Methicillin

Synopsis, Chemistry

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Also known as: Sodium methicillin, Meticillin sodium, 132-92-3, Methicillin sodium salt, Dimocillin sodium, Staphcillin

Molecular Formula

C₁₇H₁₉N₂NaO₆S

Molecular Weight

402.4 g/mol

InChI Key

MGFZNWDWOKASQZ-UMLIZJHQSA-M

FDA UNII

NBQ410S76Y

One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.

1 2D Structure

Methicillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C17H20N2O6S.Na/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4;/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23);/q;+1/p-1/t11-,12+,15-;/m1./s1

2.1.3 InChI Key

MGFZNWDWOKASQZ-UMLIZJHQSA-M

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)[O-])C.[Na+]

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)[O-])C.[Na+]

2.2 Other Identifiers

2.2.1 UNII

NBQ410S76Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dimethoxyphenyl Penicillin

2. Methicillin

3. Methicillin Hydrate, Monosodium Salt

4. Methicillin Monohydrate, Monosodium Salt

5. Meticillin

6. Metin

7. Penicillin, Dimethoxyphenyl

8. Staphcillin

2.3.2 Depositor-Supplied Synonyms

1. Sodium Methicillin

2. Meticillin Sodium

3. 132-92-3

4. Methicillin Sodium Salt

5. Dimocillin Sodium

6. Staphcillin

7. Celbenin

8. Methicillin Sodium Anhydrous

9. Meticillin Sodium Salt

10. Methicillin (sodium Salt)

11. Nbq410s76y

12. Belfacillin

13. Synticillin

14. Penaureus

15. Staficyn

16. Chebi:52065

17. Estafcilina

18. Celpilline

19. Cinopenil

20. Flabelline

21. Lucopenin

22. Penysol

23. Dimocillin-r-2

24. Chembl1164

25. Smr000539526

26. Sodium Dimethoxyphenylpencillin

27. Sq-16123

28. Einecs 205-083-9

29. 2,6-dimethoxyphenyl Penicillin Sodium

30. Unii-nbq410s76y

31. Sq 16123

32. Sodium 6beta-(2,6-dimethoxybenzamido)penicillanate

33. Sodium (2,6-dimethoxyphenyl)penicillin

34. Sodium 6beta-(2,6-dimethoxybenzamido)-2,2-dimethylpenam-3alpha-carboxylate

35. Sodium (2s,5r,6r)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

36. Schembl34135

37. Mls001304185

38. Mls002695968

39. Spectrum1500395

40. Methicillin Sodium Salt, 90%

41. Methicillin Sodium [mi]

42. Hms500e22

43. Dtxsid30872398

44. Hms1920l15

45. Hms2091d10

46. Hms3715g20

47. Meticillin Sodium [who-dd]

48. Hy-b0974

49. Ccg-39483

50. Mfcd07787409

51. Akos015900096

52. Cs-4464

53. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-, Monosodium Salt

54. Q27123143

55. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-,sodium Salt(1:1),(2s,5r,6r)-

56. Sodium (2s,5r,6r)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₉N₂NaO₆S
Molecular Weight	402.4 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	402.08615179 g/mol
Monoisotopic Mass	402.08615179 g/mol
Topological Polar Surface Area	133 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	606
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