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Loracarbef

HCID 5284585
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
76470-66-1
표준 SMILES
N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)c1ccccc1
InChIKey
JAPHQRWPEGVNBT-UTUOFQBUSA-N
분자식
C16H16ClN3O4
평균 분자량
349.77 g/mol
단동위원소 질량
349.08293367

개요

Loracarbef is a synthetic "carba" analogue of cefaclor, with carbon replacing sulfur at position 1. Used to treat a wide range of infections caused by both gram-positive and gram-negative bacteria. It has a role as an antimicrobial agent and an antibacterial drug. It is a conjugate acid of a loracarbef anion. It is a tautomer of a loracarbef zwitterion.

이름 및 식별자

우선 이름
Loracarbef
IUPAC
(6R,7S)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

이름 및 동의어

loracarbef76470-66-1LorabidLoracarbefumloracarbef anhydrousAnhydrous loracarbefLorbefLORACARBEF, ANHYDROUSKT-3777W72I5ZT78ZLY163892LY-163892
이름 더 보기
DTXSID7023223CHEBI:47544(6R,7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid1-Azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2R)-aminophenylacetyl)amino)-3-chloro-8-oxo-, (6R,7S)-1-Azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((aminophenylacetyl)amino)-3-chloro-8-oxo-, (6R-(6alpha,7beta(R*)))-(6R,7S)-7-((2R)-2-amino-2-phenylacetamido)-3-chloro-8-oxo-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:800042DTXCID503223

데이터베이스 식별자

CAS
76470-66-1
PubChem CID
5284585
DTXSID
DTXSID7023223
ChEMBL
CHEMBL1013、CHEMBL1200610
ChEBI
CHEBI:47544
UNII
W72I5ZT78Z
Nikkaji
J362.169C

물성

구조 계산 물성

XLogP
-1.7
극성 표면적
113 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
5
회전 가능 결합 수
4
무거운 원자 수
24
형식 전하
0
복잡도
600

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Antibiotics
LogP0.5
Solubility3.25e-01 g/L
Human Drugs · 3건

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

독성 정보

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Loracarbef

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

화학 및 산업

약리 정보

ATC Code · 2건

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding25%
Pharmacodynamics · 1건

Loracarbef is considered a second generation cephalosporin antibiotic. The advantages of cephalosporin antibiotics include a broad range of activity, a safe record in children with almost no dose-related toxicity, and the lack of need to monitor levels. Adverse reactions are rare and consist primarily of hypersensitivity reactions with urticaria, nonspecific rash, and pruritus. Loracarbef can be used to treat a large number of bacterial infections caused by gram-negative and gram-positive bacteria, including upper respiratory tract bacterial infections, chronic bronchitis, pneumonia, sinusitis, pharyntitis and tonsillitis, skin absceses, urinary tract infections and pyelonephritis caused by <i>E. coli</i>, <i>S. pyogenes</i>, <i>S. aureus</i>, <i>S. saprphyticus</i>, <i>S. penumoniae</i>, <i>H. influenzae</i> and <i>M. catarrhalis</i>.

Mechanism of Action · 1건

Loracarbef is an oral, synthetic beta-lactam antibiotic of the carbacephem class. Chemically, carbacephems differ from cephalosporin-class antibiotics in the dihydrothiazine ring where a methylene group has been substituted for a sulfur atom. Loracarbef has a spectrum of activity similar to that of the second generation cephalosporins. It is structurally identical to cefaclor except for a sulfur atom that has been replaced by a methylene group. This change gives greater chemical stability in solution and allows storage at room temperature. Loracarbef, like all b-lactams and cephalosporins, inhibits penicillin binding proteins, enzymes that create the cross-linkage of the peptidoglycan polymer. This binding leads to interference with the formation and remodeling of the cell wall structure.

Biological Half-Life1 hour. In subjects with moderate impairment of renal function the plasma half-life was prolonged to approximately 5.6 hours.
Metabolism/MetabolitesThere is no evidence of metabolism in humans.

관련 반응

8건
반응 기록 만들기
HRID 35994 반응식
HRID 35994생성물로uspto-grants-1995_05
HRID 35995 반응식
HRID 35995반응물로uspto-grants-1995_05
HRID 35996 반응식
HRID 35996반응물로uspto-grants-1995_05
HRID 35997 반응식
HRID 35997생성물로uspto-grants-1995_05
HRID 611754 반응식
HRID 611754생성물로uspto-grants-1999_12
HRID 611755 반응식
HRID 611755반응물로uspto-grants-1999_12
HRID 611756 반응식
HRID 611756반응물로uspto-grants-1999_12
HRID 611757 반응식
HRID 611757생성물로uspto-grants-1999_12

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
FDA Pharmacological Classification · 5건

W72I5ZT78Z

LORACARBEF ANHYDROUS

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Loracarbef anhydrous is a Cephalosporin Antibacterial.

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionWell absorbed with approximately 90% absorbed from the gastrointestinal tract after oral ingestion.
Cellular LocationsCytoplasm

용도 및 제조

UsesUse (kg; approx.) in Germany (2009): >50