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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
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 Weight 389.4 g/mol
Molecular Formula C18H19N3O5S
XLogP3-1.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Exact Mass389.10454189 g/mol
Monoisotopic Mass389.10454189 g/mol
Topological Polar Surface Area158 Ų
Heavy Atom Count27
Formal Charge0
Complexity699
Isotope Atom Count0
Defined Atom Stereocenter Count3
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 NameCefprozil
PubMed HealthCefprozil (By mouth)
Drug ClassesAntibiotic
Drug LabelCefprozil 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 IngredientCefprozil
Dosage FormTablet; For suspension
RouteOral
Strength250mg; 125mg/5ml; 500mg; 250mg/5ml
Market StatusPrescription
CompanyWockhardt; Teva Pharms; Teva; Apotex; Aurobindo Pharma; Lupin; Sandoz; Orchid Hlthcare

2 of 2  
Drug NameCefprozil
PubMed HealthCefprozil (By mouth)
Drug ClassesAntibiotic
Drug LabelCefprozil 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 IngredientCefprozil
Dosage FormTablet; For suspension
RouteOral
Strength250mg; 125mg/5ml; 500mg; 250mg/5ml
Market StatusPrescription
CompanyWockhardt; 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.


API SUPPLIERS

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01

Acs Dobfar Spa

Italy

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Medlab Asia & Asia Health
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Medlab Asia & Asia Health
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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 26354

Submission : 2012-08-22

Status : Inactive

Type : II

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Medlab Asia & Asia Health
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Medlab Asia & Asia Health
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03

Medlab Asia & Asia Health
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GDUFA

DMF Review : Complete

Rev. Date : 2014-06-24

Pay. Date : 2014-03-24

DMF Number : 18469

Submission : 2005-06-28

Status : Active

Type : II

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Hetero Drugs Ltd

India

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Medlab Asia & Asia Health
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DMF Review : N/A

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DMF Number : 18434

Submission : 2005-06-16

Status : Inactive

Type : II

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Lupin Ltd

India

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Medlab Asia & Asia Health
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Lupin Ltd

India
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Medlab Asia & Asia Health
Not Confirmed

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DMF Review : N/A

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DMF Number : 17731

Submission : 2004-09-29

Status : Active

Type : II

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Orchid Pharma Ltd

India

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Medlab Asia & Asia Health
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Medlab Asia & Asia Health
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Medlab Asia & Asia Health
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DMF Review : N/A

Rev. Date :

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DMF Number : 16973

Submission : 2003-11-21

Status : Inactive

Type : II

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Sandoz Private Ltd

Switzerland

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