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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 2349作成日:2026年11月4日

Penicillins

Beapen · Cilacil · Asillin · Anapenil · Calciopen · Apo-pen-vk · Cilicaine vk · Mykoin BF 510

https://huagongshe.com/ja/chemical/2349

Penicillins の分子構造式

識別子と物理属性

CAS No.1406-05-9
分子式C16H18N2O4S
平均分子量334.4 g/mol
単同位体質量334.09872823 g/mol
SMILESCC1(C)SC2C(NC(=O)Cc3ccccc3)C(=O)N2C1C(=O)O
InChIKeyJGSARLDLIJGVTE-UHFFFAOYSA-N
PubChem CID2349
ChEMBLCHEMBL300052
EC No.215-794-6
DTXSIDDTXSID20274362

化学・物理的性質

XLogP1.8
極性表面積112
水素結合供与体数2
水素結合受容体数5
回転可能結合数4
重原子数23
形式電荷0
複雑度530
CAS データベース1406-05-9

安全性と法規制

有害性の概要Occupational asthma reported[Malo] Allergic contact dermatitis, both immediate and delayed, have been reported in pharmaceutical, healthcare, and animal-care workers. Other sensitizing antibiotics in the penicillin family include benzyl penicillin (54836-26-8), ampicillin (69-53-4), cloxicillin (61-72-3), mezlocilin (51481-65-3), and pivampicillin (33817-20-8). [Kanerva, p. 1189-90]
有害作用Skin Sensitizer - An agent that can induce an allergic reaction in the skin.Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.Penicillin V and G can have adverse effects, including nausea, vomiting, diarrhea, rash, abdominal pain, and urticaria. In addition, Penicillin G can have other adverse reactions, including muscle spasms, fever, chills, muscle pain, headache, tachycardia, flushing, tachypnea, and hypotension.Hypersensitivity reactions: The commonly encountered adverse drug reaction with penicillin is hypersensitivity of immediate onset or delayed onset.* Immediate onset: This type of reaction occurs within 20 minutes after administering the drug and is characterized by urticaria, pruritis, edema, laryngospasm, bronchospasm, hypotension, vascular collapse, and death.* Delayed onset: This type of reaction occurs within 1 to 2 weeks of treatment, is rare, and is characterized by fever, malaise, urticaria, myalgia, arthralgia, abdominal pain, and skin rashes.Gastrointestinal system: Gastrointestinal symptoms, including nausea, vomiting, and stomatitis, were the most commonly reported in over 1% of patients and widely observed with oral administration. Pseudomembranous colitis is also observed during or after the treatment.Hematologic reactions: If the dose exceeds 10 million units per day and a patient has received a higher dose previously, then those patients can precipitate Coombs-positive hemolytic anemia and neutropenia, resolved when therapy is stopped.Metabolic reactions: The salt form of penicillin G may cause electrolyte imbalances, such as hyperkalemia, when given IV in a large dose.Nervous system: Neurological manifestations include hyperreflexia, myoclonic cramps, seizures, and coma after IV doses and are more likely in patients with impaired renal function.Urogenital system: Urological manifestations with large IV doses include renal tubular damage. Penicillins can also cause acute interstitial nephritis, a disease characterized by inflammation of the tubules and interstitium of the kidneys. Acute interstitial nephritis can also present with hematuria, fever, and rash. The recommendation is to withdraw the drug as the disease could lead to renal failure.Other reactions: Jarisch- Herxheimer reaction is precipitated when penicillin is administered in patients with syphilis due to rapid lysis of spirochetes and release of endotoxins. Procaine reactions (1 in 500 patients) are due to immediate toxic reactions to procaine due to large single-dose administration. Procaine may cause a pseudoanaphylactic reaction. Procaine can also cause methemoglobinemia.Drug-Drug Interactions* Concurrent sulfonamides, erythromycin, and chloramphenicol (bacteriostatic drugs) should be avoided due to antagonistic effects.
毒性の概要Signs and Symptoms of OverdosePenicillin has a small risk of toxicity. Clinicians can administer penicillin at relatively high doses compared to other drugs without harming patients. Estimates are that it would take 5 g/kg body weight IV to cause convulsions in a patient. However, penicillin can cause local toxicity due to high-dose injections at sensitive sites such as the eye's anterior chamber or the subarachnoid space. Reports show that pure preparations of penicillin cause no harm to the lungs and veins. Other reports indicate that topical penicillin can prevent coagulation in dental cavities.Management of OverdoseNeurotoxicity of penicillin requires discontinuation of the offending penicillin. Penicillins are hypothesized to have an inhibitory effect on GABA transmissionconsequently, IV benzodiazepines and electroencephalogram (EEG) monitoring may be necessary in refractory cases.
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)PENICILLINDILI PositiveDOI:10.1016/j.drudis.2019.09.022
毒性TDLo ims-man: 12,385 mg/kg/16D-I:SKN MJAUAJ 1,305,47
* Tubular secretion of penicillin G is blocked by probenecid- higher and longer plasma concentrations are achieved. Probenecid also decreases the volume of distribution of penicillin.
* Drugs such as aspirin, phenylbutazone, sulfonamides, indomethacin, thiazide, furosemide, and ethacrynic acid increase the half-life of penicillin by competing with tubular secretion.