Cefdinir

HCID 6915944CAS 91832-40-5

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

cefdinir91832-40-5OmnicefCefzonCFDNCefdinirumFK 482FK-482CI-983Cefdinir anhydrousDTXSID8046084BMY-28488
이름 더 보기
syn-7-[2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid7-[2-(2-AMINOTHIAZOL-4-YL)-2-HYDROXYIMINOACETYLAMINO]-8-OXO-3-VINYL-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2(6R,7R)-3-Vinyl-7-[(2-amino-4-thiazolyl)[(Z)-hydroxyimino]acetylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid8-[2-(2-amino-1,3-thiazol-4-yl)-1-hydroxy-2-nitroso-ethenyl]amino-4-ethenyl-7-oxo-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylicacid(6R,7R)-7α-[[(2-Amino-4-thiazolyl)[(Z)-hydroxyimino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo--5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid[6R-[6α,7β(Z)]]_7-[[(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyimino-acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CI0FAO63WCPD-134393NSC-758926CHEBI:3485CI983FK482DTXCID20820060(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

LogP-0.2
Solubility8.78e-02 g/L
Human Drugs · 3건

Breast Feeding; Lactation; Anti-Infective Agents; Antibacterial Agents; Cephalosporins;

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point>135
Physical DescriptionSolid

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

화학적 성질

Pale Yellow Solid

안전 및 규제

GHS 분류

GHS Classification · 4건

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

Hazard Classes and CategoriesSkin Irrit. 2 (20%)

독성 정보

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Cefdinir

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

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 · 2건

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingThe plasma protein binding of cefdinir ranges from 60% to approximately 70%.
Pharmacodynamics · 1건

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 · 1건

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.

Biological Half-LifeThe average plasma elimination half-life is about 1.7 hours in adults. In children and healthy infants, plasma elimination half-life ranges from 1.2–1.5 hours.
Metabolism/MetabolitesThis drug is not significantly metabolized and its pharmacological actions are mainly attributed to the parent drug.

용도 및 제조

UsesUse (kg) in USA (2002): 11300
응용 분야 · 2건

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

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]

추가 설명

정의ChEBI: A cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino- and 3-vinyl side groups.

관련 반응

6건

연결된 노트

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