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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level.
AcenocoumarolProcaine benzylpenicillin may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Procaine benzylpenicillin which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level.
AcrivastineProcaine benzylpenicillin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Procaine benzylpenicillin which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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Active Moieties
NameKindUNIICASInChI Key
Procainemixture4Z8Y51M43859-46-1MFDFERRIHVXMIY-UHFFFAOYSA-N
BenzylpenicillinmixtureQ42T66VG0C61-33-6JGSARLDLIJGVTE-MBNYWOFBSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ayercillin SuspensionSuspension300000 unit / mLIntramuscularAyerst Laboratories1951-12-311999-04-12Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Penicillin G ProcaineInjection1200000 [iU]/2mLIntramuscularMonarch Pharmaceuticals,Inc.1948-04-262007-09-14US flag
Penicillin G ProcaineInjection, suspension1200000 [iU]/2mLIntramuscularPfizer Laboratories Div Pfizer Inc1948-04-26Not applicableUS flag
Penicillin G ProcaineInjection600000 [iU]/1mLIntramuscularMonarch Pharmaceuticals,Inc.1948-04-262007-09-14US flag
Penicillin G ProcaineInjection, suspension600000 [iU]/1mLIntramuscularPfizer Laboratories Div Pfizer Inc1948-04-26Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BENZAPEN 6.3.3 IM ENJ TOZ ICEREN FLAKON, 1 ADETProcaine benzylpenicillin (300 IU) + Benzathine benzylpenicillin (600 IU) + Benzylpenicillin sodium (300 IU)Injection; PowderIntramuscularTÜM-EKİP İLAÇ A.Ş.2020-08-14Not applicableTurkey flag
Bicillin A-P Injection PwsProcaine benzylpenicillin (300000 unit / 2 mL) + Benzylpenicillin benzathine hydrate (600000 unit / 2 mL) + Benzylpenicillin potassium (300000 unit / 2 mL)Powder, for solutionIntramuscularWyeth Ayerst Canada Inc.1995-12-311996-09-10Canada flag
Bicillin C-R 900/300Procaine benzylpenicillin (300000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (900000 [iU]/2mL)Injection, suspensionIntramuscularPfizer Laboratories Div Pfizer Inc1953-05-18Not applicableUS flag
Bicillin CRProcaine benzylpenicillin (600000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (600000 [iU]/2mL)Injection, suspensionIntramuscularDispensing Solutions, Inc.1953-05-18Not applicableUS flag
Bicillin CRProcaine benzylpenicillin (600000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (600000 [iU]/2mL)Injection, suspensionIntramuscularPfizer Laboratories Div Pfizer Inc1953-05-18Not applicableUS flag
Bicillin CRProcaine benzylpenicillin (600000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (600000 [iU]/2mL)Injection, suspensionIntramuscularPhysicians Total Care, Inc.2008-08-28Not applicableUS flag
Bicillin CRProcaine benzylpenicillin (600000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (600000 [iU]/2mL)Injection, suspensionIntramuscularPfizer Laboratories Div Pfizer Inc1953-05-18Not applicableUS flag
Bicillin CRProcaine benzylpenicillin (600000 [iU]/2mL) + Benzylpenicillin benzathine hydrate (600000 [iU]/2mL)Injection, suspensionIntramuscularA-S Medication Solutions1953-05-18Not applicableUS flag
DEVAPEN 400 I.M. ENJEKSİYONLUK ÇÖZELTİ İÇİN TOZ İÇEREN FLAKON, 1 ADETProcaine benzylpenicillin (300000 IU) + Benzylpenicillin potassium (100000 IU)Injection, solutionIntramuscularDeva Holding A.S.2020-08-14Not applicableTurkey flag
DEVAPEN 800 I.M. ENJEKSİYONLUK ÇÖZELTİ İÇİN TOZ İÇEREN FLAKON, 1 ADETProcaine benzylpenicillin (600000 IU) + Benzylpenicillin potassium (200000 IU)Injection, solutionIntramuscularDeva Holding A.S.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CE09 — Procaine benzylpenicillin
Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. 51. (2016). In Rang & Dale's pharmacology (8th ed., pp. 626-641). Elsevier Churchill Livingstone. [ISBN:978-0-7020-5362-7]
  5. product info [Link]
  6. World Health Organization Model Prescribing Information: Drugs Used in Skin Diseases [Link]
PubChem Compound
5903
PubChem Substance
310265202
ChemSpider
5692
RxNav
7983
ChEBI
52154
ChEMBL
CHEMBL1628385
Wikipedia
Procaine_benzylpenicillin
FDA label
Download (658 KB)
MSDS
Download (44.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SuspensionIntramuscular300000 unit / mL
Injection; powderIntramuscular
Powder, for solutionIntramuscular
Injection, suspensionIntramuscular
Injection, solutionIntramuscular
Injection, powder, for solutionIntramuscular
InjectionIntramuscular
InjectionIntramuscular1200000 [iU]/2mL
InjectionIntramuscular600000 [iU]/1mL
Injection, suspensionIntramuscular1200000 [iU]/2mL
Injection, suspensionIntramuscular600000 [iU]/1mL
Injection, powder, for solution
SuspensionIntramuscular3000000 IU/10mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySlightly solubleFDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.285 mg/mLALOGPS
logP1.92ALOGPS
logP1.08ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity84.53 m3·mol-1ChemAxon
Polarizability33.5 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on November 17, 2015 17:30 / Updated on January 09, 2021 18:40