U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C15H22N2O
Molecular Weight 246.348
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPIVACAINE

SMILES

CN1CCCCC1C(=O)NC2=C(C)C=CC=C2C

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

Molecular Formula C15H22N2O
Molecular Weight 246.348
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

1960
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
Health Status: healthy
Age Group: 21 to 31 years
Sex: M+F
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
Health Status: healthy
Age Group: 5 years
Sex: F
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
Health Status: healthy
Age Group: mean age 25 years
Sex: M+F
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
Health Status: healthy
Age Group: mean age 27 years
Sex: M+F
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
Health Status: healthy
Age Group: mean age 38.8 years
Sex: M+F
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
Health Status: healthy
Age Group: 21 to 31 years
Sex: M+F
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
Health Status: healthy
Age Group: 21 to 31 years
Sex: M+F
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
Health Status: healthy
Age Group: 5 years
Sex: F
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
Health Status: healthy
Age Group: 5 years
Sex: F
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
Health Status: healthy
Age Group: 5 years
Sex: F
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
Health Status: healthy
Age Group: mean age 25 years
Sex: M+F
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
Health Status: healthy
Age Group: mean age 25 years
Sex: M+F
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
Health Status: healthy
Age Group: mean age 27 years
Sex: M+F
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
Health Status: healthy
Age Group: mean age 27 years
Sex: M+F
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
Health Status: healthy
Age Group: mean age 27 years
Sex: M+F
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
Health Status: healthy
Age Group: mean age 38.8 years
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets
PubMed

PubMed

TitleDatePubMed
Nefopam and tramadol for the prevention of shivering during neuraxial anesthesia.
2002-07-20
Effects of right stellate ganglion block on the autonomic nervous function of the heart: a study using the head-up tilt test.
2002-07
Enhancement of delayed-rectifier potassium conductance by low concentrations of local anaesthetics in spinal sensory neurones.
2002-06
Pain perception and utility: a comparison of the syringe and computerized local injection techniques.
2002-05-15
Arthroscopic removal of dorsoproximal chip fractures of the proximal phalanx in standing horses.
2002-05-08
[Diphenhydramine is useful in a parturient with hypersensitivity to local anesthetics to manage her delivery].
2002-05
[Changes of blood volume and blood propofol concentration during the anesthetic management of a pheochromocytoma patient].
2002-05
Comparison of mepivacaine and lidocaine for intravenous regional anaesthesia: pharmacokinetic study and clinical correlation.
2002-04
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction.
2002-04
Postoperative analgesia with continuous sciatic nerve block after foot surgery: a prospective, randomized comparison between the popliteal and subgluteal approaches.
2002-04
A double-blinded, randomized comparison of either 0.5% levobupivacaine or 0.5% ropivacaine for sciatic nerve block.
2002-04
Buprenorphine added to the local anesthetic for axillary brachial plexus block prolongs postoperative analgesia.
2002-03-27
Allergy to local anaesthetics in dentistry. Myth or reality?
2002-03-13
Laparoscopic cryptorchidectomy using electrosurgical instrumentation in standing horses.
2002-03-09
Mediating transurethral microwave thermotherapy by intraprostatic and periprostatic injections of mepivacaine epinephrine: effects on treatment time, energy consumption, and patient comfort.
2002-03
Clinical properties of levobupivacaine or racemic bupivacaine for sciatic nerve block.
2002-03
Topical anesthesia for minor gynecological procedures: a review.
2002-03
[Treatment of temporo-mandibular joint closed-lock using intra-articular injection of mepivacaine with immediate resolution durable in time (six months follow-up)].
2002-02-15
Randomized comparison of remifentanil-propofol with a sciatic-femoral nerve block for out-patient knee arthroscopy.
2002-02
Evaluating a dental patient for local anesthesia allergy.
2002-02
[The changes in hemodynamics and dose requirements in total intravenous anesthesia using propofol and buprenorphine].
2002-02
Retrobulbar catheter technique for postoperative titratable analgesia after glaucoma surgery.
2002-02
The neurotoxicity of local anesthetics on growing neurons: a comparative study of lidocaine, bupivacaine, mepivacaine, and ropivacaine.
2002-02
Hypoxia following interscalene block.
2002-01-19
Infraclavicular block with lateral approach and nerve stimulation: extent of anesthesia and adverse effects.
2002-01-19
Use of negatively charged cyclodextrins for the simultaneous enantioseparation of selected anesthetic drugs by capillary electrophoresis-mass spectrometry.
2002-01-15
[Maximum doses of local anesthetics. Changes due to addition of adrenaline?].
2002-01
Recurrent neurological symptoms in a patient following repeat combined spinal and epidural anaesthesia.
2002-01
Appendectomy in rabbits with extended unilateral anesthesia.
2002-01
[High dose L-dopa infusion during general anesthesia for gastrectomy in a patient with parkinsonism].
2002-01
Diffusion of mepivacaine between adjacent synovial structures in the horse. Part 2: tarsus and stifle.
2002-01
Diffusion of mepivacaine between adjacent synovial structures in the horse. Part 1: forelimb foot and carpus.
2002-01
[Surgical treatment of hydrocele with local anesthesia: 10-year experience].
2001-12
[An electrophysiological study of ropivacaine on excised cervical vagus nerves of rabbit].
2001-12
Assessment of QT interval and QT dispersion following stellate ganglion block using computerized measurements.
2001-11-15
A paravenous approach for the saphenous nerve block.
2001-11-15
Laparoscopic ovariectomy using sequential electrocoagulation and sharp transection of the equine mesovarium.
2001-11-13
Laparoscopic closure of the renosplenic space in standing horses.
2001-11-13
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001-11
[Perioperative management of a patient with systemic lupus erythematosus, myasthenia gravis, and pemphigus foliaceous].
2001-11
Effect of topical anesthesia of the laryngeal mucosa on upper airway mechanics in exercising horses.
2001-11
Long-term absence of sensitization to mepivacaine as assessed by a diagnostic protocol including patch testing.
2001-11
The use of hypotensive technique in conjunction with brachial plexus block anesthesia for surgery of the upper extremity.
2001-11
[Comparison between 1.5% lidocaine with adrenaline and 1.5% plain mepivacaine in axillary brachial plexus block].
2001-10
Middle ear problems after a Gow-Gates injection.
2001-10
Continuous post-operative regional analgesia at home.
2001-09
[Levobupivacaine for peripheral blocks of the lower limb: a clinical comparison with bupivacaine and ropivacaine].
2001-09
Mepivacaine: update on an evergreen local anaesthetic.
2001-09
The cardiotoxicity of local anesthetics: the place of ropivacaine.
2001-08
From cocaine to ropivacaine: the history of local anesthetic drugs.
2001-08
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:31:31 GMT 2025
Edited
by admin
on Mon Mar 31 18:31:31 GMT 2025
Record UNII
B6E06QE59J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBOPLYIN DENTAL
Preferred Name English
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
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
Mepivacaine [WHO-DD]
Common Name English
N-(2,6-DIMETHYLPHENYL)-1-METHYL-2-PIPERIDINECARBOXAMIDE
Systematic Name English
2',6'-PIPECOLOXYLIDIDE, 1-METHYL-
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 Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
WHO-ATC N01BB53
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
NDF-RT N0000007681
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
FDA ORPHAN DRUG 206705
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
NDF-RT N0000175682
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
WHO-VATC QN01BB03
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
CFR 21 CFR 522.1372
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
WHO-VATC QN01BB53
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
NDF-RT N0000175976
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
WHO-ATC N01BB03
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
FDA ORPHAN DRUG 206805
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
Code System Code Type Description
PUBCHEM
4062
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
LACTMED
Mepivacaine
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
RXCUI
6759
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
202-543-0
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID9023259
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
NCI_THESAURUS
C61831
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
DRUG CENTRAL
1700
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
CHEBI
6759
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
INN
988
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
CAS
96-88-8
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
IUPHAR
7224
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
MESH
D008619
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
CAS
22801-44-1
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
SUPERSEDED
EVMPD
SUB14514MIG
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
WIKIPEDIA
MEPIVACAINE
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
DRUG BANK
DB00961
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
ChEMBL
CHEMBL1087
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
MERCK INDEX
m7196
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY Merck Index
SMS_ID
100000091383
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
FDA UNII
B6E06QE59J
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
DAILYMED
B6E06QE59J
Created by admin on Mon Mar 31 18:31:31 GMT 2025 , Edited by admin on Mon Mar 31 18:31:31 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY