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Synopsis

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Chemistry

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Also known as: Cefprozil anhydrous, Cefzil, Cefprozilum, 92665-29-7, Cefprozilo, Brisoral

Molecular Formula

C₁₈H₁₉N₃O₅S

Molecular Weight

389.4 g/mol

InChI Key

WDLWHQDACQUCJR-ZAMMOSSLSA-N

FDA UNII

S1SDI2FJIY

Cefprozil Anhydrous is the anhydrous form of cefprozil, a semisynthetic, broad-spectrum, second-generation cephalosporin with antibacterial activity. Cefprozil binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

1 2D Structure

Cefprozil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(E)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/b3-2+/t12-,13-,17-/m1/s1

2.1.3 InChI Key

WDLWHQDACQUCJR-ZAMMOSSLSA-N

2.1.4 Canonical SMILES

CC=CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)SC1)C(=O)O

2.1.5 Isomeric SMILES

C/C=C/C1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)SC1)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

S1SDI2FJIY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 7-(2-amino-2-(4-hydroxyphenyl)acetamido)-3-(propenyl)-3-cephem-4-carboxylic Acid Monohydrate

2. 7-(2-amino-2-(p-hydroxyphenyl)acetamido)-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

3. Arzimol

4. Bmy 28100

5. Bmy-28100

6. Brisoral

7. Cefprozil Monohydrate

8. Cefzil

9. Procef

2.3.2 Depositor-Supplied Synonyms

1. Cefprozil Anhydrous

2. Cefzil

3. Cefprozilum

4. 92665-29-7

5. Cefprozilo

6. Brisoral

7. Cefprozilum [inn-latin]

8. Cefprozilo [inn-spanish]

9. Procef

10. Trans-cefprozil

11. 92676-86-3

12. Arzimol

13. S1sdi2fjiy

14. Cronocef

15. Serozil

16. Cefzil (tn)

17. Cefprozil Anhydrous, E-isomer

18. Bmy 28100

19. Cefprozil Hydrate (cefzil)

20. Cefprozil (e)-isomer (50 Mg)g0d341872ug/mg(ai)

21. (6s,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((e)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

22. Cefprozil (e)-isomer

23. Cefprozil (inn)

24. Cefprozil (tn)

25. Cefprozil [usan:inn]

26. Chebi:3506

27. Unii-1m698f4h4e

28. E-cefprozil

29. (e)-cefprozil

30. Bbs-1067

31. Bmy-28167

32. Unii-s1sdi2fjiy

33. Cefprozil [mart.]

34. Schembl37024

35. Bidd:gt0833

36. Cefprozil E-form [mi]

37. Chembl276568

38. Cefprozil For Peak Identification

39. Hy-b0458a

40. Dtxsid10873545

41. N,n-bisbenzylidenebenzidine

42. 1m698f4h4e

43. Hms3715p22

44. Cefprozil Anhydrous, (e)-

45. Zinc3776970

46. Akos015895989

47. Ccg-221280

48. Db01150

49. (6r,7r)-7-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

50. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2r)-amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-(1-propenyl)-, (6r,7r)-

51. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-(1-propenyl)-, (6r-(6alpha,7beta(r*)))-

52. As-14301

53. Discontinued. Please See C243933.

54. Cs-0013517

55. C06888

56. C16732

57. D07651

58. Ab01274812-01

59. Ab01274812_02

60. 665c297

61. Cefprozil, Mix Of Z (92%), And E (7%) Isomers

62. Q3231623

63. (6r,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((e)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

64. (6r,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((e)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid

65. (6r,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((e)-prop-1-enyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

66. (6r,7r)-7-((r)-2-amino-2-(p-hydroxyphenyl)acetamido)-8-oxo-3-propenyl-5-thia-1-azabicyclo(4.2.0)oct-2(e)-ene-2-carboxylic Acid

67. (6r,7r)-7-[(2r)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

68. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2r)-amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-(1e)-1-propenyl-,(6r,7r)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₉N₃O₅S
Molecular Weight	389.4 g/mol
XLogP3	-1.4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	389.10454189 g/mol
Monoisotopic Mass	389.10454189 g/mol
Topological Polar Surface Area	158 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	699
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Cefprozil
PubMed Health	Cefprozil (By mouth)
Drug Classes	Antibiotic
Drug Label	Cefprozil is a semi-synthetic broad-spectrum cephalosporin antibiotic.Cefprozil is a cis and trans isomeric mixture (90% cis). The chemical name for the monohydrate is (6R,7R)-7-[(R)-2-amino-2-(p-hydroxyphenyl)acetamido]-8-oxo-3-propenyl-5-thia-1-...
Active Ingredient	Cefprozil
Dosage Form	Tablet; For suspension
Route	Oral
Strength	250mg; 125mg/5ml; 500mg; 250mg/5ml
Market Status	Prescription
Company	Wockhardt; Teva Pharms; Teva; Apotex; Aurobindo Pharma; Lupin; Sandoz; Orchid Hlthcare

2 of 2
Drug Name	Cefprozil
PubMed Health	Cefprozil (By mouth)
Drug Classes	Antibiotic
Drug Label	Cefprozil is a semi-synthetic broad-spectrum cephalosporin antibiotic.Cefprozil is a cis and trans isomeric mixture (90% cis). The chemical name for the monohydrate is (6R,7R)-7-[(R)-2-amino-2-(p-hydroxyphenyl)acetamido]-8-oxo-3-propenyl-5-thia-1-...
Active Ingredient	Cefprozil
Dosage Form	Tablet; For suspension
Route	Oral
Strength	250mg; 125mg/5ml; 500mg; 250mg/5ml
Market Status	Prescription
Company	Wockhardt; Teva Pharms; Teva; Apotex; Aurobindo Pharma; Lupin; Sandoz; Orchid Hlthcare

4.2 Drug Indication

For the treatment of the following infections (respiratory, skin, soft tissue, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staph

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cefprozil, a semisynthetic, second-generation cephalosporin, is used to treat otitis media, soft-tissue infections, and respiratory tract infections.

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 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DC - Second-generation cephalosporins

J01DC10 - Cefprozil

5.4 Absorption, Distribution and Excretion

Absorption

Oral bioavailability is approximately 95%.

Volume of Distribution

0.23 L/kg

Clearance

3 mL/min/kg [fasting subjects]

5.5 Metabolism/Metabolites

Cefprozil is eliminated primarily by the kidneys

5.6 Biological Half-Life

1.3 hours

5.7 Mechanism of Action

Cefprozil, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefprozil interferes with an autolysin inhibitor.

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