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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

Methicillin
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 Weight 402.4 g/mol
Molecular Formula C17H19N2NaO6S
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Exact Mass402.08615179 g/mol
Monoisotopic Mass402.08615179 g/mol
Topological Polar Surface Area133 Ų
Heavy Atom Count27
Formal Charge0
Complexity606
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


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