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Cefdinir
Also known as: Omnicef, 91832-40-5, Cefzon, Cfdn, Cefdinirum, Ci-983
Molecular Formula
C14H13N5O5S2
Molecular Weight
395.4  g/mol
InChI Key
RTXOFQZKPXMALH-GHXIOONMSA-N
FDA UNII
CI0FAO63WC

A third-generation oral cephalosporin antibacterial agent that is used to treat bacterial infections of the respiratory tract and skin.
Cefdinir is a Cephalosporin Antibacterial.
1 2D Structure

Cefdinir

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
2.1.2 InChI
InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
2.1.3 InChI Key
RTXOFQZKPXMALH-GHXIOONMSA-N
2.1.4 Canonical SMILES
C=CC1=C(N2C(C(C2=O)NC(=O)C(=NO)C3=CSC(=N3)N)SC1)C(=O)O
2.1.5 Isomeric SMILES
C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\O)/C3=CSC(=N3)N)SC1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
CI0FAO63WC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 7-(2 (2-aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic Acid

2. Ci 983

3. Ci-983

4. Ci983

5. Fk 482

6. Fk-482

7. Fk482

8. Omnicef

9. Pd 134393

10. Pd-134393

2.3.2 Depositor-Supplied Synonyms

1. Omnicef

2. 91832-40-5

3. Cefzon

4. Cfdn

5. Cefdinirum

6. Ci-983

7. Fk-482

8. Fk 482

9. Cefdinir Anhydrous

10. Bmy-28488

11. Cefdinir (omnicef)

12. Chebi:3485

13. Cefdinyl

14. Ci0fao63wc

15. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

16. Nsc-758926

17. Cefdinir 100 Microg/ml In Acetonitrile

18. Pd 134393

19. Cefdirnir

20. Cefdinirum [inn-latin]

21. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

22. (6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(n-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

23. Ceftinex

24. (e)-cefdinir

25. Bmy 28488

26. Ci 983

27. (6r,7r)-7-{2-(2-amino-thiazol-4-yl)-2-[(z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

28. (6r,7r,z)-7-(2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

29. Omnicef (tn)

30. Cefzon (tn)

31. Pd-134393

32. Sr-05000001991

33. Unii-ci0fao63wc

34. Cefdinir [usan:usp:inn:ban]

35. Ci983

36. Fk482

37. Cefdinir, 97%

38. (-)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7(sup 2)-(z)-oxime

39. Fr-80482

40. Cefdinir [usan]

41. Cefdinir [inn]

42. Cefdinir [jan]

43. Cefdinir [mi]

44. Cefdinir [vandf]

45. Spectrum5_001560

46. Cefdinir [mart.]

47. Cefdinir [usp-rs]

48. Cefdinir [who-dd]

49. Chembl927

50. Schembl36995

51. Bspbio_002735

52. Mls001304703

53. Mls001424233

54. Bidd:gt0827

55. Spectrum1505208

56. Cefdinir (jp17/usp/inn)

57. Cefdinir [orange Book]

58. Cefdinir [usp Monograph]

59. Dtxsid8046084

60. Cid_6915944

61. Bcpp000293

62. Hms1922l19

63. Hms2093k20

64. Hms3715f07

65. Pharmakon1600-01505208

66. Amy22139

67. Hy-b0136

68. Bdbm50248190

69. Ccg-39455

70. Mfcd00865030

71. Nsc758926

72. S1605

73. Zinc13119676

74. Akos015951262

75. Akos032960348

76. Bcp9000503

77. Cs-1925

78. Db00535

79. Nsc 758926

80. Ncgc00178499-01

81. Ncgc00178499-02

82. Ncgc00178499-08

83. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetyl]amino}-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

84. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl) (hydroxyimino)acetyl)amino)-3-ethenyl-8-oxo-, (6r-(6alpha,7beta(z)))-

85. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(hydroxyiminoacetyl)amino)-3-ethenyl-8-oxo-, (6r-(6-alpha,7-beta(z)))-

86. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2z)-(2-amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-, (6r,7r)-

87. 7beta-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetamido]-3-ethenyl-3,4-didehydrocepham-4-carboxylic Acid

88. As-35316

89. Pd134393

90. Sbi-0206739.p001

91. C-2466

92. C08110

93. D00917

94. Ab01274720-01

95. Ab01274720_02

96. Ab01274720_03

97. Cefdinir, Antibiotic For Culture Media Use Only

98. 832c405

99. A844075

100. Sr-05000001991-1

101. Sr-05000001991-2

102. Brd-k15766189-001-05-6

103. Q27263344

104. (-)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 72-(z)-oxime

105. (6r,7r)-7-(((2z)-(2-amino-4-thiazolyl)(hydroxyimino)acetyl)amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

106. (6r,7r)-7-[[(2z)-2-(2-aminothiazol-4-yl)-2-hydroxyimino-acetyl]amino]-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;cefdinir

107. (7r)-3-vinyl-7-[[(2-amino-4-thiazolyl)[(e)-hydroxyimino]acetyl]amino]cepham-3-ene-4-carboxylic Acid

108. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl) (hydroxyimino)acetyl)amino)-3-ethenyl-8-oxo-, (6r-(6.alpha.,7.beta.(z)))-

109. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2z)-2-(2-amino-4-thiazolyl)-2-(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-, (6r,7r)-

110. Syn-7-(2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic Acid

2.4 Create Date
2006-07-15
3 Chemical and Physical Properties
Molecular Weight 395.4 g/mol
Molecular Formula C14H13N5O5S2
XLogP30
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count5
Exact Mass395.03581088 g/mol
Monoisotopic Mass395.03581088 g/mol
Topological Polar Surface Area212 Ų
Heavy Atom Count26
Formal Charge0
Complexity739
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameCefdinir
PubMed HealthCefdinir (By mouth)
Drug ClassesAntibiotic
Drug LabelCefdinir for oral suspension, USPcontains the active ingredient cefdinir USP, an extended-spectrum, semisynthetic cephalosporin, for oral administration. Chemically, cefdinir is [6R-[6,7 (Z)]]-7-[[(2-amino-4-thiazolyl)(hydroxyimino)acetyl]amino...
Active IngredientCefdinir
Dosage FormCapsule; For suspension
RouteOral
Strength300mg; 125mg/5ml; 250mg/5ml
Market StatusPrescription
CompanyTeva Pharms; Aurobindo Pharma; Lupin; Sandoz; Orchid Hlthcare

2 of 2  
Drug NameCefdinir
PubMed HealthCefdinir (By mouth)
Drug ClassesAntibiotic
Drug LabelCefdinir for oral suspension, USPcontains the active ingredient cefdinir USP, an extended-spectrum, semisynthetic cephalosporin, for oral administration. Chemically, cefdinir is [6R-[6,7 (Z)]]-7-[[(2-amino-4-thiazolyl)(hydroxyimino)acetyl]amino...
Active IngredientCefdinir
Dosage FormCapsule; For suspension
RouteOral
Strength300mg; 125mg/5ml; 250mg/5ml
Market StatusPrescription
CompanyTeva Pharms; Aurobindo Pharma; Lupin; Sandoz; Orchid Hlthcare

4.2 Drug Indication

Cefdinir is indicated to treat acute bacterial otitis media, acute maxillary sinusitis, community-acquired (CA) pneumonia, acute bacterial exacerbations of chronic bronchitis, pharyngitis/tonsillitis, and uncomplicated skin and skin structure infections in children and adults. The organisms susceptible to cefdinir have been listed below in addition to their associated clinical condition that may be treated with cefdinir. Various beta-lactamase producing organisms may be treated, as indicated in certain sections below. **Respiratory** Acute bacterial exacerbations of chronic bronchitis caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis Community-acquired pneumonia caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis **Ear, nose, and throat** Acute bacterial otitis media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pneumoniae (penicillin-susceptible only) Tonsillitis caused by Streptococcus pyogenes Pharyngitis caused by Streptococcus pyogenes Acute maxillary sinusitis caused by Haemophilus pneumoniae and Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis **Skin and skin structure infections** Uncomplicated skin and skin structure infections caused by Staphylococcus aureus and Streptococcus pyogenes


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefdinir is a bactericidal agent that treats bacterial infections by interfering with cell wall synthesis. Cefdinir exerts broad-spectrum activity against a variety of gram-positive and gram-negative bacterial infections. It is effective against several beta-lactamase enzyme producing bacteria. As a result, many organisms that are resistant to other cephalosporins may be susceptible to cefdinir.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CEFDINIR
5.3.2 FDA UNII
CI0FAO63WC
5.3.3 Pharmacological Classes
Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DD - Third-generation cephalosporins

J01DD15 - Cefdinir


5.5 Absorption, Distribution and Excretion

Absorption

Maximal plasma cefdinir concentration can be attained between 2-4 hours after an ingested dose. The bioavailability of cefdinir depends on the formulation used. The estimated bioavailability of cefdinir in the capsule form is approximately 16%-21%, depending on the dose. Absolute bioavailability after the administration of a suspension of cefdinir is 25%.. The Cmax of cefdinir is 1.60 g/mL after a 300 mg dose with an AUC of 7.05. Cmax is 2.87 g/mL after a 600 mg dose with an AUC of 11. A meal high in fat can reduce the absorption of cefdinir by up to 15%, however, this is not a cause for clinically significant changes, therefore cefdinir may be taken with or without food. When given with aluminum or magnesium-containing antacids or iron, cefdinir absorption may decrease. It is recommended to allow 2 hours between cefdinir administration and the administration of these agents.


Route of Elimination

This drug is mainly excreted by the kidneys. Dose adjustments may be required for patients with renal impairment or patients on dialysis. Approximately 18.4% of a 300 mg dose of cefdinir was found unchanged in the urine after a 300 mg dose was administered during a pharmacokinetic study of 21 individuals. A large proportion of the administered dose is excreted in the feces, although the majority is found in the urine.


Volume of Distribution

The average volume of distribution of cefdinir in adults is about 0.35 L/kg and 0.67 L/kg in children. Another resource estimates the volume of distribution in adults at 1.562.09 L/kg. Cefdinir is found to be distributed in various tissues at clinically effective concentrations. It may be found in the epithelial lining fluid, bronchial mucosa, tonsils, sinuses, skin blister fluid, as well as the middle ear fluid. Third-generation cephalosporins such as cefdinir cross the blood-brain barrier and are found in high concentrations in the cerebrospinal fluid, unlike their first and second generation counterparts. The wide tissue distribution of cefdinir allows it to treat a variety of infections throughout the body.


Clearance

The renal clearance in healthy adults in a pharmacokinetic study was 2.0 ( 1.0) mL/min/kg and the clearance in patients with renal failure was lower, decreasing in proportion to the degree of renal impairment. Dose adjustment is required in patients with renal impairment.


5.6 Metabolism/Metabolites

This drug is not significantly metabolized and its pharmacological actions are mainly attributed to the parent drug.


5.7 Biological Half-Life

The average plasma elimination half-life is about 1.7 hours in adults. In children and healthy infants, plasma elimination half-life ranges from 1.21.5 hours.


5.8 Mechanism of Action

Five-member thiazolidine rings that make up penicillins are replaced in cephalosporins by a six-member dihydrothiazine ring, conferring greater bactericidal activity. This This 6-member ring enables cefdinir and other cephalosporins to resist inactivation by certain bacterial enzymes. With a mechanism similar to other beta-lactam antibiotics, the bactericidal activity of cefdinir is caused by the inhibition of cell wall synthesis via binding to penicillin-binding proteins (PBPs). Cefdinir, like other cephalosporins, penetrates the bacterial cell wall, combats inactivation by beta-lactamase enzymes, and inactivates penicillin-binding proteins. This interferes with the final step of transpeptidation in cell walls, eventually leading to cell lysis, which eventually leads to the death of bacteria that are susceptible to this drug. Cefdinir has shown affinity to penicillin protein binding proteins 2 and 3. It has also been shown to inhibit transpeptidase enzymes of various bacteria, which may play a role in its bactericidal action. One in vitro study suggests that cefdinir inhibits myeloperoxidase release extracellularly. The impact of this potential drug target in relation to its mechanism of action is unknown.


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