ベンジルペニシリン·プロカイン
Penicillin G Procaine
基本情報
- CAS
54-35-3- 標準SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O.CCN(CC)CCOC(=O)c1ccc(N)cc1- InChIKey
WHRVRSCEWKLAHX-LQDWTQKMSA-N- 分子式
- C29H38N4O6S
- 平均分子量
- 570.7 g/mol
- 単同位体質量
- 570.25120612
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
物性
構造計算による物性
- 極性表面積
- 168 Ų
- 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
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Access group antibiotics
Animal Drugs
FDA approved animal drugs -> Active ingredient
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)
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。
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
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01CE09
Protein BindingApproximately 60% of penicillin G is bound to serum protein.
Pharmacodynamics
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
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.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
After intramuscular injection, it dissolves slowly at the site of injection, giving a plateau type of blood level at about 4 hours which falls slowly over a period of the next 15 to 20 hours.
The drug is rapidly and predominantly cleared via renal elimination, with 90% being through tubular secretion. Approximately 60 -90 % of a dose of parenteral penicillin G is excreted in the urine within 24 to 36 hours.
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