Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00271)
Name
Fentanyl
Synonyms    Click to Show/Hide the Synonyms of This API
fentanyl; Fentanil; Phentanyl; Fentora; 437-38-7; Duragesic; Fentanest; Sublimaze; Fentanylum; Fentanila; Sentonil; Duragesic-100; IONSYS; Duragesic-12; Duragesic-25; Duragesic-50; Duragesic-75; Fentanyl-12; Fentanyl-25; Fentanyl-50; Fentanyl-75; Fentanylum [INN-Latin]; N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamide; Fentanila [INN-Spanish]; Fentanyl-100; 1-Phenethyl-4-N-propionylanilinopiperidine; Matrifen; Sublimase; N-(1-Phenethyl-4-piperidyl)propionanilide; N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide; N-Phenethyl-4-(N-propionylanilino)piperidine; 1-Phenethyl-4-(N-phenylpropionamido)piperidine; R 4263; Fentanyl CII; N-(1-Phenethyl-4-piperidinyl)-N-phenylpropionamide; N-Phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide; UNII-UF599785JZ; CHEBI:119915; N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide; Propionanilide, N-(1-phenethyl-4-piperidyl)-; Durogesic; CHEMBL596; UF599785JZ; NCGC00168252-01; Propanamide, N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-; Subsys; Fentanil [DCIT]; effentora; Fentanyl buccal; PecFent; Durotep MT; HSDB 3329; EINECS 207-113-6; Fentanyl Transdermal System; JNS020QD; BRN 0494484; Fentanyl [USAN:USP:INN:BAN]; N02AB03; Duragesic (TN); Subsys (TN); FENTANYL-HCl; DSSTox_CID_3049; Epitope ID:153507; SCHEMBL8804; Fentanyl (JAN/USP/INN); DSSTox_RID_76851; DSSTox_GSID_23049; Oprea1_152073; Oprea1_207148; 5-22-08-00049 (Beilstein Handbook Reference); BIDD:GT0555; GTPL1626; IDS-NF-001; DTXSID9023049; Fentanyl 0.1 mg/ml in Methanol; Fentanyl 1.0 mg/ml in Methanol; N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide; ACN-S001735; ZINC2522669; Tox21_112611; AD 923; AD-923; BDBM50008984; CF0052; HY-U00158; PDSP1_000860; PDSP2_000846; CS-7211; DB00813; CAS-437-38-7; N-(1-Phenylethyl-4-piperidinyl)propionanilide; 9235-EP2275420A1; 9235-EP2277861A1; 9235-EP2277875A2; 9235-EP2280008A2; 9235-EP2298764A1; 9235-EP2298765A1; 9235-EP2298768A1; 9235-EP2305652A2; 9235-EP2305654A1; 9235-EP2308509A1; 9235-EP2308872A1; 9235-EP2314585A1; 9235-EP2314590A1; 9235-EP2316829A1; D00320; 1-(2-Phenylethyl)-4-(N-propananilido)piperidine; L001275; Q407541; N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide #; N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide(Fentanyl); Propanamide, N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)- (9CI)
Clinical Status
Approved
Disease Indication Anaesthesia ICD-11: 8E22 [1]
PubChem CID
3345
Formula
C22H28N2O
Canonical SMILES
CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
InChI
1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
InChIKey
PJMPHNIQZUBGLI-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=3345"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 336.5 Topological Polar Surface Area 23.6
XlogP 4 Complexity 391
Heavy Atom Count 25 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Fentanyl 0.1 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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 citric acid; Magnesium stearate; Mannitol; Sodium bicarbonate; Sodium carbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Cephalon
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Magnesium stearate; Mannitol; Croscarmellose sodium; Cellulose, microcrystalline
                   Dosage Form Sublingual Tablet
                   Company ProStrakan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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
Magnesium stearate; Mannitol; Potassium bicarbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Actavis Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Fentanyl 0.2 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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 citric acid; Magnesium stearate; Mannitol; Sodium bicarbonate; Sodium carbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Cephalon
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Magnesium stearate; Mannitol; Croscarmellose sodium; Cellulose, microcrystalline
                   Dosage Form Sublingual Tablet
                   Company ProStrakan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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
Magnesium stearate; Mannitol; Potassium bicarbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Actavis Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Fentanyl 0.4 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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 citric acid; Magnesium stearate; Mannitol; Sodium bicarbonate; Sodium carbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Cephalon
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Magnesium stearate; Mannitol; Croscarmellose sodium; Cellulose, microcrystalline
                   Dosage Form Sublingual Tablet
                   Company ProStrakan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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
Magnesium stearate; Mannitol; Potassium bicarbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Actavis Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Fentanyl 0.6 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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 citric acid; Magnesium stearate; Mannitol; Sodium bicarbonate; Sodium carbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Cephalon
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Magnesium stearate; Mannitol; Croscarmellose sodium; Cellulose, microcrystalline
                   Dosage Form Sublingual Tablet
                   Company ProStrakan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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
Magnesium stearate; Mannitol; Potassium bicarbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Actavis Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Fentanyl 0.8 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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 citric acid; Magnesium stearate; Mannitol; Sodium bicarbonate; Sodium carbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Cephalon
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Magnesium stearate; Mannitol; Croscarmellose sodium; Cellulose, microcrystalline
                   Dosage Form Sublingual Tablet
                   Company ProStrakan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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
Magnesium stearate; Mannitol; Potassium bicarbonate; Sodium starch glycolate type a potato
                   Dosage Form Buccal Tablet
                   Company Actavis Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Fentanyl 0.3 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
Magnesium stearate; Mannitol; Croscarmellose sodium; Cellulose, microcrystalline
                   Dosage Form Sublingual Tablet
                   Company ProStrakan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
References
1 FDA label for approved fentanyl from the official website of the U.S. Food and Drug Administration.
2 PubChem BioAssay data set.
3 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
4 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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