Details of Drug

Drug General Information (ID: D0916)
Drug Name	Levobupivacaine
Drug Type	Small molecule
Drug Synonymous	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 Click to Show/Hide
Disease Class	9A76-9A78: Corneal disease
Therapeutic Class	Anesthetics
Structure
Structure	3D Structure		2D Structure
Formula	C18H28N2O
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
Canonical SMILES	CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
External Link
	Pubchem ID	92253
	CAS Number	27262-47-1
	CHEBI ID	6149
	TTD ID	D09QUQ
	INTEDE ID	DR0934

Drug-Drug Interaction Network
Sunburst Graph		Legend Information AM003 Affected organization distribution AM004 Affected intra/extra-hepatic metabolism AM006 Pharmacodynamic additive effects BM013 Competitive binding of plasma proteins BM017 CYP450 enzyme inhibition BM022 CYP450 enzyme induction BM024 Competitive inhibition of metabolic enzyme BM038 Additive CNS depression effects BM042 Additive hypotensive effects BM049 Increased risk of atrioventricular block BM051 Increased risk of bradycardia BM071 Increased risk of methemoglobinemia
Relation Graph

Full list of drugs interacting with Levobupivacaine
Affected organization distribution
	Competitive binding of plasma proteins					Drug Num: 3
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0446		Desipramine	C18H22N2	2995	Minor		Inter Info	[34]
D1001		Meperidine	C15H21NO2	4058	Minor		Inter Info	[34]
D1371		Quinidine	C20H24N2O2	441074	Minor		Inter Info	[34]
Affected intra/extra-hepatic metabolism
	CYP450 enzyme inhibition					Drug Num: 74
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0080		Amprenavir	C25H35N3O6S	65016	Moderate		Inter Info	[5], [11]
D0084		Anagrelide	C10H7Cl2N3O	135409400	Moderate		Inter Info	[5], [11]
D0100		Aprepitant	C23H21F7N4O3	135413536	Moderate		Inter Info	[5], [11]
D0313		Chloramphenicol	C11H12Cl2N2O5	5959	Moderate		Inter Info	[5], [11]
D0337		Cimetidine	C10H16N6S	2756	Moderate		Inter Info	[5], [11]
D0341		Ciprofloxacin	C17H18FN3O3	2764	Moderate		Inter Info	[5], [11]
D0367		Clotrimazole	C22H17ClN2	2812	Moderate		Inter Info	[5], [11]
D0402		Cyclosporine	C62H111N11O12	5284373	Moderate		Inter Info	[5], [11]
D0439		Delavirdine	C22H28N6O3S	5625	Moderate		Inter Info	[5], [11]
D0497		Diltiazem	C22H26N2O4S	39186	Moderate		Inter Info	[5], [11]
D0597		Erythromycin	C37H67NO13	12560	Moderate		Inter Info	[5], [11]
D0667		Fluconazole	C13H12F2N6O	3365	Moderate		Inter Info	[5], [11]
D0687		Fluvoxamine	C15H21F3N2O2	5324346	Moderate		Inter Info	[5], [11]
D0793		Imatinib	C29H31N7O	5291	Moderate		Inter Info	[5], [11]
D0799		Indinavir	C36H47N5O4	5362440	Moderate		Inter Info	[5], [11]
D0858		Isoniazid	C6H7N3O	3767	Moderate		Inter Info	[5], [11]
D0002		Abametapir (topical)	C12H12N2	15664	Moderate		Inter Info	[15]
D0116		Atazanavir	C38H52N6O7	148192	Moderate		Inter Info	[5], [11]
D0180		Bicalutamide	C18H14F4N2O4S	2375	Moderate		Inter Info	[5], [11]
D0251		Capmatinib	C23H17FN6O	25145656	Moderate		Inter Info	[5], [11]
D0302		Ceritinib	C28H36ClN5O3S	57379345	Moderate		Inter Info	[5], [11]
D0349		Clarithromycin	C38H69NO13	84029	Moderate		Inter Info	[5], [11]
D0375		Cobicistat	C40H53N7O5S2	25151504	Moderate		Inter Info	[5], [11]
D0393		Crizotinib	C21H22Cl2FN5O	11626560	Moderate		Inter Info	[5], [11]
D0413		Dalfopristin	C34H50N4O9S	6323289	Moderate		Inter Info	[5], [11]
D0416		Danazol	C22H27NO2	28417	Moderate		Inter Info	[5], [11]
D0426		Darunavir	C27H37N3O7S	213039	Moderate		Inter Info	[5], [11]
D0428		Dasatinib	C22H26ClN7O2S	3062316	Moderate		Inter Info	[5], [11]
D0432		Deferasirox	C21H15N3O4	214348	Moderate		Inter Info	[5], [11]
D0534		Dronedarone	C31H44N2O5S	208898	Moderate		Inter Info	[16]
D0543		Duvelisib	C22H17ClN6O	50905713	Moderate		Inter Info	[5], [11]
D0638		Fedratinib	C27H36N6O3S	16722836	Moderate		Inter Info	[5], [11]
D0692		Fosamprenavir	C25H36N3O9PS	131536	Moderate		Inter Info	[5], [11]
D0693		Fosaprepitant	C23H22F7N4O6P	135413538	Moderate		Inter Info	[5], [11]
D0696		Fosnetupitant	C31H35F6N4O5P	71544786	Moderate		Inter Info	[5], [11]
D0699		Fostamatinib	C23H26FN6O9P	11671467	Moderate		Inter Info	[18]
D0724		Givosiran	C78H139N11O30	119058042	Moderate		Inter Info	[5], [11]
D0789		Idelalisib	C22H18FN7O	11625818	Moderate		Inter Info	[5], [11]
D0852		Isavuconazonium	C35H35F2N8O5S+	6918606	Moderate		Inter Info	[5], [11]
D0867		Itraconazole	C35H38Cl2N8O4	55283	Moderate		Inter Info	[5], [11]
D0894		Lapatinib	C29H26ClFN4O4S	208908	Moderate		Inter Info	[5], [11]
D0896		Larotrectinib	C21H22F2N6O2	46188928	Moderate		Inter Info	[5], [11]
D0899		Lefamulin	C28H45NO5S	25185057	Moderate		Inter Info	[19]
D0906		Letermovir	C29H28F4N4O4	45138674	Moderate		Inter Info	[5], [11]
D0946		Lonafarnib	C27H31Br2ClN4O2	148195	Moderate		Inter Info	[5], [11]
D1057		Miconazole	C18H14Cl4N2O	4189	Moderate		Inter Info	[5], [11]
D1117		Nefazodone	C25H32ClN5O2	4449	Moderate		Inter Info	[5], [11]
D1127		Netupitant	C30H32F6N4O	6451149	Moderate		Inter Info	[5], [11]
D1134		Nifedipine	C17H18N2O6	4485	Moderate		Inter Info	[5], [11]
D1136		Nilotinib	C28H22F3N7O	644241	Moderate		Inter Info	[5], [11]
D1155		Norfloxacin	C16H18FN3O3	4539	Moderate		Inter Info	[5], [11]
D1160		Obeticholic acid	C26H44O4	447715	Moderate		Inter Info	[5], [11]
D1189		Osilodrostat	C13H10FN3	44139752	Moderate		Inter Info	[5], [11]
D1315		Posaconazole	C37H42F2N8O4	468595	Moderate		Inter Info	[5], [11]
D1339		Primaquine	C15H21N3O	4908	Moderate		Inter Info	[5], [6], [20], [21], [9]
D1353		Propafenone	C21H27NO3	4932	Moderate		Inter Info	[5], [11]
D1398		Ribociclib	C23H30N8O	44631912	Moderate		Inter Info	[5], [11]
D1432		Rucaparib	C19H18FN3O	9931954	Moderate		Inter Info	[5], [11]
D1444		Saquinavir	C38H50N6O5	441243	Moderate		Inter Info	[5], [11]
D1459		Selpercatinib	C29H31N7O3	134436906	Moderate		Inter Info	[5], [11]
D1505		Stiripentol	C14H18O3	5311454	Moderate		Inter Info	[5], [11]
D1660		Tucatinib	C26H24N8O2	51039094	Moderate		Inter Info	[5], [11]
D1709		Voxelotor	C19H19N3O3	71602803	Moderate		Inter Info	[5], [11]
D1054		Mexiletine	C11H17NO	4178	Moderate		Inter Info	[5], [11]
D1063		Mifepristone	C29H35NO2	55245	Moderate		Inter Info	[4], [5], [25], [26]
D1119		Nelfinavir	C32H45N3O4S	64143	Moderate		Inter Info	[5], [11]
D1237		Peginterferon alfa-2a	NA	NA	Moderate		Inter Info	[5], [11]
D1415		Ritonavir	C37H48N6O5S2	392622	Moderate		Inter Info	[5], [11]
D1544		Telithromycin	C43H65N5O10	3002190	Moderate		Inter Info	[27], [28], [29]
D1571		Thiabendazole	C10H7N3S	5430	Moderate		Inter Info	[5], [11]
D1581		Ticlopidine	C14H14ClNS	5472	Moderate		Inter Info	[5], [11]
D1706		Voriconazole	C16H14F3N5O	71616	Moderate		Inter Info	[5], [11]
D1721		Zileuton	C11H12N2O2S	60490	Moderate		Inter Info	[5], [11]
D0035		Alfentanil	C21H32N6O3	51263	Minor		Inter Info	[30], [31], [32]
	CYP450 enzyme induction					Drug Num: 45
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0545		Echinacea	NA	NA	Moderate		Inter Info	[4], [17]
D1546		Telotristat ethyl	C27H26ClF3N6O3	25181577	Moderate		Inter Info	[5], [22]
D0028		Albendazole	C12H15N3O2S	2082	Minor		Inter Info	[11]
D0178		Bexarotene	C24H28O2	82146	Minor		Inter Info	[11]
D0194		Bosentan	C27H29N5O6S	104865	Minor		Inter Info	[11]
D0224		Butabarbital	C10H16N2O3	2479	Minor		Inter Info	[11]
D0255		Carbamazepine	C15H12N2O	2554	Minor		Inter Info	[11]
D0554		Efavirenz	C14H9ClF3NO2	64139	Minor		Inter Info	[11]
D0639		Felbamate	C11H14N2O4	3331	Minor		Inter Info	[11]
D0741		Griseofulvin	C17H17ClO6	441140	Minor		Inter Info	[11]
D0071		Amobarbital	C11H18N2O3	2164	Minor		Inter Info	[33], [11]
D0095		Apalutamide	C21H15F4N5O2S	24872560	Minor		Inter Info	[11]
D0106		Armodafinil	C15H15NO2S	9690109	Minor		Inter Info	[11]
D0300		Cenobamate	C10H10ClN5O2	11962412	Minor		Inter Info	[11]
D0406		Dabrafenib	C23H20F3N5O2S2	44462760	Minor		Inter Info	[11]
D0453		Dexamethasone	C22H29FO5	5743	Minor		Inter Info	[11]
D0555		Elagolix	C32H30F5N3O5	11250647	Minor		Inter Info	[33], [11]
D0578		Enzalutamide	C21H16F4N4O2S	15951529	Minor		Inter Info	[11]
D0628		Etravirine	C20H15BrN6O	193962	Minor		Inter Info	[11]
D0697		Fosphenytoin	C16H15N2O6P	56339	Minor		Inter Info	[11]
D0872		Ivosidenib	C28H22ClF3N6O3	71657455	Minor		Inter Info	[33], [11]
D0953		Lorlatinib	C21H19FN6O2	71731823	Minor		Inter Info	[11]
D1190		Osimertinib	C28H33N7O2	71496458	Minor		Inter Info	[11]
D1258		Pexidartinib	C20H15ClF3N5	25151352	Minor		Inter Info	[33], [11]
D1265		Phenobarbital	C12H12N2O3	4763	Minor		Inter Info	[5], [6], [20], [21], [9]
D1400		Rifampicin	C43H58N4O12	135398735	Minor		Inter Info	[33], [11]
D1401		Rifapentine	C47H64N4O12	135403821	Minor		Inter Info	[11]
D1433		Rufinamide	C10H8F2N4O	129228	Minor		Inter Info	[11]
D1493		Somapacitan	C54H95N13O20S2	129894493	Minor		Inter Info	[33], [11]
D1502		St. John's Wort	NA	NA	Minor		Inter Info	[11]
D1538		Tazemetostat	C34H44N4O4	66558664	Minor		Inter Info	[33], [11]
D1556		Teriflunomide	C12H9F3N2O2	54684141	Minor		Inter Info	[33], [11]
D1687		Vemurafenib	C23H18ClF2N3O3S	42611257	Minor		Inter Info	[11]
D1040		Methylphenobarbital	C13H14N2O3	8271	Minor		Inter Info	[33], [11]
D1078		Mitotane	C14H10Cl4	4211	Minor		Inter Info	[11]
D1081		Modafinil	C15H15NO2S	4236	Minor		Inter Info	[11]
D1099		Nafcillin	C21H22N2O5S	8982	Minor		Inter Info	[11]
D1128		Nevirapine	C15H14N4O	4463	Minor		Inter Info	[11]
D1179		Omeprazole	C17H19N3O3S	4594	Minor		Inter Info	[11]
D1198		Oxcarbazepine	C15H12N2O2	34312	Minor		Inter Info	[11]
D1248		Pentobarbital	C11H18N2O3	4737	Minor		Inter Info	[11]
D1340		Primidone	C12H14N2O2	4909	Minor		Inter Info	[11]
D1399		Rifabutin	C46H62N4O11	135398743	Minor		Inter Info	[11]
D1453		Secobarbital	C12H18N2O3	5193	Minor		Inter Info	[33], [11]
D1494		Somatotropin	NA	NA	Minor		Inter Info	[33], [11]
	Competitive inhibition of metabolic enzyme					Drug Num: 3
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D1549		Temsirolimus	C56H87NO16	6918289	Moderate		Inter Info	[23], [24]
D1476		Sirolimus	C51H79NO13	5284616	Moderate		Inter Info	[23], [24]
D1526		Tacrolimus	C44H69NO12	445643	Moderate		Inter Info	[23], [24]
Pharmacodynamic additive effects
	Additive CNS depression effects					Drug Num: 14
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0045		Alprazolam	C17H13ClN4	2118	Moderate		Inter Info	[4], [5], [10]
D0317		Chlordiazepoxide	C16H14ClN3O	2712	Moderate		Inter Info	[4], [5], [10]
D0356		Clobazam	C16H13ClN2O2	2789	Moderate		Inter Info	[4], [5], [10]
D0365		Clorazepic acid	C16H11ClN2O3	2809	Moderate		Inter Info	[4], [5], [10]
D0473		Diazepam	C16H13ClN2O	3016	Moderate		Inter Info	[4], [5], [10]
D0679		Flurazepam	C21H23ClFN3O	3393	Moderate		Inter Info	[4], [5], [10]
D0362		Clonazepam	C15H10ClN3O3	2802	Moderate		Inter Info	[4], [5], [10]
D0604		Estazolam	C16H11ClN4	3261	Moderate		Inter Info	[4], [5], [10]
D1367		Quazepam	C17H11ClF4N2S	4999	Moderate		Inter Info	[4], [5], [10]
D0951		Lorazepam	C15H10Cl2N2O2	3958	Moderate		Inter Info	[4], [5], [10]
D1060		Midazolam	C18H13ClFN3	4192	Moderate		Inter Info	[4], [5], [10]
D1197		Oxazepam	C15H11ClN2O2	4616	Moderate		Inter Info	[4], [5], [10]
D1547		Temazepam	C16H13ClN2O2	5391	Moderate		Inter Info	[4], [5], [10]
D1632		Triazolam	C17H12Cl2N4	5556	Moderate		Inter Info	[4], [5], [10]
	Additive hypotensive effects					Drug Num: 1
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D1752		Bupivacaine (liposome)	C18H28N2O	2474	Major		Inter Info	[1], [2]
	Increased risk of bradycardia					Drug Num: 6
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0513		Dofetilide	C19H27N3O5S2	71329	Moderate		Inter Info	[13], [14]
D0787		Ibutilide	C20H36N2O3S	60753	Moderate		Inter Info	[13], [14]
D0066		Amiodarone	C25H29I2NO3	2157	Moderate		Inter Info	[13], [14]
D0200		Bretylium	C11H17BrN+	2431	Moderate		Inter Info	[13], [14]
D1428		Ropivacaine	C17H26N2O	175805	Moderate		Inter Info	[14]
D1498		Sotalol	C12H20N2O3S	5253	Moderate		Inter Info	[13], [14]
	Increased risk of methemoglobinemia					Drug Num: 10
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D1337		Prilocaine	C13H20N2O	4906	Major		Inter Info	[3], [4], [5], [6], [7], [8], [9]
D0339		Cinchocaine (topical)	C20H29N3O2	3025	Moderate		Inter Info	[5], [6], [12]
D0377		Cocaine (nasal)	C17H21NO4	446220	Moderate		Inter Info	[5], [6], [12]
D0378		Cocaine (topical)	C17H21NO4	446220	Moderate		Inter Info	[5], [6], [12]
D0163		Benzocaine (topical)	C9H11NO2	2337	Moderate		Inter Info	[5], [6], [12]
D1904		Tetracaine (ophthalmic)	C15H24N2O2	5411	Moderate		Inter Info	[5], [6], [12]
D1835		Lidocaine (ophthalmic)	C14H22N2O	3676	Moderate		Inter Info	[5], [6], [12]
D0928		Lidocaine (topical)	C14H22N2O	3676	Moderate		Inter Info	[5], [6], [12]
D1852		Oxybuprocaine (ophthalmic)	C17H28N2O3	4633	Moderate		Inter Info	[5], [6], [12]
D1870		Proparacaine (ophthalmic)	C16H26N2O3	4935	Moderate		Inter Info	[5], [6], [12]

References
1	Product Information. Exparel (bupivacaine liposome). Pacira Pharmaceuticals Inc, San Diego, CA.
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7	Product Information. Citanest Forte (epinephrine-prilocaine) Astra-Zeneca Pharmaceuticals, Wilmington, DE.
8	Product Information. Citanest Plain (prilocaine) Astra-Zeneca Pharmaceuticals, Wilmingtoon, DE.
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11	Product Information. Chirocaine (levobupivacaine) Organon, West Orange, NJ.
12	Product Information. Hurricaine (benzocaine topical). Beutlich, Waukegan, IL.
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15	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
16	Product Information. Multaq (dronedarone). sanofi-aventis , Bridgewater, NJ.
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18	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.
19	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
20	Product Information. Marcaine HCl (bupivacaine). Hospira Inc, Lake Forest, IL.
21	Product Information. Zynrelef (bupivacaine-meloxicam). Heron Therapeutics, Redwood City, CA.
22	Product Information. Xermelo (telotristat ethyl). Lexicon Pharmaceuticals, Inc., The Woodlands, TX.
23	Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
24	Product Information. Rapamune (sirolimus) Wyeth-Ayerst Laboratories, Philadelphia, PA.
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27	Product Information. Ketek (telithromycin). Aventis Pharmaceuticals, Bridgewater, NJ.
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