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Details

Stereochemistry RACEMIC
Molecular Formula C15H22N2O.ClH
Molecular Weight 282.809
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPIVACAINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=RETIMRUQNCDCQB-UHFFFAOYSA-N
InChI=1S/C15H22N2O.ClH/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);1H

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 18:43:43 GMT 2025
Edited
by admin
on Mon Mar 31 18:43:43 GMT 2025
Record UNII
4VFX2L7EM5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARESTOCAINE HYDROCHLORIDE
Preferred Name English
MEPIVACAINE HYDROCHLORIDE
EP   GREEN BOOK   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
MEPIVACAINE HYDROCHLORIDE [USP-RS]
Common Name English
MEPIVACAINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
MEPIVACAINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
MEPIVACAINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
(±)-1-METHYL-2',6'-PIPECOLOXYLIDIDE MONOHYDROCHLORIDE
Common Name English
POLOCAINE
Brand Name English
2-PIPERIDINECARBOXAMIDE, N-(2,6-DIMETHYLPHENYL)-1-METHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
MEPIVACAINE HYDROCHLORIDE [MI]
Common Name English
MEPIVACAINE MONOHYDROCHLORIDE
Common Name English
OPTOCAIN
Brand Name English
ISOCAINE HYDROCHLORIDE
Brand Name English
SCANDONEST PLAIN
Brand Name English
Mepivacaine hydrochloride [WHO-DD]
Common Name English
NSC-758674
Code English
2-PIPERIDINECARBOXAMIDE, N-(2,6-DIMETHYLPHENYL)-1-METHYL-, MONOHYDROCHLORIDE, (±)-
Common Name English
MEPIVACAINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
MEPIVACAINE HYDROCHLORIDE [VANDF]
Common Name English
(±)-MEPIVACAINE HYDROCHLORIDE
Common Name English
MEPIVACAINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
MEPIVACAINE HYDROCHLORIDE [MART.]
Common Name English
MEPIVACAINE HCL
Common Name English
MEPIVACAINE HYDROCHLORIDE [JAN]
Common Name English
SCANDICAIN
Brand Name English
CARBOCAINE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
Code System Code Type Description
CHEBI
6759
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
CAS
38423-99-3
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
SUPERSEDED
EVMPD
SUB03158MIG
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
NSC
758674
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
SMS_ID
100000090134
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
CAS
1722-62-9
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID4031566
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
DRUG BANK
DBSALT000478
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
ChEMBL
CHEMBL1087
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
CHEBI
6760
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
RXCUI
203185
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m7196
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY Merck Index
FDA UNII
4VFX2L7EM5
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
ECHA (EC/EINECS)
217-023-9
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
CAS
16452-56-5
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
SUPERSEDED
RS_ITEM_NUM
1387002
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
NCI_THESAURUS
C47602
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
PUBCHEM
66070
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
DAILYMED
4VFX2L7EM5
Created by admin on Mon Mar 31 18:43:43 GMT 2025 , Edited by admin on Mon Mar 31 18:43:43 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Related Record Type Details
IMPURITY -> PARENT
not more than twice the area of the principal peak in the chromatogram obtained with reference solution (b) (0.2 per cent), and not more than one of the peaks has an area greater than the area of the principal peak in the chromatogram obtained with reference solution (b) (0.1 per cent);
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
not more than twice the area of the principal peak in the chromatogram obtained with reference solution (b) (0.2 per cent), and not more than one of the peaks has an area greater than the area of the principal peak in the chromatogram obtained with reference solution (b) (0.1 per cent);
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
color comparison
EP
IMPURITY -> PARENT
not more than twice the area of the principal peak in the chromatogram obtained with reference solution (b) (0.2 per cent), and not more than one of the peaks has an area greater than the area of the principal peak in the chromatogram obtained with reference solution (b) (0.1 per cent);
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
not more than twice the area of the principal peak in the chromatogram obtained with reference solution (b) (0.2 per cent), and not more than one of the peaks has an area greater than the area of the principal peak in the chromatogram obtained with reference solution (b) (0.1 per cent);
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY