Penicillin G

Base Information

• Chemical Name: Penicillin G
• CAS No.: 61-33-6
• Molecular Formula: C16H18N2O4S
• Molecular Weight: 334.396
• Hs Code.: 32041900
• European Community (EC) Number: 200-506-3
• UNII: Q42T66VG0C
• DSSTox Substance ID: DTXSID5046934
• Nikkaji Number: J2.342F
• Wikipedia: Benzylpenicillin
• Wikidata: Q258450
• NCI Thesaurus Code: C61883
• RXCUI: 7980
• Metabolomics Workbench ID: 43291
• ChEMBL ID: CHEMBL29
• Mol file: 61-33-6.mol

Synonyms:Benpen;Benzylpenicillin;Benzylpenicillin Potassium;Coliriocilina;Crystapen;Or-pen;Parcillin;Pekamin;Pengesod;Penibiot;Penicilina G Llorente;Penicillin G;Penicillin G Jenapharm;Penicillin G Potassium;Penicillin G Sodium;Penicillin Grünenthal;Penilevel;Peniroger;Pfizerpen;Sodiopen;Sodipen;Sodium Benzylpenicillin;Sodium Penicillin;Unicilina;Ursopen;Van-Pen-G

Chemical Property of Penicillin G

Chemical Property:

• Vapor Pressure: 1.69E-18mmHg at 25°C
• Melting Point: 82-83 °C
• Refractive Index: 1.655
• Boiling Point: 663.3 °C at 760 mmHg
• PKA: 2.45±0.50(Predicted)
• Flash Point: 355 °C
• PSA: 112.01000
• Density: 1.42 g/cm³
• LogP: 1.18960
• Storage Temp.: 2-8°C
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: 2.675g/L(25 oC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 334.09872823
• Heavy Atom Count: 23
• Complexity: 530

Purity/Quality:

Benzylpenicillin for system suitability European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
• Recent ClinicalTrials: Single Dose Intravenous Antibiotics for Complicated Urinary Tract Infections in Children
• Recent EU Clinical Trials: Accelerated treatment of infectious endocarditis
• Description: Penicillin was the first natural antibiotic used to treat bacterial infections and continues to be one of the most important antibiotics.The name comes from the fungus genus Penicillium from which it was isolated. Penicillus is Latin for brush and refers to the brushlike appearance of filamentous Penicillium species.Species of this genus are quite common and appear as the bluish-green mold that appears on aged bread, fruit, and cheese. The term penicillin is a generic term that refers to a number of antibiotic compounds with the same basic structure. Therefore it is more appropriate to speak of penicillins than of penicillin. The general penicillin structure consists of a β-lactam ring and thiazolidine ring fused together with a peptide bonded to a variable R group. Penicillin belongs to a group of compounds called β-lactam antibiotics. This in turn inhibits the formation of peptidoglycan cross-links in bacteria cell walls.
• Uses: Benzylpenicillin is the drug of choice for infections caused by sensitive organisms. This includes streptococci infections (except enterococci), gonococci, and meningococci that do not produce beta-lactam anaerobes. Benzylpenicillin is used for croupous and focal pneumonia, skin infections, soft tissue and mucous membranes, periotonitis, cystisis, syphilis, diphtheria, and other infectious diseases. Synonyms of this drug are megacillin, Penicillin is an antimicrobial agent. Antibacterial.
• Indications: Benzylpenicillin or penicillin G has a narrow antimicrobial spectrum. It is active with respect to Gram-positive bacteria (staphylococcus, streptococcus, and pneumococci), causative agent of diphtheria, and anthrax bacillus. Gram-negative bacteria are resistant to it. Benzylpenicillin is broken down by stomach acid and destroyed by staphylococcus penicillinase.
• Clinical Use: Serious infections caused by streptococci (including Str. pneumoniae) other than meningitis caused by penicillin-resistant pneumococci Serious infections caused by susceptible strains of staphylococci Meningococcal septicemia and meningitis Gonococcal infections caused by susceptible strains Syphilis (including neurosyphilis) and other spirochetal infections Anthrax Actinomycosis Clostridial infections Diphtheria (adjunctive therapy to antitoxin and for prevention of carrier state) Infections with other susceptible organisms, including Listeria monocytogenes, Pasteurella multocida, Erysipelothrix insidiosa and Fusobacterium For years, the most popular penicillin has been penicillin G,or benzylpenicillin. In fact, with the exception of patients allergicto it, penicillin G remains the agent of choice for thetreatment of more different kinds of bacterial infection thanany other antibiotic. It was first made available as the watersolublesalts of potassium, sodium, and calcium. These saltsof penicillin are inactivated by the gastric juice and are noteffective when administered orally unless antacids, such ascalcium carbonate, aluminum hydroxide, and magnesiumtrisilicate; or a strong buffer, such as sodium citrate, isadded. Also, because penicillin is absorbed poorly from the intestinal tract, oral doses must be very large, about fivetimes the amount necessary with parenteral administration.Only after the production of penicillin had increased enoughto make low-priced penicillin available did the oral dosageforms become popular. The water-soluble potassium andsodium salts are used orally and parenterally to achieve highplasma concentrations of penicillin G rapidly. The morewater-soluble potassium salt usually is preferred when largedoses are required. Situations in which hyperkalemia is adanger, however, as in renal failure, require use of thesodium salt; the potassium salt is preferred for patients onsalt-free diets or with congestive heart conditions.
• Drug interactions: Potentially hazardous interactions with other drugs Reduced excretion of methotrexate.

Technology Process of Penicillin G

There total 285 articles about Penicillin G which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

ampicillin (69-53-4) + 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine (41730-71-6) + sodium 2-ethylhexanoic acid → penicillin G (61-33-6)

Guidance literature:

With triethylamine; In methanol; aqueous tetrahydrofurane; water; ethyl acetate;

Reference yield: 94.0%

phosgene (75-44-5) + 5-amino-2-p-ethylanilino-4-hydroxy-pyrimidine + amoxycillin trihydrate → D-α-[3-(2-p-ethylanilino-4-hydroxy-5-pyrimidyl)-ureido]-p-hydroxy-benzyl-penicillin-sodium + penicillin G (61-33-6)

Guidance literature:

With triethylamine;

Reference yield: 88.0%

5-amino-2-ethoxycarbonyl-methylamino-4-hydroxy-pyrimidine + amoxycillin trihydrate → D-α-[3-(2-{ethoxycarbonylmethylamino}-4-hydroxy-5-pyrimidinyl)-ureido]-p-hydroxy-benzylpenicillin sodium + penicillin G (61-33-6)

Guidance literature:

With triethylamine;

upstream raw materials:

6-Aminopenicillanic Acid

phenylacetyl chloride

3,3-dimethyl-D-cysteine

2-Benzyl-4-[1-methoxy-meth-(E)-ylidene]-4H-oxazol-5-one

Downstream raw materials:

3,3-dimethyl-D-cysteine

Sodium salt of 6-{[3-(2,6-dichloro)phenyl-4-cyano-isoxazol-5-yl]acetamido}penicillanic acid

(5R,6S,3S)-benzyl-D-penicilloic acid

benzylpenicilloic acid

Refernces

• 1、 BATCHELOR,DOYLE,NAYLER,ROLINSON. "Synthesis of penicillin: 6-aminopenicillanic acid in penicillin fermentations.". . p. 257 - 258. Retrieved 1959.
• 2、 Constantinides et al.. "-". . . Retrieved 1971.
• 3、 Ilankumaran, Palanichamy,Manoj,Chandrasekaran, Srinivasan. "Prop-2-ynyl as a protective group for carboxylic acids: A mild method for the highly selective deprotection of prop-2-ynyl esters using tetrathiomolybdate". . p. 1957 - 1958. Retrieved 2007/10/03.