Cephapirin

  • CAT Number: R051064
  • CAS Number: 21593-23-7
  • Molecular Formula: C17H17N3O6S2
  • Molecular Weight: 423.458
  • Purity: ≥95%
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Cephapirin(CAS: 21593-23-7) is a semisynthetic, broad-spectrum, first-generation cephalosporin with antibacterial activity. Cephapirin 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.<br />
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Cephapirin is a cephalosporin with acetoxymethyl and 2(pyridin-4-ylsulfanyl)acetamido substituents at positions 3 and 7, respectively, of the cephem skeleton. It is used (as its sodium salt) as an antibiotic, being effective against gram-negative and gram-positive organisms. It has a role as an antibacterial drug. It is a conjugate acid of a cephapirin(1-).<br />
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Cefapirin (INN, also spelled cephapirin), commonly marketed under the trade name Cefadyl, is a first-generation cephalosporin antibiotic that is available in injectable formulations. Production for use in humans has been discontinued in the United States. Cefapirin is partly plasma-bound and is effective against gram-negative and gram-positive organisms.

Catalog Number R051064
CAS Number 21593-23-7
Molecular Formula

C17H17N3O6S2

Purity 95%
Target Antibiotic
Solubility Soluble in DMSO
Storage Store at -20°C
IUPAC Name (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChI InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
InChIKey UQLLWWBDSUHNEB-CZUORRHYSA-N
SMILES CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O
Reference

[1]. Vet Rec. 2020 Mar 21;186(11):350-352. doi: 10.1136/vr.m1049.<br />
Does intrauterine cephapirin improve subsequent fertility in cows with clinical endometritis?<br />
Hyde B(1), Brennan M(2).<br />
Author information: (1)School of Veterinary Medicine and Science, University of Nottingham, Sutton Bonington, UK. (2)Centre for Evidence-based Veterinary Medicine, University of Nottingham, Sutton Bonington, UK.<br />
DOI: 10.1136/vr.m1049 PMID: 32198250 [Indexed for MEDLINE]<br />
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[2]. Med Lett Drugs Ther. 1974 Jun 21;16(13):53-4.<br />
Cephapirin.<br />
[No authors listed]<br />
PMID: 4842601 [Indexed for MEDLINE]<br />
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[3]. Rapid Commun Mass Spectrom. 2020 Dec 15;34(23):e8948. doi: 10.1002/rcm.8948.<br />
Study of the impurity profile and characteristic fragmentation of &Delta;(3) -isomers in cephapirin sodium using dual liquid chromatography coupled with ion trap/time-of-flight mass spectrometry.<br />
Ren X(1), Zhou J(1), Hu F(2), Wang J(1)(3).<br />
Author information: (1)Zhejiang University of Technology, Hangzhou, 310014, China. (2)Zhejiang Drug Inspection Center, Hangzhou, 310013, China. (3)Key Laboratory for Core Technology of Generic Drug Evaluation National Medical Product Administration, Zhejiang Institute for Food and Drug Control, Hangzhou, 310052, China.<br />
RATIONALE: According to the requirements of the International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH), the structures of impurities in pharmaceutical products present at over 0.1% need to be confirmed. Therefore, the aim of this study is to separate and identify the impurities in cephapirin sodium drug substances, so as to guide the industry to improve the production process and storage conditions and reduce the amount of impurities in the product. METHODS: In the first chromatography dimension, a Boston Green ODS (4.6&thinsp;mm&thinsp;&times;&thinsp;250&thinsp;mm, 5&thinsp;&mu;m) column was used, with a mobile phase composed of 0.05&thinsp;M sodium dihydrogen phosphate aqueous solution and acetonitrile. In the second dimension, the column was a Shimadzu Shim-pack GISS C18 (50&thinsp;mm&thinsp;&times;&thinsp;2.1&thinsp;mm, 1.9&thinsp;&mu;m), using 10&thinsp;mM ammonium formate solution and methanol as the mobile phase. RESULTS: The fragmentation behavior of cephapirin and its impurities and isomers was studied and the structures of impurities were deduced based on the MSn data. For six unknown impurities tentative structures were proposed. The degradation behavior of cephapirin sodium was also studied. Impurities 1 to 11 were found in commercial cephapirin sodium samples, indicating that cephapirin sodium should be stored in closed containers. CONCLUSIONS: The contradiction between the non-volatile mobile phase and mass spectrometry was solved by means of multiple heart-cutting approaches and an on-line desalting technique. Twelve impurities and isomers were separated and characterized. These results could be used to improve the methods described in pharmacopoeias for the quality control of cephapirin sodium.<br />
DOI: 10.1002/rcm.8948 PMID: 32957160<br />
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[4]. J Dairy Sci. 2021 Mar;104(3):3559-3563. doi: 10.3168/jds.2020-19537. Epub 2020 Dec 25.<br />
Short communication: Efficacy of a second intrauterine cephapirin infusion for the treatment of purulent vaginal discharge and endometritis in postpartum dairy cows.<br />
Dubuc J(1), Fauteux V(2), Villettaz-Robichaud M(2), Roy JP(2), Rousseau M(2), Buczinski S(2).<br />
Author information: (1)Facult&eacute; de m&eacute;decine v&eacute;t&eacute;rinaire, Universit&eacute; de Montr&eacute;al, 3200 rue Sicotte, Saint-Hyacinthe, Qu&eacute;bec, J2S 2M2, Canada. Electronic address: [email protected]. (2)Facult&eacute; de m&eacute;decine v&eacute;t&eacute;rinaire, Universit&eacute; de Montr&eacute;al, 3200 rue Sicotte, Saint-Hyacinthe, Qu&eacute;bec, J2S 2M2, Canada.<br />
The objective of this study was to quantify the efficacy of a second intrauterine cephapirin treatment administered 14 d after the initial one on subsequent reproductive performance of postpartum dairy cows affected by purulent vaginal discharge (PVD) or endometritis (ENDO). In total, 4,140 Holstein cows from 30 commercial herds were enrolled in a randomized clinical trial. At 36 (&plusmn;7) d in milk, cows were examined using the Metricheck device to diagnose PVD. An endometrial cytology sample was also collected from each cow to perform a leukocyte esterase test for diagnosing ENDO. Diagnosis of PVD and ENDO was done cow-side. Cows diagnosed with PVD or ENDO were assigned to receive 1 of 2 treatments: (1) a single intrauterine cephapirin infusion (500 mg of cephapirin benzathin; Metricure, Merck Animal Health, Kirkland, QC, Canada) at the time of initial examination or (2) a single intrauterine infusion at the time of initial examination and a second one 14 d later. Subsequent reproductive and culling events were collected until 200 d in milk. Statistical analyses were performed using univariable and multivariable mixed logistic regression models. In cows affected by PVD, a second intrauterine cephapirin infusion increased the pregnancy risk at first insemination in comparison with cows that only received one treatment (28.0 vs. 38.8%). In cows affected by ENDO, a second treatment also increased the pregnancy risk at first insemination compared with cows that only received one treatment (30.3 vs. 39.2%). Overall, these results demonstrate that administering a second intrauterine cephapirin infusion 14 d after the initial treatment in postpartum cows affected by PVD or ENDO did improve their subsequent reproductive performance.<br />
DOI: 10.3168/jds.2020-19537 PMID: 33358808 [Indexed for MEDLINE]<br />
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[5]. Theriogenology. 2020 Oct 15;156:20-26. doi: 10.1016/j.theriogenology.2020.06.024. Epub 2020 Jun 29.<br />
Field trial on the post-insemination intrauterine treatment of dairy cows with mild endometritis with cephapirin.<br />
Schlegl R(1), Drillich M(2), Ballas P(3), Reinl&auml;nder U(1), Iwersen M(1), Baumgartner W(4), Ehling-Schulz M(5), Wagener K(1).<br />
Author information: (1)Clinical Unit for Herd Health Management in Ruminants, University Clinic for Ruminants, Department of Farm Animals and Veterinary Public Health, University of Veterinary Medicine Vienna, Veterin&auml;rplatz 1, 1210, Vienna, Austria. (2)Clinical Unit for Herd Health Management in Ruminants, University Clinic for Ruminants, Department of Farm Animals and Veterinary Public Health, University of Veterinary Medicine Vienna, Veterin&auml;rplatz 1, 1210, Vienna, Austria. Electronic address: [email protected]. (3)Clinical Unit for Herd Health Management in Ruminants, University Clinic for Ruminants, Department of Farm Animals and Veterinary Public Health, University of Veterinary Medicine Vienna, Veterin&auml;rplatz 1, 1210, Vienna, Austria; Institute for Microbiology, Functional Microbiology, Department of Pathobiology, University of Veterinary Medicine Vienna, Veterin&auml;rplatz 1, 1210, Vienna, Austria. (4)Clinical Unit for Ruminant Medicine, University Clinic for Ruminants, Department of Farm Animals and Veterinary Public Health, University of Veterinary Medicine Vienna, Veterin&auml;rplatz 1, 1210, Vienna, Austria. (5)Institute for Microbiology, Functional Microbiology, Department of Pathobiology, University of Veterinary Medicine Vienna, Veterin&auml;rplatz 1, 1210, Vienna, Austria.<br />
Cows in estrus but with signs of clinical endometritis (CE) are often not inseminated or undergo an intrauterine treatment after artificial insemination (AI). Decades ago, the so-called Astr&ouml;m method was described as intrauterine infusion of iodine-potassium solution 2-4 days after AI. Nowadays, it is common to use antibiotics instead of iodine solution and the treatment is performed only a few hours after AI. Although widespread in practice, there is only little information about the efficacy of this treatment. Thus, this study evaluated the effect of a post-breeding intrauterine treatment with cephapirin on insemination success in cows with signs of mild CE. In total, 281 cows subjected to an Ovsynch program with fixed-time AI and examined for vaginal discharge straight after AI by use of the Metricheck device were included. Cows with cloudy discharge or flecks of pus in the mucus were assigned to a treatment or a control group. The treatment group (MET; n&nbsp;=&nbsp;87) received 6&nbsp;&plusmn;&nbsp;1&nbsp;h after AI an intrauterine treatment with 500&nbsp;mg of cephapirin (Metricure, Intervet Deutschland GmbH). Control cows (CON; n&nbsp;=&nbsp;91) remained untreated. Animals with clear discharge were assigned to a healthy comparison group (HE; n&nbsp;=&nbsp;103). Pregnancy diagnosis was performed 39 days after AI. The proportion of pregnant cows after the AI directly preceding the enrollment did not differ significantly (P&nbsp;&gt;&nbsp;0.05) between HE (35.0%), CON (27.5%) and MET (32.2%). Cephapirin treatment had also no positive effect on other reproductive performance measures, i.e, the percentage of pregnant cows 200 days after enrollment (HE: 64.1%, CON: 73.6%, and MET: 73.6%) or the mean interval from enrollment to conception (HE: 25.4 days, CON: 30.0 days, and MET: 29.7 days). The binary logistic regression showed that the only risk factors with a detrimental effect on fertility were a history of CE 28-34 days postpartum and season. Although cows in MET and HE were 1.74 and 1.37 times more likely to conceive after AI than CON, this effect was not significant. Uterine sampling of a subset of cows with CE (n&nbsp;=&nbsp;50) revealed 127 bacterial isolates. The most frequently found genera were Staphylococcus (19.7%), Bacillus (12.6%), Streptococcus (10.2%), Corynebacterium (8.7%), and Lysinibacillus (7.9%). The finding that common uterine pathogenic bacteria were rarely detected additionally questions an intrauterine antibiotic treatment of cows with mild CE at AI.<br />
DOI: 10.1016/j.theriogenology.2020.06.024 PMID: 32650251 [Indexed for MEDLINE] Conflict of interest statement: Declaration of competing interest The authors declare that they have no competing interests. The author RS is an employee of MSD. However, this work was completely done outside of his service. MSD is neither financially involved nor provided any MSD products.

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