Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00028)
Name
Ambrisentan
Synonyms    Click to Show/Hide the Synonyms of This API
Ambrisentan; 177036-94-1; Letairis; Volibris; BSF 208075; LU-208075; (S)-2-(4,6-Dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoic acid; BSF-208075; UNII-HW6NV07QEC; (S)-2-((4,6-Dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoic acid; HW6NV07QEC; CHEMBL1111; (2S)-2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-diphenylpropanoic acid; DSSTox_CID_26282; DSSTox_RID_81508; DSSTox_GSID_46282; Benzenepropanoic acid, alpha-[(4,6-dimethyl-2-pyrimidinyl)oxy]-beta-methoxy-beta-phenyl-, (alphaS)-; LU 208075; LU208075; (s)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic acid; CAS-177036-94-1; Ambrisentan [INN:BAN:JAN]; NCGC00160662-01; Letairis (TN); Volibris (TN); GSK1325760A; GSK-1325760A; GSK1325760; GSK-1325760; PubChem18318; Ambrisentan (JAN/INN); SCHEMBL3679; cc-160; MLS006010218; GTPL3951; DTXSID4046282; CHEBI:135949; ZINC538627; EX-A3315; Tox21_111967; ANW-59416; BDBM50146710; CA0131; FD7219; MFCD08672619; AKOS015994540; Tox21_111967_1; AC-9015; CCG-268386; CS-0447; DB06403; DE-0223; SB17358; (+-)-(2S)-2-((4,6-Dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoic acid; NCGC00160662-02; NCGC00346730-01; HY-13209; SMR004701307; AB0009811; SW219060-1; D07077; K-5435; AB01566890_01; A812234; Q410789; J-519579; UNII-7B43003091 component OUJTZYPIHDYQMC-LJQANCHMSA-N; (?S)-?-[(4,6-Dimethyl-2-pyrimidinyl)oxy]-?-methoxy-?-phenylbenzenepropanoic acid; (2S)-2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-di(phenyl)propanoic acid; (2S)-2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-diphenyl-propanoic acid; (2S)-2-[(4,6-dimethyl-2-pyrimidinyl)oxy]-3-methoxy-3,3-diphenylpropanoic acid; (2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy- 3,3-diphenylpropanoic acid; (S)-2-(4,6-Dimethyl-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl-propionic acid
Clinical Status
Approved
Disease Indication Pulmonary hypertension ICD-11: BB01 [1]
PubChem CID
6918493
Formula
C22H22N2O4
Canonical SMILES
CC1=CC(=NC(=N1)O[C@H](C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)C
InChI
1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26)22(27-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1
InChIKey
OUJTZYPIHDYQMC-LJQANCHMSA-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=6918493"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 378.4 Topological Polar Surface Area 81.5
XlogP 3.8 Complexity 475
Heavy Atom Count 28 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Ambrisentan 10 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
Lactose monohydrate; Fd&c red no. 40; Magnesium stearate; Talc; Titanium dioxide; Croscarmellose sodium; Lecithin, soybean; Polyethylene glycol 3350; Polyvinyl alcohol; Aluminum oxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Gilead Sciences
                   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]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [6]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
          Ambrisentan 5 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
Lactose monohydrate; Fd&c red no. 40; Magnesium stearate; Talc; Titanium dioxide; Croscarmellose sodium; Lecithin, soybean; Polyethylene glycol 3350; Polyvinyl alcohol; Aluminum oxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Gilead Sciences
                   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]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [6]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
References
1 FDA label for approved ambrisentan 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 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
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 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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