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CHEMISTRY
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ACTIVE PHARMA INGREDIENTS

4 API Suppliers, 4 USDMF, 1 NDC API

4 API Suppliers
4 USDMF
1 NDC API

FINISHED DOSAGE FORMULATIONS

2 FDF Dossiers, 2 FDA Orange Book

2 FDF Dossiers
2 FDA Orange Book

Synopsis

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Chemistry

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Also known as: Natacillin, 5321-32-4, Potassium hetacillin, Versapen-k, Hetacillin (potassium), Versatrex

Molecular Formula

C₁₉H₂₂KN₃O₄S

Molecular Weight

427.6 g/mol

InChI Key

QRSPJBLLJXVPDD-XFAPPKAWSA-M

FDA UNII

95PFX5932Y

Hetacillin Potassium is the potassium salt of hetacillin, a semi-synthetic penicillin antibiotic with bactericidal activity. Hetacillin is a prodrug that is converted to ampicillin via esterases. Ampicillin binds to and inactivated penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall, thereby preventing the cross-linkage of peptidoglycans, which are critical components of the bacterial cell wall. This leads to an interruption of the bacterial cell wall and causes bacterial cell lysis.

1 2D Structure

Hetacillin Potassium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

potassium;(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-carboxylate

2.1.2 InChI

InChI=1S/C19H23N3O4S.K/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);/q;+1/p-1/t11-,12-,13+,16-;/m1./s1

2.1.3 InChI Key

QRSPJBLLJXVPDD-XFAPPKAWSA-M

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.[K+]

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.[K+]

2.2 Other Identifiers

2.2.1 UNII

95PFX5932Y

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Natacillin

2. 5321-32-4

3. Potassium Hetacillin

4. Versapen-k

5. Hetacillin (potassium)

6. Versatrex

7. Hetacin-k

8. Chebi:34789

9. 95pfx5932y

10. Nsc-757046

11. Potassium 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

12. Potassium;(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-carboxylate

13. Hetacin-k (veterinary)

14. H-k Mastitis (veterinary)

15. Unii-95pfx5932y

16. Einecs 226-182-3

17. Hetacin-k (tn)

18. Hetacillin Potassium [usan:usp:jan]

19. Hetacillin Potassium Salt

20. Schembl192601

21. Chembl1201121

22. Hetacillin Potassium (jan/usan)

23. Hetacillin Potassium [jan]

24. Hetacillin Potassium [usan]

25. Hetacillin Potassium [mart.]

26. Hetacillin Potassium [who-dd]

27. Hetacillin Potassium Salt [mi]

28. Cs-4871

29. Nsc 757046

30. Hetacillin Potassium [green Book]

31. Hetacillin Potassium [orange Book]

32. Hy-16251

33. D02203

34. Q27116274

35. Potassium 6beta-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanate

36. 26939-80-0

37. 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-, Monopotassium Salt, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

38. 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-, Monopotassium Salt, (2s-(2alpha,5alpha,6beta(s*)))-

39. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2,2-dimethyl-5-oxo-4-phenyl-imidazolinyl)-3,3-dimethyl-7-oxo-, Monopotassium Salt

40. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[(4r)-2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl]-3,3-dimethyl-7-oxo-,potassium Salt(1:1),(2s,5r,6r)-

41. Potassium (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-carboxylate

42. Potassium (2s-(2alpha,5alpha,6beta(s*)))-6-(2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

43. Potassium 6beta-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-2,2-dimethylpenam-3alpha-carboxylate

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₂KN₃O₄S
Molecular Weight	427.6 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	427.09680885 g/mol
Monoisotopic Mass	427.09680885 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	695
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	2