기본 정보
- 표준 SMILES
C=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\O)c3csc(N)n3)[C@H]2SC1- InChIKey
RTXOFQZKPXMALH-GHXIOONMSA-N- 분자식
- C14H13N5O5S2
- 평균 분자량
- 395.4 g/mol
- 단동위원소 질량
- 395.03581052
개요
Cefdinir is a cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino- and 3-vinyl side groups. It has a role as an antibacterial drug. It is a cephalosporin and a ketoxime.
이름 및 식별자
- 우선 이름
- Cefdinir
- IUPAC
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 영어명
- Cefdinir
- 분자식
- C14H13N5O5S2
- 분자량
- 395.41
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
91832-40-5- PubChem CID
- 6915944
- DTXSID
DTXSID8046084- ChEMBL
CHEMBL927- ChEBI
CHEBI:3485- UNII
- CI0FAO63WC
- EC Number
- 643-088-1
- Nikkaji
- J227.563E
물성
구조 계산 물성
- XLogP
- 0
- 극성 표면적
- 212 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 10
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 26
- 형식 전하
- 0
- 복잡도
- 739
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Anti-Infective Agents; Antibacterial Agents; Cephalosporins;
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Dissociation Constants
3.35
9.7
물리화학적 성질
- 녹는점
- 180 °C · >180°C dec.
- 밀도
- 1.89 · 1.89±0.1 g/cm3(Predicted)
- 저장 조건
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 용해도
- 묽은 HCl: 약간 용해됨
- 산도 계수 (pKa)
- 9.7 · 9.70(at 25℃)
- 물리적 상태
- 고체
- 색상
- 연한 노란색에서 밝은 노란색까지
- 수용성
- 물에 용해됨
- Merck
- 14 · 14,1920
- BCS Class
- 4 · 4
- 주요 응용
- 제약
- InChIKey
- RTXOFQZKPXMALH-GHXIOONMSA-N
- SMILES
- N12[C@@]([H])([C@H](NC(/C(/C3=CSC(N)=N3)=N\O)=O)C1=O)SCC(C=C)=C2C(O)=O
화학적 성질
Pale Yellow Solid
안전 및 규제
GHS 분류
GHS Classification
Danger
H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
독성 정보
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Cefdinir
vLess-DILI-concern
7
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
안전 데이터
- wgk
- 3
- rtecs
- XI0367250
- 독성
- LD50 orl-rat: >5600 mg/kg IYKEDH 23,93,1992
- HS 번호
- 2941906000
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Pharmacodynamics
Cefdinir is a bactericidal agent that treats bacterial infections by interfering with cell wall synthesis. Cefdinir exerts broad-spectrum activity against a variety of gram-positive and gram-negative bacterial infections. It is effective against several beta-lactamase enzyme producing bacteria. As a result, many organisms that are resistant to other cephalosporins may be susceptible to cefdinir.
Mechanism of Action
Five-member thiazolidine rings that make up penicillins are replaced in cephalosporins by a six-member dihydrothiazine ring, conferring greater bactericidal activity. This 6-member ring enables cefdinir and other cephalosporins to resist inactivation by certain bacterial enzymes. With a mechanism similar to other beta-lactam antibiotics, the bactericidal activity of cefdinir is caused by the inhibition of cell wall synthesis via binding to penicillin-binding proteins (PBPs). Cefdinir, like other cephalosporins, penetrates the bacterial cell wall, combats inactivation by beta-lactamase enzymes, and inactivates penicillin-binding proteins. This interferes with the final step of transpeptidation in cell walls, eventually leading to cell lysis, which eventually leads to the death of bacteria that are susceptible to this drug. Cefdinir has shown affinity to penicillin protein binding proteins 2 and 3. It has also been shown to inhibit transpeptidase enzymes of various bacteria, which may play a role in its bactericidal action. One in vitro study suggests that cefdinir inhibits myeloperoxidase release extracellularly. The impact of this potential drug target in relation to its mechanism of action is unknown.
FDA Pharmacological Classification
CI0FAO63WC
CEFDINIR
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefdinir is a Cephalosporin Antibacterial.
CEFDINIR
MeSH Pharmacological Classification
Agents that are structurally similar to other CEPHALOSPORINS but have a broader spectrum of activity against bacteria than the first and second generation cephalosporins. These agents cover more resistant STREPTOCOCCUS, STAPHYLOCOCCUS, gram-positive anaerobes, and more resistant strains of HAEMOPHILUS, NEISSERIA, PROTEUS, ESCHERICHIA COLI, and KLEBSIELLA (HNPEK).
Absorption, Distribution and Excretion
Maximal plasma cefdinir concentration can be attained between 2-4 hours after an ingested dose. The bioavailability of cefdinir depends on the formulation used. The estimated bioavailability of cefdinir in the capsule form is approximately 16%-21%, depending on the dose. Absolute bioavailability after the administration of a suspension of cefdinir is 25%.. The Cmax of cefdinir is 1.60 μg/mL after a 300 mg dose with an AUC of 7.05. Cmax is 2.87 μg/mL after a 600 mg dose with an AUC of 11. A meal high in fat can reduce the absorption of cefdinir by up to 15%, however, this is not a cause for clinically significant changes, therefore cefdinir may be taken with or without food. When given with aluminum or magnesium-containing antacids or iron, cefdinir absorption may decrease. It is recommended to allow 2 hours between cefdinir administration and the administration of these agents.
This drug is mainly excreted by the kidneys. Dose adjustments may be required for patients with renal impairment or patients on dialysis. Approximately 18.4% of a 300 mg dose of cefdinir was found unchanged in the urine after a 300 mg dose was administered during a pharmacokinetic study of 21 individuals. A large proportion of the administered dose is excreted in the feces, although the majority is found in the urine.
The average volume of distribution of cefdinir in adults is about 0.35 L/kg and 0.67 L/kg in children. Another resource estimates the volume of distribution in adults at 1.56–2.09 L/kg. Cefdinir is found to be distributed in various tissues at clinically effective concentrations. It may be found in the epithelial lining fluid, bronchial mucosa, tonsils, sinuses, skin blister fluid, as well as the middle ear fluid. Third-generation cephalosporins such as cefdinir cross the blood-brain barrier and are found in high concentrations in the cerebrospinal fluid, unlike their first and second generation counterparts. The wide tissue distribution of cefdinir allows it to treat a variety of infections throughout the body.
The renal clearance in healthy adults in a pharmacokinetic study was 2.0 (± 1.0) mL/min/kg and the clearance in patients with renal failure was lower, decreasing in proportion to the degree of renal impairment. Dose adjustment is required in patients with renal impairment.
용도 및 제조
응용 분야
개요Cefdinir is an orally active, beta-lactamase stable cephalosporin with a broad spectrum of activity. Compared to other oral cephalosporins, cefdinir is more potent against Gram-positive bacteria, especially Staphylococci. Its activity against Gram-negative bacteria such as E.coli,K. pneumoniae and P.mirabilis is similar to cefixime, but superior to cefaclor and cephalexin.
용도A Cephalosporin antibiotic structurally similar to Cefixime
상·하류 제품 정보
상류 원료
공급사50 곳
추가 설명
정의ChEBI: A cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino- and 3-vinyl side groups.
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