Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00740)
Name
Zileuton
Synonyms    Click to Show/Hide the Synonyms of This API
ZILEUTON; 111406-87-2; Leutrol; 1-(1-(Benzo[b]thiophen-2-yl)ethyl)-1-hydroxyurea; Zileutonum; Abbott 64077; Zileutonum [INN-Latin]; A-64077; 1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea; N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyurea; A 64077; Zyflo (TN); Urea, N-(1-benzo[b]thien-2-ylethyl)-N-hydroxy-; ABBOTT-64077; CHEMBL93; 1-[1-(1-benzothien-2-yl)ethyl]-1-hydroxyurea; N-[1-(benzo[b]thiophen-2-yl)ethyl]-N-hydroxyurea; (+-)-1-(1-Benzo(b)thien-2-ylethyl)-1-hydroxyurea; (+/-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea; Zyflo CR; CHEBI:10112; (+-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea; MFCD00866097; NCGC00159453-02; DSSTox_CID_3752; n-(1-benzo[b]thien-2-ylethyl)-n-hydroxyurea; DSSTox_RID_77185; DSSTox_GSID_23752; Urea, N-(1-benzo(b)thien-2-ylethyl)-N-hydroxy-; Ziluton; Zyflo Filmtab; ( inverted exclamation markA)-1(1-Benzo[b]thien-2-ylethyl)-1-hydroxyure; SMR000466377; CAS-111406-87-2; Zileuton (USP/INN); SR-01000759349; CTI-02; ABT-077; Zileuton [USAN:USP:INN:BAN]; PubChem14804; ACMC-20n1mn; ACMC-20n2ac; Prestwick0_001090; ACMC-1C7JU; 1-(1-benzothiophen-2-ylethyl)-1-hydroxy-urea; Urea, N-[(1R)-1-benzo[b]thien-2-ylethyl]-N-hydroxy-; Urea, N-[(1S)-1-benzo[b]thien-2-ylethyl]-N-hydroxy-; SCHEMBL4209; MLS000759510; MLS001424079; MLS006011971; Urea,N-(1-benzo[b]thien-2-ylethyl)-N'-hydroxy-; GTPL5297; Zileuton, >=98% (HPLC); DTXSID9023752; SCHEMBL18251470; Urea, N-(1-benzo(b)thien-2-ylethyl)-N-hydroxy-, (+-)-; HMS2051M20; HMS2089J12; HMS2093H06; HMS2235O04; HMS3369I17; HMS3393M20; HMS3654J08; HMS3714E07; HMS3872F13; Pharmakon1600-01505906; 142606-21-1; 143200-94-6; BCP16199; Tox21_111680; Tox21_301148; ANW-61226; BBL029070; BDBM50000541; NSC730712; NSC759277; STL373010; AKOS000280127; AKOS016340558; Tox21_111680_1; CCG-100901; CCG-213571; CS-1563; DB00744; KS-1195; MCULE-7670046922; NC00151; NSC-730712; NSC-759277; SB19083; MRF-0000030; NCGC00159453-03; NCGC00159453-04; NCGC00159453-05; NCGC00159453-06; NCGC00255046-01; AC-13198; AC-31490; AK-54597; HY-14164; SBI-0206869.P001; AB0012645; DB-015071; BB 0261152; FT-0601582; FT-0675903; SW197531-3; D00414; J90033; K-0925; N-(1-benzo[b]thien-2-ylethyl)-N-hydroxy-urea; AB00639921-06; AB00639921-08; AB00639921-09; AB00639921_10; AB00639921_11; 406Z872; Q202998; J-002574; J-525169; SR-01000759349-4; SR-01000759349-5; SR-01000759349-6; Zileuton, commercially available as 600 mg tablets; (+/-)-N-hydroxy-N-(1-benzo[b]thien-2-ylethyl)urea; BRD-A56359832-001-04-6; N-(1-BENZO(B)THIEN-2-YL-ETHYL)-N-HYDROXYUREA; Z1551429725; Zileuton, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Asthma ICD-11: CA23 [1]
PubChem CID
60490
Formula
C11H12N2O2S
Canonical SMILES
CC(C1=CC2=CC=CC=C2S1)N(C(=O)N)O
InChI
1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)
InChIKey
MWLSOWXNZPKENC-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=60490"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 236.29 Topological Polar Surface Area 94.8
XlogP 1.6 Complexity 275
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Zileuton 600 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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; Mannitol; Ferric oxide yellow; Titanium dioxide; Crospovidone; Polyethylene glycol 400; Silicon dioxide; Hypromellose 2910 (6 mpa.s); Hypromelloses; Microcrystalline cellulose; Sodium starch glycolate type a corn; Starch, corn
                   Dosage Form 12 HR Extended Release Oral Tablet
                   Company Rising 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]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
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
Glyceryl dibehenate; Magnesium stearate; Mannitol; Ferric oxide red; Propylene glycol; Talc; Crospovidone; Povidone; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Hypromelloses; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form 12 HR Extended Release Oral Tablet
                   Company Prasco
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone 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
Magnesium stearate; Propylene glycol; Talc; Titanium dioxide; Crospovidone; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Hypromelloses; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Chiesi USA
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved zileuton 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 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
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 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
6 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.