Basic information
- Standard 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- Molecular formula
- C29H38N4O6S
- Average molar mass
- 570.7 g/mol
- Monoisotopic mass
- 570.25120594
Overview
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.
Names & identifiers
- Preferred name
- 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
- English name
- Procaine penicillin G
- Molecular formula
- C16H18N2O4S.C13H20N2O2
- Molecular weight
- 570.7
Names & synonyms
Procaine penicillin GProcaine BenzylpenicillinDepocillinDuphapenHostacillinHydracillinNopcaineRetardillinVitablendVetspenJenacillin OMicro-Pen
Show more names
PENICILLIN G PROCAINEbenzylpenicillin procaineBenzyl Pencillin Procainerocaine penicillin
Penicillin procainePenzal N 300Procaine benzylpenicillinateBenzylpenicillin novocaine saltPenicillin procaine (anhydrous)Benzilpenillina procainicaUNII-1LW5K9CIR1EINECS 200-205-7
Database identifiers
- CAS
54-35-3- PubChem CID
- 5903
- DTXSID
DTXSID30883227- ChEMBL
CHEMBL1200936、CHEMBL1628385- UNII
- 1LW5K9CIR1
Properties
Computed structural properties
- Topological polar surface area
- 168 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 11
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 752
Experimental & physicochemical properties
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
Active Ingredients (Penicillin G Procaine) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Physicochemical properties
- Melting point
- 129 · 129-130 °C
- Density
- 1.1335 · 1.1335 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 100 mg/mL · DMSO: 100 mg/mL (175.22 mM);Ethanol: 20 mg/mL (35.04 mM)
- Water Solubility
- 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 DataBase Reference
- 54 · 54-35-3
- FDA UNII
- 1 LW5K9CIR1 · 1LW5K9CIR1
- ATC code
- 1 CE09 · J01CE09
- EPA Substance Registry System
- 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)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- TSCA
- TSCA listed
- Toxicity
- 50 orl-rat: · LD50 orl-rat: >2 g/kg ABANAE 3,534,55/56
Safety & regulation
Hazard information
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
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- tsca
- TSCA listed
- Toxicity
- LD50 orl-rat: >2 g/kg ABANAE 3,534,55/56
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
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.
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.
Uses & manufacturing
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
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
Applications
UsesAntibacterial.
General DescriptionThe 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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
医格尔（上海）药业有限公司+86-2160290089 +86-13884467586 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
Hebei baicao biology science and technology co., ltd+86-19131911055 17824879454 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
山东雨禾医药科技有限公司15263077727
湖北海克斯生化有限公司17362916295; 17362916295 · [email protected]
Shaanxi Haibo Biotechnology Co., Ltd+86-18629295024 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
湖北辰心化工有限公司18696113233 · [email protected]
江西瑞威尔生物科技有限公司400-880-2824 18107960669 · [email protected]
湖南瑞威尔生物科技有限公司15608648206 13297919155 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
武汉菲越生物科技有限公司027-87002654 15827563343
福建盛世嘉泰药业有限公司13385921167
湖北魏氏化学试剂股份有限公司027-59102966 18717199209 · [email protected]
United Life Science020-82099279 18988941402 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
北京博奥森生物技术有限公司400-901-9800 18611424007 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
河北茹麒科技有限公司176-03256889 17603256889 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
山东铭枫医药科技有限公司053155551677 15315114555 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
LUYUNJIA CHEMISTRY XIAMEN LIMITED+86-592-5360779 +86-13055435203
武汉贝乐叶生物医药科技有限公司18086118078 · [email protected]
湖北源梦生物科技有限公司027-68897569 18120462897 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
湖北威德利化学科技有限公司027-83989310 18627915365
武汉鑫儒化工有限公司15927387915 15337108568
泰安嘉岳生物化工有限公司15318151873 · [email protected]
湖南瑞威尔生物科技有限公司19359985961 · [email protected]
湖北辰心化工有限公司17362916295
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
湖北万业众诚化学试剂有限责任公司18671296875 · [email protected]
石家庄瑞田生化有限公司15831127780 · [email protected]
武汉福鑫化工有限公司+86-2759207851; +86-18007136271 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
BOC Sciences16314854226 · [email protected]
河北方乾新材料科技有限公司86-180-3439-5858-5858 18034395858
南通市苏北化工原料有限公司0513-85290972 18762756250 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
华北制药集团先泰药业有限公司(0311)83098230/83098186
Related reactions
1 records
Linked notes
Loading…