procaine benzylpenicillin

Trade name: novocaine

Small moleculeapproved

Approved

Feb 6, 1947

Procaine benzylpenicillin also known as penicillin G procaine, is an antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for syphilis, anthrax, mouth infections, pneumonia, diphtheria, cellulitis, and animal bites. It is given by injection into a muscle. — Wikipedia

Clinical trial activity

448 trials · 465 clinical orgs · 68 marketing orgs

Phase 1
49
Phase 2
133
Phase 3
103
Phase 4
163

Earliest trial started Aug 1, 1983 (NCT00000585)

Timeline

1940s

  1. Feb 6, 1947

    Earliest FDA Approval

  2. Feb 6, 1947

    Pfizer — Marketing Organization

  3. Apr 26, 1948

    King Pharmaceuticals — NDA Secondary Org

  4. Apr 26, 1948

    King Pharmaceuticals — Marketing Organization

1950s

  1. Apr 26, 1951

    Merck — First NDA Organization

  2. Apr 26, 1951

    Merck — NDA Organization

  3. Nov 22, 1951

    American Home Products — NDA Secondary Org

  4. Dec 16, 1952

    Casper Pharma LLC — NDA Secondary Org

1960s

  1. May 27, 1964

    Teva — Marketing Organization

  2. Dec 17, 1965

    American Home Products — Marketing Organization

1970s

  1. May 7, 1970

    GlaxoSmithKline — Marketing Organization

  2. Mar 3, 1971

    Apothecon — Marketing Organization

  3. Mar 3, 1971

    Bristol-Myers Squibb — Marketing Organization

  4. Mar 3, 1971

    Sandoz — Marketing Organization

  5. Nov 9, 1971

    Heritage Pharma — Marketing Organization

  6. Nov 9, 1971

    Chartwell Pharmaceuticals — Marketing Organization

  7. Oct 10, 1973

    G & W Laboratories Inc. — Marketing Organization

  8. Oct 10, 1973

    Cosette — Marketing Organization

  9. Oct 10, 1973

    ACP Nimble — Marketing Organization

  10. Jan 21, 1974

    Belcher Pharmaceuticals — Marketing Organization

  11. Jan 21, 1974

    American Antibiotics — Marketing Organization

  12. Apr 7, 1975

    Watson Pharmaceuticals — Marketing Organization

  13. Jan 13, 1976

    Mylan — Marketing Organization

  14. Mar 11, 1976

    Beecham — Marketing Organization

  15. May 4, 1976

    Puracap Pharmaceutical — Marketing Organization

  16. Jul 29, 1976

    Lannett Company, Inc. — Marketing Organization

  17. Jun 12, 1978

    Ani Pharmaceuticals — Marketing Organization

  18. Aug 2, 1979

    Neopharma — NDA Secondary Org

  19. Sep 6, 1979

    Lederle — Marketing Organization

  20. Sep 6, 1979

    American Cyanamid — Marketing Organization

1980s

  1. Jan 1, 1983

    Earliest Phase 3 Sponsor(trial)

  2. Aug 7, 1985

    Atral — Marketing Organization

  3. Jun 24, 1986

    West-Ward Pharmaceutical — Marketing Organization

  4. Dec 31, 1986

    Pfizer — NDA Secondary Org

  5. May 12, 1987

    Istituto Bio Ita Spa — Marketing Organization

  6. Feb 25, 1988

    DAVA Pharmaceuticals — Marketing Organization

  7. Feb 25, 1988

    Strides Pharma Science — Marketing Organization

  8. Feb 10, 1989

    Endo Pharmaceuticals — Marketing Organization

1990s

  1. Jun 25, 1990

    Baxalta — NDA Secondary Org

  2. Jun 25, 1990

    Baxter — NDA Secondary Org

  3. Jan 1, 1993

    Earliest Phase 2 Sponsor(trial)

  4. Apr 15, 1993

    Hanford Pharmaceuticals — Marketing Organization

  5. Apr 15, 1993

    Hq Speciality Pharma — Marketing Organization

  6. Dec 2, 1997

    Takeda — Marketing Organization

  7. Jan 1, 1999

    Earliest Phase 1 Sponsor(trial)

  8. Apr 8, 1999

    Sun Pharmaceuticals — Marketing Organization

2000s

  1. Aug 30, 2002

    Novartis — Marketing Organization

  2. Aug 11, 2003

    Ranbaxy — Marketing Organization

  3. Nov 9, 2005

    Aurobindo Pharma — Marketing Organization

  4. Mar 29, 2006

    Hikma — Marketing Organization

  5. Jun 18, 2007

    Wockhardt — Marketing Organization

  6. Jun 29, 2007

    Pharmaceutical Associates — Marketing Organization

  7. Jun 29, 2007

    Mustafa Nevzat Pharmaceuticals — Marketing Organization

  8. Jun 29, 2007

    Medimetriks — Marketing Organization

  9. Jan 23, 2008

    Pragma Therapeutics — NDA Secondary Org

  10. May 13, 2008

    Novast Labs — Marketing Organization

  11. Oct 20, 2008

    Apotex — Marketing Organization

  12. Dec 22, 2009

    ACS Dobfar — Marketing Organization

  13. Dec 28, 2009

    Antibiotice — Marketing Organization

2010s

  1. Aug 17, 2010

    Eugia Pharma — Marketing Organization

  2. Feb 8, 2011

    Cumberland Pharmaceuticals — Marketing Organization

  3. Dec 21, 2011

    Hospira — Marketing Organization

  4. Apr 7, 2014

    STERISCIENCE — Marketing Organization

  5. Oct 20, 2015

    Sagent Pharmaceuticals, Inc. — Marketing Organization

  6. Jan 8, 2016

    Astral — Marketing Organization

  7. Oct 7, 2016

    Rising Pharmaceuticals — Marketing Organization

  8. Dec 30, 2016

    Micro Labs Ltd India — Marketing Organization

  9. Nov 1, 2019

    RedHill Biopharma — NDA Secondary Org

2020s

  1. Oct 25, 2024

    Iterum Therapeutics — NDA Secondary Org

Indications

Studied for

Mechanism of action

Combination products

  • probampacin

    with probenecid

    Also known as polycillin-prb, principen w/ probeneci

  • unasyn

    with sulbactam

    Also known as ampicillin and sulbactam

Approval history

  • approvedFeb 6, 1947

Chemistry & pharmacology

Loading structure…

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-].[Na+]
Mol. weight
356.38 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Parenteral
Availability
Prescription Only

Oral

No

Parenteral

Yes

Topical

No

Sources

Also known as

  • (2s,5r,6r)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2s,5r,6r)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2s,5r,6r)-6-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2s,5r,6r)-6-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2s,6r)-6-{[(2r)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2s,6r)-6-{[(2r)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 4-(di-n-propylsulfamoyl)benzoesaeure
  • 4-(di-n-propylsulfamoyl)benzoesaeure
  • 4-((dipropylamino)sulfonyl)benzoic acid
  • 4-((dipropylamino)sulfonyl)benzoic acid
  • 4-(n,n-dipropylsulfamoyl)benzoesaeure
  • 4-(n,n-dipropylsulfamoyl)benzoesaeure
  • 6-(2-phenylacetamido)penicillanic acid
  • 6-(2-phenylacetamido)penicillanic acid
  • 6-(d-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • 6-(d-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • 6-(p-hydroxy-α-aminophenylacetamido)penicillanic acid
  • 6-(p-hydroxy-α-aminophenylacetamido)penicillanic acid
  • abpc
  • abpc
  • alpha-aminobenzylpenicillin
  • alpha-aminobenzylpenicillin
  • amcill
  • amcill
  • amfipen
  • amfipen
  • aminobenzylpenicillin
  • aminobenzylpenicillin
  • aminobenzylpenicillin
  • amp equine
  • ampicilina
  • ampicilina
  • ampicillin
  • ampicillin
  • ampicillin
  • ampicillin
  • ampicillin
  • ampicillin
  • ampicillin
  • ampicillin
  • ampicillin acid
  • ampicillin acid
  • ampicillin/ampicillin trihydrate
  • ampicillin/ampicillin trihydrate
  • ampicillin/ampicillin trihydrate
  • ampicillin anhydrous
  • ampicillin anhydrous
  • ampicillin (anhydrous)
  • ampicillin (anhydrous)
  • ampicillin, anhydrous
  • ampicillin, anhydrous
  • ampicilline
  • ampicilline
  • ampicillin hydrate
  • ampicillin hydrate
  • ampicillin hydrate
  • ampicillin hydrate
  • ampicillin hydrate
  • ampicillin sodium
  • ampicillin sodium
  • ampicillin sodium
  • ampicillin sodium
  • ampicillin trihydrate
  • ampicillinum
  • ampicillinum
  • ampilar
  • anhydrous ampicillin
  • anhydrous ampicillin
  • ap
  • ap
  • ax
  • ax
  • ay-6108
  • ay-6108
  • bencilpenicilina
  • bencilpenicilina
  • benecid
  • benemid
  • benemid
  • benemid
  • bensylpenicillin
  • bensylpenicillin
  • benuryl
  • benuryl
  • benzathine benzylpenicillin
  • benzathine benzylpenicillin
  • benzathine benzylpenicillin
  • benzathine benzylpenicillin
  • benzathine benzylpenicillin
  • benzathine benzylpenicillin
  • benzathine penicillin
  • benzathine penicillin
  • benzathine penicillin
  • benzathine penicillin
  • benzathine penicillin g
  • benzathine penicillin g
  • benzathine phenoxymethylpenicillin
  • benzathine phenoxymethylpenicillin
  • benzathine phenoxymethylpenicillin
  • benzethacil
  • benzyl benicillin
  • benzyl benicillin
  • benzylpenicillin
  • benzylpenicillin
  • benzylpenicillin
  • benzylpenicillin
  • benzylpenicillin
  • benzylpenicillin
  • benzylpenicillin
  • benzyl penicillin
  • benzyl penicillin
  • benzylpenicillin benzathine
  • benzylpenicillin benzathine
  • benzylpénicilline
  • benzylpénicilline
  • benzylpenicillin g
  • benzylpenicillinic acid
  • benzylpenicillinic acid
  • benzylpenicillinic acid
  • benzylpenicillin potassium
  • benzylpenicillin potassium
  • benzylpenicillin potassium
  • benzylpenicillin procaine
  • benzylpenicillin procaine
  • benzylpenicillinum
  • benzylpenicillinum
  • bicilin
  • bicillin
  • bicillin
  • bicillin
  • bicillin l-a
  • bicillin l-a
  • bicillin l-a tubex
  • britcin
  • brl-1341
  • brl-1341
  • cilicaine syringe
  • cilloral
  • cilloral
  • crystapen g
  • crysticillin
  • crysticillin
  • d-(−)-6-(α-aminophenylacetamido)penicillanic acid
  • d-(−)-6-(α-aminophenylacetamido)penicillanic acid
  • d-(−)-ampicillin
  • d-(−)-ampicillin
  • depocillin
  • depocillin
  • duracillin
  • duracillin
  • duracillin a.s.
  • duracillin a.s.
  • e705
  • e705
  • e707
  • e707
  • e708
  • e708
  • extencilline
  • extencilline
  • free penicillin g
  • free penicillin ii
  • free penicillin ii
  • liquapen
  • liquapen
  • omnipen
  • omnipen
  • omnipen-n
  • omnipen-n
  • p-50
  • p-50
  • pcg
  • pcg
  • p-(dipropylsulfamoyl)benzoic acid
  • p-(dipropylsulfamoyl)benzoic acid
  • penadur 6-3-3
  • penbritin
  • penbritin
  • penbritin
  • penbritin-s
  • penbritin-s
  • penicillin
  • penicillin
  • penicillin
  • penicillin
  • penicillin-2
  • penicillin-2
  • penicillin g
  • penicillin g
  • penicillin g
  • penicillin g
  • penicillin g
  • penicillin g
  • penicillin g
  • penicillin g benzathine
  • penicillin g benzathine
  • penicillin g benzathine
  • penicillin g benzathine
  • penicillin g benzathine
  • penicillin-g-benzathine
  • penicillin-g-benzathine
  • penicillin g potassium
  • penicillin g potassium
  • penicillin g potassium
  • penicillin g potassium
  • penicillin g procaine
  • penicillin g procaine
  • penicillin g procaine
  • penicillin g procaine
  • penicillin g procaine
  • penicillin g procaine
  • penicillin g procaine
  • penicillin potassium g, crystalline
  • penicillin potassium g, crystalline
  • penicillin v benzathine
  • penicillin v benzathine
  • penicllin
  • penidural
  • penidural
  • penidural la
  • pentids
  • pentids
  • pentids '200'
  • pentids '200'
  • pentids '250'
  • pentids '250'
  • pentids '400'
  • pentids '400'
  • pentids '800'
  • pentids '800'
  • permapen
  • permapen
  • pfizerpen
  • pfizerpen
  • pfizerpen-a
  • pfizerpen-a
  • pfizerpen-as
  • pfizerpen g
  • pfizerpen g
  • pg
  • pg
  • p-hydroxyampicillin
  • p-hydroxyampicillin
  • polycillin
  • polycillin
  • polycillin-n
  • polycillin-n
  • polycillin-prb
  • polycillin-prb
  • principen
  • principen
  • principen-n
  • probalan
  • probalan
  • probampacin
  • probampacin
  • probampicin
  • probecid
  • probecid
  • probecid
  • probenacid
  • probenacid
  • probenecid
  • probenecid
  • probenecid
  • probenecid
  • probenecid
  • probenecid
  • probenecid
  • probenecid
  • probenecid
  • probenecid
  • probenecid
  • probenecida
  • probenecida
  • probenecid acid
  • probenecid acid
  • probenecid acid
  • probenecide
  • probenecide
  • probenecidum
  • probenecidum
  • probenicid
  • probenicid
  • procaine benzylpenicillin
  • procaine benzylpenicillin
  • procaine benzylpenicillin
  • procaine benzylpenicillin
  • procaine benzylpenicillin
  • procaine benzylpenicillin
  • procaine penicillin
  • procaine penicillin
  • procaine penicillin
  • procaine penicillin g
  • procaine penicillin g
  • retarpen
  • scotcil
  • scotcil
  • sultamicillin
  • sultamicillin
  • totacillin
  • totacillin
  • totacillin-n
  • totacillin-n
  • vidopen
  • vidopen
  • wycillin
  • wycillin
  • α-amino-p-hydroxybenzylpenicillin
  • α-amino-p-hydroxybenzylpenicillin

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06025344Phase 1Dec 31, 2023TrippBio, Inc.
NCT05365451Early Phase 1 (Phase 1)Apr 11, 2022National Institutes of Health (NIH), Washington State University
NCT04506801N/ASep 25, 2018University of Zagreb
NCT03692819N/AMay 2, 2018Sao Paulo State University
NCT03572777N/AApr 15, 2018University of Split
NCT03490123Phase 4Apr 1, 2018Government of Papua New Guinea, Harvard University, Lihir Medical Centre, University of Barcelona, University of Masarykova, World Health Organization
NCT03431337Phase 4Feb 26, 2018Albany Medical College
NCT03174184Phase 2Sep 1, 2017Johns Hopkins University
NCT03172676Phase 4Jul 1, 2017Assiut University
NCT02381470Phase 2Jul 1, 2017National University of Singapore
NCT03202511Early Phase 1 (Phase 1)Jun 23, 2017Indiana University
NCT03031210Phase 2/Phase 3 (Phase 3)Jun 11, 2017Sainte-Justine Hospital, University of Montreal
NCT03174236Phase 3Jun 5, 2017Coast General Hospital, Mombasa, Kenya, Kenya Medical Research Institute, Mbale Regional Referral Hospital, Swansea University, University of London, University of Nairobi, University of Oxford
NCT03177629Phase 3May 23, 2017Hallym University, Seoul National University
NCT03108690Phase 4May 1, 2017University of Copenhagen
NCT02988089Phase 4Apr 20, 2017Binzhou Medical University, Liaocheng People's Hospital, People's Liberation Army of China, Shandong Provincial Hospital, Shandong University
NCT03050307Phase 3Apr 17, 2017Takeda
NCT03105986Phase 1Apr 10, 2017Johnson and Johnson
NCT03050359Phase 3Apr 4, 2017Takeda
NCT02783404Phase 4Feb 27, 2017Santiago de Compostela University, University of Santiago, University of Santiago de Compostela
Showing 20 of 448 trials
Page 1 / 23

Organizations

Research & Development (465)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Institute of Allergy and Infectious Diseases (NIAID)Government161151999
National Taiwan UniversityAcademic/Hospital131131996
GlaxoSmithKlineFor profit12641998
Kaohsiung Medical UniversityAcademic/Hospital11232007
PfizerFor profit101032002
Taichung Veterans General HospitalAcademic/Hospital10932007
World Health OrganizationGovernment10051998
Jiao Tong UniversityAcademic/Hospital9922011
BayerFor profit8722001
Johnson and JohnsonFor profit8722001
Seoul National UniversityAcademic/Hospital8832003
University of ParisAcademic/Hospital8632003
People's Liberation Army of ChinaGovernment7422010
Aga Khan UniversityAcademic/Hospital6632003
Government of TaiwanGovernment6231996
Harvard UniversityAcademic/Hospital6422011
University of PittsburghAcademic/Hospital6632006
Baylor UniversityAcademic/Hospital5132006
Duke UniversityAcademic/Hospital5131983
RanbaxyFor profit5512002
465 organizations
Page 1 / 24

Marketing (89)

OrganizationOrg typeRelationshipDate
ACP NimbleFor profitMKTGOct 10, 1973
ACS DobfarFor profitMKTGDec 22, 2009
ACS DobfarFor profitSYNApr 3, 2013
American AntibioticsFor profitMKTGJan 21, 1974
American CyanamidFor profitMKTGSep 6, 1979
American Home ProductsFor profitNDA2Nov 22, 1951
American Home ProductsFor profitMKTGDec 17, 1965
Ani PharmaceuticalsFor profitMKTGJun 12, 1978
Ani PharmaceuticalsFor profitSYNJun 12, 1978
AntibioticeFor profitMKTGDec 28, 2009
ApotexFor profitMKTGOct 20, 2008
ApotheconFor profitMKTGMar 3, 1971
ApotheconFor profitNDA2
AstralFor profitMKTGJan 8, 2016
AtralFor profitMKTGAug 7, 1985
Aurobindo PharmaFor profitMKTGNov 9, 2005
Aurobindo PharmaFor profitSYNAug 17, 2010
Aurobindo PharmaFor profitSYNJan 17, 2007
Aurobindo PharmaFor profitSYNJan 13, 1976
BaxaltaFor profitNDA2Jun 25, 1990
BaxterFor profitNDA2Jun 25, 1990
BeechamFor profitMKTGMar 11, 1976
Belcher PharmaceuticalsFor profitMKTGJan 21, 1974
Bristol-MyersFor profitNDA2
Bristol-Myers SquibbFor profitMKTGMar 3, 1971
Casper Pharma LLCFor profitNDA2Dec 16, 1952
Chartwell PharmaceuticalsFor profitMKTGNov 9, 1971
Consolidated MidlandFor profitMKTG
CosetteFor profitMKTGOct 10, 1973
Cumberland PharmaceuticalsFor profitMKTGFeb 8, 2011
DAVA PharmaceuticalsFor profitMKTGFeb 25, 1988
Eli LillyFor profitMKTG
Endo PharmaceuticalsFor profitMKTGFeb 10, 1989
Eugia PharmaFor profitMKTGAug 17, 2010
G & W Laboratories Inc.For profitMKTGOct 10, 1973
GlaxoSmithKlineFor profitMKTGMay 7, 1970
Hanford PharmaceuticalsFor profitMKTGApr 15, 1993
Heritage PharmaFor profitMKTGNov 9, 1971
HikmaFor profitMKTGMar 29, 2006
HikmaFor profitSYNJan 25, 2005
HospiraFor profitMKTGDec 21, 2011
HospiraFor profitSYNSep 4, 2015
Hq Speciality PharmaFor profitMKTGApr 15, 1993
Impax LaboratoriesFor profitMKTG
International MedicationFor profitMKTG
Istituto Bio Ita SpaFor profitMKTGMay 12, 1987
Iterum TherapeuticsFor profitNDA2Oct 25, 2024
King PharmaceuticalsFor profitNDA2Apr 26, 1948
King PharmaceuticalsFor profitMKTGApr 26, 1948
Lannett Company, Inc.For profitMKTGJul 29, 1976
LederleFor profitMKTGSep 6, 1979
MedimetriksFor profitMKTGJun 29, 2007
MerckFor profitNDAApr 26, 1951
Micro Labs Ltd IndiaFor profitMKTGDec 30, 2016
Mustafa Nevzat PharmaceuticalsFor profitMKTGJun 29, 2007
MylanFor profitMKTGJan 13, 1976
MylanFor profitSYNApr 7, 2014
NeopharmaFor profitNDA2Aug 2, 1979
NovartisFor profitMKTGAug 30, 2002
Novast LabsFor profitMKTGMay 13, 2008
Parke-DavisFor profitMKTG
PfizerFor profitMKTGFeb 6, 1947
PfizerFor profitNDA2Dec 31, 1986
Pharmaceutical AssociatesFor profitMKTGJun 29, 2007
Pragma TherapeuticsFor profitNDA2Jan 23, 2008
Puracap PharmaceuticalFor profitMKTGMay 4, 1976
RanbaxyFor profitMKTGAug 11, 2003
RedHill BiopharmaFor profitSYNNov 1, 2019
RedHill BiopharmaFor profitNDA2Nov 1, 2019
Rising PharmaceuticalsFor profitMKTGOct 7, 2016
Rising PharmaceuticalsFor profitSYNOct 7, 2016
STERISCIENCEFor profitMKTGApr 7, 2014
STERISCIENCEFor profitSYNApr 7, 2014
Sagent Pharmaceuticals, Inc.For profitSYNOct 20, 2015
Sagent Pharmaceuticals, Inc.For profitMKTGOct 20, 2015
SandozFor profitMKTGMar 3, 1971
SandozFor profitSYNNov 21, 2002
Strides Pharma ScienceFor profitMKTGFeb 25, 1988
Sun PharmaceuticalsFor profitMKTGApr 8, 1999
TakedaFor profitMKTGDec 2, 1997
TevaFor profitSYNMay 9, 1984
TevaFor profitMKTGMay 27, 1964
TevaFor profitSYNOct 29, 2002
TevaFor profitSYNMar 2, 1977
VitarineFor profitMKTG
Watson PharmaceuticalsFor profitMKTGApr 7, 1975
Watson PharmaceuticalsFor profitSYNSep 13, 1988
West-Ward PharmaceuticalFor profitMKTGJun 24, 1986
WockhardtFor profitMKTGJun 18, 2007