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Penicillins

HCID 2349
노트반응
기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
1406-05-9
표준 SMILES
CC1(C)SC2C(NC(=O)Cc3ccccc3)C(=O)N2C1C(=O)O
InChIKey
JGSARLDLIJGVTE-UHFFFAOYSA-N
분자식
C16H18N2O4S
평균 분자량
334.4 g/mol
단동위원소 질량
334.09872823

이름 및 식별자

우선 이름
Penicillins
IUPAC
3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
영어명
Penicillin
분자식
C16H20N2O3S
분자량
320.411

이름 및 동의어

CHEBI:17334penicillinsPenicillin AntibioticsAntibiotics, PenicillinRefChem:126139DTXSID501017130215-794-61406-05-9PenicillinCillin7005-30-3Benzopenicillin
이름 더 보기
BeapenCilacilAsillinAnapenilCalciopenApo-pen-vkCilicaine vkMykoin BF 510Abbocillin vkLisa Caldarone
(5S)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidBenzylpenicillin GFree benzylpenicillin(Phenylmethyl)penicillin3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidPenicillinic acid, benzyl-1232134-74-5(Phenylmethyl)penicillinic acid

데이터베이스 식별자

CAS
1406-05-9、61-33-6、7005-30-3
PubChem CID
2349
DTXSID
DTXSID20274362
ChEMBL
CHEMBL300052
EC Number
215-794-6
Nikkaji
J25.642K

물성

구조 계산 물성

XLogP
1.8
극성 표면적
112 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
5
회전 가능 결합 수
4
무거운 원자 수
23
형식 전하
0
복잡도
530

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

유해성 정보

Hazards Summary · 1건

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]

독성 정보

Adverse Effects · 2건

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.;* 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.

화학 및 산업

약리 정보

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.

용도 및 제조

UsesUse (kg) in USA (2002): 102000;Consumption (g per capita) in the USA (2002): 0.362;Calculated removal (%): 22.6
Use ClassificationVeterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

관련 반응

2건
반응 기록 만들기
HRID 284835 반응식
HRID 284835생성물로반응물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 1133621 반응식
HRID 1133621반응물로Training data from https://doi.org/10.1039/C8SC04228D (7/10)

화합물 노트

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이 페이지에서기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Toxicity Summary · 1건

Signs and Symptoms of Overdose;Penicillin 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 Overdose;Neurotoxicity of penicillin requires discontinuation of the offending penicillin. Penicillins are hypothesized to have an inhibitory effect on GABA transmission; consequently, IV benzodiazepines and electroencephalogram (EEG) monitoring may be necessary in refractory cases.

Drug Induced Liver Injury · 4건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

PENICILLIN

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

안전 데이터

독성
TDLo ims-man: 12,385 mg/kg/16D-I:SKN MJAUAJ 1,305,47