Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1339)
Drug Name
Primaquine
Synonyms
Primachin; Primachina [DCIT]; Primachinum; Primaquin; Primaquina; Primaquina [INN-Spanish]; Primaquine [INN:BAN]; Primaquinum; Primaquinum [INN-Latin]; S. N. 13272; SN 13,272; WR 2975; 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-; Neo-Quipenyl; PRIMAQUINE; PRIMAQUINE PHOSPHATE; 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline; 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline; 90-34-6; CCRIS 4109; CHEBI:8405; EINECS 201-987-2; HSDB 6516; N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; NSC 27296
Indication Malaria [ICD11: 1F40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 259.35 Topological Polar Surface Area 60.2
Heavy Atom Count 19 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
4908
PubChem SID
9829 ; 87834 ; 598065 ; 602722 ; 604501 ; 5227598 ; 7980381 ; 8153019 ; 10537677 ; 11335981 ; 11361220 ; 11363724 ; 11366286 ; 11368848 ; 11371823 ; 11374106 ; 11377010 ; 11405430 ; 11410276 ; 11462192 ; 11466504 ; 11467624 ; 11484410 ; 11486287 ; 11488703 ; 11490368 ; 11492299 ; 11494644 ; 14798934 ; 24715072 ; 24715073 ; 29223986 ; 46508222 ; 47291261 ; 47291262 ; 47291263 ; 47440410 ; 47885557 ; 47959923 ; 47959924 ; 48035284 ; 48110597 ; 48416468 ; 49698880 ; 50042258 ; 50123426 ; 50123427 ; 50725468 ; 53790596 ; 56312914
ChEBI ID
CHEBI:8405
CAS Number
90-34-6
TTD Drug ID
D0T1LK
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2OH-PQ DM002954 N. A. Oxidation - Hydroxylation 1 [4] , [5]
3OH-PQ DM002955 N. A. Oxidation - Hydroxylation 1 [4] , [5]
4OH-PQ DM002956
11778154
Oxidation - Hydroxylation 1 [4] , [5]
5OH-PQ DM002958
135516690
Oxidation - Hydroxylation 1 [5]
CPQ DM002960
127542
Unclear 1 [4] , [6] , [7] , [8]
PQ-Alc DM002953 N. A. Unclear 1 [4]
PQ-N-CG DM002957 N. A. Conjugation - Glucuronidation 1 [4] , [6]
PQQI DM002964 N. A. Unclear 1 [4]
5-hydroxy-6-desmethylprimaquine DM002959
135457941
Oxidation - Hydroxylation 2 [5]
CPOQ DM002962 N. A. Unclear 2 [4]
CPQ-G DM002963 N. A. Conjugation - Glucuronidation 2 [4]
CPQ-lac DM002961 N. A. Unclear 2 [4]
MQPQ DM002965
253686
Unclear 2 [4]
POQ DM002966
73744341
Unclear 2 [4]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002141 Primaquine PQ-Alc Unclear Unclear [4]
MR002142 Primaquine 2OH-PQ Oxidation - Hydroxylation CYP2D6 [4], [5]
MR002143 Primaquine 3OH-PQ Oxidation - Hydroxylation CYP2D6 [4], [5]
MR002144 Primaquine 4OH-PQ Oxidation - Hydroxylation CYP2D6 [4], [5]
MR002145 Primaquine PQ-N-CG Conjugation - Glucuronidation Unclear [4], [6]
MR002146 Primaquine 5OH-PQ Oxidation - Hydroxylation CYP2D6 [5]
MR002147 Primaquine CPQ Unclear Unclear [4], [6], [7], [8]
MR002148 Primaquine PQQI Unclear Unclear [4]
MR002135 5OH-PQ 5-hydroxy-6-desmethylprimaquine Oxidation - Hydroxylation Unclear [5]
MR002136 CPQ CPQ-lac Unclear Unclear [4]
MR002137 CPQ CPOQ Unclear Unclear [4]
MR002138 CPQ CPQ-G Conjugation - Glucuronidation Unclear [4]
MR002139 PQQI MQPQ Unclear Unclear [4]
MR002140 PQQI POQ Unclear Unclear [4]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
⏷ Show the Full List of 12  DME(s)
References
1 Primaquine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Quantitative analysis of primaquine and its metabolites in human urine using liquid chromatography coupled with tandem mass spectrometry J Chromatogr B Analyt Technol Biomed Life Sci. 2022 Dec 15;1213:123517. doi: 10.1016/j.jchromb.2022.123517.
5 Enantioselective metabolism of primaquine by human CYP2D6 Malar J. 2014 Dec 17;13:507. doi: 10.1186/1475-2875-13-507.
6 Comparative single dose pharmacokinetics and metabolism of racemic primaquine and its enantiomers in human volunteers. Drug Metab Pharmacokinet. 2022 Aug;45:100463. doi: 10.1016/j.dmpk.2022.100463.
7 Synthesis, Biological Activity and In Silico Pharmacokinetic Prediction of a New 2-Thioxo-Imidazoldidin-4-One of Primaquine. Pharmaceuticals (Basel). 2021 Feb 27;14(3):196. doi: 10.3390/ph14030196.
8 Quantitative determination of primaquine-5,6-ortho-quinone and carboxyprimaquine-5,6-ortho-quinone in human erythrocytes by UHPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Jan 15;1163:122510. doi: 10.1016/j.jchromb.2020.122510.

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