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Loracarbef

HCID 5284585
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
76470-66-1
標準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
分子式
C16H16ClN3O4
平均分子量
349.77 g/mol
単同位体質量
349.08293367

概要

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.

名称と識別子

優先名称
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

名称と別名

loracarbef76470-66-1LorabidLoracarbefumloracarbef anhydrousAnhydrous loracarbefLorbefLORACARBEF, ANHYDROUSKT-3777W72I5ZT78ZLY163892LY-163892
名称をさらに表示
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

データベース識別子

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

物性

構造計算による物性

XLogP
-1.7
極性表面積
113 Ų
水素結合供与体数
3
水素結合受容体数
5
回転可能結合数
4
重原子数
24
形式電荷
0
複雑度
600

実験および物理化学的性質

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

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Drug Induced Liver Injury · 6 件

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

化学と産業

薬理情報

ATC Code · 2 件

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding25%
Pharmacodynamics · 1 件

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 · 1 件

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.

関連反応

8 件
反応記録を作成
HRID 35994 の反応式
HRID 35994生成物としてuspto-grants-1995_05
HRID 35995 の反応式
HRID 35995反応物としてuspto-grants-1995_05
HRID 35996 の反応式
HRID 35996反応物としてuspto-grants-1995_05
HRID 35997 の反応式
HRID 35997生成物としてuspto-grants-1995_05
HRID 611754 の反応式
HRID 611754生成物としてuspto-grants-1999_12
HRID 611755 の反応式
HRID 611755反応物としてuspto-grants-1999_12
HRID 611756 の反応式
HRID 611756反応物としてuspto-grants-1999_12
HRID 611757 の反応式
HRID 611757生成物としてuspto-grants-1999_12

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
FDA Pharmacological Classification · 5 件

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

用途と製造

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