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2D Structure
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

2D Structure

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 Weight 514.6 g/mol
Molecular Formula C22H22N6O5S2
XLogP30.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Exact Mass514.10931017 g/mol
Monoisotopic Mass514.10931017 g/mol
Topological Polar Surface Area208 Ų
Heavy Atom Count35
Formal Charge0
Complexity955
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


4.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DE - Fourth-generation cephalosporins

J01DE02 - Cefpirome