24356-60-3 Usage
Description
Cephapirin sodium (Cefapirin sodium), a semisynthetic cephalosporin antibiotic, is bactericidal against strains of gram-positive and gram-negative bacteria.Cephapirin is closely resembles cephalothin in chemical and pharmacokinetic properties. Cephapirin, have cephalosporanic acid core with the acetyloxymethyl group at the 3rd position and having IUPAC name (6R,7R)-3-(Acetoxymethy)-8- oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia- 1-azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid. It is unstable in acid and must be administered parenteral. It has similar mechanism as other cephalosporins. It is marketed under the trade name Cefadyl. It is effective against a wide variety of gram-positive and gramnegative bacteria; used as the sodium salt. Among the most serious adverse reactions of cefapirin, that is， neutropenia, leukopenia, anemia, bone marrowdepression, and allergic reactions, it has been discontinued in the United States (Wiesner, 1972).
Chemical Properties
White or pale yellow powder.
Uses
Cefapirin sodium is very similar to cephalothin (Bran et al., 1972). Cephapirin is
now used almost exclusively in veterinary practice.
Definition
ChEBI: Cephapirin sodium is the sodium salt of cephapirin. A first-generation cephalosporin antibiotic, it is effective against gram-negative and gram-positive organisms. Being more resistant to beta-lactamases than penicillins, it is effective agains most staphylococci, though not methicillin-resistant staphylococci. It has a role as an antibacterial drug. It is a cephalosporin and an organic sodium salt. It contains a cephapirin(1-).
Therapeutic Function
Antibacterial
Synthesis
Cephapirin, (6R-trans)-3-[(acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)
acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.4), is synthesized by acylating 7-aminocephalosporanic acid with 4-pyridylthioacetic acid chloride
(32.1.2.3), which is synthesized by reacting 4-chloropyridine with mercaptoacetic acid in
the presence of a base, forming 4-pyridylthioacetic acid (32.1.22), and further transforming the resulting acid to the acid chloride by reacting it with phosphorous pentachloride.
An alternative way of making cephapirin is the acylation of 7-aminocephalosporanic acid
by bromoacetyl bromide, which gives a bromoacetyl derivative (32.1.2.5), and which is
then reacted with 4-mercaptopyridine in the presence of triethylamine, forming the desired
cephapirin (32.1.2.4).
Check Digit Verification of cas no
The CAS Registry Mumber 24356-60-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,3,5 and 6 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 24356-60:
(7*2)+(6*4)+(5*3)+(4*5)+(3*6)+(2*6)+(1*0)=103
103 % 10 = 3
So 24356-60-3 is a valid CAS Registry Number.
InChI:InChI=1/C17H17N3O6S2.Na/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);/q;+1/p-1/t13-,16-;/m1./s1
24356-60-3Relevant articles and documents
Cephapirin sodium refining method
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Paragraph 0015; 0017; 0018; 0020; 0021, (2018/03/01)
The invention relates to the technical field of veterinary antibiotic synthesis, and particularly discloses a cephapirin sodium refining method. The cephapirin sodium refining method takes a cephapirin sodium crude product as a treatment object, and is characterized in that the cephapirin sodium crude product is dissolved in a dilute acid solution, activated carbon is added for decolorization, the filtrate is retained, and alkali liquor is slowly dropwise added to the filtrate, and then cooling, stirring and crystallizing are performed to obtain cephapirin acid; the cephapirin acid is washed, and then dissolved in a solvent containing dimethyl sulfoxide, the sodium salt is added into the cephapirin acid solution, and is stirred, cooled, and filtered to remove mother liquor to obtain a cephapirin sodium wet product, and the wet product is dried to obtain a product. The method of the invention has the characteristics of simple operation steps, high product purity, high yield, light color, cheap materials and low production cost, and can fully meet the requirements on the cephapirin sodium of European Pharmacopoeia.
