Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00684)
Name
Tolazamide
Synonyms    Click to Show/Hide the Synonyms of This API
tolazamide; 1156-19-0; Tolinase; Norglycin; Tolanase; Diabewas; Tolazolamide; Tolazamida; Tolazamidum; 1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylurea; N-(p-Toluenesulfonyl)-N'-hexamethyleniminourea; U-17835; 4-(p-Tolylsulfonyl)-1,1-hexamethylenesemicarbazide; NCI-C03327; 1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; U 17835; CCRIS 591; NSC-70762; 1-(azepan-1-yl)-3-(4-methylphenyl)sulfonylurea; UNII-9LT1BRO48Q; Urea, 1-(hexahydroazepin-1-yl)-3-p-tolylsulfonyl-; EINECS 214-588-3; Benzenesulfonamide, N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methyl-; Urea, 1-(hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)-; BRN 1323565; 9LT1BRO48Q; MLS000028534; CHEBI:9613; N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide; N-(((Hexahydro-1H-azepin-1-yl)-amino)carbonyl)-4-methylbenzenesulfonamide; NSC70762; N-(azepan-1-ylcarbamoyl)-4-methylbenzenesulfonamide; Benzenesulfonamide, N-(((hexahydro-1H-azepin-1-yl)amino)carbonyl)-4-methyl-; 1-(Hexahydro-1H-azepin-1-yl)-3-(p-toluenesulfonyl)urea; NCGC00016009-10; SMR000058290; CAS-1156-19-0; DSSTox_CID_1358; DSSTox_RID_76105; DSSTox_GSID_21358; Tolazamidum [INN-Latin]; Tolazamida [INN-Spanish]; 1-(((((4-Methylphenyl)sulfonyl)amino)carbonyl)amino)azepane; Tolinase (TN); HSDB 3192; SR-01000003105; NSC 70762; 1-[(Azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide; 1-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]azepane; Ronase; (azaperhydroepinylamino)-N-[(4-methylphenyl)sulfonyl]carboxamide; AI3-50826; N-{[(hexahydro-1H-azepin-1-yl)-amino]carbonyl}-4-methylbenzenesulfonamide; Prestwick_865; Tolazamide [USAN:USP:INN:BAN:JAN]; Spectrum_001269; Opera_ID_1740; Prestwick0_000554; Prestwick1_000554; Prestwick2_000554; Prestwick3_000554; Spectrum2_001449; Spectrum3_001473; Spectrum4_000240; Spectrum5_001204; Lopac-T-2408; CHEMBL817; Benzenesulfonamide, N-(((hexahydro-1H-azepin-1-yl)-amino)carbonyl)-4-methyl-; T 2408; 3-azepan-1-yl-1-(4-methylphenyl)sulfonyl-urea; NCIOpen2_008361; CBiol_001918; Lopac0_001195; Oprea1_061180; SCHEMBL34417; BSPBio_000627; BSPBio_001505; BSPBio_003025; KBioGR_000225; KBioGR_000939; KBioSS_000225; KBioSS_001749; Tolazamide (JAN/USP/INN); 1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea; 5-20-04-00062 (Beilstein Handbook Reference); MLS001076161; DivK1c_000212; SPECTRUM1501201; SPBio_001317; SPBio_002548; BPBio1_000691; GTPL6847; WLN: T7NTJ AMVMSWR D1; DTXSID3021358; BCBcMAP01_000061; HMS500K14; KBio1_000212; KBio2_000225; KBio2_001749; KBio2_002793; KBio2_004317; KBio2_005361; KBio2_006885; KBio3_000449; KBio3_000450; KBio3_002525; ZINC57512; NINDS_000212; Bio1_000204; Bio1_000693; Bio1_001182; Bio2_000225; Bio2_000705; HMS1361L07; HMS1569P09; HMS1791L07; HMS1921P19; HMS1989L07; HMS2089L10; HMS2092L09; HMS2096P09; HMS2232L21; HMS3259O18; HMS3263P11; HMS3369L04; HMS3402L07; HMS3713P09; Pharmakon1600-01501201; BCP23550; HY-B0920; Tox21_110281; Tox21_201507; Tox21_300416; Tox21_501195; 2761AH; CCG-39178; MFCD00083504; NSC758149; SBB058190; AKOS015913823; N-[[(Hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide; Tox21_110281_1; ACN-053046; DB00839; KS-1438; LP01195; MCULE-9265102499; NC00590; NSC-758149; SDCCGSBI-0051162.P004; Benzenesulfonamide, {N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methyl-}; IDI1_000212; IDI1_033975; NCGC00016009-01; NCGC00016009-02; NCGC00016009-03; NCGC00016009-04; NCGC00016009-05; NCGC00016009-06; NCGC00016009-07; NCGC00016009-08; NCGC00016009-09; NCGC00016009-11; NCGC00016009-12; NCGC00016009-13; NCGC00016009-14; NCGC00016009-15; NCGC00016009-16; NCGC00016009-17; NCGC00016009-19; NCGC00016009-24; NCGC00023701-03; NCGC00023701-04; NCGC00023701-05; NCGC00023701-06; NCGC00023701-07; NCGC00023701-08; NCGC00023701-09; NCGC00023701-10; NCGC00254501-01; NCGC00259058-01; NCGC00261880-01; AK546472; 1-(azepan-1-yl)-3-(p-tolylsulfonyl)urea; SBI-0051162.P003; AB00052247; EU-0101195; FT-0675268; ST51015133; SW196991-3; D00379; AB00052247-15; AB00052247_16; AB00052247_17; 1-(azepan-1-yl)-3-[(4-methylbenzene)sulfonyl]urea; Q7814101; SR-01000003105-2; SR-01000003105-4; SR-01000003105-5; SR-01000003105-8; W-109110; BRD-K32164935-001-06-8; BRD-K32164935-001-17-5; BRD-K32164935-001-28-2; F2173-1137; 1-[(([(4-Methylphenyl)sulfonyl]amino)carbonyl)amino]azepane #; Tolazamide, United States Pharmacopeia (USP) Reference Standard; Benzenesulfonamide, N-[[(hexahydro-1-azepinyl)amino]carbonyl]-4-methyl-
Clinical Status
Approved
Disease Indication Diabetes mellitus ICD-11: 5A10 [1]
PubChem CID
5503
Formula
C14H21N3O3S
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CCCCCC2
InChI
1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)
InChIKey
OUDSBRTVNLOZBN-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=5503"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 311.4 Topological Polar Surface Area 86.9
XlogP 1.5 Complexity 431
Heavy Atom Count 21 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Tolazamide 250 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
Sodium lauryl sulfate; Magnesium stearate; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company American Health Packaging; Mylan Pharamceuticals; PD-Rx Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Tolazamide 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
Sodium lauryl sulfate; Magnesium stearate; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved tolazamide from the official website of the U.S. Food and Drug Administration.
2 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.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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