Cefapirin

Các tên gọi khác (9 ) :

(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefapirin
Cefapirina
Cefapirine
Cefapirinum
Cefaprin
Cephapirin
Cephapirine
CEPR

Thuốc trị ký sinh trùng, chống nhiễm khuẩn

Thuốc Gốc

Small Molecule

CAS: 21593-23-7

ĐG : Bristol-Myers Squibb Co. , http://www.bms.com

CTHH: C₁₇H₁₇N₃O₆S₂

PTK: 423.463

Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. 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.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₇H₁₇N₃O₆S₂

Phân tử khối

423.463

Monoisotopic mass

423.055876671

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

InChI Key

InChIKey=UQLLWWBDSUHNEB-CZUORRHYSA-N

IUPAC Name

(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional IUPAC Name

cephapirin

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O

Độ hòa tan

1030 mg/L

logP

-1.15

logS

-3.5

pKa (strongest acidic)

3.54

pKa (Strongest Basic)

PSA

125.9 Å²

Refractivity

102.43 m³·mol^-1

Polarizability

40.63 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

-1

Number of Rings

Bioavailability

Rule of Five

true

MDDR-Like Rule

true

pKa

2.15

Dược Lực Học : Cephapirin is a first-generation cephalosporin that has a wide spectrum of activity against gram-positive and gram-negative organisms. Cephapirin is more resistant to beta-lactamases than are the penicillins and so is effective against staphylococci, with the exception of methicillin-resistant staphylococci.

Cơ Chế Tác Dụng : Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. 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. The bactericidal activity of cephapirin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).

Dược Động Học :

▧ Metabolism :
Major metabolite detected is desacetylcephapirin.

Độc Tính : Rats exposed via the oral route to cephapirin displayed low acute toxicity (LD₅₀ = 14000 mg/kg). The most common adverse reactions are hypersensitivity reactions and alterations to liver function. Evidence of white blood cell disorders and anaemia were noted in some subjects.

Chỉ Định : For treatment of infections caused by susceptible bacteria.

Tương Tác Thuốc :

Amikacin Increased risk of nephrotoxicity
Gentamicin Increased risk of nephrotoxicity
Netilmicin Increased risk of nephrotoxicity
Tobramycin Increased risk of nephrotoxicity

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty :

Sản phẩm biệt dược : Cefadyl

Đóng gói

Công ty : Bristol-Myers Squibb Co.

Website : http://www.bms.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01139

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=30699

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505227

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C06896

ChemSpider

http://www.chemspider.com/Chemical-Structure.28486.html

PharmGKB

http://www.pharmgkb.org/drug/PA164749340

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