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Chemistry

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Also known as: Cefadole, 34444-01-4, Cephamandole, Cefamandol, Cephadole, Cefamandolum
Molecular Formula
C18H18N6O5S2
Molecular Weight
462.5  g/mol
InChI Key
OLVCFLKTBJRLHI-AXAPSJFSSA-N
FDA UNII
5CKP8C2LLI

Cefamandole
Semisynthetic wide-spectrum cephalosporin with prolonged action, probably due to beta-lactamase resistance. It is used also as the nafate.
1 2D Structure

Cefamandole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]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/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
2.1.3 InChI Key
OLVCFLKTBJRLHI-AXAPSJFSSA-N
2.1.4 Canonical SMILES
CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(C4=CC=CC=C4)O)SC2)C(=O)O
2.1.5 Isomeric SMILES
CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)O)SC2)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
5CKP8C2LLI
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cephamandole

2. Compound 83405

2.3.2 Depositor-Supplied Synonyms

1. Cefadole

2. 34444-01-4

3. Cephamandole

4. Cefamandol

5. Cephadole

6. Cefamandolum

7. L-cefamandole

8. Compound 83405

9. Chebi:3480

10. (6r,7r)-7-(r)-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic Acid

11. 5ckp8c2lli

12. (6r,7r)-7-{[(2r)-2-hydroxy-2-phenylacetyl]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

13. Compound-83405

14. (6r,7r)-7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

15. J01dc03

16. Kefdole

17. 7-d-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic Acid

18. Kefamandol

19. Mancef

20. (6r,7r)-7-((r)-2-hydroxy-2-phenylacetamido)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

21. 7-[(2-hydroxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

22. 30034-03-8

23. Unii-5ckp8c2lli

24. Cefamandol [inn-spanish]

25. Cefamandole (usan/inn)

26. Cefamandolum [inn-latin]

27. Free Form

28. Cefamandole [usan:inn:ban]

29. Einecs 252-030-0

30. Brn 0598510

31. Cefamandole [mi]

32. Prestwick0_000747

33. Prestwick1_000747

34. Prestwick2_000747

35. Prestwick3_000747

36. Cefamandole [inn]

37. Cefamandole [usan]

38. Epitope Id:141490

39. Cefamandole [vandf]

40. Cefamandole [mart.]

41. Chembl1146

42. Schembl37287

43. Bspbio_000734

44. Cefamandole [who-dd]

45. Spbio_002673

46. Bpbio1_000808

47. Dtxsid7022750

48. Gtpl12210

49. Hy-b1128

50. Zinc3830394

51. Bdbm50350468

52. Akos025401365

53. Ac-1294

54. Cs-4724

55. Db01326

56. (6r,7r)-7-[[(2r)-2-hydroxy-2-phenyl-acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

57. (6r,7r)-7-{[(2r)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

58. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7beta(r*)))-

59. 7beta-[(2r)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic Acid

60. C06879

61. D02344

62. 444c014

63. Cefamandole, Antibiotic For Culture Media Use Only

64. Q2601530

65. W-106736

66. Brd-k27130738-236-03-4

67. (6r,7r)-7-((r)-2-hydroxy-2-phenylacetamido)-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

68. (6r,7r)-7-[(2r)-2-hydroxy-2-phenylacetamido]-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

69. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6.alpha.,7.beta.(r*)))-

70. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-, (6r,7r)-

71. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-, 6r,7r)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 462.5 g/mol
Molecular Formula C18H18N6O5S2
XLogP3-0.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count7
Exact Mass462.07801004 g/mol
Monoisotopic Mass462.07801004 g/mol
Topological Polar Surface Area201 Ų
Heavy Atom Count31
Formal Charge0
Complexity777
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 the treatment of serious infections caused by susceptible strains of microorganisms.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The parenteral prodrug formate ester cefamandole nafate is a broad-spectrum cephalosporin antibiotic. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.


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

J01DC03 - Cefamandole


5.4 Biological Half-Life

The half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.


5.5 Mechanism of Action

Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of 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 cefamandole interferes with an autolysin inhibitor.


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ABOUT THIS PAGE

Cefamandole Manufacturers

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

Cefamandole Suppliers

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

Cefamandole GMP

Cefamandole 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 Cefamandole 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 Cefamandole GMP manufacturer or Cefamandole GMP API supplier for your needs.

Cefamandole CoA

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

Cefamandole CoA mostly includes findings from lab analyses of a specific batch. For each Cefamandole 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.

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