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Procaine Penicillin G

Procaine Penicillin G

Synopsis, 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 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 Formula	C₂₉H₃₈N₄O₆S
Molecular Weight	570.7 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	11
Exact Mass	570.25120612 g/mol
Monoisotopic Mass	570.25120612 g/mol
Topological Polar Surface Area	168 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	752
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.