Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00567)
Name
Protriptyline
Synonyms    Click to Show/Hide the Synonyms of This API
protriptyline; Protryptyline; Amimetilina; 438-60-8; Triptil; Vivactil; 7-(3-Methylaminopropyl)-1,2:5,6-dibenzocycloheptatriene; 3-(5H-dibenzo[a,d][7]annulen-5-yl)-N-methylpropan-1-amine; N-Methyl-5H-dibenzo[a,d]cycloheptene-5-propanamine; 5-(3-Methylaminopropyl)-5H-Dibenzo[a,d]cycloheptene; Vivactyl; UNII-4NDU154T12; N-Methyl-5H-dibenzo[a,d]cycloheptene-5-propylamine; PROTRYPTYLINE HYDROCHLORIDE; N-3-(5H-Dibenzo(a,d)cyclohepten-5-yl)propyl-N-methylamine; CHEMBL668; N-Methyl-5H-dibenzo(a,d)cycloheptene-5-propylamine; 5-(3-Methylaminopropyl)-5H-dibenzo(a,d)cycloheptene; 5H-Dibenzo(a,d)cycloheptene-5-propanamine, N-methyl-; 5H-Dibenzo[a,d]cycloheptene-5-propanamine, N-methyl-; CHEBI:8597; 3-(5H-Dibenzo[a,d]cyclohepten-5-yl)-N-methyl-1-propanamine; 4NDU154T12; Concordin; 5H-Dibenzo(a,d)cycloheptene-5-propylamine, N-methyl-; Protriptilina; Protriptylinum; Protriptyline [INN:BAN]; Protriptylinum [INN-Latin]; Protriptilina [INN-Spanish]; N-methyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)propan-1-amine; Protriptyline (INN); NSC169912; HSDB 3391; NCGC00015851-02; EINECS 207-119-9; CAS-1225-55-4; 5H-Dibenzo[a,d]cycloheptene-5-propylamine, N-methyl-; BRN 2217411; Vivactil (Salt/Mix); Concordin (Salt/Mix); Prestwick0_000930; Prestwick1_000930; Prestwick2_000930; Prestwick3_000930; Lopac-P-8813; BIDD:PXR0157; Lopac0_000974; SCHEMBL34267; BSPBio_000840; SPBio_003019; BPBio1_000924; GTPL7285; DTXSID0023535; ZINC1530764; 5H-Dibenzo[a, d]cycloheptene-5-propanamine, N-methyl-, hydrochloride; BDBM50176062; MK 240; PDSP1_001390; PDSP2_001374; AKOS015962184; CCG-205054; DB00344; MCULE-6023848462; SDCCGSBI-0050947.P003; NCGC00015851-01; NCGC00015851-03; NCGC00015851-04; NCGC00015851-05; NCGC00015851-06; NCGC00015851-07; NCGC00015851-15; NCGC00024439-03; AC-15971; SBI-0050947.P002; AB00489964; C07408; D08447; AB00489964_10; L000913; Q408432; BRD-K42098891-003-03-1; 3-(5H-Dibenzo[a,d]cyclohepten-5-yl)-N-methyl-1-propanamine #; 3-(11H-dibenzo[[?],[?]][7]annulen-11-yl)-N-methyl-propan-1-amine; 3-(11H-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-N-methylpropan-1-amine; methyl(3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl}propyl)amine
Clinical Status
Approved
Disease Indication Major depressive disorder ICD-11: 6A70 [1]
PubChem CID
4976
Formula
C19H21N
Canonical SMILES
CNCCCC1C2=CC=CC=C2C=CC3=CC=CC=C13
InChI
1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3
InChIKey
BWPIARFWQZKAIA-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=4976"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 263.4 Topological Polar Surface Area 12
XlogP 4.4 Complexity 296
Heavy Atom Count 20 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Full List of Drug Formulations (DFMs) Containing This API
          Protriptyline 10 mg tablet 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; D&c yellow no. 10; Fd&c yellow no. 6; Magnesium stearate; Anhydrous dibasic calcium phosphate; Talc; Titanium dioxide; Crospovidone; Polyethylene glycol 3350; Polyvinyl alcohol; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Rising Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             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
Anhydrous lactose; Fd&c red no. 40; Fd&c yellow no. 6; Magnesium stearate; Propylene glycol; Titanium dioxide; Polyethylene glycol 400; Polysorbate 80; Aluminum oxide; Calcium phosphate, dibasic, anhydrous; Carnauba wax; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Hypromellose 2910 (6 mpa.s); Polyethylene glycol 8000; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Barr Laboratories; Teva Women's Health
                   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) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [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 monohydrate; Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Triacetin; Polysorbate 80; Calcium phosphate, dibasic, anhydrous; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols; Sodium starch glycolate type a potato; Starch, potato
                   Dosage Form Oral Tablet
                   Company Epic Pharma; Hi-Tech Pharmacal
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Anhydrous lactose; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Protriptyline 5 mg tablet 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; Fd&c yellow no. 6; Magnesium stearate; Anhydrous dibasic calcium phosphate; Talc; Titanium dioxide; Crospovidone; Polyethylene glycol 3350; Polyvinyl alcohol; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Rising Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             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
Anhydrous lactose; Fd&c red no. 40; Fd&c yellow no. 6; Magnesium stearate; Propylene glycol; Titanium dioxide; Polyethylene glycol 400; Polysorbate 80; Aluminum oxide; Calcium phosphate, dibasic, anhydrous; Carnauba wax; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Hypromellose 2910 (6 mpa.s); Polyethylene glycol 8000; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Barr Laboratories; Teva Women's Health
                   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) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [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 monohydrate; Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Triacetin; Polysorbate 20; Calcium phosphate, dibasic, anhydrous; Cellulose, microcrystalline; Hypromelloses; Sodium starch glycolate type a potato; Starch, tapioca
                   Dosage Form Oral Tablet
                   Company Epic Pharma; Hi-Tech Pharmacal
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Anhydrous lactose; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Protriptyline Hydrochloride 5mg tablet 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
Cellulose, Microcrystalline; Starch, Potato; Lactose Monohydrate; Calcium Phosphate, Dibasic, Anhydrous; Sodium Starch Glycolate Type A Potato; Magnesium Stearate; Hypromelloses; Titanium Dioxide; Polysorbate 80; Triacetin; Fd&C Yellow No. 6
                   Dosage Form Tablet
                   Company Epic Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             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
Cellulose, Microcrystalline; Starch, Tapioca; Lactose Monohydrate; Calcium Phosphate, Dibasic, Anhydrous; Sodium Starch Glycolate Type A Potato; Magnesium Stearate; Hypromelloses; Triacetin; Polysorbate 20; Titanium Dioxide; Fd&C Yellow No. 6
                   Dosage Form Tablet
                   Company Hi-Tech Pharmacal Co.
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Protriptyline Hydrochloride 10mg 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
Anhydrous Lactose; Silicon Dioxide; Magnesium Stearate; Microcrystalline Cellulose
                   Dosage Form Tablet
                   Company Bryant Ranch Prepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved protriptyline 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 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
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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