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

General Information of Drug (ID: DR1442)
Drug Name
Ropivacaine hydrochloride
Synonyms
Ropivacaine hydrochloride hydrate; Ropivacaine monohydrochloride; UNII-35504LBE2T; (S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride; (S)-Ropivacaine hydrochloride; (S)-ropivacaine hydrochloride (anhydrous); Ropivacaina; Ropivacaina [INN-Spanish]; Ropivacaina [Spanish]; Ropivacaine; Ropivacaine (INN); Ropivacaine [INN]; Ropivacainum; Ropivacainum [INN-Latin]; S-Ropivacaine; UNII-7IO5LYA57N; (-)-1-Propyl-2',6'-pipecoloxylidide; (2S)-N-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide; (2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide; (S)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide; (S)-Ropivacaine; 7IO5LYA57N; 84057-95-4; CHEBI:8890; 132112-35-7; 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, monohydrochloride, (S)-; 35504LBE2T; 98717-15-8; C17H26N2O.HCl.H2O; CAS-98717-15-8; CHEBI:60803; DSSTox_CID_28353; DSSTox_GSID_48379; DSSTox_RID_82753; NCGC00164597-01; ROPIVACAINE HCl
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 310.9 Topological Polar Surface Area 32.299
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
175804
ChEBI ID
CHEBI:60803
CAS Number
98717-15-8
TTD Drug ID
D09RHQ
Formula
C17H27ClN2O
Canonical SMILES
CCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
InChI
1S/C17H26N2O.ClH/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3;/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20);1H/t15-;/m0./s1
InChIKey
NDNSIBYYUOEUSV-RSAXXLAASA-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
2-Hydroxymethylropivacaine DM016419
91810632
Oxidation - Methylhydroxylation 1 [5]
3-hydroxyropivacaine DM016036
24892799
Oxidation - 3-hydroxylation 1 [6]
4-Hydroxyropivacaine DM016037
24892800
Oxidation - 4-hydroxylation 1 [5]
PPX DM015595
10014180
Oxidation - N-dealkylation 1 [7] , [8]
3-OH-PPX DM016420
91810633
Oxidation - 3-hydroxylation 2 [9]
3-OH-PPX DM016420
91810633
Oxidation - N-dealkylation 2 [9]
4-OH-PPX DM016327
71748964
Oxidation - 4-hydroxylation 2 [9]
4-OH-PPX DM016327
71748964
Oxidation - N-dealkylation 2 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009568 Ropivacaine hydrochloride 3-hydroxyropivacaine Oxidation - 3-hydroxylation CYP1A2 [6]
MR009570 Ropivacaine hydrochloride 4-Hydroxyropivacaine Oxidation - 4-hydroxylation CYP1A2 [5]
MR009572 Ropivacaine hydrochloride PPX Oxidation - N-dealkylation CYP1A2 [7], [8]
MR009575 Ropivacaine hydrochloride 2-Hydroxymethylropivacaine Oxidation - Methylhydroxylation Unclear [5]
MR009569 3-hydroxyropivacaine 3-OH-PPX Oxidation - N-dealkylation Unclear [9]
MR009571 4-Hydroxyropivacaine 4-OH-PPX Oxidation - N-dealkylation Unclear [9]
MR009573 PPX 3-OH-PPX Oxidation - 3-hydroxylation Unclear [9]
MR009574 PPX 4-OH-PPX Oxidation - 4-hydroxylation Unclear [9]
⏷ Show the Full List of 8 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 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
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
[4]
References
1 Ropivacaine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of ropivacaine in humans is mediated by CYP1A2 and to a minor extent by CYP3A4: an interaction study with fluvoxamine and ketoconazole as in vivo inhibitors. Clin Pharmacol Ther. 1998 Nov;64(5):484-91.
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
4 Metabolism of a new local anesthetic, ropivacaine, by human hepatic cytochrome P450. Anesthesiology. 1995 Jan;82(1):214-20.
5 Metabolism and excretion of ropivacaine in humans
6 Lack of metabolic racemisation of ropivacaine, determined by liquid chromatography using a chiral AGP column
7 Regional transport and metabolism of ropivacaine and its CYP3A4 metabolite PPX in human intestine. J Pharm Pharmacol. 2003 Jul;55(7):963-72.
8 Effect of propofol on ropivacaine metabolism in human liver microsomes
9 LABEL:Ropivacaine hydrochloride

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