MEPIVACAINE

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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	Potency
Sodium channel protein type X alpha subunit 9	Inhibitor 8,297	285.2 µM [IC50]
Potassium channel subfamily K member 3 10	Inhibitor 8,297	709.0 µM [IC50]
HERG 92	Inhibitor 8,297
Voltage-Gated Sodium Channels, mouse 2	Inhibitor 8,297	3.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614	Palliative		Approved 8,429	CARBOCAINE

C_max

Value	Dose	Co-administered	Analyte	Population
435.3 ng/mL	20 mg single, intraoral submucosal injection		MEPIVACAINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1982.3 ng × h/mL	20 mg single, intraoral submucosal injection		MEPIVACAINE plasma	Homo sapiens
440 μg × min/mL	250 mg single, intravenous		MEPIVACAINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.63 h	20 mg single, intraoral submucosal injection		MEPIVACAINE plasma	Homo sapiens
125 min	250 mg single, intravenous		MEPIVACAINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
25%			MEPIVACAINE serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
3 % 1 times / day single, parenteral Recommended	healthy, 21 to 31 years	Other AEs: Herpes lesion intra-oral, Oral mucosa hematoma...
270 mg 1 times / day single, parenteral Recommended	healthy, 5 years	Other AEs: Seizures, Pneumonia...
3 % 1 times / day single, parenteral Recommended	healthy, mean age 25 years	Other AEs: Diplopia, Numbness of lip...
3 % 1 times / day single, parenteral Recommended	healthy, mean age 27 years	Other AEs: Swelling & soreness of mouth, Incision site paraesthesia...
3 % 1 times / day single, submucosal Recommended	healthy, mean age 38.8 years	Other AEs: Syncope...

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AEs

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AE	Significance	Dose	Population
Herpes lesion intra-oral	3.2%	3 % 1 times / day single, parenteral Recommended	healthy, 21 to 31 years
Oral mucosa hematoma	3.2%	3 % 1 times / day single, parenteral Recommended	healthy, 21 to 31 years
Pneumonia		270 mg 1 times / day single, parenteral Recommended	healthy, 5 years
Seizures		270 mg 1 times / day single, parenteral Recommended	healthy, 5 years
Death	grade 5	270 mg 1 times / day single, parenteral Recommended	healthy, 5 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6759	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6759
ChemicalBook	CB8460318	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8460318
ChemicalBook	CB9907386	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9907386
eMolecules	902098	https://www.emolecules.com/cgi-bin/more?vid=902098
MolPort	MolPort-005-935-383	https://www.molport.com/shop/molecule-link/MolPort-005-935-383

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PubMed

Show entries

Title	Date	PubMed
[Anesthetic management of a patient with a history of acute intermittent porphyria and an elevation of urinary porphobilinogen].	2001 Aug	11554022
[Surgical treatment of hydrocele with local anesthesia: 10-year experience].	2001 Dec	11852515
The acute effects of stellate ganglion block on circulation in human ocular fundus.	2001 Feb	11167286
Standing laparoscopic herniorrhaphy in stallions using cylindrical polypropylene mesh prosthesis.	2001 Jan	11191617
Effects of vasoconstrictors in dentistry upon systolic and diastolic arterial pressure.	2001 Jan-Feb	11488132

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Patents

Sample Use Guides

In Vivo Use Guide

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

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