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Drug Details

General Information of the Drug (ID: DR4718)
Name
Primaquin
Synonyms
PRIMAQUINE; 90-34-6; 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline; Primachin; 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; NCI60_001035; NCI60_005887; SN-13272; SBI-0051491.P003; AB00053529; FT-0687514; W9302; 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; 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
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Molecular Type
Small molecule
Disease Malaria [ICD-11: 1F40] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C15H21N3O
PubChem CID
4908
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
CAS Number
CAS 90-34-6
ChEBI ID
CHEBI:8405
TTD Drug ID
D0T1LK
DrugBank ID
DB01087
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Tretinoin      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
                    In-vivo Model C57BL/6 micemice were transtracheally instilled with 2*106 of Pc organisms in 50 uL sterile PBS.
                    Experimental
                    Result(s)
All-trans retinoic acid in combination with primaquine clears pneumocystis infection.
Target and Pathway
Target(s) Plasmodium Deoxyribonucleic acid (Malaria DNA)  Molecule Info  [3]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 008316.
Reference 2 All-trans retinoic acid in combination with primaquine clears pneumocystis infection. PLoS One. 2013;8(1):e53479.
Reference 3 Primaquine-induced differential gene expression analysis in mice liver using DNA microarrays. Toxicology. 2007 Sep 24;239(1-2):96-107.
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Cite NPCDR
Visitor Map
Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China