Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00554)
Name
Primaquine
Synonyms    Click to Show/Hide the Synonyms of This API
PRIMAQUINE; 90-34-6; Primachin; 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline; Neo-Quipenyl; Primaquin; Primachinum; Primaquinum; Primaquina; 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-; 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline; SN 13,272; S. N. 13272; WR 2975; (RS)-primaquine; NSC 27296; CHEBI:8405; 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; 8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline; N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine; l-Primaquine; N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; NSC27296; NSC-27296; 1,4-Pentanediamine, N(4)-(6-methoxy-8-quinolinyl)-; 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline; Primachina [DCIT]; Primachina; dl-Primaquine; Primaquine [INN:BAN]; BRN 0019337; Maliride; NSC 27296; Neo-Quipenyl; Primachin; N4-(6-methoxy-8-quinolyl)pentane-1,4-diamine; Primaquinum [INN-Latin]; Primaquina [INN-Spanish]; 6-Methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline; N~4~-[6-(methyloxy)quinolin-8-yl]pentane-1,4-diamine; (+/-)-Primaquine; CHEMBL506; MLS001334045; (+)-Primaquine; (-)-Primaquine; Kanaprim (TN); Primaquine (INN); CCRIS 4109; HSDB 6516; 4-22-00-05817 (Beilstein Handbook Reference); 57152-58-6; NCGC00178754-06; N~4~-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; SMR000875314; EINECS 201-987-2; 6-Methoxy-8-((4-amino-1-methylbutyl)amino)quinoline; Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-; Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-; Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy; TG1-296; TG1-297; Spectrum_000830; Prestwick0_000476; Prestwick1_000476; Prestwick2_000476; Prestwick3_000476; Spectrum2_000887; Spectrum3_000552; Spectrum4_000484; Spectrum5_001363; Epitope ID:131792; Oprea1_546209; SCHEMBL22207; BSPBio_000612; BSPBio_002223; KBioGR_000967; KBioSS_001310; DivK1c_000806; N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; SPBio_000674; SPBio_002551; (+)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine; (-)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine; BPBio1_000674; cid_359247; GTPL9952; Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy-; DTXSID8023509; BDBM71542; KBio1_000806; KBio2_001310; KBio2_003878; KBio2_006446; KBio3_001723; NINDS_000806; HMS2090J17; BCP29271; ANW-50074; BBL011330; MFCD00598906; STL146416; 1, N4-(6-methoxy-8-quinolinyl)-; AKOS005721199; DB01087; MCULE-1557087031; WLN: T66 BNJ HO1 JMY1&3Z; WR-2975; IDI1_000806; SMP1_000263; NCGC00178754-01; NCGC00178754-02; NCGC00178754-03; AC-23007; AS-30679; BR-51335; NCI60_001035; NCI60_005887; SN-13272; SBI-0051491.P003; AB00053529; FT-0687514; C07627; D08420; S-4508; AB00053529-11; AB00053529_12; AB00053529_14; N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; 598P906; A843518; N4-(6-methoxy-8-quinolinyl)pentane-1,4-diamine; Q419834; BRD-A55913614-316-06-2; (4-amino-1-methyl-butyl)-(6-methoxy-8-quinolyl)amine; 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)- (9CI); N-[(S)-4-Amino-1-methylbutyl]-6-methoxy-8-quinolinamine; N4-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine (2 H3PO4); N4-(6-methoxy-8-quinolinyl)pentane-1,4-diamine;phosphoric acid; N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid; (4-amino-1-methyl-butyl)-(6-methoxy-8-quinolyl)amine;phosphoric acid
Clinical Status
Approved
Disease Indication Malaria ICD-11: 1F40 [1]
PubChem CID
4908
Formula
C15H21N3O
Canonical SMILES
CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2
InChI
1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
InChIKey
INDBQLZJXZLFIT-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=4908"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 259.35 Topological Polar Surface Area 60.2
XlogP 2.2 Complexity 262
Heavy Atom Count 19 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Primaquine 26.3 mg tablet 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
Lactose monohydrate; Fd&c red no. 40; Fd&c blue no. 2; Fd&c yellow no. 5; Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Silicon dioxide; Aluminum oxide; Cellulose, microcrystalline; Starch, corn
                   Dosage Form Oral Tablet
                   Company Alvogen
                   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]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide 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
Lactose monohydrate; Fd&c red no. 40; Fd&c blue no. 2; Magnesium stearate; Titanium dioxide; Water; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols; Starch, corn
                   Dosage Form Oral Tablet
                   Company Aidarex Pharmaceuticals; Bayshore Pharmaceuticals; Liberty Pharmaceuticals; PD-Rx 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. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Fd&c red no. 40; Fd&c blue no. 2; Magnesium stearate; Titanium dioxide; Water; Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified; Starch, corn
                   Dosage Form Oral Tablet
                   Company Golden State Medical Supply
                   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. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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 monohydrate; Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Triacetin; Cellulose, microcrystalline; Hypromellose 2910 (15 mpa.s); Starch, pregelatinized corn
                   Dosage Form Oral Tablet
                   Company Ingenus 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) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose; Magnesium stearate; Ferric oxide red; Talc; Titanium dioxide; Polyethylene glycol 400; Polysorbate 80; Carnauba wax; Cellulose, microcrystalline; Hypromellose 2910 (15000 mpa.s); Starch, corn
                   Dosage Form Oral Tablet
                   Company PD-Rx Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [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
Lactose, unspecified form; Magnesium stearate; Ferric oxide red; Talc; Titanium dioxide; Polyethylene glycol 400; Polysorbate 80; Carnauba wax; Hypromellose 2910 (15000 mpa.s); Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company Avera McKennan Hospital; Bryant Ranch Prepack; Sanofi-Aventis
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
References
1 FDA label for approved primaquine 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 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
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.

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