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

General Information of Drug (ID: DR0093)
Drug Name
Amiodarone hydrochloride
Synonyms
Amiodar; Amiodarone (hydrochloride); Amiodarone HCL; Amiodarone hydrochloride; Amiodaronum hydrochloride; Angoron; Atlansil; Amiodarona; Amiodarone; Amiodarona [INN-Spanish]; Amiodarone Base; Amiodaronum; Amiodaronum [INN-Latin]; Amjodaronum; BRN 1271711; C25H29I2NO3; CHEMBL633; Cordarone; EINECS 217-772-1; L 3428; L-3428; N3RQ532IUT; UNII-N3RQ532IUT; (2-butyl-1-benzofuran-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone; 1951-25-3; 2-Butyl-3-(3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl)benzofuran; 2-n-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuran; CPD000058296; DSSTox_CID_17185; DSSTox_GSID_37185; DSSTox_RID_79304; EINECS 243-293-2; HSDB 6525; L 3428 labaz; MFCD00069204; MLS000028520; Miodrone; NSC 85442; Nexterone; Renodoron; Ritmocardyl; Rythmarone; SKF 33134 A; SMR000058296; Trangorex; UNII-976728SY6Z; (2-Butylbenzofuran-3-yl)(4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl)methanone hydrochloride; 19774-82-4; 51087 N HCl; 976728SY6Z
Indication Ventricular tachyarrhythmia [ICD11: BC71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 681.8 Topological Polar Surface Area 42.7
Heavy Atom Count 32 Rotatable Bond Count 11
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
441325
ChEBI ID
CHEBI:2664
CAS Number
19774-82-4
TTD Drug ID
D0L5WM
Formula
C25H30ClI2NO3
Canonical SMILES
CCCCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)I)OCCN(CC)CC)I.Cl
InChI
1S/C25H29I2NO3.ClH/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3;/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3;1H
InChIKey
ITPDYQOUSLNIHG-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
Amiodarone hydrochloride Metabolite M1 DM018037 N. A. Oxidation - O-deakylation 1 [8]
Amiodarone hydrochloride Metabolite M2 DM018035 N. A. Oxidation - HYDROXYLATION 1 [8]
B2-O-Et-N-dipropyl DM016570
129267289
Reduction - Deiodination 1 [8]
Mono-N-desethylamiodarone DM018033 N. A. Oxidation - N-dealkylation 1 [9] , [10] , [7]
Amiodarone hydrochloride Metabolite M3 DM018036 N. A. Unclear - Unclear 2 [8]
Di-N-desethylamiodarone DM018034 N. A. Unclear - Unclear 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013093 Amiodarone hydrochloride Mono-N-desethylamiodarone Oxidation - N-dealkylation CYP1A1 ... [9], [10], [7]
MR013095 Amiodarone hydrochloride Amiodarone hydrochloride Metabolite M2 Oxidation - HYDROXYLATION Unclear [8]
MR013097 Amiodarone hydrochloride Amiodarone hydrochloride Metabolite M1 Oxidation - O-deakylation Unclear [8]
MR013098 Amiodarone hydrochloride B2-O-Et-N-dipropyl Reduction - Deiodination Unclear [8]
MR013096 Amiodarone hydrochloride Metabolite M2 Amiodarone hydrochloride Metabolite M3 Unclear - Unclear Unclear [8]
MR013094 Mono-N-desethylamiodarone Di-N-desethylamiodarone Unclear - Unclear Unclear [8]
⏷ Show the Full List of 6 MR(s)
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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
⏷ Show the Full List of 7  DME(s)
References
1 Amiodarone Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 A significant role of human cytochrome P450 2C8 in amiodarone N-deethylation: an approach to predict the contribution with relative activity factor. Drug Metab Dispos. 2000 Nov;28(11):1303-10.
3 Role of desethylamiodarone in the anticoagulant effect of concurrent amiodarone and warfarin therapy. J Cardiovasc Pharmacol Ther. 2001 Oct;6(4):363-7.
4 Functional characterization of five novel CYP2C8 variants, G171S, R186X, R186G, K247R, and K383N, found in a Japanese population. Drug Metab Dispos. 2005 May;33(5):630-6.
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
6 Potentially significant drug interactions of class III antiarrhythmic drugs. Drug Saf. 2003;26(6):421-38.
7 The metabolism of amiodarone by various CYP isoenzymes of human and rat, and the inhibitory influence of ketoconazole. J Pharm Pharm Sci. 2008;11(1):147-59.
8 Pharmacology and pharmacokinetics of amiodarone
9 Determination of the cardiac drug amiodarone and its N-desethyl metabolite in sludge samples
10 Amiodarone and concurrent antiretroviral therapy: a case report and review of the literature

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