Company Carilion Materials Management
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 7 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c yellow no. 5; Magnesium stearate; Povidones; Saccharin sodium
                   Dosage Form Oral Tablet
                   Company Leading Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 8 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Povidone; Saccharin sodium
                   Dosage Form Oral Tablet
                   Company Aurobindo Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 9 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Povidone, unspecified; Saccharin sodium
                   Dosage Form Oral Tablet
                   Company Alvogen; County Line Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Methenamine 500 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c blue no. 1; Magnesium stearate; Anhydrous dibasic calcium phosphate; Magnesium aluminum silicate; Titanium dioxide; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Edenbridge Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved methenamine from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
6 Carbonic anhydrase inhibitors: copper(II) complexes of polyamino-polycarboxylamido aromatic/heterocyclic sulfonamides are very potent inhibitors of the tumor-associated isoforms IX and XII. Bioorg Med Chem Lett. 2008 Jan 15; 18(2):836-41.

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