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

General Information of Drug (ID: DR0301)
Drug Name
Chloroquine
Synonyms
Chemochin; Chingamin; Chloraquine; Chlorochin; Chloroquina; Chloroquinium; Chloroquinum; Chlorquin; Cidanchin; Clorochina; Cloroquina; Cocartrit; Dichinalex; Elestol; Gontochin; Heliopar; Imagon; Iroquine; Klorokin; Lapaquin; Amokin; Aralen; Arthrochin; Artrichin; Bemaco; Bemaphate; Bemasulph; Benaquin; Bipiquin; Capquin; Malaquin; Malaren; Malarex; Mesylith; Neochin; Nivaquine B; Pfizerquine; Quinachlor; Quinercyl; Quinilon; Quinoscan; Resoquine; Reumachlor; Roquine; Sanoquin; Silbesan; Siragan; Solprina; Sopaquin; Tresochin; Trochin; chloroquine;
Indication Malaria [ICD11: 1F40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 319.9 Topological Polar Surface Area 28.2
Heavy Atom Count 22 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2719
PubChem SID
9827 ; 447935 ; 596572 ; 5050990 ; 7849425 ; 7978921 ; 8151759 ; 10526125 ; 11335579 ; 11360818 ; 11363006 ; 11365568 ; 11368130 ; 11371321 ; 11373917 ; 11376292 ; 11404351 ; 11405289 ; 11461790 ; 11466576 ; 11467696 ; 11483910 ; 11486252 ; 11487943 ; 11490157 ; 11492094 ; 11493946 ; 11528736 ; 14776983 ; 26675665 ; 29221876 ; 46506925 ; 47217037 ; 47291356 ; 47440521 ; 47440522 ; 47885638 ; 48035387 ; 48110720 ; 48185227 ; 48259487 ; 49635547 ; 49681217 ; 49698849 ; 49846799 ; 50111008 ; 53787949 ; 53788124 ; 56310729 ; 57321414
ChEBI ID
ChEBI:3638
CAS Number
54-05-7
TTD Drug ID
D09EGZ
Formula
C18H26ClN3
Canonical SMILES
CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl
InChI
1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
InChIKey
WHTVZRBIWZFKQO-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
(R)-chloroquine, N-desethyl DM001816
38989112
Oxidation - N-Dealkylation 1 [7] , [3] , [6]
N-bidesethylchloroquine DM001817
40579070
Oxidation - N-Dealkylation 2 [7]
4-amino-7 chloroquinoline DM001818
94711
Unclear 3 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000628 Chloroquine (R)-chloroquine, N-desethyl Oxidation - N-Dealkylation CYP3A4 ... [7], [3], [6]
MR000626 (R)-chloroquine, N-desethyl N-bidesethylchloroquine Oxidation - N-Dealkylation Unclear [7]
MR000627 N-bidesethylchloroquine 7-chloro-4-aminoquinoline Unclear Unclear [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
⏷ Show the Full List of 11  DME(s)
References
1 Chloroquine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab Dispos. 2003 Jun;31(6):748-54.
3 Metabolism and Interactions of Chloroquine and Hydroxychloroquine with Human Cytochrome P450 Enzymes and Drug Transporters Curr Drug Metab. 2020;21(14):1127-1135. doi: 10.2174/1389200221999201208211537.
4 Short communication: high prevalence of the cytochrome P450 2C8*2 mutation in Northern Ghana. Trop Med Int Health. 2005 Dec;10(12):1271-3.
5 Halofantrine and chloroquine inhibit CYP2D6 activity in healthy Zambians. Br J Clin Pharmacol. 1998 Mar;45(3):315-7.
6 Cytochrome P450 2C8 and CYP3A4/5 are involved in chloroquine metabolism in human liver microsomes. Arch Pharm Res. 2003 Aug;26(8):631-7.
7 Clinical pharmacokinetics and metabolism of chloroquine. Focus on recent advancements Clin Pharmacokinet. 1996 Oct;31(4):257-74. doi: 10.2165/00003088-199631040-00003.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.