Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00385)
Name
Mebendazole
Synonyms    Click to Show/Hide the Synonyms of This API
mebendazole; 31431-39-7; Vermox; Telmin; Mebenvet; Pantelmin; Vermirax; Mebenoazole; Ovitelmin; Bantenol; Mebutar; Lomper; Besantin; Vermicidin; Verpanyl; Noverme; Mebendazol; Methyl (5-benzoyl-1H-benzo[d]imidazol-2-yl)carbamate; Mebendazolum; 5-Benzoyl-2-benzimidazolecarbamic acid methyl ester; Carbamic acid, (5-benzoyl-1H-benzimidazol-2-yl)-, methyl ester; Methyl 5-benzoyl-2-benzimidazolecarbamate; Methyl 5-benzoyl-2-benzimidazolylcarbamate; Methyl 5-benzoyl benzimidazole-2-carbamate; R 17635; methyl (5-benzoyl-1H-benzimidazol-2-yl)carbamate; (5-Benzoyl-1H-benzimidazol-2-yl)-carbamic acid methyl ester; R 17,635; Methyl N-(5-benzoyl-1H-benzimidazol-2-yl)carbamate; CCRIS 4479; methyl N-(6-benzoyl-1H-benzimidazol-2-yl)carbamate; MFCD00057872; methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate; NSC 184849; UNII-81G6I5V05I; 2-Benzimidazolecarbamic acid, 5-benzoyl-, methyl ester; CHEMBL685; N-2 (5-Benzoyl-benzimidazole) carbamate de methyle; N-(Benzoyl-5, benzimidazolyl)-2, carbamate de methyle; CHEBI:6704; Carbamic acid, N-(5-benzoylbenzimidazol-2-yl)-, methyl ester; Versid; Methyl 6-benzoyl-1H-benzimidazol-2-ylcarbamate; 81G6I5V05I; 5-Benzoyl-2-benzimidazolecarbamic acid, methyl ester; NSC184849; NSC-184849; methyl [5-(phenylcarbonyl)-1H-benzimidazol-2-yl]carbamate; NCGC00016806-01; (5-Benzoyl-1H-benzimidazol-2-yl)carbamic acid methyl ester; 2-Benzimidazolecarbamic acid, 5-benzoyl-, methyl ester (8CI); CAS-31431-39-7; Equivurm Plus; DSSTox_CID_20682; DSSTox_RID_79538; DSSTox_GSID_40682; Mebendazol [INN-Spanish]; Mebendazolum [INN-Latin]; Vermox (TN); Emverm; SMR000036734; HSDB 3232; Mebendazole Polymorph C; SR-01000003109; EINECS 250-635-4; Methyl N-(5-benzoyl-2-benzimidazolyl)carbamate; Mebatreat; Mebendazole (JAN/USP/INN); Equivurmp Plus; N-2 (5-Benzoyl-benzimidazole) carbamate de methyle [French]; Mebendazole,(S); N-(Benzoyl-5, benzimidazolyl)-2, carbamate de methyle [French]; Prestwick_310; Mebendazole [USAN:USP:INN:BAN:JAN]; Spectrum_001298; CPD000036734; Prestwick0_000217; Prestwick1_000217; Prestwick2_000217; Prestwick3_000217; Spectrum2_001401; Spectrum3_001439; Spectrum4_000416; Spectrum5_001381; Probes1_000013; Probes2_000149; Cambridge id 5250893; Methyl [5-(Benzoyl)benzimidazol-2-yl]carbamate; TimTec1_000869; Oprea1_278237; Oprea1_768530; R-17635; SCHEMBL15860; BSPBio_000233; BSPBio_003178; CBDivE_010559; KBioGR_000712; KBioSS_001778; MLS000028491; MLS006011879; BIDD:GT0087; DivK1c_000751; SPECTRUM1501110; SPBio_001442; SPBio_002154; BPBio1_000257; DTXSID4040682; HMS502F13; KBio1_000751; KBio2_001778; KBio2_004346; KBio2_006914; KBio3_002398; NINDS_000751; HMS1536H11; HMS1568L15; HMS1921F03; HMS2090B03; HMS2092B15; HMS2095L15; HMS3259B11; HMS3604N11; HMS3712L15; N-(6-benzoyl-1H-benzimidazol-2-yl)carbamic acid methyl ester; Pharmakon1600-01501110; ZINC121541; EBD12117; Tox21_110620; ANW-54402; BBL008298; BDBM50180753; CCG-39628; MMV003152; NSC757838; SBB057003; STK093862; AKOS000539066; AKOS015896232; Carbamic acid, (5-benzoyl-1H-benzimidazol-2-yl)-, methyl ester (9CI); Tox21_110620_1; CS-3974; DB00643; MCULE-4133611535; NC00639; NE41992; NSC-757838; IDI1_000751; NCGC00016806-02; NCGC00016806-03; NCGC00016806-04; NCGC00016806-05; NCGC00016806-06; NCGC00016806-07; NCGC00016806-08; NCGC00016806-09; NCGC00016806-10; NCGC00016806-12; NCGC00016806-13; NCGC00021698-03; NCGC00021698-04; NCGC00021698-05; NCGC00021698-06; NCGC00021698-07; AC-12064; AK-97348; AS-12272; HY-17595; ST011967; SY051142; SBI-0051641.P002; AB00052203; FT-0628179; FT-0628180; EN300-50844; D00368; W-6804; 5-Benzoyl-2-benzimidazolylcarbamicacidmethylester; AB00052203-09; AB00052203_10; Mebendazole, VETRANAL(TM), analytical standard; 431M397; A820852; AG-205/04588045; Mebendazole, analytical standard, >=98% (HPLC); Methyl (6-benzoyl-1H-benzimidazol-2-yl)carbamate; Q422194; methyl 5-benzoyl-1H-benzo[d]imidazol-2-ylcarbamate; SR-01000003109-2; SR-01000003109-3; W-106901; BRD-K77987382-001-01-7; BRD-K77987382-001-06-6; BRD-K77987382-001-08-2; methyl N-(5-benzoyl-1H-1,3-benzimidazol-2-yl)carbamate; Z234895185; 5-benzoyl-1H-benzimidazol-2-yl carbamic acid methyl ester; Mebendazole, European Pharmacopoeia (EP) Reference Standard; methoxy-N-[5-(phenylcarbonyl)benzimidazol-2-yl]carboxamide; methoxy-N-[6-(phenylcarbonyl)benzimidazol-2-yl]carboxamide; methyl N-[6-(phenylcarbonyl)-1H-benzimidazol-2-yl]carbamate; (5-benzoyl-1(3)H-benzoimidazol-2-yl)-carbamic acid methyl ester;; Mebendazole, United States Pharmacopeia (USP) Reference Standard; Mebendazole Polymorph C, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Ascariasis ICD-11: 1F62 [1]
PubChem CID
4030
Formula
C16H13N3O3
Canonical SMILES
COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3
InChI
1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21)
InChIKey
OPXLLQIJSORQAM-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=4030"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 295.29 Topological Polar Surface Area 84.1
XlogP 2.8 Complexity 423
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Mebendazole 100 mg tablet Click to Show/Hide the Full List of Formulation(s):          4 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
Stearic acid; Anhydrous lactose; Sodium lauryl sulfate; Saccharin sodium dihydrate; Fd&c yellow no. 6; Magnesium stearate; Cellulose, microcrystalline; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Chewable Tablet
                   Company Bryant Ranch Prepack
                   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) [2]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [4]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             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
Stearic acid; Anhydrous lactose; Sodium lauryl sulfate; Fd&c yellow no. 6; Magnesium stearate; Cellulose, microcrystalline; Saccharin sodium; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Chewable Tablet
                   Company Physicians Total Care; Teva Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [4]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             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
Stearic acid; Anhydrous lactose; Sodium lauryl sulfate; Fd&c yellow no. 6; Magnesium stearate; Cellulose, microcrystalline; Saccharin sodium; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Chewable Tablet
                   Company Amedra Pharmaceuticals; Impax Specialty Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [4]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             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
Sodium lauryl sulfate; Fd&c yellow no. 6; Magnesium stearate; Talc; Silicon dioxide; Microcrystalline cellulose; Orange; Saccharin sodium; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Chewable Tablet
                   Company Johnson & Johnson
                   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) [4]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Mebendazole 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
Sucralose; Magnesium stearate; Water; Crospovidone (15 mpa.s at 5%); Microcrystalline cellulose; Povidone, unspecified; Strawberry
                   Dosage Form Chewable Tablet
                   Company Janssen Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sucralose DIG Info Carbonic anhydrase II (Ki = 300 nM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved mebendazole from the official website of the U.S. Food and Drug Administration.
2 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.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 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.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
6 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.

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