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Hetacillin

Synopsis, Chemistry

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Also known as: 3511-16-8, Hetacillinum, Phenazacillin, Hetacilina, Hetacilline, Versapen

Molecular Formula

C₁₉H₂₃N₃O₄S

Molecular Weight

389.5 g/mol

InChI Key

DXVUYOAEDJXBPY-NFFDBFGFSA-N

FDA UNII

TN4JSC48CV

Hetacillin is a semi-synthetic penicillin compound with bactericidal properties. Hetacillin is a prodrug that is converted to ampicillin via esterases. Ampicillin binds to inactivated penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs, including transpeptidases, carboxypeptidases, and endopeptidases, participate in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. This results in the weakening of the bacterial cell wall and eventually causes cell lysis. (NCI05)

1 2D Structure

Hetacillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2.1.2 InChI

InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1

2.1.3 InChI Key

DXVUYOAEDJXBPY-NFFDBFGFSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)N3C(=O)C(NC3(C)C)C4=CC=CC=C4)C(=O)O)C

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)C4=CC=CC=C4)C(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

TN4JSC48CV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hetacillin, (2s-(2alpha,5alpha,6alpha))-isomer

2. Hetacillin, Aluminum Salt (3:1), (2s-(2alpha,5alpha,6beta(s*)))-isomer

3. Hetacillin, Monopotassium Salt, (2s-(2alpha,5alpha,6beta(s*)))-isomer

4. Hetacillin, Monosodium Salt, (2s-(2alpha,5alpha,6beta(s*)))-isomer

5. Hetacillin, Monosodium Salt, (2s-(2alpha,5alpha,6beta))-isomer

6. Phenazacillin

2.3.2 Depositor-Supplied Synonyms

1. 3511-16-8

2. Hetacillinum

3. Phenazacillin

4. Hetacilina

5. Hetacilline

6. Versapen

7. Bl-p 804

8. Hetacillin Acid

9. Brl-804

10. Tn4jsc48cv

11. Chebi:5683

12. (2s,5r,6r)-6-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

13. Blp-804

14. Bl-p-804

15. 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

16. 7-(2,2-dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-3,3-dimethyl-6-oxo-2-thia-5-azabicyclo[3.2.0]heptane-4-carboxylic Acid

17. Etacillina

18. 6beta-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic Acid

19. Etacillina [dcit]

20. Brl 804

21. Unii-tn4jsc48cv

22. Hetacilina [inn-spanish]

23. Hetacilline [inn-french]

24. Hetacillinum [inn-latin]

25. Hetacillin [usan:usp:inn:ban]

26. Versapen (tn)

27. Einecs 222-512-5

28. Hetacillin [mi]

29. Hetacillin [inn]

30. Hetacillin (usan/inn)

31. Hetacillin [usan]

32. N,n'-isopropylidene-a-amino-benzyl Penicillin

33. Hetacillin [mart.]

34. Hetacillin [who-dd]

35. Schembl34131

36. Chembl1201116

37. Dtxsid4023121

38. Hetacillin [orange Book]

39. Zinc4102186

40. 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillansaeure

41. Hy-16251a

42. Cs-4870

43. Db00739

44. (2s,%r,6r)-6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure

45. D01074

46. Q5746710

47. (2s,5r,6r)-6-((r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

48. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((4r)-2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-, (2s,5r,6r)-

49. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

50. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6beta(s*)))-

51. 6beta-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-2,2-dimethylpenam-3alpha-carboxylic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₃N₃O₄S
Molecular Weight	389.5 g/mol
XLogP3	-0.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	389.14092740 g/mol
Monoisotopic Mass	389.14092740 g/mol
Topological Polar Surface Area	115 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	688
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections. In the body it gets converted to ampicillin.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs).

5.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CA - Penicillins with extended spectrum

J01CA18 - Hetacillin

5.3 Metabolism/Metabolites

Hydrolyzed to active ampicillin via esterases

5.4 Mechanism of Action

Hetacillin is a semisynthetic penicillin prodrug which itself has no antibacterial activity, but is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. Hetacillin is prepared by reacting ampicillin with acetone. Ampicillin rapidly decomposes because of the intramolecular attack of the side chain amino group on the lactam ring. _In vitro_ studies have shown that hetacillin is resistant to beta lactamase activity. However, this effect is transient, as the hydrolysis product, ampicillin, is readily inactivated by beta lactamase. Hetacillin locks up the offending amino group and prevents the decomposition of Hetacillin. Once hydrolyzed to ampicillin (and acetone), ampicillin binds to the penicillin binding proteins found in susceptible bacteria. This inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.