Grundinformationen
- Standard-SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O.CCN(CC)CCOC(=O)c1ccc(N)cc1- InChIKey
WHRVRSCEWKLAHX-LQDWTQKMSA-N- Summenformel
- C29H38N4O6S
- Durchschnittliche Molmasse
- 570,7 g/mol
- Monoisotopische Masse
- 570,25120594
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Penicillin G Procaine
- IUPAC
- 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
- Lokaler Name
- Procain-Penicillin
- Englischer Name
- Procaine penicillin G
- Summenformel
- C16H18N2O4S.C13H20N2O2
- Molmasse
- 570.7
Namen und Synonyme
Procaine penicillin GProcaine BenzylpenicillinDepocillinDuphapenHostacillinHydracillinNopcaineRetardillinVitablendVetspenJenacillin OMicro-Pen
Weitere Namen anzeigen
PENICILLIN G PROCAINEbenzylpenicillin procaineBenzyl Pencillin Procainerocaine penicillin
Penicillin procainePenzal N 300Procaine benzylpenicillinateBenzylpenicillin novocaine saltPenicillin procaine (anhydrous)Benzilpenillina procainicaUNII-1LW5K9CIR1EINECS 200-205-7
Datenbank-Bezeichner
- CAS
54-35-3- PubChem CID
- 5903
- DTXSID
DTXSID30883227- ChEMBL
CHEMBL1200936、CHEMBL1628385- UNII
- 1LW5K9CIR1
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 168 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 40
- Formalladung
- 0
- Komplexität
- 752
Experimentelle und physikochemische Eigenschaften
SolubilitySlightly soluble
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Access group antibiotics
Animal Drugs
Active Ingredients (Penicillin G Procaine) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Physikochemische Eigenschaften
- Schmelzpunkt
- 129 · 129-130 °C
- Dichte
- 1.1335 · 1.1335 (rough estimate)
- Brechungsindex
- 1.6 · 1.6000 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- 100 mg/mL · DMSO: 100 mg/mL (175.22 mM);Ethanol: 20 mg/mL (35.04 mM)
- Wasserlöslichkeit
- 10 mg/mL · Water: 10 mg/mL (17.52 mM)
- InChIKey
- WHRVRSCEWKLAHX-RLWRCNEPNA-N
- SMILES
- N12[C@@H](C(=O)O)C(C)(C)S[C@@]1([C@H](NC(CC1C=CC=CC=1)=O)C2=O)[H].C1(=CC=C(N)C=C1)C(=O)OCCN(CC)CC |&1:1,9,10,r|
- CAS Datenbank
- 54 · 54-35-3
- EPA chemische Informationen
- 4 · 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) (54-35-3)
Sicherheit und Regulatorisches
Gefahrenhinweise
Other Safety InformationIMAP assessments - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- [2S-(2.alpha.,5.alpha.,6.beta.)]-, compound with 2-(diethylamino)ethyl 4-aminobenzoate (1:1): Environment tier I assessment
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- tsca
- TSCA listed
- Toxizität
- LD50 orl-rat: >2 g/kg ABANAE 3,534,55/56
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01CE09
Protein BindingApproximately 60% of penicillin G is bound to serum protein.
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.
Biological Half-LifeIntramuscular injection of benzylpenicillin has a plasma half-life of 30 minutes.
Metabolism/MetabolitesProcaine is rapidly hydrolyzed by plasma esterases to nontoxic metabolites.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
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.
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.
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.
Verwendung und Herstellung
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
General Manufacturing Information4-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): ACTIVE
Anwendungen
VerwendenAntibacterial.
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