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Drug

D0387 | Primaquine

Molecular Formula C15H21N3O
Molecular Weight 259.35
Structure
State solid
Half life 3.7-7.4 hours

P

P01BA03 Primaquine


[P01BA] Aminoquinolines


[P01B] ANTIMALARIALS


[P01] ANTIPROTOZOALS


[P] Antiparasitic products, insecticides and repellents

Toxicity Dose Time Species Model Method Action Positive criterion Reference
UNCOUPLING increase 35
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex I activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex II + III activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex II + III activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex IV activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex V activity Negative p < 0.05 3

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 50 μM bovine heart mitochondria Measurement of complex I activity Negative p < 0.05 3
Succinate dehydrogenase 50 μM bovine heart mitochondria Measurement of complex II + III activity Negative p < 0.05 3
Quinol--cytochrome-c reductase 50 μM bovine heart mitochondria Measurement of complex II + III activity Negative p < 0.05 3
Cytochrome c oxidase 50 μM bovine heart mitochondria Measurement of complex IV activity Negative p < 0.05 3
ATP synthase 50 μM bovine heart mitochondria Measurement of complex V activity Negative p < 0.05 3

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 intravenous 15900ug/kg (15.9mg/kg) Antibiotics and Chemotherapy Vol. 12, Pg. 103, 1962.
mouse LD50 oral 100mg/kg (100mg/kg) Antimicrobial Agents and Chemotherapy. Vol. 12, Pg. 51, 1977.
mouse LD50 unreported 68800ug/kg (68.8mg/kg) Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 16, Pg. 502, 1981.
monkey LDLo oral 96mg/kg (96mg/kg) behavioral: convulsions or effect on seizure threshold Antibiotics and Chemotherapy Vol. 12, Pg. 103, 1962.

  • Plasmodium vivax infection

    • (+)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine (+)-Primaquine (+/-)-Primaquine
    (-)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine (-)-Primaquine (4-amino-1-methyl-butyl)-(6-methoxy-8-quinolyl)amine;phosphoric acid
    (RS)-primaquine 1, N4-(6-methoxy-8-quinolinyl)- 1,4-Pentanediamine, N(4)-(6-methoxy-8-quinolinyl)-
    1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)- 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)- (9CI) 4-22-00-05817 (Beilstein Handbook Reference)
    4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid 4CH-006983
    598P906 6-Methoxy-8-((4-amino-1-methylbutyl)amino)quinoline 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline
    6-Methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline 66616-84-0 8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline
    8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline 90-34-6
    A843518 AB00053529 AB00053529-11
    AB00053529_12 AB00053529_14 AC-23007
    AK-51335 AKOS005721199 ANW-50074
    API0009074 AS-30679 AX8110977
    BBL011330 BDBM71542 BPBio1_000674
    BR-51335 BRD-A55913614-316-06-2 BRN 0019337
    BSPBio_000612 BSPBio_002223 C07627
    CCRIS 4109 CHEBI:8405 CHEMBL506
    CTK8B5781 D08420 DB01087
    DTXSID8023509 DivK1c_000806 EINECS 201-987-2
    EN300-144245 Epitope ID:131792 FT-0687514
    GTPL9952 HMS2090J17 HSDB 6516
    IDI1_000806 INDBQLZJXZLFIT-UHFFFAOYSA-N KBio1_000806
    KBio2_001310 KBio2_003878 KBio2_006446
    KBio3_001723 KBioGR_000967 KBioSS_001310
    Kanaprim (TN) LS-141312 MCULE-1557087031
    MLS001334045 N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamine N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine
    N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine N4-(6-methoxy-8-quinolinyl)pentane-1,4-diamine
    N4-(6-methoxy-8-quinolinyl)pentane-1,4-diamine;phosphoric acid N4-(6-methoxy-8-quinolyl)pentane-1,4-diamine N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
    N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid NCGC00178754-01 NCGC00178754-02
    NCGC00178754-03 NCGC00178754-06 NCI60_001035
    NCI60_005887 NINDS_000806 NSC 27296
    NSC-27296 NSC27296 Neo-Quipenyl
    N~4~-(6-methoxyquinolin-8-yl)pentane-1,4-diamine N~4~-[6-(methyloxy)quinolin-8-yl]pentane-1,4-diamine Oprea1_546209
    PRIMAQUINE Prestwick0_000476 Prestwick1_000476
    Prestwick2_000476 Prestwick3_000476 Primachin
    Primachina Primachina [DCIT] Primachinum
    Primaquin Primaquina Primaquina [INN-Spanish]
    Primaquine (INN) Primaquine [INN:BAN] Primaquinum
    Primaquinum [INN-Latin] Q419834 Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-
    Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy- Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-
    S-4508 S. N. 13272 SBI-0051491.P003
    SC-46746 SCHEMBL22207 SMP1_000263
    SMR000875314 SN 13,272 SPBio_000674
    SPBio_002551 ST24029985 STL146416
    Spectrum2_000887 Spectrum3_000552 Spectrum4_000484
    Spectrum5_001363 Spectrum_000830 TG1-296
    TG1-297 TR-028405 TX-012465
    W9302 WLN: T66 BNJ HO1 JMY1&3Z WR 2975
    cid_359247 dl-Primaquine

    DrugBank Name Primaquine
    DrugBank DB01087
    CAS Number 105901-53-9, 57152-58-6, 63-45-6, 66616-84-0, 90-34-6
    PubChem Compound 4908
    KEGG Compound ID C07627
    KEGG Drug D08420
    PubChem.Substance 46508222
    ChEBI 8405
    PharmGKB PA451103
    ChemSpider 4739
    BindingDB 71542.0
    TTD DAP000216
    Wikipedia Primaquine
    DPD 3336