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Chemistry

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Also known as: Dicloxacillin sodium, 13412-64-1, Dicloxacillin sodium salt monohydrate, Dicloxacillin sodium hydrate, Dynapen, Pathocil
Molecular Formula
C19H18Cl2N3NaO6S
Molecular Weight
510.3  g/mol
InChI Key
SIGZQNJITOWQEF-VICXVTCVSA-M
FDA UNII
4HZT2V9KX0

Sodium Dicloxacillin
One of the PENICILLINS which is resistant to PENICILLINASE.
1 2D Structure

Sodium Dicloxacillin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrate
2.1.2 InChI
InChI=1S/C19H17Cl2N3O5S.Na.H2O/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24;;/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1
2.1.3 InChI Key
SIGZQNJITOWQEF-VICXVTCVSA-M
2.1.4 Canonical SMILES
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].O.[Na+]
2.1.5 Isomeric SMILES
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].O.[Na+]
2.2 Other Identifiers
2.2.1 UNII
4HZT2V9KX0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cilpen

2. Dichloroxacillin

3. Diclocil

4. Dicloxaciclin

5. Dicloxacillin

6. Dicloxacillin Sodium

7. Dicloxacillin, Monosodium Salt, Anhydrous

8. Dicloxacillin, Monosodium Salt, Mono-hydrate

9. Dicloxacycline

10. Dicloxsig

11. Distaph

12. Ditterolina

13. Dycill

14. Dynapen

15. Infectostaph

16. Pathocil

17. Posipen

18. Sodium, Dicloxacillin

2.3.2 Depositor-Supplied Synonyms

1. Dicloxacillin Sodium

2. 13412-64-1

3. Dicloxacillin Sodium Salt Monohydrate

4. Dicloxacillin Sodium Hydrate

5. Dynapen

6. Pathocil

7. Dycill

8. Dicloxacillin Sodium Salt Hydrate

9. Diclocil

10. Sodium Dicloxacillin Monohydrate

11. Dicloxacillin (sodium Hydrate)

12. Chebi:52019

13. P-1011

14. 4hzt2v9kx0

15. Brispen

16. Nsc-756726

17. Monosodium (2s,5r,6r)-6-(3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate Monohydrate

18. Digloxilline

19. Biocloxin

20. Constaphyl

21. Novapen

22. Noxaben

23. Stampen

24. Ciclex

25. Clocil

26. Diflor

27. P 1011

28. Pen-sint

29. Dsstox_cid_28928

30. Dsstox_rid_83194

31. Dsstox_gsid_49002

32. Staphcillin A Banyu

33. Sodium Dicloxacillin Hydrate

34. Dichlorstapenor Sodium

35. Mdi-pc

36. Bayer 5488

37. Blp-1011

38. Smr000875239

39. Sodium (2s,5r,6r)-6-(3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Hydrate

40. R 13423

41. Ncgc00178782-02

42. 343-55-5

43. Sodium;(2s,5r,6r)-6-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrate

44. Unii-4hzt2v9kx0

45. Dycill (tn)

46. Mfcd00056865

47. Dicloxacillinum Natricum

48. Dicloxacillin Sodium [usan:usp:ban:jan]

49. 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl Penicillin Sodium Monohydrate

50. Dicloxacillin Sodium (usp)

51. Cas-13412-64-1

52. Schembl41515

53. Mls001332403

54. Mls001332404

55. Mls002153818

56. Chembl1200701

57. Dtxsid2049002

58. Hms2096i22

59. Hms2234c13

60. Hms3713i22

61. Dicloxacillin Sodium [usan]

62. Bcp28581

63. Hy-b0977

64. Dicloxacillin Sodium [vandf]

65. Tox21_113495

66. Bdbm50005106

67. Dicloxacillin Sodium [mart.]

68. Dicloxacillin Sodium Hydrate (jp17)

69. S4111

70. Dicloxacillin Sodium [usp-rs]

71. Dicloxacillin Sodium [who-ip]

72. Akos015962897

73. Tox21_113495_1

74. Ccg-220450

75. Ccg-269777

76. Cs-4467

77. Nsc 756726

78. Ncgc00178782-04

79. Ncgc00180956-01

80. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, Monohydrate, (2s,5r,6r)-

81. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, Monohydrate, (2s-(2alpha,5alpha,6beta))-

82. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-, Monosodium Salt, Monohydrate

83. Ac-18976

84. Dicloxacillin Sodium [orange Book]

85. Dicloxacillin Sodium Hydrate [jan]

86. Dicloxacillin Sodium [ep Monograph]

87. Dicloxacillin Sodium [usp Impurity]

88. Dicloxacillin Sodium [usp Monograph]

89. D02137

90. D81863

91. Dicloxacillinum Natricum [who-ip Latin]

92. Dicloxacillin Sodium Monohydrate [who-dd]

93. Dicloxacillin Sodium Salt Monohydrate [mi]

94. Dicloxacillin Sodium Monohydrate [green Book]

95. Q27887689

96. Dicloxacillin Sodium, European Pharmacopoeia (ep) Reference Standard

97. Dicloxacillin Sodium Salt Hydrate, Vetranal(tm), Analytical Standard

98. Dicloxacillin Sodium, United States Pharmacopeia (usp) Reference Standard

99. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, Monohydrate, (2s-(2.alpha.,5.alpha.,6.beta.))-

100. Sodium (2s,5r,6r)-6-({[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Hydrate

101. Sodium 6beta-{[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carboxamido}-2,2-dimethylpenam-3alpha-carboxylate--water (1/1)

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 510.3 g/mol
Molecular Formula C19H18Cl2N3NaO6S
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass509.0191061 g/mol
Monoisotopic Mass509.0191061 g/mol
Topological Polar Surface Area142 Ų
Heavy Atom Count32
Formal Charge0
Complexity752
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDicloxacillin sodium
Drug LabelDicloxacillin sodium is a semisynthetic antibiotic substance which resists destruction by the enzyme penicillinase(beta - lactamase). It is monosodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)- 5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-...
Active IngredientDicloxacillin sodium
Dosage FormCapsule
RouteOral
Strengtheq 500mg base; eq 125mg base; eq 250mg base
Market StatusPrescription
CompanyTeva; Sandoz

2 of 2  
Drug NameDicloxacillin sodium
Drug LabelDicloxacillin sodium is a semisynthetic antibiotic substance which resists destruction by the enzyme penicillinase(beta - lactamase). It is monosodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)- 5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-...
Active IngredientDicloxacillin sodium
Dosage FormCapsule
RouteOral
Strengtheq 500mg base; eq 125mg base; eq 250mg base
Market StatusPrescription
CompanyTeva; Sandoz

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Penicillins [CS]; Penicillin-class Antibacterial [EPC]

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