levobupivacaine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
local anaesthetics	4	27262-47-1

Description:

Molecule

Description

Molfile Inchi Smiles

Synonyms:

levobupivacaine
chirocain
levobupivacaine hydrochloride
levobupivacaine HCl

S-enantiomer of bupivacaine, local anaesthetic

Molecular weight: 288.44
Formula: C18H28N2O
CLOGP: 3.69
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 32.34
ALOGS: -3.47
ROTB: 5

Status: OFM

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	100 mg/mL	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	13.00 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.49 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	8.70 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.03 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.79 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Aug. 5, 1999	FDA	PURDUE PHARMA LP

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Mental status changes postoperative	66.26	45.09	9	663	191	63488159
Confusion postoperative	64.40	45.09	9	663	237	63488113
Acute generalised exanthematous pustulosis	62.93	45.09	16	656	11083	63477267

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Anaphylactic reaction	90.25	39.75	34	843	83709	79659802
Mental status changes postoperative	58.25	39.75	8	869	177	79743334
Confusion postoperative	56.80	39.75	8	869	214	79743297
Acute generalised exanthematous pustulosis	55.29	39.75	16	861	17238	79726273
Injection site calcification	42.52	39.75	5	872	29	79743482
Cauda equina syndrome	42.06	39.75	8	869	1395	79742116
Anaphylactic shock	40.04	39.75	15	862	35981	79707530

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	N01BB10	NERVOUS SYSTEM ANESTHETICS ANESTHETICS, LOCAL Amides
MeSH PA	D000777	Anesthetics
MeSH PA	D000779	Anesthetics, Local
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D002492	Central Nervous System Depressants
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D018689	Sensory System Agents
CHEBI has role	CHEBI:36333	local anesthetics
CHEBI has role	CHEBI:37733	EC 3.1.1.8 inhibitor
CHEBI has role	CHEBI:37887	adrenergic blockers
CHEBI has role	CHEBI:59941	amphiphiles
CHEBI has role	CHEBI:60186	SERCA inhibitor

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Anesthesia for cesarean section	indication	4847005
Local anesthesia	indication	386761002
Regional Anesthesia for Surgery	indication
Regional Anesthesia for Labor Pain	indication
Major Nerve Block for Surgery	indication
Regional Anesthesia for Postoperative Pain	indication
Disorder of cardiovascular system	contraindication	49601007	DOID:1287
Kidney disease	contraindication	90708001	DOID:557
Myasthenia gravis	contraindication	91637004	DOID:437
Disease of liver	contraindication	235856003	DOID:409
Deficiency of cholinesterase	contraindication	360607009

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.24	acidic
pKa2	7.92	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Sodium channel protein type 4 subunit alpha	Ion channel	P35499	SCN4A_HUMAN	BLOCKER				WOMBAT-PK	CHEMBL
Sodium channel protein type 1 subunit alpha	Ion channel	P35498	SCN1A_HUMAN		IC50	5.79		WOMBAT-PK
Prostaglandin E2 receptor EP1 subtype	GPCR	P34995	PE2R1_HUMAN					WOMBAT-PK
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN		IC50	6.71		DRUG MATRIX
5-hydroxytryptamine receptor 3A	Ion channel	P46098	5HT3A_HUMAN					WOMBAT-PK
Potassium voltage-gated channel subfamily D member 3	Ion channel	Q9UK17	KCND3_HUMAN		IC50	4.50		WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	4.89		CHEMBL
Potassium voltage-gated channel subfamily A member 5	Ion channel	P22460	KCNA5_HUMAN					WOMBAT-PK

External reference:

ID	Source
4021287	VUID
N0000148724	NUI
D01287	KEGG_DRUG
259453	RXNORM
C0873118	UMLSCUI
CHEBI:6149	CHEBI
OJ0	PDB_CHEM_ID
CHEMBL1201193	ChEMBL_ID
DB01002	DRUGBANK_ID
D000077554	MESH_DESCRIPTOR_UI
92253	PUBCHEM_CID
7211	IUPHAR_LIGAND_ID
7465	INN_ID
27262-48-2	SECONDARY_CAS_RN
A5H73K9U3W	UNII
116103003	SNOMEDCT_US
387011006	SNOMEDCT_US
412237003	SNOMEDCT_US
CHEMBL1200749	ChEMBL_ID
4021287	VANDF
4021288	VANDF
8289	MMSL
d04449	MMSL
008081	NDDF
008082	NDDF

Pharmaceutical products:

None