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Details

Stereochemistry RACEMIC
Molecular Formula C15H22N2O
Molecular Weight 246.3485
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPIVACAINE

SMILES

Cc1cccc(C)c1N=C(C2CCCCN2C)O

InChI

InChIKey=INWLQCZOYSRPNW-UHFFFAOYSA-N
InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/cdi/mepivacaine.html

Mepivicaine is a local anesthetic of the amide type. Mepivicaine as a reasonably rapid onset and medium duration and is known by the proprietary names as Carbocaine and Polocaine. Mepivicaine is used in local infiltration and regional anesthesia. Systemic absorption of local anesthetics produces effects on the cardiovascular and central nervous systems. At blood concentrations achieved with normal therapeutic doses, changes in cardiac conduction, excitability, refractoriness, contractility, and peripheral vascular resistance are minimal. Mepivicaine is used for production of local or regional analgesia and anesthesia by local infiltration, peripheral nerve block techniques, and central neural techniques including epidural and caudal blocks.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
285.2 µM [IC50]
709.0 µM [IC50]
Target ID: Voltage-Gated Sodium Channels, mouse
3.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CARBOCAINE

Approved Use

CARBOCAINE is indicated for production of local or regional analgesia and anesthesia by local infiltration, peripheral nerve block techniques, and central neural techniques including epidural and caudal blocks.

Launch Date

-3.03868805E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
435.3 ng/mL
20 mg single, intraoral submucosal injection
dose: 20 mg
route of administration: Intraoral Submucosal Injection
experiment type: SINGLE
co-administered:
MEPIVACAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
440 μg × min/mL
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MEPIVACAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1982.3 ng × h/mL
20 mg single, intraoral submucosal injection
dose: 20 mg
route of administration: Intraoral Submucosal Injection
experiment type: SINGLE
co-administered:
MEPIVACAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
125 min
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MEPIVACAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.63 h
20 mg single, intraoral submucosal injection
dose: 20 mg
route of administration: Intraoral Submucosal Injection
experiment type: SINGLE
co-administered:
MEPIVACAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
MEPIVACAINE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, 21 to 31 years
n = 31
Health Status: healthy
Age Group: 21 to 31 years
Sex: M+F
Population Size: 31
Sources:
Other AEs: Herpes lesion intra-oral, Oral mucosa hematoma...
Other AEs:
Herpes lesion intra-oral (3.2%)
Oral mucosa hematoma (3.2%)
Sources:
270 mg 1 times / day single, parenteral
Recommended
Dose: 270 mg, 1 times / day
Route: parenteral
Route: single
Dose: 270 mg, 1 times / day
Sources:
healthy, 5 years
n = 1
Health Status: healthy
Age Group: 5 years
Sex: F
Population Size: 1
Sources:
Other AEs: Seizures, Pneumonia...
Other AEs:
Seizures
Pneumonia
Death (grade 5)
Sources:
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 25 years
n = 50
Health Status: healthy
Condition: pain
Age Group: mean age 25 years
Sex: M+F
Population Size: 50
Sources:
Other AEs: Diplopia, Numbness of lip...
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 27 years
n = 40
Health Status: healthy
Age Group: mean age 27 years
Sex: M+F
Population Size: 40
Sources:
Other AEs: Swelling & soreness of mouth, Incision site paraesthesia...
Other AEs:
Swelling & soreness of mouth (28%)
Incision site paraesthesia (18%)
Other and unspecified diseases of pulp and periapical tissues (2%)
Sources:
3 % 1 times / day single, submucosal
Recommended
Dose: 3 %, 1 times / day
Route: submucosal
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 38.8 years
n = 66
Health Status: healthy
Age Group: mean age 38.8 years
Sex: M+F
Population Size: 66
Sources:
Other AEs: Syncope...
AEs

AEs

AESignificanceDosePopulation
Herpes lesion intra-oral 3.2%
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, 21 to 31 years
n = 31
Health Status: healthy
Age Group: 21 to 31 years
Sex: M+F
Population Size: 31
Sources:
Oral mucosa hematoma 3.2%
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, 21 to 31 years
n = 31
Health Status: healthy
Age Group: 21 to 31 years
Sex: M+F
Population Size: 31
Sources:
Pneumonia
270 mg 1 times / day single, parenteral
Recommended
Dose: 270 mg, 1 times / day
Route: parenteral
Route: single
Dose: 270 mg, 1 times / day
Sources:
healthy, 5 years
n = 1
Health Status: healthy
Age Group: 5 years
Sex: F
Population Size: 1
Sources:
Seizures
270 mg 1 times / day single, parenteral
Recommended
Dose: 270 mg, 1 times / day
Route: parenteral
Route: single
Dose: 270 mg, 1 times / day
Sources:
healthy, 5 years
n = 1
Health Status: healthy
Age Group: 5 years
Sex: F
Population Size: 1
Sources:
Death grade 5
270 mg 1 times / day single, parenteral
Recommended
Dose: 270 mg, 1 times / day
Route: parenteral
Route: single
Dose: 270 mg, 1 times / day
Sources:
healthy, 5 years
n = 1
Health Status: healthy
Age Group: 5 years
Sex: F
Population Size: 1
Sources:
Diplopia 16%
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 25 years
n = 50
Health Status: healthy
Condition: pain
Age Group: mean age 25 years
Sex: M+F
Population Size: 50
Sources:
Numbness of lip 26%
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 25 years
n = 50
Health Status: healthy
Condition: pain
Age Group: mean age 25 years
Sex: M+F
Population Size: 50
Sources:
Incision site paraesthesia 18%
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 27 years
n = 40
Health Status: healthy
Age Group: mean age 27 years
Sex: M+F
Population Size: 40
Sources:
Other and unspecified diseases of pulp and periapical tissues 2%
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 27 years
n = 40
Health Status: healthy
Age Group: mean age 27 years
Sex: M+F
Population Size: 40
Sources:
Swelling & soreness of mouth 28%
3 % 1 times / day single, parenteral
Recommended
Dose: 3 %, 1 times / day
Route: parenteral
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 27 years
n = 40
Health Status: healthy
Age Group: mean age 27 years
Sex: M+F
Population Size: 40
Sources:
Syncope 2%
3 % 1 times / day single, submucosal
Recommended
Dose: 3 %, 1 times / day
Route: submucosal
Route: single
Dose: 3 %, 1 times / day
Sources:
healthy, mean age 38.8 years
n = 66
Health Status: healthy
Age Group: mean age 38.8 years
Sex: M+F
Population Size: 66
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets
PubMed

PubMed

TitleDatePubMed
[Comparative study between 5% prilocaine and 2% mepivacaine by the subarachnoid route in transurethral resections].
2000 May
Hemidiaphragmatic paresis after interscalene supplementation of insufficient axillary block with 3 mL of 2% mepivacaine.
2000 Oct
Inhibition of the Na,K-ATPase of canine renal medulla by several local anesthetics.
2001 Apr
[Recurrence of bullous pemphigoid after surgery: report of a case].
2001 Apr
From cocaine to ropivacaine: the history of local anesthetic drugs.
2001 Aug
[Anesthetic management of a patient with a history of acute intermittent porphyria and an elevation of urinary porphobilinogen].
2001 Aug
[Incidence of transient neurologic symptoms after subarachnoid anesthesia with mepivacaine in ambulatory major surgery].
2001 Aug-Sep
[Surgical treatment of hydrocele with local anesthesia: 10-year experience].
2001 Dec
[An electrophysiological study of ropivacaine on excised cervical vagus nerves of rabbit].
2001 Dec
Successful euthanasia of a juvenile fin whale.
2001 Feb
Blood concentrations of tetracaine and its metabolite following spinal anesthesia.
2001 Feb 1
[Patient-controlled epidural analgesia with bupivacaine and fentanyl suppresses postoperative delirium following hepatectomy].
2001 Jul
Left ventricular contractility is reduced by hypercapnic acidosis and thoracolumbar epidural anesthesia in rabbits.
2001 Jun
Clonidine as adjuvant for mepivacaine, ropivacaine and bupivacaine in axillary, perivascular brachial plexus block.
2001 Jun
The effect of bilateral palmar digital nerve analgesia on the compressive force experienced by the navicular bone in horses with navicular disease.
2001 Mar
Pain perception and utility: a comparison of the syringe and computerized local injection techniques.
2001 Mar-Apr
[Anesthetic management of two patients with essential thrombocythemia].
2001 May
A comparison of the effects of two volumes of local analgesic solution in the distal interphalangeal joint of horses with lameness caused by solar toe or solar heel pain.
2001 May
Pulsioxymetry monitorization during lower third molar extraction. A comparative study of three local anesthetics with epinephrine 1:100,000.
2001 May-Jul
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
A paravenous approach for the saphenous nerve block.
2001 Nov-Dec
Supramalleolar ankle block anesthesia and ankle tourniquet for foot surgery.
2001 Oct
Mepivacaine: update on an evergreen local anaesthetic.
2001 Sep
[Effects of low reactive level laser, linear polarized light and Xenon-ray irradiation on the stellate ganglion in dogs].
2001 Sep
The effects of single and fractionated doses of mepivacaine on the extent of thoracic epidural block.
2001 Sep-Oct
The neurotoxicity of local anesthetics on growing neurons: a comparative study of lidocaine, bupivacaine, mepivacaine, and ropivacaine.
2002 Feb
[Maximum doses of local anesthetics. Changes due to addition of adrenaline?].
2002 Jan
Recurrent neurological symptoms in a patient following repeat combined spinal and epidural anaesthesia.
2002 Jan
Appendectomy in rabbits with extended unilateral anesthesia.
2002 Jan
Allergy to local anaesthetics in dentistry. Myth or reality?
2002 Jan-Feb
[Treatment of temporo-mandibular joint closed-lock using intra-articular injection of mepivacaine with immediate resolution durable in time (six months follow-up)].
2002 Jan-Feb
Hypoxia following interscalene block.
2002 Jan-Feb
Infraclavicular block with lateral approach and nerve stimulation: extent of anesthesia and adverse effects.
2002 Jan-Feb
Effects of right stellate ganglion block on the autonomic nervous function of the heart: a study using the head-up tilt test.
2002 Jul
Nefopam and tramadol for the prevention of shivering during neuraxial anesthesia.
2002 Jul-Aug
Topical anesthesia for minor gynecological procedures: a review.
2002 Mar
Buprenorphine added to the local anesthetic for axillary brachial plexus block prolongs postoperative analgesia.
2002 Mar-Apr
Laparoscopic cryptorchidectomy using electrosurgical instrumentation in standing horses.
2002 Mar-Apr
[Diphenhydramine is useful in a parturient with hypersensitivity to local anesthetics to manage her delivery].
2002 May
Patents

Sample Use Guides

The recommended single adult dose (or the total of a series of doses given in one procedure) of CARBOCAINE (Mepivicaine) for unsedated, healthy, normal-sized individuals should not usually exceed 400 mg.
Route of Administration: Parenteral
Mepivacaine produced tonic contraction in endothelium-denuded rat aorta (3 × 10(−4) to 3 × 10(−3) mol/L mepivacaine; P < 0.05 compared with 10(−5) mol/L mepivacaine
Name Type Language
MEPIVACAINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
2-PIPERIDINECARBOXAMIDE, N-(2,6-DIMETHYLPHENYL)-1-METHYL-
Systematic Name English
MEPIVACAINE [VANDF]
Common Name English
(+/-)-MEPIVACAINE
Common Name English
CARBOPLYIN DENTAL
Brand Name English
MEPISV
Brand Name English
1-METHYL-2',6'-PIPECOLOXYLIDIDE
Common Name English
DL-MEPIVACAINE
Common Name English
(+/-)-1-METHYL-2',6'-PIPECOLOXYLIDIDE
Common Name English
N-(2,6-DIMETHYLPHENYL)-1-METHYL-2-PIPERIDINECARBOXAMIDE
Systematic Name English
2',6'-PIPECOLOXYLIDIDE, 1-METHYL-
Common Name English
MEPIVACAINE [WHO-DD]
Common Name English
TEVACAINE
Brand Name English
APF-135
Code English
SCANDICAINE
Brand Name English
2-PIPERIDINECARBOXAMIDE, N-(2,6-DIMETHYLPHENYL)-1-METHYL-, (+/-)-
Systematic Name English
MEPIVACAINE [INN]
Common Name English
MEPIVACAINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
WHO-ATC N01BB53
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
NDF-RT N0000007681
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
FDA ORPHAN DRUG 206705
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
NDF-RT N0000175682
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
WHO-VATC QN01BB03
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
CFR 21 CFR 522.1372
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
WHO-VATC QN01BB53
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
NDF-RT N0000175976
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
WHO-ATC N01BB03
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
FDA ORPHAN DRUG 206805
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
Code System Code Type Description
PUBCHEM
4062
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
LACTMED
Mepivacaine
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
RXCUI
6759
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
202-543-0
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
EPA CompTox
96-88-8
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
NCI_THESAURUS
C61831
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
DRUG CENTRAL
1700
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
INN
988
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
CAS
96-88-8
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
IUPHAR
7224
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
MESH
D008619
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
CAS
22801-44-1
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
SUPERSEDED
EVMPD
SUB14514MIG
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
WIKIPEDIA
MEPIVACAINE
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
DRUG BANK
DB00961
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
ChEMBL
CHEMBL1087
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY
MERCK INDEX
M7196
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY Merck Index
FDA UNII
B6E06QE59J
Created by admin on Sat Jun 26 11:02:29 UTC 2021 , Edited by admin on Sat Jun 26 11:02:29 UTC 2021
PRIMARY