Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00526)
Name
Phenoxybenzamine
Synonyms    Click to Show/Hide the Synonyms of This API
phenoxybenzamine; Dibenyline; Dibenzyline; Dibenylin; 59-96-1; Bensylyt; Benzylyt; Fenoxibenzamina; Fenossibenzamina [DCIT]; Fenossibenzamina; Fenoxibenzamina [INN-Spanish]; Phenoxybenzaminum [INN-Latin]; Benzenemethanamine, N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)-; N-benzyl-N-(2-chloroethyl)-1-phenoxypropan-2-amine; NSC 37448; 2-(N-Benzyl-2-chloroethylamino)-1-phenoxypropane; N-(2-Chloroethyl)-N-(1-methyl-2-phenoxyethyl)benzenemethanamine; Benzyl(2-chloroethyl)-(1-methyl-2-phenoxyethyl)amine; N-(2-Chloroethyl)-N-(1-methyl-2-phenoxyethyl)benzylamine; Dibenylene; CHEMBL753; CHEBI:8077; 59-96-1 (free); Benzylamine, N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)-; NCGC00015121-08; Bensylyte; Phenoxybenzaminum; DSSTox_CID_3458; DSSTox_RID_77034; benzyl(2-chloroethyl)(1-phenoxypropan-2-yl)amine; DSSTox_GSID_23458; Phenoxybenzamine [INN:BAN]; CAS-59-96-1; CCRIS 505; HSDB 4005; Phenoxybenzamine (INN); EINECS 200-446-8; N-Phenoxyisopropyl-N-benzyl-beta-chloroethylamine; BRN 2129697; Spectrum_000378; Prestwick0_000944; Prestwick1_000944; Prestwick2_000944; Prestwick3_000944; Spectrum2_001815; Spectrum4_000769; Spectrum5_001370; SCHEMBL5722; Lopac0_000235; BSPBio_000908; BSPBio_001278; BSPBio_002356; KBioGR_000618; KBioGR_001158; KBioSS_000618; KBioSS_000858; 4-12-00-02204 (Beilstein Handbook Reference); DivK1c_000800; SPBio_001829; SPBio_003067; BPBio1_001000; GTPL7268; DTXSID0023458; KBio1_000800; KBio2_000618; KBio2_000858; KBio2_003186; KBio2_003426; KBio2_005754; KBio2_005994; KBio3_001095; KBio3_001096; NINDS_000800; Bio2_000479; Bio2_000959; HMS1362P19; HMS1792P19; HMS1990P19; HMS2089J09; HMS3403P19; N-(2-chloroethyl)-N-(phenylmethyl)-1-(phenyloxy)propan-2-amine; Tox21_110087; BDBM50017679; AKOS015961144; Tox21_110087_1; CCG-204330; DB00925; MCULE-1084779069; SDCCGSBI-0050223.P004; IDI1_000800; IDI1_002234; MRF-0000619; NCGC00015121-03; NCGC00015121-04; NCGC00015121-05; NCGC00015121-06; NCGC00015121-07; NCGC00015121-09; NCGC00015121-11; NCGC00015121-12; NCGC00015121-13; NCGC00015121-14; NCGC00015121-16; NCGC00015121-17; NCGC00089748-03; NCGC00089748-04; NCGC00089748-05; NCGC00089748-07; AC-13214; SBI-0050223.P003; AB00053702; FT-0778642; C07435; D08358; AB00053702-12; AB00053702_13; AB00053702_14; L001197; Q419824; N-Phenoxyisopropyl-N-benzyl-.beta.-chloroethylamine; Q-201556; N-benzyl-N-(2-chloroethyl)-1-phenoxy-propan-2-amine; N-Benzyl-N-(2-chloroethyl)-1-phenoxy-2-propanamine #; Benzyl-(2-chloro-ethyl)-(1-methyl-2-phenoxy-ethyl)-amine; 102737-84-8
Clinical Status
Approved
Disease Indication Essential hypertension ICD-11: BA00 [1]
PubChem CID
4768
Formula
C18H22ClNO
Canonical SMILES
CC(COC1=CC=CC=C1)N(CCCl)CC2=CC=CC=C2
InChI
1S/C18H22ClNO/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3
InChIKey
QZVCTJOXCFMACW-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=4768"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 303.8 Topological Polar Surface Area 12.5
XlogP 4.4 Complexity 262
Heavy Atom Count 21 Rotatable Bond Count 8
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Phenoxybenzamine 10 mg capsule Click to Show/Hide the Full List of Formulation(s):          4 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
Anhydrous lactose; Sodium lauryl sulfate; Fd&c red no. 40; Butyl alcohol; Isopropyl alcohol; Ammonia; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Water; Silicon dioxide; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company West-Ward Pharmaceticals
                   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]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             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
Lactose; Sodium lauryl sulfate; D&c red no. 33; Fd&c yellow no. 6; Fd&c red no. 3; Silicon dioxide; Gelatin
                   Dosage Form Oral Capsule
                   Company WellSpring Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 33 DIG Info Solute carrier SLCO2B1 (Ki = 58.1 uM) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             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
Lactose; D&c red no. 33; Fd&c yellow no. 6; Fd&c red no. 3; Gelatin
                   Dosage Form Oral Capsule
                   Company Concordia Pharmaceuticals; Prasco
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 33 DIG Info Solute carrier SLCO2B1 (Ki = 58.1 uM) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
             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
Lactose; Talc
                   Dosage Form Oral Capsule
                   Company Par Pharmaceutical
          Phenoxybenzamine Hydrochloride 10mg/capsule capsule Click to Show/Hide the Full List of Formulation(s):          2 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
Alcohol; Ammonia; Butyl Alcohol; D&C Red No. 33; Fd&C Red No. 3; Ferric Oxide Yellow; Gelatin, Unspecified; Isopropyl Alcohol; Lactose Monohydrate; Potassium Hydroxide; Propylene Glycol; Shellac; Silicon Dioxide; Sodium Lauryl Sulfate; Titanium Dioxide
                   Dosage Form Capsule
                   Company Amneal Pharmaceuticals Ny
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 33 DIG Info Solute carrier SLCO2B1 (Ki = 58.1 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [7]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             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
D&C Red No. 33; Fd&C Red No. 3; Fd&C Yellow No. 6; Gelatin; Lactose
                   Dosage Form Capsule
                   Company Concordia Pharmaceuticals ; Prasco Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 33 DIG Info Solute carrier SLCO2B1 (Ki = 58.1 uM) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [7]
References
1 FDA label for approved phenoxybenzamine 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 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
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 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
7 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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