Cephapirin benzathine
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| Category | Antibiotics |
| Catalog number | BBF-04147 |
| CAS | 97468-37-6 |
| Molecular Weight | 1087.27 |
| Molecular Formula | C50H54N8O12S4 |
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Description
Cephapirin benzathine is a first-generation cephalosporin with a broad spectrum of activity against gram-positive and gram-negative organisms. Its resistance to β-lactamase is higher than that of the penicillin family. commonly used in the veterinary field.
Specification
| Synonyms | Cefapirin benzathine |
| Storage | Store at -20°C (dark) |
| 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;N,N'-dibenzylethane-1,2-diamine |
| Canonical SMILES | CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O.CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O.C1=CC=C(C=C1)CNCCNCC2=CC=CC=C2 |
| InChI | InChI=1S/2C17H17N3O6S2.C16H20N2/c2*1-9(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;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25);1-10,17-18H,11-14H2/t2*13-,16-;/m11./s1 |
| InChI Key | JAHKOXGROZNHHG-RACYMRPCSA-N |
Properties
| Appearance | Pale Beige to Light Brown Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 783.9°C at 760 mmHg |
| Melting Point | 166-170°C (dec.) |
| Solubility | Soluble in DMSO |
Reference Reading
1. Prepartum antibiotic therapy with a cephapirin dry-cow product against naturally occurring intramammary infections in heifers
C H Ray, S C Nickerson, P J Washburn, W E Owens Zentralbl Veterinarmed B . 1994 Apr;41(2):90-100. doi: 10.1111/j.1439-0450.1994.tb00212.x.
Intramammary infusion of a dry-cow antibiotic preparation containing 300 mg of cephapirin benzathine into 18 Jersey heifers, 10-12 weeks prepartum, resulted in cure rates of existing intramammary infection (IMI) of 96% (24/25), 100% (4/4), and 90% (28/31) for Staphylococcus aureus, Streptococcus species, and Staphylococcus species, respectively. Cure rates of IMI that had been treated with a lactating-cow therapy containing 200 mg cephapirin benzathine at parturition were 62.5% (15/24), 100% (22/22), and 100% (3/3) for Staphylococcus aureus, Streptococcus species, and Staphylococcus species, respectively. Initial somatic cell counts (SCC) of secretions from infected quarters were greater than from uninfected quarters. At 2 months postpartum, the SCC of milk from treated and cured quarters were reduced in comparison with quarters that remained infected. Cephapirin benzathine was present at detectable concentrations in 94, 80, 68, and 61% of treated quarters at 1, 2, 3, and 4 weeks after infusion of the cephapirin dry-cow product, respectively. At parturition, 24% of treated quarters were positive for antibiotic, however, no quarters remained positive for antibiotic at 5 days postpartum. An additional 40 heifers from a commercial herd were sampled and infused in all quarters with the cephapirin dry-cow product at 16-20 weeks prepartum. Cure rates for the commercial herd were 94% (29/31), 94% (16/17), 100% (44/44), and 100% (3/3), respectively, for quarters infected by S. aureus, Streptococcus species, Staphylococcus species, and coliforms.
2. Comparison of tilmicosin and cephapirin as therapeutics for Staphylococcus aureus mastitis at dry-off
S C Nickerson, T R Shryock, C C Scheifinger, T E Spike, L K Fox, W E Owens J Dairy Sci . 1999 Apr;82(4):696-703. doi: 10.3168/jds.S0022-0302(99)75286-0.
Forty-four cows (26 Jerseys and 18 Holsteins) that had at least 1 mammary quarter that was naturally (n = 12) or experimentally (n = 84) infected with Staphylococcus aureus were allotted to three treatment groups of approximately equal number at the end of lactation. Cows were dried off by abrupt cessation of milking, and dry cow therapy was administered as an intramammary infusion of cephapirin benzathine at 10 ml per quarter, an intramammary infusion of tilmicosin (solution containing 300 mg/ml) at 5 ml per quarter, or a subcutaneous injection of tilmicosin at 5 mg/kg of body weight on the day of drying off and another injection 4 d later. Mammary secretions were monitored during the dry period and postpartum for antimicrobial residues, intramammary infection (IMI) status, and somatic cell counts. Results demonstrated the following percentage cures for IMI caused by Staph. aureus at 28 d postcalving based on individual mammary quarters: cephapirin benzathine, 78.1%; tilmicosin infused, 74.2%; and tilmicosin injected, 9.1%. During the first 4 wk after drying off, the mean concentration of tilmicosin in mammary secretions from cows infused with the antibiotic remained approximately 10-fold higher than that in secretions from cows injected with the antibiotic (3.43 vs. 0.32 ppm), and, by the time of calving, concentrations for cows treated with both methods were below the dilution limit of the assay (< 0.1 ppm). Results demonstrated that intramammary infusion of tilmicosin was equally as effective as cephapirin benzathine in curing IMI caused by Staph. aureus at drying off; however, the subcutaneous injection of tilmicosin at the dose used was not effective as a dry cow therapeutic against Staph. aureus.
3. The effect of a single administration of cephapirin or cloprostenol on the reproductive performance of dairy cows with subclinical endometritis
W H Johnson, R A Foster, R Kasimanickam, T F Duffield, J S Walton, C J Gartley, K E Leslie Theriogenology . 2005 Feb;63(3):818-30. doi: 10.1016/j.theriogenology.2004.05.002.
This study examined the effect of a single administration of cephapirin iu or cloprostenol im on the reproductive performance of dairy cows with subclinical endometritis. Cows (n = 228) at 20-33 days in milk (DIM) from two commercial dairy farms, determined to be normal for clinical endometritis (based on absence of abnormal uterine discharge on vaginoscopic examination) were enrolled. At enrollment, a thorough reproductive examination was performed, including rectal palpation, ultrasonography (US) and endometrial cytology (EC). The case definition for subclinical endometritis was the presence of >18% neutrophils on EC examination or fluid in uterus (FIU) on US examination. All cows were randomly assigned to receive one of three treatments: 500 mg benzathine cephapirin iu, 500 microg cloprostenol im, or control (no treatment). Reproductive performance was monitored for a minimum of 8 months after treatment. Cows with subclinical endometritis treated with cephapirin or cloprostenol had a significantly increased relative pregnancy rate compared to control [hazard ratios 1.89 (P = 0.01) and 1.70 (P = 0.05), respectively]. In conclusion, a single treatment with cephapirin or cloprostenol at 20-33 DIM significantly improved the reproductive performance of cows with subclinical endometritis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
