mepivacaine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
local anaesthetics 1700 96-88-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mepivacaine
  • (+/-)-Mepivacaine
  • carbocain
  • carbocaine
  • DL-Mepivacaine
  • mepicaine
  • tevacaine
  • mepivacaine hydrochloride
  • mepivacaine HCl
A local anesthetic that is chemically related to BUPIVACAINE but pharmacologically related to LIDOCAINE. It is indicated for infiltration, nerve block, and epidural anesthesia. Mepivacaine is effective topically only in large doses and therefore should not be used by this route. (From AMA Drug Evaluations, 1994, p168)
  • Molecular weight: 246.35
  • Formula: C15H22N2O
  • CLOGP: 2.10
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 32.34
  • ALOGS: -2.60
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 2.40 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 23.19 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 55 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.95 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 6.80 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.30 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 6, 1960 FDA EASTMAN KODAK

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Monoplegia 80.32 40.20 18 1305 3097 53344646
Anaphylactic shock 52.82 40.20 20 1303 21873 53325870
Anaesthetic complication 48.77 40.20 11 1312 1943 53345800
Lip oedema 46.93 40.20 12 1311 3595 53344148
Mycobacterium chelonae infection 43.71 40.20 8 1315 497 53347246
Oedema mouth 40.77 40.20 10 1313 2532 53345211

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Artery dissection 55.30 39.82 8 672 133 32512713
Drug ineffective 48.98 39.82 49 631 383428 32129418
Anaphylactic shock 47.37 39.82 16 664 15018 32497828

Pharmacologic Action:

SourceCodeDescription
ATC N01BB03 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
ATC N01BB53 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
FDA CS M0000897 Amides
MeSH PA D000777 Anesthetics
MeSH PA D000779 Anesthetics, Local
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:36333 local anaesthetics
CHEBI has role CHEBI:88188 allergenic drug
FDA EPC N0000175682 Amide Local Anesthetic
FDA PE N0000175976 Local Anesthesia

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Local anesthesia, by infiltration indication 44596000
Local anesthesia indication 386761002
Administration of Regional Anesthesia indication
Administration of Local Anesthetic Nerve Block indication
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Disease of liver contraindication 235856003 DOID:409
Deficiency of cholinesterase contraindication 360607009

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.06 acidic
pKa2 7.81 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 1 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 2 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 3 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 4 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 8 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 9 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL

External reference:

IDSource
4019815 VUID
N0000147904 NUI
D00738 KEGG_DRUG
1722-62-9 SECONDARY_CAS_RN
4018232 VANDF
4019815 VANDF
C0025384 UMLSCUI
CHEBI:6759 CHEBI
CHEMBL1087 ChEMBL_ID
DB00961 DRUGBANK_ID
CHEMBL1200440 ChEMBL_ID
D008619 MESH_DESCRIPTOR_UI
988 INN_ID
4062 PUBCHEM_CID
7224 IUPHAR_LIGAND_ID
B6E06QE59J UNII
2021 RXNORM
1899 MMSL
5050 MMSL
64048 MMSL
d01398 MMSL
001352 NDDF
004567 NDDF
391673008 SNOMEDCT_US
59560006 SNOMEDCT_US
65741009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Carbocaine HUMAN PRESCRIPTION DRUG LABEL 1 0362-0753 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 20 sections
Carbocaine with Neo-Cobefrin HUMAN PRESCRIPTION DRUG LABEL 2 0362-0931 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 20 sections
Scandonest 2% L HUMAN PRESCRIPTION DRUG LABEL 2 0362-1097 INJECTION, SOLUTION 20 mg SUBCUTANEOUS ANDA 2 sections
Scandonest 3% Plain HUMAN PRESCRIPTION DRUG LABEL 1 0362-1098 injection, solution 30 mg SUBCUTANEOUS ANDA 19 sections
Mepivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0404-6730 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 20 sections
Carbocaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1036 INJECTION, SOLUTION 10 mg EPIDURAL NDA 22 sections
Carbocaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1038 INJECTION, SOLUTION 10 mg INFILTRATION NDA 22 sections
Carbocaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1041 INJECTION, SOLUTION 15 mg EPIDURAL NDA 22 sections
Carbocaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1067 INJECTION, SOLUTION 20 mg EPIDURAL NDA 22 sections
Carbocaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-2047 INJECTION, SOLUTION 20 mg INFILTRATION NDA 22 sections
Carbocaine HUMAN PRESCRIPTION DRUG LABEL 1 31382-753 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 20 sections
Carbocaine with Neo-Cobefrin HUMAN PRESCRIPTION DRUG LABEL 2 31382-931 INJECTION, SOLUTION 20 mg SUBCUTANEOUS ANDA 20 sections
IQ Dental Mepivacaine HUMAN PRESCRIPTION DRUG LABEL 1 42756-1080 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 19 sections
Mepivacaine HUMAN PRESCRIPTION DRUG LABEL 1 43128-005 injection, solution 30 mg SUBCUTANEOUS ANDA 19 sections
Pearson Mepivacaine HUMAN PRESCRIPTION DRUG LABEL 1 43305-1080 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 19 sections
Polocaine HUMAN PRESCRIPTION DRUG LABEL 1 50090-4408 INJECTION, SOLUTION 20 mg INFILTRATION ANDA 23 sections
Polocaine HUMAN PRESCRIPTION DRUG LABEL 1 50090-4517 INJECTION, SOLUTION 10 mg INFILTRATION ANDA 22 sections
Mepivacaine HUMAN PRESCRIPTION DRUG LABEL 1 50227-1080 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 20 sections
POLOCAINE(R) -MPF (MEPIVACAINE HCI) HUMAN PRESCRIPTION DRUG LABEL 1 51662-1403 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 12 sections
POLOCAINE (MEPIVACAINE HCl) HUMAN PRESCRIPTION DRUG LABEL 1 51662-1534 INJECTION, SOLUTION 10 mg INFILTRATION ANDA 12 sections
POLOCAINE (MEPIVACAINE HCl) HUMAN PRESCRIPTION DRUG LABEL 1 51662-1535 INJECTION, SOLUTION 20 mg INFILTRATION ANDA 12 sections
Polocaine-MPF HUMAN PRESCRIPTION DRUG LABEL 1 63323-260 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 22 sections
Polocaine HUMAN PRESCRIPTION DRUG LABEL 1 63323-283 INJECTION, SOLUTION 10 mg INFILTRATION ANDA 22 sections
Polocaine-MPF HUMAN PRESCRIPTION DRUG LABEL 1 63323-293 INJECTION, SOLUTION 15 mg EPIDURAL ANDA 22 sections
Polocaine-MPF HUMAN PRESCRIPTION DRUG LABEL 1 63323-294 INJECTION, SOLUTION 20 mg EPIDURAL ANDA 22 sections
Polocaine HUMAN PRESCRIPTION DRUG LABEL 1 63323-296 INJECTION, SOLUTION 20 mg INFILTRATION ANDA 22 sections
Polocaine HUMAN PRESCRIPTION DRUG LABEL 1 66312-441 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 20 sections
Mepivacaine HUMAN PRESCRIPTION DRUG LABEL 1 66467-9760 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 20 sections
Mepivacaine HUMAN PRESCRIPTION DRUG LABEL 1 66975-406 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 20 sections
MEPIVACAINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 67239-0201 INJECTION, SOLUTION 30 mg SUBCUTANEOUS ANDA 19 sections