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levobupivacaine

Trade name: chirocaine

Small moleculeapproved

Approved

Oct 3, 1972

Levobupivacaine (CHIROCAINE®) is a (S)-enantiomer of bupivacaine and it is related chemically and pharmacologically to the amino amide class of local anesthetics. Local anesthetics block the generation and the conduction of nerve impulses by increasing the threshold for electrical excitation in the nerve, by slowing propagation of the nerve impulse, and by reducing the rate of rise of the action potential. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: 1) pain, 2) temperature, 3) touch, 4) proprioception and 5) skeletal muscle tone. Levobupivacaine (CHIROCAINE®) is a safer alternative for regional anesthesia than bupivacaine. It demonstrated less affinity and strength of depressant effects onto myocardial and central nervous vital centers in pharmacodynamic studies, and a superior pharmacokinetic profile. — NCATS

Clinical trial activity

932 trials · 552 clinical orgs · 28 marketing orgs

Phase 1
48
Phase 2
204
Phase 3
128
Phase 4
355

Earliest trial started Jul 1, 1997 (NCT00001088)

Timeline

1970s

  1. Oct 3, 1972

    Earliest FDA Approval

  2. Oct 3, 1972

    Hospira — NDA Secondary Org

1980s

  1. Dec 30, 1981

    Fresenius — NDA Secondary Org

  2. May 21, 1986

    Fresenius — Marketing Organization

  3. Feb 17, 1987

    Hospira — Marketing Organization

1990s

  1. Jan 1, 1997

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 1998

    Earliest Phase 3 Sponsor(trial)

  3. Aug 5, 1999

    Purdue Pharmaceuticals — First NDA Organization

  4. Aug 5, 1999

    Purdue Pharmaceuticals — NDA Organization

  5. Aug 5, 1999

    Purdue Pharmaceuticals — NDA Secondary Org

2000s

  1. Jan 1, 2002

    Earliest Phase 2 Sponsor(trial)

  2. Jan 9, 2002

    International medicated systems ltd. — Marketing Organization

  3. May 23, 2003

    Amphastar Pharmaceuticals — Marketing Organization

  4. May 23, 2003

    Amphastar Pharmaceuticals — NDA Secondary Org

  5. Sep 27, 2006

    Septodont — Marketing Organization

  6. Sep 27, 2006

    Deproco — Marketing Organization

2010s

  1. Oct 18, 2011

    Mylan — Marketing Organization

  2. Oct 18, 2011

    STERISCIENCE — Marketing Organization

  3. Oct 18, 2011

    ONESOURCE SPECIALTY — Marketing Organization

  4. Oct 28, 2011

    Pacira Pharmaceuticals — NDA Secondary Org

  5. Nov 5, 2013

    Aurobindo Pharma — Marketing Organization

  6. Nov 5, 2013

    Eugia Pharma — Marketing Organization

  7. Jul 25, 2016

    Baxalta — Marketing Organization

  8. Jul 25, 2016

    Shire — Marketing Organization

  9. Feb 19, 2019

    CIVICA — Marketing Organization

  10. Apr 2, 2019

    B. Braun — Marketing Organization

  11. Dec 30, 2019

    Huons Co.,Ltd. — Marketing Organization

2020s

  1. Aug 28, 2020

    Innocoll — Marketing Organization

  2. Aug 28, 2020

    Innocoll — NDA Secondary Org

  3. Feb 1, 2021

    Durect — Marketing Organization

  4. Feb 11, 2021

    Hikma — Marketing Organization

  5. May 12, 2021

    Heron Therapeutics — NDA Secondary Org

  6. Jun 23, 2023

    KINDOS — Marketing Organization

  7. Jun 23, 2023

    Meitheal — Marketing Organization

  8. Nov 20, 2023

    Somerset Pharmaceuticals — Marketing Organization

  9. Mar 27, 2024

    Aspiro — Marketing Organization

  10. Jul 1, 2024

    Hengrui Therapeutics, Inc. — Marketing Organization

  11. Apr 22, 2026

    ANTHEA PHARMA — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • duocaine

    with lidocaine

  • marcaine hydrochloride w/ epinephrine preservative free

    with epinephrine

    Also known as bupivacaine hydrochloride and epinephrine, marcaine hydrochloride w/ epinephrine, sensorcaine

  • zynrelef

    with meloxicam

Approval history

  • approvedPriority reviewOct 3, 1972

Chemistry & pharmacology

Loading structure…

SMILES

CCCCN1CCCC[C@H]1C(=O)NC2=C(C)C=CC=C2C
Mol. weight
288.4277 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Racemic Mixture
Inorganic
No
Polymer
No
Delivery
Parenteral
Availability
Prescription Only

Oral

No

Parenteral

Yes

Topical

No

Black box warning

Sources

Also known as

  • 1-butyl-2',6'-pipecoloxylidide
  • 1-butyl-2',6'-pipecoloxylidide
  • 1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamide
  • 1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamide
  • anekain
  • anekain
  • bucain
  • bucain
  • bucain
  • bupivacaina
  • bupivacaina
  • bupivacaine
  • bupivacaine
  • bupivacaine
  • bupivacaine
  • bupivacaine
  • bupivacaine
  • bupivacaine
  • bupivacaine
  • bupivacaine
  • (-)-bupivacaine
  • (-)-bupivacaine
  • (+/-)-bupivacaine
  • (±)-bupivacaine
  • (±)-bupivacaine
  • bupivacaine hcl
  • bupivacaine hcl
  • bupivacaine hcl
  • bupivacaine hydrochloride
  • bupivacaine hydrochloride
  • bupivacaine hydrochloride
  • bupivacaine hydrochloride
  • bupivacaine hydrochloride anhydrous
  • bupivacaine hydrochloride anhydrous
  • bupivacaine hydrochloride anhydrous
  • bupivacaine hydrochloride anhydrous
  • bupivacaine hydrochloride anhydrous
  • bupivacaine hydrochloride anhydrous
  • bupivacaine hydrochloride kit
  • bupivacaine hydrochloride kit
  • bupivacaine / lidocaine
  • bupivacainum
  • bupivacainum
  • bupivac hcl
  • bupivaciane
  • bupivan
  • bupivicaine
  • carbostesin
  • carbostesin
  • carbostesin
  • chirocain
  • chirocaine
  • chirocaine
  • chirocaine
  • chirocaine
  • chirocaine
  • dl-1-butyl-2',6'-pipecoloxylidide
  • dl-1-butyl-2',6'-pipecoloxylidide
  • dl-bupivacaine
  • dl-bupivacaine
  • dl-bupivacaine
  • exparel
  • exparel
  • exparel
  • l-(-)-1-butyl-2',6'-pipecoloxylidide
  • l-(-)-1-butyl-2',6'-pipecoloxylidide
  • lac-43
  • lac-43
  • l-(-)-bupivacaine
  • l-(-)-bupivacaine
  • levobupivac
  • levobupivacaine
  • levobupivacaine
  • levobupivacaine
  • levobupivacaine
  • levobupivacaine
  • levobupivacaine
  • levobupivacaine
  • levobupivacaine
  • levobupivacaine
  • levobupivacaine
  • levo-bupivacaine
  • levobupivacaine hcl
  • levobupivacaine hcl
  • levobupivacaine hcl
  • levobupivacaine hydrochloride
  • levobupivacaine hydrochloride
  • levobupivacaine hydrochloride
  • levobupivacaine hydrochloride
  • levobupivacaine hydrochloride
  • levobupivicaine
  • marcain
  • marcain
  • marcaine
  • marcaine
  • marcaine
  • marcaine
  • marcaine hcl
  • marcaine hcl
  • racemic bupivacaine
  • racemic bupivacaine
  • (rs)-bupivacaine
  • (rs)-bupivacaine
  • (s)-1-butyl-2',6'-pipecoloxylidide
  • (s)-1-butyl-2',6'-pipecoloxylidide
  • (s)-bupivacaine
  • (s)-bupivacaine
  • sensorcaine
  • sensorcaine
  • sensorcaine
  • sky0402
  • sky0402
  • sky-0402
  • sky-0402
  • win-11318
  • win-11318

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06926764N/ANov 30, 2025Chinese University of Hong Kong, Government of Hong Kong
NCT06695468Phase 4Dec 1, 2024Assiut University
NCT06611176N/AOct 24, 2024St. Antonius Hospital, Nieuwegein
NCT06369870Phase 4Sep 1, 2024Algemeen Ziekenhuis Maria Middelares
NCT06577155Phase 2Sep 1, 2024Asklepieion General Hospital
NCT06410404N/AJun 15, 2024Assiut University
NCT07046052N/AMar 28, 2024National University of Ireland
NCT06266767Phase 4Feb 21, 2024Hamad Medical Corporation
NCT06446960Phase 3Feb 12, 2024Institut National de la Santé Et de la Recherche Médicale, France
NCT06002217N/AJan 31, 2024Clinique Saint Jean, Montpellier
NCT05848375N/ANov 13, 2023Elsan
NCT06864312Phase 4Oct 16, 2023National University of Ireland
NCT06011746Phase 4Aug 30, 2023Tanta University
NCT05877131Phase 4Jun 1, 2023Fundación Althaia Manresa
NCT05863221Phase 4May 9, 2023Heron Therapeutics, Holyoke Medical Center
NCT05816538N/AApr 30, 2023University Hospital, Rijeka
NCT05728151N/AFeb 12, 2023Research Institute of Ophthalmology, Egypt
NCT05707169N/AJan 4, 2023Mansoura University
NCT05600296Phase 1Nov 1, 2022Mansoura University
NCT05559437Phase 1Oct 1, 2022Mansoura University
Showing 20 of 932 trials
Page 1 / 47

Organizations

Research & Development (552)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Assiut UniversityAcademic/Hospital494952007
Pacira PharmaceuticalsFor profit474052004
Mansoura UniversityAcademic/Hospital201742014
Cairo UniversityAcademic/Hospital181842013
Northwestern UniversityAcademic/Hospital181732006
University of CopenhagenAcademic/Hospital141252001
University of RochesterAcademic/Hospital141242005
Icahn School of Medicine at Mount SinaiAcademic/Hospital131222005
Mahidol UniversityAcademic/Hospital131332007
University of Sao PauloAcademic/Hospital131042004
Mayo ClinicAcademic/Hospital121052006
University of TorontoAcademic/Hospital121152006
Aarhus UniversityAcademic/Hospital9522001
National University of IrelandAcademic/Hospital9932010
University of Texas at HoustonAcademic/Hospital9542003
DurectFor profit8722006
Emory UniversityAcademic/Hospital8722009
Harvard UniversityAcademic/Hospital8642013
Premier Research GroupFor profit8032007
Rockefeller UniversityAcademic/Hospital8832006
552 organizations
Page 1 / 28

Marketing (38)

OrganizationOrg typeRelationshipDate
ANTHEA PHARMAFor profitMKTGApr 22, 2026
Amphastar PharmaceuticalsFor profitMKTGMay 23, 2003
Amphastar PharmaceuticalsFor profitNDA2May 23, 2003
AspiroFor profitMKTGMar 27, 2024
Aurobindo PharmaFor profitMKTGNov 5, 2013
B. BraunFor profitMKTGApr 2, 2019
B. BraunFor profitSYNApr 2, 2019
BaxaltaFor profitMKTGJul 25, 2016
CIVICAFor profitMKTGFeb 19, 2019
DeprocoFor profitMKTGSep 27, 2006
DurectFor profitMKTGFeb 1, 2021
Eugia PharmaFor profitMKTGNov 5, 2013
FreseniusFor profitNDA2Dec 30, 1981
FreseniusFor profitMKTGMay 21, 1986
Hengrui Therapeutics, Inc.For profitMKTGJul 1, 2024
Heron TherapeuticsFor profitNDA2May 12, 2021
Heron TherapeuticsFor profitSYNMay 12, 2021
HikmaFor profitMKTGFeb 11, 2021
HospiraFor profitNDA2Oct 3, 1972
HospiraFor profitMKTGFeb 17, 1987
Huons Co.,Ltd.For profitMKTGDec 30, 2019
InnocollFor profitMKTGAug 28, 2020
InnocollFor profitSYNFeb 1, 2021
InnocollFor profitNDA2Aug 28, 2020
International medicated systems ltd.For profitMKTGJan 9, 2002
KINDOSFor profitMKTGJun 23, 2023
MeithealFor profitMKTGJun 23, 2023
MylanFor profitMKTGOct 18, 2011
ONESOURCE SPECIALTYFor profitMKTGOct 18, 2011
Pacira PharmaceuticalsFor profitNDA2Oct 28, 2011
Purdue PharmaceuticalsFor profitNDAAug 5, 1999
Purdue PharmaceuticalsFor profitNDA2Aug 5, 1999
STERISCIENCEFor profitMKTGOct 18, 2011
STERISCIENCEFor profitSYNOct 18, 2011
SeptodontFor profitMKTGSep 27, 2006
SeptodontFor profitSYNFeb 19, 2019
ShireFor profitMKTGJul 25, 2016
Somerset PharmaceuticalsFor profitMKTGNov 20, 2023