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
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
| 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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00961Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/mepivacaine.html
Sources: http://www.drugbank.ca/drugs/DB00961
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.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5451 Sources: http://www.drugbank.ca/drugs/DB00961 |
285.2 µM [IC50] | ||
Target ID: CHEMBL2321613 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10201682 |
709.0 µM [IC50] | ||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15983462 |
|||
Target ID: Voltage-Gated Sodium Channels, mouse Sources: https://www.ncbi.nlm.nih.gov/pubmed/23744419 |
3.7 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | CARBOCAINE Approved UseCARBOCAINE 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 Date1960 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
435.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27976931 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1982.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27976931 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/380609 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.63 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27976931 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/380609 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
25% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6478740 |
MEPIVACAINE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse 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%) Sources: Oral mucosa hematoma (3.2%) |
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 |
Other AEs: Seizures, Pneumonia... |
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... Other AEs: Diplopia (16%) 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 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%) Sources: Incision site paraesthesia (18%) Other and unspecified diseases of pulp and periapical tissues (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: |
Other AEs: Syncope... Other AEs: Syncope (2%) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
|
| 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 |
|
| 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 |
| 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: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/carbocaine-injection.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23627840
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
Edited
Mon Mar 31 18:43:43 GMT 2025
by
admin
on
Mon Mar 31 18:43:43 GMT 2025
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| Record UNII |
4VFX2L7EM5
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C245
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6759
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38423-99-3
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SUB03158MIG
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758674
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100000090134
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1722-62-9
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DTXSID4031566
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DBSALT000478
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CHEMBL1087
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6760
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203185
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m7196
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4VFX2L7EM5
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217-023-9
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16452-56-5
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1387002
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C47602
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66070
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4VFX2L7EM5
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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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
|
||
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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
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |