기본 정보
- 표준 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- 분자식
- C29H38N4O6S
- 평균 분자량
- 570.7 g/mol
- 단동위원소 질량
- 570.25120594
개요
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.
이름 및 식별자
- 우선 이름
- 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
- 현지명
- 페니실린 G 프로카인
- 영어명
- Procaine penicillin G
- 분자식
- C16H18N2O4S.C13H20N2O2
- 분자량
- 570.7
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
54-35-3- PubChem CID
- 5903
- DTXSID
DTXSID30883227- ChEMBL
CHEMBL1200936、CHEMBL1628385- UNII
- 1LW5K9CIR1
물성
구조 계산 물성
- 극성 표면적
- 168 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 9
- 회전 가능 결합 수
- 11
- 무거운 원자 수
- 40
- 형식 전하
- 0
- 복잡도
- 752
실험 및 물리화학적 성질
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
Active Ingredients (Penicillin G Procaine) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
물리화학적 성질
- 녹는점
- 129 · 129-130 °C
- 밀도
- 1.1335 · 1.1335 (rough estimate)
- 굴절률
- 1.6 · 1.6000 (estimate)
- 저장 조건
- -20 °C · Store at -20°C
- 용해도
- 100 mg/mL · DMSO: 100 mg/mL (175.22 mM);Ethanol: 20 mg/mL (35.04 mM)
- 수용성
- 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|
- EPA
- 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)
화학적 성질
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.
안전 및 규제
유해성 정보
독성 정보
안전 데이터
- tsca
- TSCA listed
- 독성
- LD50 orl-rat: >2 g/kg ABANAE 3,534,55/56
- 기존화학 물질
- KE-05-1271
화학 및 산업
약리 정보
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01CE09
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.
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.
The drug is distributed throughout the body tissues in widely varying amounts and spinal fluid to a lesser degree. Highest levels are found in the kidneys with lesser amounts in the liver, skin, and intestines. It displays low solubility thus results in blood serum levels much lower but more prolonged than other parenteral penicillins.
용도 및 제조
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
응용 분야
용도Antibacterial.
일반 설명The 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.
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