Cefpirome

Synopsis, Chemistry

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Also known as: 84957-29-9, Cefpiroma, Cefpiromum, Cefrom, Cefir, Cefpirome sulfate

Molecular Formula

C₂₂H₂₂N₆O₅S₂

Molecular Weight

514.6 g/mol

InChI Key

DKOQGJHPHLTOJR-WHRDSVKCSA-N

FDA UNII

S72Q2F09HY

Cefpirome is a semisynthetic, broad-spectrum, fourth-generation cephalosporin with antibacterial activity. Cefpirome 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

Cefpirome

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20-/m1/s1

2.1.3 InChI Key

DKOQGJHPHLTOJR-WHRDSVKCSA-N

2.1.4 Canonical SMILES

CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCC5)C(=O)[O-]

2.1.5 Isomeric SMILES

CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCC5)C(=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

S72Q2F09HY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-((2,3-cyclopenteno-1-pyridinium)methyl)-7-(2-syn-methoximino-2-(2-aminothiazole-4-yl)acetamido)ceph-3-em-4-carboxylate

2. Cefpirome Sulfate

3. Cefrom

4. Hr 810

5. Hr-810

6. Metran

2.3.2 Depositor-Supplied Synonyms

1. 84957-29-9

2. Cefpiroma

3. Cefpiromum

4. Cefrom

5. Cefir

6. Cefpirome Sulfate

7. Hr 810

8. Hr-810 Free Base

9. Chebi:3503

10. S72q2f09hy

11. Hr-810

12. Cefpirome (inn)

13. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5h-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

14. Cefpirome Sulphate

15. Cefpirome [inn]

16. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5h-cyclopenta[b]pyridinium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

17. 5h-cyclopenta[b]pyridinium,1-[[(6r,7r)-7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-, Inner Salt

18. Cefpiromum [latin]

19. Cefpiroma [spanish]

20. Cefpirome [inn:ban]

21. Ncgc00181339-01

22. Unii-s72q2f09hy

23. Broact

24. Keiten

25. Keiten, Cefpiroma

26. Cefir (tn)

27. Cefpirome [mi]

28. Cefpirome [who-dd]

29. Schembl49406

30. Mls006010792

31. Chembl65794

32. Dtxsid2048244

33. Schembl22207951

34. Akos016013926

35. Db13682

36. 1-(((6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-5h-1-pyridinium Hydroxide, Inner Salt

37. 5h-1-pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-, Hydroxide, Inner Salt, (6r-(6alpha,7beta(z)))-

38. Smr004701476

39. 98753-19-6

40. D07649

41. (6r,7r)-7-((2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-8-oxo-3-(2beta-trimethylenpyridinio)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carboxylat

42. 1-(((6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-5h-1-pyrindinium Hydroxide, Inner Salt, 72-(z)-(o-methyloxime)

43. 1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5h,6h,7h-cyclopenta[b]pyridin-1-ium

44. 5h-1-pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, Hydroxide, Inner Salt, (6r-(6alpha,7beta(z)))-

45. 5h-1-pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-, Hydroxide, Inner Salt, (6r-(6.alpha.,7.beta.(z)))-

46. 7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5h-cyclopenta[b]pyridinium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylic Acid

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₂N₆O₅S₂
Molecular Weight	514.6 g/mol
XLogP3	0.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	6
Exact Mass	514.10931017 g/mol
Monoisotopic Mass	514.10931017 g/mol
Topological Polar Surface Area	208 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	955
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1