Procaine benzylpenicillin
Identification
- Summary
Procaine benzylpenicillin is a local anesthetic and antibiotic combination for intramuscular injection to treat a variety of bacterial infections while reducing pain from a deep intramuscular injection.
- Brand Names
- Bicillin
- Generic Name
- Procaine benzylpenicillin
- DrugBank Accession Number
- DB09320
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
- Weight
- Average: 570.71
Monoisotopic: 570.251206134 - Chemical Formula
- C29H38N4O6S
- Synonyms
- Bencilpenicilina procaína
- Penicillin G procaine
Pharmacology
- Indication
For the treatment of a number of bacterial infections such as syphilis, anthrax, mouth infections, pneumonia and diphtheria.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Anthrax •••••••••••• ••••••••• Prophylaxis of Anthrax •••••••••••• ••••••••• Treatment of Bacterial infections •••••••••••• ••••••••• Prevention of Diphtheria •••••••••••• ••••••••• Treatment of Erysipelas •••••••••••• ••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
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.
- 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 4.
- 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.
- 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.
- Protein binding
Approximately 60% of penicillin G is bound to serum protein.
- Metabolism
Procaine is rapidly hydrolyzed by plasma esterases to nontoxic metabolites.
- 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.
- Half-life
Intramuscular injection of benzylpenicillin has a plasma half-life of 30 minutes 6.
- Clearance
Not Available
- Adverse Effects
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- Toxicity
Procaine benzylpenicillin is associated with the pain at the injection site, blood clotting problems, and seizures. Treatment targeted against syphilis is often associated with Jarisch-Herxheimer reaction. The main unwanted effects are hypersensitivity reactions caused by the degradation products of penicillin, which combine with host protein and become antigenic. Other common adverse effects include skin rashes, fever and delayed serum sickness. Rare but fatal anaphylactic shock may occur. Oral LD50 values in mouse and rat are > 2000 mg/kg. Overdosage can cause convulsions, paralysis and even death. Emesis and gastric lavage may be of value if begun within a few hours of injection. Excessive blood concentrations can be lowered by haemodialysis 6.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level. Acenocoumarol Procaine benzylpenicillin may increase the anticoagulant activities of Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Active Moieties
Name Kind UNII CAS InChI Key Procaine mixture 4Z8Y51M438 59-46-1 MFDFERRIHVXMIY-UHFFFAOYSA-N Benzylpenicillin mixture Q42T66VG0C 61-33-6 JGSARLDLIJGVTE-MBNYWOFBSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ayercillin Suspension Suspension 300000 unit / mL Intramuscular Ayerst Laboratories 1951-12-31 1999-04-12 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Penicillin G Procaine Injection 1200000 [iU]/2mL Intramuscular Monarch Pharmaceuticals,Inc. 1948-04-26 2007-09-14 US Penicillin G Procaine Injection, suspension 1200000 [iU]/2mL Intramuscular Pfizer Laboratories Div Pfizer Inc 1948-04-26 Not applicable US Penicillin G Procaine Injection 600000 [iU]/1mL Intramuscular Monarch Pharmaceuticals,Inc. 1948-04-26 2007-09-14 US Penicillin G Procaine Injection, suspension 600000 [iU]/1mL Intramuscular Pfizer Laboratories Div Pfizer Inc 1948-04-26 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BENZAPEN 6.3.3 IM ENJ TOZ ICEREN FLAKON, 1 ADET Procaine benzylpenicillin (300 IU) + Benzathine benzylpenicillin (600 IU) + Benzylpenicillin sodium (300 IU) Injection; Powder Intramuscular TÜM-EKİP İLAÇ A.Ş. 2001-01-31 Not applicable Turkey Bicillin A-P Injection Pws Procaine benzylpenicillin (300000 unit / 2 mL) + Benzylpenicillin benzathine hydrate (600000 unit / 2 mL) + Benzylpenicillin potassium (300000 unit / 2 mL) Powder, for solution Intramuscular Wyeth Ayerst Canada Inc. 1995-12-31 1996-09-10 Canada Bicillin C-R 900/300 Procaine benzylpenicillin (300000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (900000 [iU]/2mL) Injection, suspension Intramuscular Pfizer Laboratories Div Pfizer Inc 1953-05-18 Not applicable US Bicillin CR Procaine benzylpenicillin (600000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (600000 [iU]/2mL) Injection, suspension Intramuscular Dispensing Solutions, Inc. 1953-05-18 Not applicable US Bicillin CR Procaine benzylpenicillin (600000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (600000 [iU]/2mL) Injection, suspension Intramuscular Pfizer Laboratories Div Pfizer Inc 1953-05-18 Not applicable US
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Acids, Carbocyclic
- Amides
- Aminobenzoates
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Benzene Derivatives
- Benzoates
- Beta-Lactam Antibacterials
- Beta-Lactamase Sensitive Penicillins
- beta-Lactams
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Lactams
- para-Aminobenzoates
- Penicillin G
- Penicillins
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Penicillins / N-acyl-alpha amino acids and derivatives / Phenylacetamides / Thiazolidines / Tertiary carboxylic acid amides / Azetidines / Secondary carboxylic acid amides / Azacyclic compounds / Thiohemiaminal derivatives / Carboxylic acids show 7 more
- Substituents
- Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Beta-lactam / Carbonyl group / Carboxamide group / Carboxylic acid show 21 more
- Molecular Framework
- Not Available
- External Descriptors
- procaine(1+) salt (CHEBI:52154)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1LW5K9CIR1
- CAS number
- 54-35-3
- InChI Key
- WHRVRSCEWKLAHX-LQDWTQKMSA-N
- 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
- IUPAC Name
- (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 2-(diethylamino)ethyl 4-aminobenzoate
- SMILES
- CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O
References
- General References
- Olsen L, Ingvast-Larsson C, Brostrom H, Larsson P, Tjalve H: Clinical signs and etiology of adverse reactions to procaine benzylpenicillin and sodium/potassium benzylpenicillin in horses. J Vet Pharmacol Ther. 2007 Jun;30(3):201-7. [Article]
- Uboh CE, Soma LR, Luo Y, McNamara E, Fennell MA, May L, Teleis DC, Rudy JA, Watson AO: Pharmacokinetics of penicillin G procaine versus penicillin G potassium and procaine hydrochloride in horses. Am J Vet Res. 2000 Jul;61(7):811-5. [Article]
- Papich MG, Korsrud GO, Boison JO, Yates WD, MacNeil JD, Janzen ED, McKinnon JJ, Landry DA: Disposition of penicillin G after administration of benzathine penicillin G, or a combination of benzathine penicillin G and procaine penicillin G in cattle. Am J Vet Res. 1994 Jun;55(6):825-30. [Article]
- 51. (2016). In Rang & Dale's pharmacology (8th ed., pp. 626-641). Elsevier Churchill Livingstone. [ISBN:978-0-7020-5362-7]
- product info [Link]
- World Health Organization Model Prescribing Information: Drugs Used in Skin Diseases [Link]
- External Links
- PubChem Compound
- 5903
- PubChem Substance
- 310265202
- ChemSpider
- 5692
- 7983
- ChEBI
- 52154
- ChEMBL
- CHEMBL1628385
- Wikipedia
- Procaine_benzylpenicillin
- FDA label
- Download (658 KB)
- MSDS
- Download (44.8 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suspension Intramuscular 300000 unit / mL Injection; powder Intramuscular Powder, for solution Intramuscular Injection, suspension Intramuscular Injection, solution Intramuscular Injection, powder, for solution Intramuscular Injection Intramuscular 1200000 [iU]/2mL Injection Intramuscular 600000 [iU]/1mL Injection, suspension Intramuscular 1200000 [iU]/2mL Injection, suspension Intramuscular 600000 [iU]/1mL Injection, powder, for solution Injection Intramuscular Suspension Intramuscular 3000000 IU/10mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Slightly soluble FDA Label - Predicted Properties
Property Value Source Water Solubility 0.285 mg/mL ALOGPS logP 1.92 ALOGPS logP 1.08 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 3.53 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 86.71 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 84.53 m3·mol-1 Chemaxon Polarizability 33.5 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 223.24452 predictedDeepCCS 1.0 (2019) [M+H]+ 225.06941 predictedDeepCCS 1.0 (2019) [M+Na]+ 230.67523 predictedDeepCCS 1.0 (2019)
Drug created at November 17, 2015 17:30 / Updated at January 09, 2021 18:40