Piperacillin

Piperacillin · PIPERACILLIN SODIUM · Pipracil · Pipercillin · (2S,5R,6R)-6-[[(2R)-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid · (2S,5R,6R)-6-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrate · 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-,(2S,5R,6R)- · PIPC

https://huagongshe.com/ko/chemical/43672

식별자 및 물리적 특성

CAS No.	61477-96-1
분자식	C23H27N5O7S
평균 분자량	517.6 g/mol
단동위원소 질량	517.1631192 g/mol
SMILES	CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3[C@@H]2SC(C)(C)[C@@H]3C(=O)O)c2ccccc2)C(=O)C1=O
InChIKey	IVBHGBMCVLDMKU-GXNBUGAJSA-N
PubChem CID	43672
ChEMBL	CHEMBL702
ChEBI	CHEBI:8232
EC No.	262-811-8
DTXSID	DTXSID2023482

화학 및 물리적 성질

XLogP	0.5
극성 표면적	182
수소 결합 공여자 수	3
수소 결합 수용자 수	8
회전 가능 결합 수	6
무거운 원자 수	36
형식 전하	0
복잡도	982
물질 분류	Other Uses -> Pharmaceuticals
의약품	Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland
LogP(분배 계수)	0.3
용해도	1.19e-01 g/L메탄올에 자유롭게 용해됩니다. 0.119 mg/mL의 수용액에는 난용성입니다.
Human Drugs	Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsPenicillins
Physical Description	White to off-white solid[Bristol-Myers Squibb]
Collision Cross Section	227.2 Å² [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]222.2 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]221.26 Å² [M-H]-
녹는점	183-185C (dec.)
밀도	1.51±0.1 g/cm3(Predicted)
증기압	0Pa at 20℃
저장 조건	Sealed in dry,2-8°C
pKa(산도 계수)	2.44±0.50(Predicted)
물리적 상태	고체
색상	흰색에서 황백색까지
용해도	256.8mg/L at 20℃
안정성	흡습성
InChIKey	IVBHGBMCVLDMKU-GXNBUGAJSA-N
SMILES	N12[C@@]([H])([C@H](NC([C@H](NC(N3CCN(CC)C(=O)C3=O)=O)C3=CC=CC=C3)=O)C1=O)SC(C)(C)[C@@H]2C(O)=O
LogP(분배 계수)	-1.55 at 20℃

화학적 성질

White Crystalline Solid; odorless; slightly hygroscopic. It is easily soluble in methanol, soluble in absolute ethanol or acetone, and very slightly soluble in water. It is a semi-synthetic penicillin antibiotic with broad-spectrum antibacterial effect.

안전 및 규제

GHS 분류	DangerH317 (93.8%): 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, P403, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 16 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보	Status: Active Update: 15-06-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/27459
기타 안전 정보	IMAP assessments - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-, [2S-[2.alpha.,5.alpha.,6.beta.(S*)]]-: Environment tier I assessment
유해성 요약	A dermal and respiratory sensitizer[Bristol-Myers Squibb] Occupational asthma confirmed in a pharmaceutical worker[Malo] Causes contact urticaria[Kanerva, p. 219]
Hazard Classes and Categories	Skin Sens. 1 (93.8%)
Hepatotoxicity	Patients on intravenous piperacillin may have transient and mild-to-moderate serum aminotransferase elevations in up to 12% of patients, but these are of little clinical significance and not more common than with comparative parenteral antibiotics. Hepatic injury was more commonly reported with mezlocillin, a related extended spectrum ureidopenicillin which has been withdrawn from use. Rare instances of idiosyncratic liver injury have been reported in persons receiving piperacillin. The liver injury is typically cholestatic arising within 1 to 6 weeks of starting therapy. The injury can be severe, but is generally self-limited once piperacillin is stopped. The features of the hepatotoxicity resemble those of other penicillins. The cholestatic hepatitis caused by piperacillin and other penicillins can be prolonged and lead to persistent cholestasis (vanishing bile duct syndrome) or persistent elevations in serum alkaline phosphatase suggestive of partial bile duct loss. Most cases of liver injury related to piperacillin are linked to the combination of piperacillin with the beta-lactamase inhibitor tazobactam (Zosyn and generics), which is more commonly used than piperacillin alone.
유해 작용	Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.

용도

Piperacillin is a semisynthetic penicillin with wide spectrum of antimicrobial activity, particularly pseudomonas strains. It is used to treat moderate-to-severe infections due to susceptible organisms.