6-(2-Phenylacetamido)penicillansure

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

Log Kow = 1.83

1.5

Slightly soluble (210 mg/L)

WHITE, CRYSTALLINE POWDER; PH OF 3% AQ SOLN 5.0-7.5; SPECIFIC OPTICAL ROTATION: +285-310 DEG @ 22 °C/D (0.7%); DECOMP 214-217 °C; MODERATELY HYGROSCOPIC; FREELY SOL IN WATER, IN ISOTONIC NACL SOLN, IN DEXTROSE SOLN; MODERATELY SOL IN GLYCEROL & ALCOHOLS /PENICILLIN G POTASSIUM/

PRACTICALLY INSOL IN WATER; SOL IN PEANUT OIL; FREELY SOL IN METHANOL, BENZENE, CHLOROFORM, AMYL ACETATE /METHYL ESTER/

SPARINGLY SOL IN WATER; INSOL IN PETROLEUM ETHER; SOL IN METHANOL, ETHANOL, ETHER, ETHYL ACETATE, BENZENE, CHLOROFORM, ACETONE

2.85e-01 g/L

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins

Access group antibiotics

214-217 °C

214 - 217 °C

Danger

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P233, P260, P261, P271, P272, P273, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P391, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 75 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Oral Dosage Form New Animal Drugs. Specifications and conditions of use provided for turkeys. /Penicillin G potassium in drinking water/

Implantation or Injectable Dosage Form New Animal Drugs. Specifications and conditions of use provided for horses, dogs, and beef cattle. /Penicillin G benzathine and penicillin G procaine sterile suspension/

Implantation or Injectable Dosage Form New Animal Drugs. Specifications and conditions of use provided for dogs, cats, cattle, sheep, swine, and horses. /Penicillin G procaine aqueous suspension/

Implantation or Injectable Dosage Form New Animal Drugs. Specifications and conditions of use provided for horses, dogs, and cats. /Penicillin G procaine in oil/

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

MARKED POTENTIATION OF HYPOPROTHROMBINEMIC EFFECT OF WARFARIN BY LARGE DOSES OF PARENTERAL PENICILLIN G DESCRIBED IN 49-YR-OLD MALE. PENICILLIN G CAUSED WARFARIN PROTEIN BINDING DISPLACEMENT INTERACTION.

Penicillins are generally inactivated in the presence of heat, alkaline or acid pH, oxidizing agents, alcohols, glycols, and metal ions such as copper, mercury, or zinc. In currently available penicillins, cleavage at any point in the penicillin nucleus, including the beta-lactam ring, results in complete loss of antibacterial activity. The major cause of inactivation of penicillins is hydrolysis of the beta-lactam ring. The course of hydrolysis and nature of the degradation products can vary and are generally influenced by pH. /Penicillins/

Penicillin G is potentially physically and/or chemically incompatible with some drugs, including aminoglycosides and tetracyclines, but the compatibility depends on several factors (eg, concn of the drugs, specific diluents used, resulting pH, temp).

Penicillins are generally inactivated in the presence of heat, alkaline or acid pH, oxidizing agents, alcohols, glycols, and metal ions such as copper, mercury, or zinc. In currently available penicillins, cleavage at any point in the penicillin nucleus, including the beta-lactam ring, results in complete loss of antibacterial activity. The major cause of inactivation of penicillins is hydrolysis of the beta-lactam ring. The course of hydrolysis and nature of the degradation products can vary and are generally influenced by pH. /Penicillins/

For more Interactions (Complete) data for PENICILLIN G (18 total), please visit the HSDB record page.

... Milk is contaminated by penicillin through intramammary infusion of the drug in the treatment of bovine mastitis. ... Administration of penicillin by other routes can also result in contamination of milk.

Depletion of aqueous penicillin (100,000 units/quarter) in milk of dairy cattle requires 48 hr, and the same dose in oil requires 72hr. Low production in cows (less than 9 kg milk/day) has a delaying effect upon the excretion or depletion rate of antibiotics in milk.

ANAPHYLAXIS HAS MOST OFTEN FOLLOWED INJECTION...ALTHOUGH IT HAS ALSO BEEN OBSERVED AFTER ORAL INGESTION OF DRUG... CLINICAL PICTURES...SUDDEN, SEVERE HYPOTENSION & RAPID DEATH. ...BRONCHOCONSTRICTION WITH SEVERE ASTHMA, OR ABDOMINAL PAIN, NAUSEA, & VOMITING, OR EXTREME WEAKNESS & FALL IN BLOOD PRESSURE...SKIN ERUPTIONS...

SYMPTOMS FOLLOWING INTRATHECAL ADMIN INCL LISTLESSNESS, HEADACHE, NAUSEA, VOMITING, RESPIRATORY DIFFICULTY, CYANOSIS, FALL IN BLOOD PRESSURE, THREADY PULSE, MUSCULAR TWITCHING, & CONVULSIONS. THESE ARE ALL REDUCED OR ELIMINATED BY LOWERING DOSE. /PENICILLIN/

MOST SERIOUS HYPERSENSITIVITY REACTIONS...ARE ANGIOEDEMA, SERUM SICKNESS, ANAPHYLAXIS, & ARTHUS PHENOMENON. ... ACUTE ANAPHYLACTIC OR ANAPHYLACTOID REACTIONS...CONSTITUTE MOST IMPORTANT IMMEDIATE DANGER CONNECTED WITH THEIR USE. /PENICILLINS/

SKIN RASHES OF ALL TYPES...CONTACT DERMATITIS...ORAL LESIONS...FEVER... EOSINOPHILIA...INTERSTITIAL NEPHRITIS MAY...BE PRODUCED BY PENICILLINS. ... IN PATIENTS WITH UNDERLYING RENAL DISEASE, PENICILLIN MAY PRODUCE NEPHROPATHY WITH ABNORMAL URINE SEDIMENT OR ACUTE GLOMERULONEPHRITIS. /PENICILLINS/

For more Human Toxicity Excerpts (Complete) data for PENICILLIN G (58 total), please visit the HSDB record page.

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

penicillin g

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

PENICILLIN G INJECTED SC IN WISTAR RATS FOR 700 DAYS (DOSE, 2 MG X 92, TWICE WEEKLY, IN ARACHIS OIL) PRODUCED 1/4 LOCAL SARCOMA, 1/4 REMOTE FIBROMA, 1/4 THYROID ALVEOLAR CARCINOMA. /FROM TABLE/

The mutagenic or carcinogenic potentials of penicillin G or penicillin V have not been fully determined. In one study, evidence of carcinogenicity was present following long-term subcutaneous admin of penicillin G in peanut oil to rats.

◉ Summary of Use during Lactation

◈ What is penicillin G?

Oral Dosage Form New Animal Drugs. Specifications and conditions of use provided for turkeys. /Penicillin G potassium in drinking water/

Implantation or Injectable Dosage Form New Animal Drugs. Specifications and conditions of use provided for horses, dogs, and beef cattle. /Penicillin G benzathine and penicillin G procaine sterile suspension/

Implantation or Injectable Dosage Form New Animal Drugs. Specifications and conditions of use provided for dogs, cats, cattle, sheep, swine, and horses. /Penicillin G procaine aqueous suspension/

Implantation or Injectable Dosage Form New Animal Drugs. Specifications and conditions of use provided for horses, dogs, and cats. /Penicillin G procaine in oil/

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

J01CE01

S - Sensory organs

J - Antiinfectives for systemic use

QS - Sensory organs

QJ - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Penicillin G is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Penicillin G has <i>in vitro</i> activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of penicillin G results from the inhibition of cell wall synthesis and is mediated through penicillin G binding to penicillin binding proteins (PBPs). Penicillin G is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, penicillin G inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that penicillin G interferes with an autolysin inhibitor.

The penicillins and their metabolites are potent immunogens because of their ability to combine with proteins and act as haptens for acute antibody-mediated reactions. The most frequent (about 95 percent) or "major" determinant of penicillin allergy is the penicilloyl determinant produced by opening the beta-lactam ring of the penicillin. This allows linkage of the penicillin to protein at the amide group. "Minor" determinants (less frequent) are the other metabolites formed, including native penicillin and penicilloic acids. /Penicillins/

Bactericidal; inhibit bacterial cell wall synthesis. Action is dependent on the ability of penicillins to reach and bind penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Penicillin-binding proteins (which include transpeptidases, carboxypeptidases, and endopeptidases) are enzymes that are involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Penicillins bind to, and inactivate, penicillin-binding proteins, resulting in the weakening of the bacterial cell wall and lysis. /Penicillins/

In adults with normal renal function is reportedly 0.4–0.9 hours

ELIMINATION HALF-LIFE IS ABOUT 30 MIN IN NORMAL ADULTS.

PENICILLIN HALF-LIFE IN HUMAN SERUM INCR FROM ABOUT 25 MIN IN YOUNG ADULTS TO 2 HR IN ELDERLY SUBJECTS & IS ALSO MARKEDLY INCR BY DRUGS WHICH ARE ACTIVELY SECRETED BY KIDNEY TUBULES. /PENICILLIN/

The serum half-life of penicillin G in adults with normal renal function is reportedly 0.4-0.9 hr.

The serum half-life of penicillin G in neonates varies inversely with age and appears to be independent of birthweight. The serum half-life of the drug is reportedly 3.2-3.4 hr in neonates 6 days of age or younger, 1.2-2.2 hr in neonates 7-13 days of age, and 0.9-1.9 hr in neonates 14 days of age or older.

About 16-30% of an intramuscular dose is metabolized to penicilloic acid, an inactive metabolite. Small amounts of 6-aminopenicillanic acid have been recovered in the urine of patients on penicillin G. A small percentage of the drug appears to be hydroxylated into one or more active metabolites, which are also excreted via urine.

Approx 16-30% of an IM dose of penicillin G sodium is metabolized to penicilloic acid which is microbiologically inactive. Small amt of 6-aminopenicillanic acid (6-APA) have also been found in the urine of patients receiving penicillin G. In addition, the drug appears to be hydroxylated to a small extent to one or more microbiologically active metabolites which are also excreted in urine.

Q42T66VG0C

PENICILLIN G

Established Pharmacologic Class [EPC] - Penicillin-class Antibacterial

Chemical Structure [CS] - Penicillins

Penicillin g is a Penicillin-class Antibacterial.

PENICILLIN G

Rapidly absorbed following both intramuscular and subcutaneous injection. Initial blood levels following parenteral administration are high but transient. Oral absorption in fasting, healthy humans is only about 15-30% as it is very susceptible to acid-catalyzed hydrolysis.

Penicillin G is eliminated by the kidneys. Nonrenal clearance includes hepatic metabolism and, to a lesser extent, biliary excretion.

0.53–0.67 L/kg in adults with normal renal function

560ml/min in healthy humans

...WIDELY DISTRIBUTED THROUGHOUT BODY... ITS APPARENT VOL OF DISTRIBUTION IS IN ABOUT 50% OF TOTAL BODY WATER. MORE THAN 90%...IN BLOOD IS IN PLASMA & LESS THAN 10% IS IN ERYTHROCYTES; APPROX 65% IS REVERSIBLY BOUND TO PLASMA ALBUMIN. LOW CONCN OF PROTEIN...LOW DEGREE OF BINDING...DRUG EFFICACY.

SIGNIFICANT AMT APPEAR IN LIVER, BILE, KIDNEY, SEMEN, LYMPH, & INTESTINE. ... PENICILLIN DOES NOT READILY ENTER CSF WHEN MENINGES ARE NORMAL.

MEDICATION

MEDICATION (VET)

Use (kg; approx.) in Germany (2009): >2500

MOLD IS GROWN IN NUTRIENT SOLN... AFTER SEVERAL DAYS OF CULTIVATION MOLD EXCRETES PENICILLIN INTO ITS LIQ CULTURE MEDIUM. THIS LIQ IS THEN FILTERED OFF & PENICILLIN EXTRACTED & PURIFIED BY COUNTERCURRENT EXTRACTION... DIFFERENT VARIETIES...ARE PRODUCED BIOSYNTHETICALLY BY ADDING PROPER PRECURSORS TO NUTRIENT SOLN.

OBTAINED BY EXTRACTION @ ICE TEMP OF ACIDIFIED (PH 2) AQ SOLN OF SODIUM BENZYLPENICILLIN WITH ETHER OR CHLOROFORM. SHOWS CORRECT ANALYTICAL COMPOSITION ONLY IF MOISTURE IS EXCLUDED COMPLETELY DURING ITS ISOLATION FROM ETHER EXTRACT (BY LYOPHILIZING FROM BENZENE).

...DESIGNED FOR SC, IM, IV, OR INTRATHECAL INJECTION. ... TWO OFFICIAL PENICILLIN SALTS FOR INJECTION ARE PENICILLIN G POTASSIUM FOR INJECTION, USP, & PENICILLIN G SODIUM FOR INJECTION, NF. PREPN...ARE CRYSTALLINE POWDERS...IN STERILE DRY FORM IN VIALS OR AMPULS CONTAINING 20,000-20 MILLION UNITS EACH.

STERILE PENICILLIN G PROCAINE SUSPENSION, USP (CRYSTICILLIN, DIURNAL-PENICILLIN, DURACILLIN AS, WYCILLIN SUSPENSION), IS AQ PREPN OF CRYSTALLINE SALT...SOL IN WATER ONLY TO EXTENT OF 0.4%. STERILE PENICILLIN G PROCAINE WITH ALUMINUM STEARATE SUSPENSION, USP, CONTAINS ALUMINUM MONOSTEARATE (2% WT/VOL)...

OFFICIAL ORAL PREPN ARE PENICILLIN G POTASSIUM TABLETS, USP, PENICILLIN G POTASSIUM TABLETS FOR SOLN, USP, & PENICILLIN G BENZATHINE TABLETS, USP. /POTASSIUM, BENZATHINE/

BENZYLPENICILLIN POTASSIUM, CRYSTALLINE PENICILLIN G POTASSIUM, AQUEOUS PENICILLIN G POTASSIUM, PFIZERPEN, SUGRACILLIN, KESSO-PEN, G-RECILLIN, BENZYL PENICILLANIC ACID. /PENICILLIN G POTASSIUM/

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

PHARMACEUTICAL INCOMPATIBILITIES: MUST NOT BE FORMULATED WITH ACIDS, SALTS OF HEAVY METALS, GLYCEROL, NAPHTHALENE OILS, RESORCINOL, ZINC OXIDE, VITAMIN B1, PROCAINE, EPHEDRINE, IODINE & IODIDES, ALC & OXIDIZING AGENTS. /PENICILLIN G SODIUM/

PREPN OF METHYL ESTER: DANISH PATENT 85,976 (1958 TO LEO PHARM).

ONE INTERNATIONAL OR USP PENICILLIN UNIT IS EQUIV TO 0.6 UG OF BENZYLPENICILLIN SODIUM. 1 MG OF BENZYLPENICILLIUM SODIUM IS EQUIV TO 1670 UNITS /PENICILLIN G POTASSIUM/