Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00008)
Name
Acebutolol
Synonyms    Click to Show/Hide the Synonyms of This API
acebutolol; 37517-30-9; Acetobutolol; Neptal; dl-Acebutolol; Acebutololo; Acebutololum; (+-)-Acebutolol; Sectral; N-(3-Acetyl-4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)butyramide; 5'-Butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone; CHEBI:2379; 3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide; 1-(2-Acetyl-4-n-butyramidophenoxy)-2-hydroxy-3-isopropylaminopropane; N-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]butanamide; N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide; N-(3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide; Acebrutololum; N-{3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}butanamide; N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide; Acebutololum [INN-Latin]; Acebrutololum [INN-Latin]; Acetobutolol [INN-Spanish]; Acebutolol [USAN:INN:BAN]; (+/-)-acebutolol; CCRIS 9214; RP 21823; Acebutolol (USAN/INN); EINECS 253-539-0; BRN 2162244; 3'-Acetyl-4'-(2-hydroxy-3-isopropylaminopropoxy)butyranilid; 3'-(Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide; C07AB04; (+-)-3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide; (+-)-N-(3-Acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)butanamide; Sectral (Salt/Mix); Wesfalin (Salt/Mix); Spectrum_000491; Prestwick0_000069; Prestwick1_000069; Prestwick2_000069; Prestwick3_000069; Spectrum2_001340; Spectrum3_000573; Spectrum4_000802; Spectrum5_001399; (.+/-.)-Acebutolol; CHEMBL642; Epitope ID:146105; SCHEMBL3772; BSPBio_000257; BSPBio_001986; KBioGR_001283; KBioSS_000971; DivK1c_000612; SPBio_001499; SPBio_002178; BPBio1_000283; GTPL7107; IL 17803A (Salt/Mix); DTXSID2048539; BDBM25755; KBio1_000612; KBio2_000971; KBio2_003539; KBio2_006107; KBio3_001486; NINDS_000612; AKOS015963037; DB01193; DS-3129; MCULE-6278379694; IDI1_000612; NCGC00018215-02; SBI-0051584.P003; DB-069556; AB00053574; FT-0660954; C06803; D02338; AB00053574_13; AB00053574_14; 197A639; L000998; Q418857; BRD-A29260609-003-05-4; BRD-A29260609-003-15-3; 1-[2-Acetyl-4-(butyrylamino)phenoxy]-3-(isopropylamino)-2-propanol; (.+/-.)-3'-Acetyl-4'-[2-hydroxy-3-(isopropylamino)propoxy]butyranilide; N-(3-Acetyl-4-(2-hydroxy-3-(isopropylamino)-propoxy)phenyl)butyramide; N-(3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide #; N-[3-Acetyl-4-(2-hydroxy-3-propan-2-ylaminopropoxy)-phenyl] butanamide; (.+/-.)-3'-Acetyl-4'-[2-hydroxy-3-(1-methylethylamino)propoxy]butyranilide; Butanamide, N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]-; Butanamide,N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]-; N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanimidic acid; 28197-63-9
Clinical Status
Approved
Disease Indication Essential hypertension ICD-11: BA00 [1]
PubChem CID
1978
Formula
C18H28N2O4
Canonical SMILES
CCCC(=O)NC1=CC(=C(C=C1)OCC(CNC(C)C)O)C(=O)C
InChI
1S/C18H28N2O4/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23)
InChIKey
GOEMGAFJFRBGGG-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=1978"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 336.4 Topological Polar Surface Area 87.7
XlogP 1.7 Complexity 401
Heavy Atom Count 24 Rotatable Bond Count 10
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Acebutolol 200 mg capsule Click to Show/Hide the Full List of Formulation(s):          7 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; D&c red no. 28; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Fd&c blue no. 2; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Gelatin; Povidones; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Mylan Pharamceuticals
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [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
Stearic acid; D&c red no. 28; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Fd&c blue no. 1; Titanium dioxide; Povidone; Corn oil; Gelatin
                   Dosage Form Oral Capsule
                   Company Major Pharmaceuticals
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [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; D&c red no. 28; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Marlex Pharmaceuticals
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [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
Stearic acid; D&c red no. 28; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company AvPAK
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
             Drug Formulation 5 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; D&c red no. 28; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company AvKARE
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
             Drug Formulation 6 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; D&c red no. 22; D&c red no. 28; Fd&c blue no. 1; Fd&c yellow no. 6; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Promius Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 22 DIG Info Organic anion transporter 1 (Ki = 89.13 nM) [6]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
             Drug Formulation 7 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
Fd&c blue no. 1
                   Dosage Form Oral Capsule
                   Company Amneal Pharmaceuticals; Bryant Ranch Prepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
          Acebutolol 400 mg capsule Click to Show/Hide the Full List of Formulation(s):          6 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; D&c red no. 28; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Fd&c blue no. 2; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Gelatin; Povidones; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Mylan Pharamceuticals
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [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
Stearic acid; D&c red no. 28; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Marlex Pharmaceuticals
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [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; D&c red no. 28; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company AvPAK
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [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
Stearic acid; D&c red no. 28; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company AvKARE
                   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]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
             Drug Formulation 5 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; D&c red no. 22; Fd&c red no. 40; Fd&c blue no. 1; Fd&c yellow no. 6; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Promius Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 22 DIG Info Organic anion transporter 1 (Ki = 89.13 nM) [6]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
             Drug Formulation 6 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
Fd&c blue no. 1
                   Dosage Form Oral Capsule
                   Company Amneal Pharmaceuticals; Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
          Acebutolol Hydrochloride eq 200mg 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
D&C Red 22; Fd&C Blue 1; Fd&C Yellow 6; Gelatin; Povidone; Starch; Stearic Acid; Titanium Dioxide; D&C Red 28; Fd&C Red 40
                   Dosage Form Capsule
                   Company Promius Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 22 DIG Info Organic anion transporter 1 (Ki = 89.13 nM) [6]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [5]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Pregelatinized starch DIG Info Multidrug resistance protein 1 (Protein expression downregulation) [7]
References
1 FDA label for approved acebutolol 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 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
5 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
6 Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members. J Biol Chem. 2007 Aug 17; 282(33):23841-53.
7 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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