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    Procaine Penicillin G

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    MARKET PLACE

    PharmaCompass
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    2D Structure
    Also known as: 54-35-3, Duphapen, Hostacillin, Hydracillin, Procaine benzylpenicillin, 1lw5k9cir1
    Molecular Formula
    C29H38N4O6S
    Molecular Weight
    570.7  g/mol
    InChI Key
    WHRVRSCEWKLAHX-LQDWTQKMSA-N
    FDA UNII
    1LW5K9CIR1
    Procaine benzylpenicillin (INN), also known as procaine G penicillin, is an injectable antiobiotic. It is a poorly soluble salt form of penicillin which is a combination of naturally occuring benzylpenicillin (penicillin G) and the local anaesthetic agent procaine in equimolar amounts. Procaine benzylpenicillin is administered by deep intramuscular injection. It is slowly absorbed and hydrolyzed to benzylpenicillin. This drug is used where prolonged exposure to benzylpenicillin at a low concentration is required. This combination is aimed at reducing the pain and discomfort associated with a large intramuscular injection of penicillin. It is widely used in veterinary settings. Benzylpenicillin is active against a wide range of organisms and is the drug of first choice for many infections.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-(diethylamino)ethyl 4-aminobenzoate;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C16H18N2O4S.C13H20N2O2/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);5-8H,3-4,9-10,14H2,1-2H3/t11-,12+,14-;/m1./s1
    2.1.3 InChI Key
    WHRVRSCEWKLAHX-LQDWTQKMSA-N
    2.1.4 Canonical SMILES
    CCN(CC)CCOC(=O)C1=CC=C(C=C1)N.CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
    2.1.5 Isomeric SMILES
    CCN(CC)CCOC(=O)C1=CC=C(C=C1)N.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    1LW5K9CIR1
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 54-35-3

    2. Duphapen

    3. Hostacillin

    4. Hydracillin

    5. Procaine Benzylpenicillin

    6. 1lw5k9cir1

    7. Retardillin

    8. Depocillin

    9. Nopcaine

    10. Vetspen

    11. Vitablend

    12. Jenacillin O

    13. Micro-pen

    14. Penicillin Procaine

    15. 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    16. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2s,5r,6r)-, Compd. With2-(diethylamino)ethyl 4-aminobenzoate (1:1)other Ca Index Names:benzoic Acid, 4-amino-, 2-(diethylamino)ethyl Ester,mono[(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2

    17. Penzal N 300

    18. Procain-penicillin

    19. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((2-phenylacetyl)amino)- (2s,5r,6r)-, Compd. With 2-(diethylamino)ethyl 4-aminobenzoate (1:1)

    20. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)- (2s,5r,6r)-, Compd. With 2-(diethylamino)ethyl 4-aminobenzoate (1:1)

    21. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2s,5r,6r)-, Compd. With 2-(diethylamino)ethyl 4-aminobenzoate (1:1)

    22. Benzylpenicillin Novocaine Salt

    23. Benzilpenillina Procainica [dcit]

    24. Benzilpenillina Procainica

    25. Einecs 200-205-7

    26. Unii-1lw5k9cir1

    27. Procainebenzylpenicillin

    28. Penicillin G. Procaine

    29. Chembl1628385

    30. Dtxsid30883227

    31. Anhydrous Procaine Penicillin

    32. Mfcd00079285

    33. S4979

    34. Akos015896161

    35. Penicillin G Procaine Anhydrous

    36. Penicillin G Procaine Salt Monohydrate

    37. Db09320

    38. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-, Compd. With 2-(diethylamino)ethyl P-aminobenzoate (1:1)

    39. As-15252

    40. E707

    41. 130p649

    42. A830119

    43. Q3435660

    44. 2-(diethylamino)ethyl 4-azanylbenzoate; (2s,5r,6r)-3,3-dimethyl-7-oxidanylidene-6-(2-phenylethanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    45. 4-aminobenzoic Acid 2-(diethylamino)ethyl Ester; (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(1-oxo-2-phenylethyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 570.7 g/mol
    Molecular Formula C29H38N4O6S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count11
    Exact Mass570.25120612 g/mol
    Monoisotopic Mass570.25120612 g/mol
    Topological Polar Surface Area168 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity752
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of a number of bacterial infections such as syphilis, anthrax, mouth infections, pneumonia and diphtheria.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    It is an antibiotic against penicillin-susceptible microorganisms with bactericidal effect. Like all penicillins, procaine benzylpenicillin interferes with the synthesis of the bacterial cell wall peptidoglycan. It acts through the inhibition of biosynthesis of cell-wall peptidoglycan, rendering the cell wall osmotically unstable. It is part of the penicillin and beta lactam family of antibacterial drugs.

    5.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01C - Beta-lactam antibacterials, penicillins

    J01CE - Beta-lactamase sensitive penicillins

    J01CE09 - Procaine benzylpenicillin

    5.3 Absorption, Distribution and Excretion

    Absorption

    After intramuscular injection, it dissolves slowly at the site of injection, giving a plateau type of blood level at about 4 hours which falls slowly over a period of the next 15 to 20 hours.

    Route of Elimination

    The drug is rapidly and predominantly cleared via renal elimination, with 90% being through tubular secretion. Approximately 60 -90 % of a dose of parenteral penicillin G is excreted in the urine within 24 to 36 hours.

    Volume of Distribution

    The drug is distributed throughout the body tissues in widely varying amounts and spinal fluid to a lesser degree. Highest levels are found in the kidneys with lesser amounts in the liver, skin, and intestines. It displays low solubility thus results in blood serum levels much lower but more prolonged than other parenteral penicillins.

    5.4 Metabolism/Metabolites

    Procaine is rapidly hydrolyzed by plasma esterases to nontoxic metabolites.

    5.5 Biological Half-Life

    Intramuscular injection of benzylpenicillin has a plasma half-life of 30 minutes.

    5.6 Mechanism of Action

    Procaine benzylpenicillin is hydrolyzed into penicillin G once it is released from the injection site. Penicillin G attaches to the penicillin-binding proteins on bacterial cell wall and inhibit the transpeptidation enzyme that crosslinks the peptide chains attached to the backbone of the peptidoglycan. The final bactericidal event involves the inactivation of an inhibitor of autolytic enzymes in the cell wall, leading to lysis of the bacterium.