General Information of API (ID: D00052)
Name
Avanafil
Synonyms    Click to Show/Hide the Synonyms of This API
Avanafil; 330784-47-9; STENDRA; TA 1790; TA-1790; UNII-DR5S136IVO; CHEBI:66876; (S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide; DR5S136IVO; (S)-2-(2-Hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine; (S)-4-(3-Chloro-4-methoxybenzylamino)-2-(2-hydroxymethylpyrrolidin-1-yl)-N-pyrimidin-2-ylmethyl-5-pyrimidinecarboxamide; Spedra; 4-[(3-chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide; 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide; (S)-4-[(3-Chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2pyrimidinylmethyl)-5-pyrimidinecarboxamide; Stendra (TN); Avanafil [USAN:INN]; Zepeed; ine-5-carboxamide; 4-((3-Chloro-4-methoxybenzyl)amino)-2-((2S)-2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide; Spedra (TN); Avanafil (USAN/INN); SCHEMBL118799; GTPL7448; CHEMBL1963681; DTXSID50186727; BDBM50036629; MFCD11977961; ZINC11677857; AKOS024462448; CCG-229896; DB06237; PB28365; VI-0162; NCGC00386241-01; AS-20106; HY-18252; SW219217-1; D03217; Q-4413; AB01565827_02; J-019006; Q2873270; BRD-K65781196-001-01-4; (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidylmethyl)carbamoyl]-pyrimidine; (S)-4-[(3-Chlor-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1- pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamid; 4-[(3-chloranyl-4-methoxy-phenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimid; 4-[(3-chloranyl-4-methoxy-phenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimid ine-5-carboxamide; 5-Pyrimidinecarboxamide, 4-(((3-chloro-4-methoxyphenyl)methyl)amino)-2-((2S)-2-(hydroxymethyl)-1-pyrrolidinyl)-N-(2-pyrimidinylmethyl)-; Avanafil; (S)-4-chloro-6-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
Clinical Status
Approved
Disease Indication Erectile dysfunction ICD-11: HA01 [1]
PubChem CID
9869929
Formula
C23H26ClN7O3
Canonical SMILES
COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCC[C@H]4CO)Cl
InChI
1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
InChIKey
WEAJZXNPAWBCOA-INIZCTEOSA-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=9869929"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 483.9 Topological Polar Surface Area 125
XlogP 2.6 Complexity 642
Heavy Atom Count 34 Rotatable Bond Count 9
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Avanafil 100 mg 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
Calcium carbonate; Fumaric acid; Magnesium stearate; Mannitol; Ferric oxide yellow; Hydroxypropyl cellulose (type h)
                   Dosage Form Oral Tablet
                   Company VIVUS
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Calcium carbonate DIG Info Carbonic anhydrase IX (Ki = 8600 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Fumaric acid DIG Info HIF-prolyl hydroxylase 2 (IC50 = 19000 nM) [4]
Magnesium stearate 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
Calcium carbonate; Fumaric acid; Magnesium stearate; Mannitol; Ferric oxide yellow; Hydroxypropyl cellulose, unspecified; Low-substituted hydroxypropyl cellulose (11% hydroxypropyl 130000 mw)
                   Dosage Form Oral Tablet
                   Company Mist Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Calcium carbonate DIG Info Carbonic anhydrase IX (Ki = 8600 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Fumaric acid DIG Info HIF-prolyl hydroxylase 2 (IC50 = 19000 nM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Avanafil 200 mg 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
Calcium carbonate; Fumaric acid; Magnesium stearate; Mannitol; Ferric oxide yellow; Hydroxypropyl cellulose (type h)
                   Dosage Form Oral Tablet
                   Company VIVUS
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Calcium carbonate DIG Info Carbonic anhydrase IX (Ki = 8600 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Fumaric acid DIG Info HIF-prolyl hydroxylase 2 (IC50 = 19000 nM) [4]
Magnesium stearate 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
Calcium carbonate; Fumaric acid; Magnesium stearate; Mannitol; Ferric oxide yellow; Hydroxypropyl cellulose, unspecified; Low-substituted hydroxypropyl cellulose (11% hydroxypropyl 130000 mw)
                   Dosage Form Oral Tablet
                   Company Mist Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Calcium carbonate DIG Info Carbonic anhydrase IX (Ki = 8600 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Fumaric acid DIG Info HIF-prolyl hydroxylase 2 (IC50 = 19000 nM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Avanafil 50 mg 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
Calcium carbonate; Fumaric acid; Magnesium stearate; Mannitol; Ferric oxide yellow; Hydroxypropyl cellulose (type h)
                   Dosage Form Oral Tablet
                   Company VIVUS
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Calcium carbonate DIG Info Carbonic anhydrase IX (Ki = 8600 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Fumaric acid DIG Info HIF-prolyl hydroxylase 2 (IC50 = 19000 nM) [4]
Magnesium stearate 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
Calcium carbonate; Fumaric acid; Magnesium stearate; Mannitol; Ferric oxide yellow; Hydroxypropyl cellulose, unspecified; Low-substituted hydroxypropyl cellulose (11% hydroxypropyl 130000 mw)
                   Dosage Form Oral Tablet
                   Company Mist Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Calcium carbonate DIG Info Carbonic anhydrase IX (Ki = 8600 nM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Fumaric acid DIG Info HIF-prolyl hydroxylase 2 (IC50 = 19000 nM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved avanafil from the official website of the U.S. Food and Drug Administration.
2 Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V, and IX with anions isosteric and isoelectronic with sulfate, nitrate, and carbonate. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):567-71.
3 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
4 Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases. J Med Chem. 2008 Nov 27; 51(22):7053-6.
5 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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