Penicillin G Procaine (HCID 5903)

概要

Procaine benzylpenicillin (INN), also known as procaine G penicillin, is an injectable antiobiotic. It is a poorly soluble salt form of penicillin which is a combination of naturally occuring benzylpenicillin (penicillin G) and the local anaesthetic agent procaine in equimolar amounts. Procaine benzylpenicillin is administered by deep intramuscular injection. It is slowly absorbed and hydrolyzed to benzylpenicillin. This drug is used where prolonged exposure to benzylpenicillin at a low concentration is required. This combination is aimed at reducing the pain and discomfort associated with a large intramuscular injection of penicillin. It is widely used in veterinary settings. Benzylpenicillin is active against a wide range of organisms and is the drug of first choice for many infections.

名称と識別子

優先名称: Penicillin G Procaine
IUPAC: 2-(diethylamino)ethyl 4-aminobenzoate;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
現地名: ベンジルペニシリン·プロカイン
英語名: Procaine penicillin G
分子式: C16H18N2O4S.C13H20N2O2
分子量: 570.7

名称と別名

Procaine penicillin GProcaine BenzylpenicillinDepocillinDuphapenHostacillinHydracillinNopcaineRetardillinVitablendVetspenJenacillin OMicro-Pen

名称をさらに表示

プロカイン/ペニシリンG,(1:1)ベンジルペニシリン·プロカインプロカインペニシリンGベンジルペニシリンプロカインペニシリンG/プロカイン(2S,5β)-3,3-ジメチル-7-オキソ-6α-[(フェニルアセチル)アミノ]-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2β-カルボン酸·4-アミノ安息香酸2-(ジエチルアミノ)エチルプロカイン/ペニシリンGベンジルペニシリン/プロカインプロカインペニシリン GPENICILLIN G PROCAINEbenzylpenicillin procaineBenzyl Pencillin Procainerocaine penicillin

Penicillin procainePenzal N 300Procaine benzylpenicillinateBenzylpenicillin novocaine saltPenicillin procaine (anhydrous)Benzilpenillina procainicaUNII-1LW5K9CIR1EINECS 200-205-7

データベース識別子

CAS: 54-35-3
PubChem CID: 5903
DTXSID: DTXSID30883227
ChEMBL: CHEMBL1200936、CHEMBL1628385
UNII: 1LW5K9CIR1

物性

構造計算による物性

極性表面積: 168 Å²
水素結合供与体数: 3
水素結合受容体数: 9
回転可能結合数: 11
重原子数: 40
形式電荷: 0
複雑度: 752

実験および物理化学的性質

SolubilitySlightly soluble

Human Drugs · 4 件

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

FDA approved drugs -> Active ingredient

Access group antibiotics

Animal Drugs · 2 件

Active Ingredients (Penicillin G Procaine) -> FDA Greenbook

Pharmaceuticals -> UK Veterinary Medicines Directorate List

物理化学的性質

融点: 129 · 129-130 °C
比重(密度): 1.1335 · 1.1335 (rough estimate)
屈折率: 1.6 · 1.6000 (estimate)
貯蔵温度: -20 °C · Store at -20°C
溶解性: 100 mg/mL · DMSO: 100 mg/mL (175.22 mM);Ethanol: 20 mg/mL (35.04 mM)
水溶解度: 10 mg/mL · Water: 10 mg/mL (17.52 mM)
InChIKey: WHRVRSCEWKLAHX-RLWRCNEPNA-N
SMILES: N12[C@@H](C(=O)O)C(C)(C)S[C@@]1([C@H](NC(CC1C=CC=CC=1)=O)C2=O)[H].C1(=CC=C(N)C=C1)C(=O)OCCN(CC)CC |&1:1,9,10,r|
CAS データベース: 54 · 54-35-3
EPAの化学物質情報: 4 · 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, compd. with 2-(diethylamino)ethyl 4-aminobenzoate (1:1) (54-35-3)

化学的性質

化学的特性White, fine crystals or powder; odorless; relatively stable to air and light; solutions dextroro- tatory. Sparingly soluble in water; slightly soluble in alcohol; fairly soluble in chloroform.

安全と法規制

危険有害性情報

Other Safety InformationIMAP assessments - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- [2S-(2.alpha.,5.alpha.,6.beta.)]-, compound with 2-(diethylamino)ethyl 4-aminobenzoate (1:1): Environment tier I assessment

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

tsca: TSCA listed
毒性: LD50 orl-rat: >2 g/kg ABANAE 3,534,55/56

化学と産業

薬理情報

ATC Code · 4 件

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

J01CE09

Protein BindingApproximately 60% of penicillin G is bound to serum protein.

Pharmacodynamics · 1 件

It is an antibiotic against penicillin-susceptible microorganisms with bactericidal effect. Like all penicillins, procaine benzylpenicillin interferes with the synthesis of the bacterial cell wall peptidoglycan. It acts through the inhibition of biosynthesis of cell-wall peptidoglycan, rendering the cell wall osmotically unstable. It is part of the penicillin and beta lactam family of antibacterial drugs.

Mechanism of Action · 1 件

Procaine benzylpenicillin is hydrolyzed into penicillin G once it is released from the injection site. Penicillin G attaches to the penicillin-binding proteins on bacterial cell wall and inhibit the transpeptidation enzyme that crosslinks the peptide chains attached to the backbone of the peptidoglycan. The final bactericidal event involves the inactivation of an inhibitor of autolytic enzymes in the cell wall, leading to lysis of the bacterium.

Biological Half-LifeIntramuscular injection of benzylpenicillin has a plasma half-life of 30 minutes.

Metabolism/MetabolitesProcaine is rapidly hydrolyzed by plasma esterases to nontoxic metabolites.

用途と製造

Use Classification · 3 件

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

General Manufacturing Information4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]- (2S,5R,6R)-, compd. with 2-(diethylamino)ethyl 4-aminobenzoate (1:1): ACTIVE

応用分野 · 2 件

使用Antibacterial.

一般的な説明The first widely used amine salt of penicillin G wasmade with procaine. Penicillin G procaine (Crysticillin,Duracillin, Wycillin) can be made readily from penicillin Gsodium by treatment with procaine hydrochloride. This saltis considerably less soluble in water than the alkali metalsalts, requiring about 250 mL to dissolve 1 g. Free penicillinis released only as the compound dissolves and dissociates.It has an activity of 1,009 units/mg. A large number ofpreparations for injection of penicillin G procaine are commerciallyavailable. Most of these are either suspensions inwater to which a suitable dispersing or suspending agent, a buffer, and a preservative have been added or suspensions inpeanut oil or sesame oil that have been gelled by theaddition of 2% aluminum monostearate. Some commercialproducts are mixtures of penicillin G potassium or sodiumwith penicillin G procaine; the water-soluble salt providesrapid development of a high plasma concentration of penicillin,and the insoluble salt prolongs the duration of effect.

上流・下流製品情報

上流原料

酢酸ヘキシルペニシリンGカリウムプロカイン塩酸塩プロカインベンジルペニシリン

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ベンジルペニシリン·プロカイン

基本情報

概要