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

General Information of Drug (ID: DR1394)
Drug Name
Ranolazine
Synonyms
Ranexa; Ranolazine (Ranexa); (-)-Ranolazine; 142387-99-3; 95635-55-5; C24H33N3O4; CHEBI:87690; CVT 303; CVT-303; DSSTox_CID_25196; Latixa; RANOLAZINE; RS-43285-003; DSSTox_GSID_45196; DSSTox_RID_80743; N-(2,6-dimethylphenyl)-2-(4-(2-hydroxy-3-(2-methoxyphenoxy)propyl)piperazin-1-yl)acetamide; N-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl]acetamide; N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide; NCGC00015897-02; RAN D; Ran4
Indication Angina pectoris [ICD11: BA40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 427.5 Topological Polar Surface Area 74.3
Heavy Atom Count 31 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
56959
PubChem SID
7980486 ; 8184974 ; 12013498 ; 14856376 ; 26612929 ; 26749060 ; 26749061 ; 43114706 ; 46505145 ; 47207361 ; 47795040 ; 48169373 ; 50070803 ; 50107515 ; 51004683 ; 56463697 ; 57313861 ; 81040983 ; 85171832 ; 85789241 ; 90340842 ; 92124680 ; 92307911 ; 92309225 ; 92712119 ; 103482101 ; 104171232 ; 104253386 ; 104311416 ; 117573069 ; 121363701 ; 124750209 ; 124757504 ; 124799345 ; 124881338 ; 124881339 ; 125164308 ; 125360240 ; 126583887 ; 126622101 ; 126630205 ; 126656915 ; 126666839 ; 126724363 ; 129701807 ; 134338152 ; 135015431 ; 135684171 ; 135692283 ; 136375567
ChEBI ID
CHEBI:87690
CAS Number
142387-99-3
TTD Drug ID
D03HYQ
Formula
C24H33N3O4
Canonical SMILES
CC1=C(C(=CC=C1)C)NC(=O)CN2CCN(CC2)CC(COC3=CC=CC=C3OC)O
InChI
1S/C24H33N3O4/c1-18-7-6-8-19(2)24(18)25-23(29)16-27-13-11-26(12-14-27)15-20(28)17-31-22-10-5-4-9-21(22)30-3/h4-10,20,28H,11-17H2,1-3H3,(H,25,29)
InChIKey
XKLMZUWKNUAPSZ-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
CVT-2512 DM016113
46781239
Conjugation - O-arylation 1 [3]
CVT-2513 DM015412
3159843
Oxidation - N-dealkylation 1 [3]
CVT-2534 DM014865
3516
Oxidation - N-dealkylation 1 [3]
CVT-2535 DM016360
82112001
Oxidation - N-dealkylation 1 [3]
CVT-2551 DM016417
91810629
Oxidation - Hydroxylation 1 [3]
CVT-2738 DM015362
2608606
Oxidation - N-dealkylation 1 [3] , [4]
CVT-3369 DM016418
91810630
Hydrolysis - Hydrolysis 1 [3]
RS-88390 (CVT-2514) DM015947
16717165
Oxidation - O-demethylation 1 [3] , [5]
CVT-2537 DM016233
62232045
Oxidation - Carboxylation 2 [3]
CVT-3248 DM016407
91799726
Oxidation - N-dealkylation 2 [3]
CVT-4786 DM015199
151727
Unclear - Unclear 2 [3] , [6]
Ranolazine M1 DM017902 N. A. Multi-steps Reaction - O-glucuronidation; sulfation 2 [3]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009498 Ranolazine RS-88390 (CVT-2514) Oxidation - O-demethylation CYP3A4 ... [3], [5]
MR009500 Ranolazine CVT-2534 Oxidation - N-dealkylation CYP3A4 ... [3]
MR009502 Ranolazine CVT-2535 Oxidation - N-dealkylation Unclear [3]
MR009504 Ranolazine CVT-2551 Oxidation - Hydroxylation CYP3A4 ... [3]
MR009506 Ranolazine CVT-2738 Oxidation - N-dealkylation CYP3A4 ... [3], [4]
MR009507 Ranolazine CVT-2513 Oxidation - N-dealkylation Unclear [3]
MR009508 Ranolazine CVT-2512 Conjugation - O-arylation CYP3A4 ... [3]
MR009509 Ranolazine CVT-3369 Hydrolysis - Hydrolysis CYP3A4 ... [3]
MR009501 CVT-2534 CVT-4786 Unclear - Unclear Unclear [3], [6]
MR009503 CVT-2535 CVT-2537 Oxidation - Carboxylation Unclear [3]
MR009505 CVT-2551 CVT-3248 Oxidation - N-dealkylation Unclear [3]
MR009499 RS-88390 (CVT-2514) Ranolazine M1 Multi-steps Reaction - O-glucuronidation; sulfation Unclear [3]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
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]
References
1 Ranolazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Ranolazine: a contemporary review. J Am Heart Assoc. 2016 Mar 15;5(3):e003196.
3 Ranolazine for the treatment of chronic angina and potential use in other cardiovascular conditions
4 Comparison of pharmacokinetic parameters of ranolazine between diabetic and non-diabetic rats
5 Fatal, Intentional Overdose of Ranolazine: Post-Mortem Distribution of Parent Drug and its Major Metabolite
6 Development and validation of a sensitive LC-MS/MS assay for simultaneous quantitation of ranolazine and its three metabolites in human plasma

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