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Chemistry

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Also known as: 70797-11-4, Cefpiramide acid, Cefpiramido, Cefpiramidum, Wy-44635, Wy-44,635
Molecular Formula
C25H24N8O7S2
Molecular Weight
612.6  g/mol
InChI Key
PWAUCHMQEXVFJR-PMAPCBKXSA-N
FDA UNII
P936YA152N

Cefpiramide
Cefpiramide is a third-generation, semi-synthetic, beta-lactam cephalosporin antibiotic with antibacterial activity. Cefpiramide binds to penicillin-binding proteins (PBPs), transpeptidases that are responsible for crosslinking of peptidoglycan. By preventing crosslinking of peptidoglycan, cell wall integrity is lost and cell wall synthesis is halted.
1 2D Structure

Cefpiramide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-7-[[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1H-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
2.1.2 InChI
InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1
2.1.3 InChI Key
PWAUCHMQEXVFJR-PMAPCBKXSA-N
2.1.4 Canonical SMILES
CC1=CC(=O)C(=CN1)C(=O)NC(C2=CC=C(C=C2)O)C(=O)NC3C4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
2.1.5 Isomeric SMILES
CC1=CC(=O)C(=CN1)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@H]3[C@@H]4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
P936YA152N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cefpiramide Sodium

2. Cefpiramide, Sodium Salt

3. Sm 1652

4. Sm-1652

5. Sumcefal

2.3.2 Depositor-Supplied Synonyms

1. 70797-11-4

2. Cefpiramide Acid

3. Cefpiramido

4. Cefpiramidum

5. Wy-44635

6. Wy-44,635

7. (6r,7r)-7-[[(2r)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1h-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

8. Chebi:59213

9. P936ya152n

10. Nsc-759869

11. Ncgc00167444-01

12. Sm 1652

13. Sm-1652

14. (7r)-7-[[(2r)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1h-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

15. (6r,7r)-7-((r)-2-(4-hydroxy-6-methylnicotinamido)-2-(4-hydroxyphenyl)acetamido)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

16. Wy 44,635

17. Cefpiramidum [inn-latin]

18. Cefpiramido [inn-spanish]

19. Unii-p936ya152n

20. Cefpiramide [usan:usp:inn]

21. Wy 44635

22. Cefpiramide (usp/inn)

23. Cefpiramide [mi]

24. Cefpiramide [inn]

25. Cefpiramide [usan]

26. Cefpiramide [mart.]

27. Dsstox_cid_26630

28. Dsstox_rid_81778

29. Dsstox_gsid_46630

30. Schembl49253

31. Cefpiramide [usp-rs]

32. Cefpiramide [who-dd]

33. Chembl1201204

34. Dtxsid6046630

35. Gtpl12027

36. Cefpiramide [usp Impurity]

37. Hms3715h12

38. Hy-b1354

39. Zinc4215257

40. Tox21_112448

41. Mfcd00864893

42. S5186

43. Akos025311237

44. Ccg-221235

45. Db00430

46. Nsc 759869

47. Ncgc00167444-04

48. (6r,7r)-7-((r)-2-(4-hydroxy-6-methylnicotinamido)-2-(p-hydroxyphenyl)acetamido)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

49. As-14170

50. Cas-70797-11-4

51. Cs-0013097

52. D03428

53. 797c114

54. Q4921174

55. Brd-k92872987-001-02-9

56. Cefpiramide Acid;cefpiramido;cefpiramidum;wy-44635;sm-1652

57. (6r,7r)-7-((r)-2-(4-hydroxy-6-methylnicotinamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

58. (6r,7r)-7-[(2r)-2-[(4-hydroxy-6-methylpyridin-3-yl)formamido]-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1h-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

59. (6r,7r)-7-{[(2r)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

60. (7r)-7-((r)-2-(4-hydroxy-6-methylnicotinamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

61. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((((4-hydroxy-6-methyl-3-pyridinyl)carbonyl)amino)(4-hydroxyphenyl)acetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7beta(r*)))-

62. 7beta-[(2r)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic Acid

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 612.6 g/mol
Molecular Formula C25H24N8O7S2
XLogP3-0.1
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count13
Rotatable Bond Count9
Exact Mass612.12093748 g/mol
Monoisotopic Mass612.12093748 g/mol
Topological Polar Surface Area259 Ų
Heavy Atom Count42
Formal Charge0
Complexity1270
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For treatment of severe infections caused by susceptible bacteria such as P. aeruginosa.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefpiramide is a cephalosporin active against Pseudomonas aeruginosa. It has a broad spectrum of antibacterial activity. Cefpiramide works by inhibiting bacterial cell wall biosynthesis. The plasma half-lives of cefpiramide in rabbits, dogs, and rhesus monkeys were much longer than those of cefoperazone and cefazolin.


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

J01DD - Third-generation cephalosporins

J01DD11 - Cefpiramide


5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following intramuscular injection.


5.5 Biological Half-Life

4.44 hours


5.6 Mechanism of Action

The bactericidal activity of cefpiramide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).


REF. STANDARDS & IMPURITIES

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ABOUT THIS PAGE

Cefpiramide Manufacturers

A Cefpiramide manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Cefpiramide, including repackagers and relabelers. The FDA regulates Cefpiramide manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Cefpiramide API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Cefpiramide manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Cefpiramide Suppliers

A Cefpiramide supplier is an individual or a company that provides Cefpiramide active pharmaceutical ingredient (API) or Cefpiramide finished formulations upon request. The Cefpiramide suppliers may include Cefpiramide API manufacturers, exporters, distributors and traders.

click here to find a list of Cefpiramide suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Cefpiramide USDMF

A Cefpiramide DMF (Drug Master File) is a document detailing the whole manufacturing process of Cefpiramide active pharmaceutical ingredient (API) in detail. Different forms of Cefpiramide DMFs exist exist since differing nations have different regulations, such as Cefpiramide USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Cefpiramide DMF submitted to regulatory agencies in the US is known as a USDMF. Cefpiramide USDMF includes data on Cefpiramide's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Cefpiramide USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Cefpiramide suppliers with USDMF on PharmaCompass.

Cefpiramide GMP

Cefpiramide Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Cefpiramide GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Cefpiramide GMP manufacturer or Cefpiramide GMP API supplier for your needs.

Cefpiramide CoA

A Cefpiramide CoA (Certificate of Analysis) is a formal document that attests to Cefpiramide's compliance with Cefpiramide specifications and serves as a tool for batch-level quality control.

Cefpiramide CoA mostly includes findings from lab analyses of a specific batch. For each Cefpiramide CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Cefpiramide may be tested according to a variety of international standards, such as European Pharmacopoeia (Cefpiramide EP), Cefpiramide JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Cefpiramide USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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