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Chemistry

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Also known as: 54-35-3, Duphapen, Hostacillin, Hydracillin, Procaine benzylpenicillin, 1lw5k9cir1
Molecular Formula
C29H38N4O6S
Molecular Weight
570.7  g/mol
InChI Key
WHRVRSCEWKLAHX-LQDWTQKMSA-N
FDA UNII
1LW5K9CIR1

Procaine Penicillin G
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.
1 2D Structure

Procaine Penicillin G

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
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
2.1.2 InChI
InChI=1S/C16H18N2O4S.C13H20N2O2/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);5-8H,3-4,9-10,14H2,1-2H3/t11-,12+,14-;/m1./s1
2.1.3 InChI Key
WHRVRSCEWKLAHX-LQDWTQKMSA-N
2.1.4 Canonical SMILES
CCN(CC)CCOC(=O)C1=CC=C(C=C1)N.CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
2.1.5 Isomeric SMILES
CCN(CC)CCOC(=O)C1=CC=C(C=C1)N.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
2.2 Other Identifiers
2.2.1 UNII
1LW5K9CIR1
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 54-35-3

2. Duphapen

3. Hostacillin

4. Hydracillin

5. Procaine Benzylpenicillin

6. 1lw5k9cir1

7. Retardillin

8. Depocillin

9. Nopcaine

10. Vetspen

11. Vitablend

12. Jenacillin O

13. Micro-pen

14. Penicillin Procaine

15. 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

16. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2s,5r,6r)-, Compd. With2-(diethylamino)ethyl 4-aminobenzoate (1:1)other Ca Index Names:benzoic Acid, 4-amino-, 2-(diethylamino)ethyl Ester,mono[(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2

17. Penzal N 300

18. Procain-penicillin

19. 4-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)

20. 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)

21. 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)

22. Benzylpenicillin Novocaine Salt

23. Benzilpenillina Procainica [dcit]

24. Benzilpenillina Procainica

25. Einecs 200-205-7

26. Unii-1lw5k9cir1

27. Procainebenzylpenicillin

28. Penicillin G. Procaine

29. Chembl1628385

30. Dtxsid30883227

31. Anhydrous Procaine Penicillin

32. Mfcd00079285

33. S4979

34. Akos015896161

35. Penicillin G Procaine Anhydrous

36. Penicillin G Procaine Salt Monohydrate

37. Db09320

38. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-, Compd. With 2-(diethylamino)ethyl P-aminobenzoate (1:1)

39. As-15252

40. E707

41. 130p649

42. A830119

43. Q3435660

44. 2-(diethylamino)ethyl 4-azanylbenzoate; (2s,5r,6r)-3,3-dimethyl-7-oxidanylidene-6-(2-phenylethanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

45. 4-aminobenzoic Acid 2-(diethylamino)ethyl Ester; (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(1-oxo-2-phenylethyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 570.7 g/mol
Molecular Formula C29H38N4O6S
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count11
Exact Mass570.25120612 g/mol
Monoisotopic Mass570.25120612 g/mol
Topological Polar Surface Area168 Ų
Heavy Atom Count40
Formal Charge0
Complexity752
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Indication

For the treatment of a number of bacterial infections such as syphilis, anthrax, mouth infections, pneumonia and diphtheria.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CE - Beta-lactamase sensitive penicillins

J01CE09 - Procaine benzylpenicillin


5.3 Absorption, Distribution and Excretion

Absorption

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.


Route of Elimination

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.


Volume of Distribution

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.


5.4 Metabolism/Metabolites

Procaine is rapidly hydrolyzed by plasma esterases to nontoxic metabolites.


5.5 Biological Half-Life

Intramuscular injection of benzylpenicillin has a plasma half-life of 30 minutes.


5.6 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.


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ABOUT THIS PAGE

Procaine Penicillin G Manufacturers

A Procaine Penicillin G manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Procaine Penicillin G, including repackagers and relabelers. The FDA regulates Procaine Penicillin G manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Procaine Penicillin G API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Procaine Penicillin G manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Procaine Penicillin G Suppliers

A Procaine Penicillin G supplier is an individual or a company that provides Procaine Penicillin G active pharmaceutical ingredient (API) or Procaine Penicillin G finished formulations upon request. The Procaine Penicillin G suppliers may include Procaine Penicillin G API manufacturers, exporters, distributors and traders.

click here to find a list of Procaine Penicillin G suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Procaine Penicillin G GMP

Procaine Penicillin G Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Procaine Penicillin G GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Procaine Penicillin G GMP manufacturer or Procaine Penicillin G GMP API supplier for your needs.

Procaine Penicillin G CoA

A Procaine Penicillin G CoA (Certificate of Analysis) is a formal document that attests to Procaine Penicillin G's compliance with Procaine Penicillin G specifications and serves as a tool for batch-level quality control.

Procaine Penicillin G CoA mostly includes findings from lab analyses of a specific batch. For each Procaine Penicillin G CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Procaine Penicillin G may be tested according to a variety of international standards, such as European Pharmacopoeia (Procaine Penicillin G EP), Procaine Penicillin G JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Procaine Penicillin G USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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