Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00623)
Name
Simeprevir
Synonyms    Click to Show/Hide the Synonyms of This API
SIMEPREVIR; Olysio; 923604-59-5; TMC435350; TMC-435; TMC 435; TMC 435350; TMC435; TMC-435350; CHEMBL501849; UNII-9WS5RD66HZ; (1R,4R,6S,7Z,15R,17R)-N-cyclopropylsulfonyl-17-[7-methoxy-8-methyl-2-(4-propan-2-yl-1,3-thiazol-2-yl)quinolin-4-yl]oxy-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide; (2R,3aR,10Z,11aS,12aR,14aR)-N-(cyclopropylsulfonyl)-2-({7-methoxy-8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)-5-methyl-4,14-dioxo-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxamide; 9WS5RD66HZ; HCV-PI; SCHEMBL826061; GTPL7367; C38H47N5O7S2; CHEBI:134743; N-cyclopropylsulfonyl-[[2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methyl-4-quinolyl]oxy]-methyl-dioxo-[?]carboxamide; 4041AH; BDBM50336504; ZINC85540268; AKOS025401966; CCG-270435; AC-27651; AS-56205; TMC-00435350; TMC-435, TMC-435350; W-6083; US8741926, 47; US8754106, 47; Q7517689; (2R,3aR,10Z,11aS,12aR,14aR)-N-(Cyclopropylsulfonyl)-2-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)-5-methyl-4,14-dioxo-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxamide; (2R,3aR,10Z,12S,13R,15aR)-N-(Cyclopropylsulfonyl)-2-[[2-(4-isopropylthiazole-2-yl)-7-methoxy-8-methyl-4-quinolyl]oxy]-5-methyl-4,15-dioxo-2,3,3a,4,5,6,7,8,9,12,13,14,15,15a-tetradecahydro-12,13-methano-5,14-diaza-1H-cyclopentacyclotetradecene-13-carboxamide; (2R,3aR,11aS,12aR,14aR)-N-(cyclopropylsulfonyl)-2-(2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxamide; (2R,3aR,11aS,12aR,14aR,Z)-N-(cyclopropylsulfonyl)-2-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxamide; (2R,3aR,11aS,12aR,14aR,Z)-N-(cyclopropylsulfonyl)-2-(2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxamide; N-[17-[2-(4-isopropylthiazole-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo [13.3.0.0''4,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamide
Clinical Status
Approved
Disease Indication Viral hepatitis ICD-11: 1E51 [1]
PubChem CID
24873435
Formula
C38H47N5O7S2
Canonical SMILES
CC1=C(C=CC2=C1N=C(C=C2O[C@@H]3C[C@@H]4[C@@H](C3)C(=O)N(CCCC/C=C\\[C@@H]5C[C@]5(NC4=O)C(=O)NS(=O)(=O)C6CC6)C)C7=NC(=CS7)C(C)C)OC
InChI
1S/C38H47N5O7S2/c1-21(2)30-20-51-35(40-30)29-18-32(26-13-14-31(49-5)22(3)33(26)39-29)50-24-16-27-28(17-24)36(45)43(4)15-9-7-6-8-10-23-19-38(23,41-34(27)44)37(46)42-52(47,48)25-11-12-25/h8,10,13-14,18,20-21,23-25,27-28H,6-7,9,11-12,15-17,19H2,1-5H3,(H,41,44)(H,42,46)/b10-8-/t23-,24-,27-,28-,38-/m1/s1
InChIKey
JTZZSQYMACOLNN-VDWJNHBNSA-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=24873435"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 749.9 Topological Polar Surface Area 194
XlogP 4.8 Complexity 1490
Heavy Atom Count 52 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 10
Full List of Drug Formulations (DFMs) Containing This API
          Simeprevir 150 mg capsule 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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Ferrosoferric oxide; Titanium dioxide; Croscarmellose sodium; Silicon dioxide; Gelatin, unspecified; Shellac
                   Dosage Form Oral Capsule
                   Company Janssen Products
                   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]
          Simeprevir Sodium eq 150mg base capsule 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
Colloidal Anhydrous Silica; Croscarmellose Sodium; Lactose Monohydrate; Magnesium Stearate; Sodium Lauryl Sulphate; Gelatin; Titanium Dioxide (E171); Iron Oxide Black (E172); Shellac (E904)
                   Dosage Form Capsule
                   Company Janssen Prods
                   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]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
References
1 FDA label for approved simeprevir 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.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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