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Loracarbef

Loracarbef

Synopsis, Chemistry

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Also known as: 76470-66-1, Loracarbefum, Loracarbef anhydrous, Loracarbefum [inn-latin], Anhydrous loracarbef, Loracarbef, anhydrous

Molecular Formula

C₁₆H₁₆ClN₃O₄

Molecular Weight

349.77 g/mol

InChI Key

JAPHQRWPEGVNBT-UTUOFQBUSA-N

FDA UNII

W72I5ZT78Z

Loracarbef Anhydrous is an anhydrous form of loracarbef, a semi-synthetic, broad-spectrum, beta-lactamase resistant, second-generation cephalosporin antibiotic derived from cephasporium.

Loracarbef anhydrous is a Cephalosporin Antibacterial.

1 2D Structure

Loracarbef

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7S)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12+/m1/s1

2.1.3 InChI Key

JAPHQRWPEGVNBT-UTUOFQBUSA-N

2.1.4 Canonical SMILES

C1CC(=C(N2C1C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)Cl

2.1.5 Isomeric SMILES

C1CC(=C(N2[C@H]1[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)Cl

2.2 Other Identifiers

2.2.1 UNII

W72I5ZT78Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Carbac

2. Kt 3777

3. Kt-3777

4. Lorabid

5. Loracarbef Monohydrate

6. Lorafem

7. Lorax

8. Ly 163892

9. Ly-163892

10. Ly163892

2.3.2 Depositor-Supplied Synonyms

1. 76470-66-1

2. Loracarbefum

3. Loracarbef Anhydrous

4. Loracarbefum [inn-latin]

5. Anhydrous Loracarbef

6. Loracarbef, Anhydrous

7. W72i5zt78z

8. (6r,7s)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

9. Chebi:47544

10. Loracarbef (inn)

11. Ly-163892

12. 1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-, (6r,7s)-

13. Loracarbef [inn]

14. (6r,7s)-7-{[(2r)-2-amino-2-phenylacetyl]amino}-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

15. Kt 3777

16. Unii-w72i5zt78z

17. Ly163892

18. Lorbef

19. Loracarbef [usan:inn:ban]

20. Ly 163892

21. Lorbef (tn)

22. Loracabef

23. Loracarbef [mi]

24. Chembl1013

25. Loracarbef [who-dd]

26. Schembl34153

27. Bidd:gt0753

28. Dtxsid7023223

29. Hms3713l04

30. Hy-b1682

31. Zinc1530993

32. Akos015895936

33. Ccg-220611

34. Db00447

35. 7beta-[(2r)-2-amino-2-phenylacetyl]nitrilo-3-chloro-3,4-didehydrocepham-4-carboxylic Acid

36. Ncgc00510749-15

37. 1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((aminophenylacetyl)amino)-3-chloro-8-oxo-, (6r-(6alpha,7beta(r*)))-

38. Cs-0013651

39. D08143

40. Q979521

41. Brd-k28935038-001-01-4

42. (6r,7s)-7-[(2r)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

43. 1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2r)-aminophenylacetyl)amino)-3-chloro-8-oxo-, (6r,7s)-

2.4 Create Date

2005-11-20

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₆ClN₃O₄
Molecular Weight	349.77 g/mol
XLogP3	-1.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	349.0829337 g/mol
Monoisotopic Mass	349.0829337 g/mol
Topological Polar Surface Area	113 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	600
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used to treat upper respiratory tract bacterial infections, chronic bronchitis, pneumonia, sinusitis, pharyntitis and tonsillitis, skin absceses, urinary tract infections and pyelonephritis caused by E. coli, S. pyogenes, S. aureus, S. saprphyticus, S. penumoniae, H. influenzae and M. catarrhalis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Loracarbef is considered a second generation cephalosporin antibiotic. The advantages of cephalosporin antibiotics include a broad range of activity, a safe record in children with almost no dose-related toxicity, and the lack of need to monitor levels. Adverse reactions are rare and consist primarily of hypersensitivity reactions with urticaria, nonspecific rash, and pruritus. Loracarbef can be used to treat a large number of bacterial infections caused by gram-negative and gram-positive bacteria, including upper respiratory tract bacterial infections, chronic bronchitis, pneumonia, sinusitis, pharyntitis and tonsillitis, skin absceses, urinary tract infections and pyelonephritis caused by E. coli, S. pyogenes, S. aureus, S. saprphyticus, S. penumoniae, H. influenzae and M. catarrhalis.

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

LORACARBEF ANHYDROUS

5.3.2 FDA UNII

W72I5ZT78Z

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Cephalosporins

5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DC - Second-generation cephalosporins

J01DC08 - Loracarbef

5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed with approximately 90% absorbed from the gastrointestinal tract after oral ingestion.

5.6 Metabolism/Metabolites

There is no evidence of metabolism in humans.

5.7 Biological Half-Life

1 hour. In subjects with moderate impairment of renal function the plasma half-life was prolonged to approximately 5.6 hours.

5.8 Mechanism of Action

Loracarbef is an oral, synthetic beta-lactam antibiotic of the carbacephem class. Chemically, carbacephems differ from cephalosporin-class antibiotics in the dihydrothiazine ring where a methylene group has been substituted for a sulfur atom. Loracarbef has a spectrum of activity similar to that of the second generation cephalosporins. It is structurally identical to cefaclor except for a sulfur atom that has been replaced by a methylene group. This change gives greater chemical stability in solution and allows storage at room temperature. Loracarbef, like all b-lactams and cephalosporins, inhibits penicillin binding proteins, enzymes that create the cross-linkage of the peptidoglycan polymer. This binding leads to interference with the formation and remodeling of the cell wall structure.