General Information of Drug (ID: DM783CH)

Drug Name
Levobupivacaine Drug Info
Synonyms
Novabupi; Chirocaine (TN); Levobupivacaine (INN); Levobupivacaine [INN:BAN]; Novabupi (TN); L(-)-Bupivacaine; L-(-)-bupivacaine; L-(-)-1-Butyl-2',6'-pipecoloxylidide; (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; (S)-1-Butyl-2',6'-pipecoloxylidide; (S)-bupivacaine
Indication
Disease Entry ICD 11 Status REF
Anaesthesia 9A78.6 Approved [1]
Therapeutic Class
Anesthetics
Cross-matching ID
PubChem CID
92253
ChEBI ID
CHEBI:6149
CAS Number
CAS 27262-47-1
TTD Drug ID
DM783CH
INTEDE Drug ID
DR0934

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [5]
Carbamazepine DMZOLBI Epilepsy 8A60-8A68 Approved [6]
Zonisamide DM0DTF7 Alcohol dependence 6C40.2 Approved [7]
Eslicarbazepine DMZREFQ Seizure disorder 8A6Z Approved [8]
LIDOFLAZINE DMV23GL Angina pectoris BA40 Approved [9]
LOMERIZINE DME0TC8 Migraine 8A80 Approved [10]
Tetrodotoxin DMWMPRG Bacterial infection 1A00-1C4Z Approved [11]
Permethrin DMZ0Q1G Pediculus capitis infestation 1G00.0 Approved [12]
Rufinamide DMWE60C Epilepsy 8A60-8A68 Approved [13]
Butacaine DM584TM Pain MG30-MG3Z Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [15]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [16]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [17]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [18]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [19]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [20]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [21]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [22]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [16]
Verapamil DMA7PEW Angina pectoris BA40 Approved [23]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 1A2 (CYP1A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [24]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [25]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [26]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [27]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [28]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [29]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [21]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [30]
Verapamil DMA7PEW Angina pectoris BA40 Approved [31]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [32]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sodium channel unspecific (NaC) TTRK8B9 NOUNIPROTAC Blocker [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) Main DME DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 1A2 (CYP1A2) Main DME DEJGDUW CP1A2_HUMAN Substrate [4]

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7211).
2 Block of neuronal tetrodotoxin-resistant Na+ currents by stereoisomers of piperidine local anesthetics. Anesth Analg. 2000 Dec;91(6):1499-505.
3 Clinical profile of levobupivacaine in regional anesthesia: A systematic review. J Anaesthesiol Clin Pharmacol. 2013 Oct;29(4):530-9.
4 Pharmacokinetics of levobupivacaine after caudal epidural administration in infants less than 3 months of age. Br J Anaesth. 2005 Oct;95(4):524-9.
5 Lacosamide: a new approach to target voltage-gated sodium currents in epileptic disorders. CNS Drugs. 2009;23(7):555-68.
6 Sidedness of carbamazepine accessibility to voltage-gated sodium channels. Mol Pharmacol. 2014 Feb;85(2):381-7.
7 Antiepileptic drugs and relapse after epilepsy surgery. Epileptic Disord. 2008 Sep;10(3):193-8.
8 Progress report on new antiepileptic drugs: a summary of the Ninth Eilat Conference (EILAT IX). Epilepsy Res. 2009 Jan;83(1):1-43.
9 Synthesis and pharmacological evaluation of phenylacetamides as sodium-channel blockers. J Med Chem. 1994 Jan 21;37(2):268-74.
10 Medicinal chemistry of neuronal voltage-gated sodium channel blockers. J Med Chem. 2001 Jan 18;44(2):115-37.
11 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
12 In vitro assays for repellents and deterrents for ticks: differing effects of products when tested with attractant or arrestment stimuli. Med Vet Entomol. 2003 Dec;17(4):370-8.
13 Emerging drugs for epilepsy. Expert Opin Emerg Drugs. 2007 Sep;12(3):407-22.
14 WO patent application no. 2008,0857,11, Synergy of sodium channel blockers and calcium channel blockers.
15 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
16 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
17 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
18 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
19 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
20 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
21 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
22 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
23 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.
24 Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
25 Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8.
26 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
27 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
28 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
29 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
30 The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46.
31 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
32 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.