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

General Information of Drug (ID: DR0934)
Drug Name
Levobupivacaine
Synonyms
Levobupivacaine; Levobupivacaine [INN:BAN]; Levobupivacaine hydrochloride; (2S)-1-butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide; L(-)-Bupivacaine; (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; (S)-1-Butyl-2',6'-pipecoloxylidide; (S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; (S)-bupivacaine; 2',6'-Pipecoloxylidide, 1-butyl-, L-(-)-; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)-; 27262-47-1; A5H73K9U3W; CHEBI:6149; L-(-)-1-Butyl-2',6'-pipecoloxylidide; UNII-A5H73K9U3W
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 288.4 Topological Polar Surface Area 32.299
Heavy Atom Count 21 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
92253
PubChem SID
10089 ; 10225294 ; 11112642 ; 14775644 ; 14800000 ; 29215441 ; 44423110 ; 46505295 ; 50010834 ; 50070564 ; 50071325 ; 57335205 ; 80394341 ; 93166629 ; 96024806 ; 104222110 ; 104406939 ; 123092444 ; 126592946 ; 126669543 ; 126669544 ; 128475942 ; 131308447 ; 134338472 ; 135048182 ; 136357477 ; 137248692 ; 160964338 ; 162174730 ; 163366975 ; 175271332 ; 178103786 ; 179150260 ; 185974045 ; 187072685 ; 198980870 ; 218903197 ; 223535869 ; 223666603 ; 223666604 ; 223850360 ; 226420984 ; 251916836 ; 251918075 ; 252451169
ChEBI ID
CHEBI:6149
CAS Number
27262-47-1
TTD Drug ID
D09QUQ
Formula
C18H28N2O
Canonical SMILES
CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
InChI
1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1
InChIKey
LEBVLXFERQHONN-INIZCTEOSA-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',6'-pipecoloxylidide DM000664
115282
Unclear 1 [3]
3-hydroxy levobupivacaine DM000261 N. A. Oxidation - N-Dealkylation 1 [3]
Desbutyl levobupivacaine DM000262 N. A. Oxidation - Deamination 1 [3]
Unclear DM009999 N. A. Conjugation - Sulfation 2 [3]
Unclear DM009999 N. A. Conjugation - Glucuronidation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001468 Levobupivacaine 3-hydroxy levobupivacaine Oxidation - N-Dealkylation CYP1A2 [3]
MR001469 Levobupivacaine Desbutyl levobupivacaine Oxidation - Deamination CYP3A4 [3]
MR001470 Levobupivacaine N-desbutylbupivacaine Unclear Unclear [3]
MR001467 3-hydroxy levobupivacaine . Conjugation - Glucuronidation Unclear [3]
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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Levobupivacaine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetics of levobupivacaine after caudal epidural administration in infants less than 3 months of age. Br J Anaesth. 2005 Oct;95(4):524-9.
3 Clinical profile of levobupivacaine in regional anesthesia: A systematic review. J Anaesthesiol Clin Pharmacol. 2013 Oct;29(4):530-9.

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