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ピペラシリン

Piperacillin

HCID 43672
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
61477-96-1
標準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
分子式
C23H27N5O7S
平均分子量
517.6 g/mol
単同位体質量
517.1631192

概要

Piperacillin is a penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a piperacillin(1-).

名称と識別子

優先名称
Piperacillin
IUPAC
(2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
現地名
ピペラシリン
英語名
Piperacillin
分子式
C23H27N5O7S
分子量
517.55

名称と別名

piperacillin61477-96-1Piperacillin anhydrousPiperacillinePiperacilinaPeracinPiperacillinaPiperacillinumPIPCCHEBI:8232Pipercillin(2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
名称をさらに表示
ピペルシリン6α-[[(R)-α-オキソ-β-[[(2,3-ジオキソ-4-エチル-1-ピペラジニル)カルボニル]アミノ]フェネチル]アミノ]ペニシラン酸(2S,5R,6R)-6-[[(R)-α-[(4-エチル-2,3-ジオキソピペラジン-1-イル)カルボニルアミノ]ベンジル]カルボニルアミノ]-3,3-ジメチル-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2-カルボン酸6α-[[(R)-(4-エチル-2,3-ジオキソ-1-ピペラジニルカルボニルアミノ)フェニルアセチル]アミノ]ペニシラン酸ピペラシリンピプラシール(2S,5R,6R)-6-[(2R)-2-[(4-エチル-2,3-ジオキソピペラジン-1-カルボニル)アミノ]-2-フェニルアセトアミド]-3,3-ジメチル-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2-カルボン酸(6R)-6-[[(R)-(4-エチル-2,3-ジオキソ-1-ピペラジニルカルボニルアミノ)フェニルアセチル]アミノ]ペニシラン酸PIPERACILLIN SODIUMPipracil(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

物性

構造計算による物性補完中

XLogP
0.5
極性表面積
182 Ų
水素結合供与体数
3
水素結合受容体数
8
回転可能結合数
6
重原子数
36
形式電荷
0
複雑度
982

実験および物理化学的性質

Chemical ClassesOther Uses -> Pharmaceuticals
Drugs · 4 件

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

LogP0.3
Solubility1.19e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins
Physical Description · 2 件

White to off-white solid; [Bristol-Myers Squibb]

Solid

Collision Cross Section · 3 件

227.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

222.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

221.26 Ų [M-H]-

物理化学的性質

融点
183 · 183-185C (dec.)
比重(密度)
1.51 · 1.51±0.1 g/cm3(Predicted)

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H317 (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.

危険有害性情報

Regulatory InformationStatus: Active Update: 15-06-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/27459
Other Safety InformationIMAP 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
Hazards SummaryA dermal and respiratory sensitizer; [Bristol-Myers Squibb] Occupational asthma confirmed in a pharmaceutical worker; [Malo] Causes contact urticaria; [Kanerva, p. 219]
Hazard Classes and CategoriesSkin Sens. 1 (93.8%)

毒性情報

Hepatotoxicity · 1 件

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.

化学と産業

薬理情報

ATC Code · 3 件

J01CR05

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Pharmacodynamics · 1 件

Piperacillin 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. Piperacillin has <i>in vitro</i> activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Piperacillin results from the inhibition of cell wall synthesis and is mediated through Piperacillin binding to penicillin binding proteins (PBPs). Piperacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.

Mechanism of Action · 1 件

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Piperacillin 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 Piperacillin interferes with an autolysin inhibitor.

Biological Half-Life36-72 minutes
Metabolism/MetabolitesLargely not metabolized.
FDA Pharmacological Classification · 5 件

9I628532GX

PIPERACILLIN ANHYDROUS

Established Pharmacologic Class [EPC] - Penicillin-class Antibacterial

Chemical Structure [CS] - Penicillins

Piperacillin anhydrous is a Penicillin-class Antibacterial.

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion · 4 件

関連反応

3 件
反応記録を作成
HRID 377529 の反応式
HRID 377529反応物としてuspto-grants-2000_02
HRID 970294 の反応式
HRID 970294反応物としてuspto-grants-2007_12
HRID 1955488 の反応式
HRID 1955488反応物としてuspto-grants-1998_07

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
(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)-
C14034
Pipraci
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid9I628532GXDTXSID2023482AB Piperacillin4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-7-oxo-, (2S-(2-alpha,5-alpha,6-beta(S*)))-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-(2alpha,5alpha,6beta(S*)))-(2S,5R,6R)-6-[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetamido]-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-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid monohydrate

データベース識別子

CAS
61477-96-1、66258-76-2
PubChem CID
43672
DTXSID
DTXSID2023482
ChEMBL
CHEMBL702
ChEBI
CHEBI:8232
UNII
9I628532GX
EC Number
262-811-8
Nikkaji
J18.442J
蒸気圧
0 Pa · 0Pa at 20℃
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
0.119 mg/mL · メタノールに易溶。 0.119 mg/mL で水溶液にわずかにしか溶けない
酸解離定数(Pka)
2.44 · 2.44±0.50(Predicted)
外見
個体
色
ホワイトからオフホワイト
水溶解度
256.8 mg/L · 256.8mg/L at 20℃
安定性
吸湿性
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
-1.55 at · -1.55 at 20℃
CAS データベース
61477 · 61477-96-1(CAS DataBase Reference)
化学的性質 · 1 件

化学的特性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.

Adverse EffectsAsthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

piperacillin

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

risk_code
42/43
hazard_code
Xi
safety_code
36/37

Not absorbed following oral administration.

As with other penicillins, PIPRACIL is eliminated primarily by glomerular filtration and tubular secretion; it is excreted rapidly as unchanged drug in high concentrations in the urine. Because PIPRACIL is excreted by the biliary route as well as by the renal route, it can be used safely in appropriate dosage in patients with severely restricted kidney function.

101 mL/kg [intravenous administration of 50 mg/kg (5-minute infusion) in neonates]

32 - 41 mL/min/1.73 m2

Cellular LocationsMembrane

用途と製造

Uses · 2 件

A beta-lactam antibiotic; [Bristol-Myers Squibb]

Use (kg) in Switzerland (2009): >1000

応用分野 · 2 件

用途ピペラシリン(Piperacillin)は広域スペクトラムの β-ラクタム抗生物質 、中でもウレイドペニシリン?クラスのひとつ。ピペラシリンとその他のウレイドペニシリンの化学構造は、極性側鎖を持つ。これはグラム陰性菌に対して高い浸透性と、グラム陰性菌βラクタマーゼによる分解感受性を低下させる。 これらの性質は病院での重要な病原菌である緑膿菌に対する活性を持つ。 このような性質から、ピペラシリンはときに「抗緑膿菌ペニシリン」と呼ばれる。 ピペラシリンは単独で用いられる時には 黄色ブドウ球菌のなどのグラム陽性菌への強い活性を持たない。またβ-ラクタム構造は細菌の β-ラクタマーゼで加水分解される。

使用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.

上流・下流製品情報

上流原料

6-アミノペニシラン酸Bromide塩化カルボニルしゅう酸ジエチルクロロトリメチルシラン2-エチルヘキサン酸ナトリウムN-エチルエチレンジアミン
補足説明 · 1 件

定義ChEBI: Piperacillin is a penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a piperacillin(1-).