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Chemistry

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Also known as: 56796-20-4, Cefmetazolo, Cefmetazolum, Cefmetazolum [inn-latin], Cefmetazolo [inn-spanish], (6r,7s)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Formula
C15H17N7O5S3
Molecular Weight
471.5  g/mol
InChI Key
SNBUBQHDYVFSQF-HIFRSBDPSA-N
FDA UNII
3J962UJT8H

Cefmetazole
A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.
1 2D Structure

Cefmetazole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-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/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
2.1.3 InChI Key
SNBUBQHDYVFSQF-HIFRSBDPSA-N
2.1.4 Canonical SMILES
CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
2.1.5 Isomeric SMILES
CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
3J962UJT8H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cefmetazole Monosodium Salt

2. Cefmetazole Sodium

3. Cefmetazon

4. Cs 1170

5. Cs-1170

6. Cs1170

7. Monosodium Salt, Cefmetazole

8. Salt, Cefmetazole Monosodium

9. Sodium, Cefmetazole

10. U 72791a

11. U-72791a

12. U72791a

13. Zefazone

2.3.2 Depositor-Supplied Synonyms

1. 56796-20-4

2. Cefmetazolo

3. Cefmetazolum

4. Cefmetazolum [inn-latin]

5. Cefmetazolo [inn-spanish]

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

7. Chebi:3489

8. U-72791

9. 3j962ujt8h

10. (6r,7s)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

11. (6r,7s)-7-(2-((cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

12. 56796-20-4 (free)

13. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((((cyanomethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-cis)-

14. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-, (6r,7s)-

15. Cs 1170

16. Skf 83088

17. U 72791

18. Cefmetazole (usp/inn)

19. Einecs 260-384-2

20. Brn 0634647

21. Unii-3j962ujt8h

22. Cefmetazole [usan:usp:inn]

23. Cefmetazolesodium

24. Cefmetazole [mi]

25. Prestwick0_000700

26. Prestwick1_000700

27. Prestwick2_000700

28. Prestwick3_000700

29. Cefmetazole [inn]

30. Cefmetazole [usan]

31. Epitope Id:116204

32. Cefmetazole [vandf]

33. Cefmetazole [mart.]

34. Lopac0_000266

35. Bspbio_000859

36. Cefmetazole [usp-rs]

37. Cefmetazole [who-dd]

38. Schembl147832

39. Spbio_002780

40. Bpbio1_000945

41. Cefmetazole Sodium [jan]

42. Chembl1201195

43. Dtxsid7022756

44. Gtpl12215

45. Cefmetazole [usp Impurity]

46. Cefmetazole [usp Monograph]

47. Bcp11998

48. Hy-b1595

49. Zinc3830417

50. Bdbm50350471

51. Mfcd00865068

52. Akos015896219

53. Db00274

54. Sdccgsbi-0050254.p002

55. (6r,7s)-7-({[(cyanomethyl)thio]acetyl}amino)-7-(methyloxy)-3-{[(1-methyl-1h-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

56. (6r,7s)-7-(2-((cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, Sodium Salt

57. Ac-13154

58. Bs-42476

59. 2,6-difluoro-4-methoxyacetophenone

60. Cs-0013513

61. C08103

62. D00910

63. A831178

64. J-700159

65. Q5057238

66. (6r,7s)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia

67. (6r,7s)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-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,7s)-7-[[2-(cyanomethylthio)-1-oxoethyl]amino]-7-methoxy-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

69. (6r,7s)-7-[2-(cyanomethylsulfanyl)ethanoylamino]-7-methoxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanylmethyl]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

70. (6r,7s)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-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

71. 7beta-{[(cyanomethyl)sulfanyl]acetamido}-7alpha-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic Acid

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 471.5 g/mol
Molecular Formula C15H17N7O5S3
XLogP3-0.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count9
Exact Mass471.04533019 g/mol
Monoisotopic Mass471.04533019 g/mol
Topological Polar Surface Area239 Ų
Heavy Atom Count30
Formal Charge0
Complexity818
Isotope Atom Count0
Defined Atom Stereocenter Count2
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 infections caused by susceptible organisms.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefmetazole is a second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins. Cefmetazole is more active than 1st-generation cephalosporins against indole-positive Proteus, Serratia, anaerobic gram-negative bacilli (including B. fragilis), and some E. coli, Klebsiella, and P. mirabilis, but is less active than cefoxitin or cefotetan against most gram-negative bacilli.


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

J01DC09 - Cefmetazole


5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability is approximately 100% following intramuscular injection.


5.5 Metabolism/Metabolites

No appreciable metabolism.


5.6 Biological Half-Life

1.50 ±0.14 hours


5.7 Mechanism of Action

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


JDMF

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Cefmetazole Acid

Registration Number : 305MF10064

Registrant's Address : No. 1688 Shixian Road, Jining City, Shandong Province

Initial Date of Registration : 2023-05-17

Latest Date of Registration : 2023-05-17

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Cefmetazole

Registration Number : 231MF10089

Registrant's Address : No. 1688 Shixian Road, Jining City, Shandong Province

Initial Date of Registration : 2019-04-11

Latest Date of Registration : 2019-04-11

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Cefmetazole

Registration Number : 229MF10137

Registrant's Address : No. 6, Gaogang Avenue, Jiangyin Industrial Estate, Fuqing, Fuzhou, Fujian, China

Initial Date of Registration : 2017-07-24

Latest Date of Registration : 2017-07-24

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Cefmetazole

Registration Number : 227MF10099

Registrant's Address : No. 1688 Shixian Road, Jining City, Shandong Province

Initial Date of Registration : 2015-04-09

Latest Date of Registration : 2015-04-09

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Cefmetazole

Brand Name : Metafar

Dosage Form : Cephmetazol 1.000Mg 4Ml 1 Units Parenteral Use

Dosage Strength : 1 vial IM 1 g + 1 ampoule solv 4 ml

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Approval Date :

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Regulatory Info :

Registration Country : Italy

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Cefmetazole

Brand Name : Metafar

Dosage Form : Cephmetazol 1.000Mg 4Ml 1 Units Parenteral Use

Dosage Strength : 1 vial IM 1 g + 1 ampoule solv 4 ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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ABOUT THIS PAGE

Cefmetazole Manufacturers

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

Cefmetazole Suppliers

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

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

Cefmetazole USDMF

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

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

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

Cefmetazole JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Cefmetazole Drug Master File in Japan (Cefmetazole JDMF) empowers Cefmetazole API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Cefmetazole JDMF during the approval evaluation for pharmaceutical products. At the time of Cefmetazole JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Cefmetazole suppliers with JDMF on PharmaCompass.

Cefmetazole GMP

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

Cefmetazole CoA

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

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

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