基本情報
- CAS
50-59-9- 標準SMILES
O=C(Cc1cccs1)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12- InChIKey
CZTQZXZIADLWOZ-CRAIPNDOSA-N- 分子式
- C19H17N3O4S2
- 平均分子量
- 415.5 g/mol
- 単同位体質量
- 415.06604838
概要
Cefaloridine is a cephalosporin compound having pyridinium-1-ylmethyl and 2-thienylacetamido side-groups. A first-generation semisynthetic derivative of cephalosporin C. It has a role as an antibacterial drug. It is a cephalosporin, a semisynthetic derivative and a beta-lactam antibiotic allergen.
名称と識別子
- 優先名称
- Cephaloridine
- IUPAC
- (6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
- 現地名
- セファロリジン
- 英語名
- Cephaloridine
- 分子式
- C19H17N3O4S2
- 分子量
- 415.48
名称と別名
cephaloridinecefaloridine50-59-9CephaloridinCephaloridinumCefaloridinCefalorizinCepaloridinCephalomycineLoridineCefaloridinaCeflorin
名称をさらに表示
7-[(2-チエニル)アセトアミド]-3-(1-ピリジルメチル)-3-セフェム-4-カルボン酸ベタイン1-[[(6R,7R)-2-カルボキシラト-8-オキソ-7-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-3-イル]メチル]ピリジニウムセファシンケフロルジンセファロリジンセポリンセポランケフロジンセフロリンセファロリジン (JAN)1-{[(6R,7R)-2-カルボキシラト-8-オキソ-7-[2-(チオフェン-2-イル)アセトアミド]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-3-イル]メチル}ピリジン-1-イウムSefacinCeporanKeflodinKeflordinSch 11527Cephaloridine IICephaloridine USP/EP/BP
CepalorinKefloridinCeporinCefaloridinumGlaxoridinAmpligramCeporineDeflorin
データベース識別子
物性
構造計算による物性
- XLogP
- 1.9
- 極性表面積
- 147 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 6
- 回転可能結合数
- 5
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 687
実験および物理化学的性質
DrugsPharmaceuticals -> Antibiotics
pHAQ SOLN ARE SLIGHTLY ACID (PH 4.5-5)
LogPLogP = -1.70 at pH = 2
Color/Form
CRYSTALS
WHITE TO OFF-WHITE, CRYSTALLINE POWDER
Solubility
SOL IN WATER
PRACTICALLY INSOL IN MOST ORG SOLVENTS
In water, >2.0X10+4 at 21 °C
Flash PointNo data
Optical RotationSPECIFIC OPTICAL ROTATION: +47.7 °FOR D (SODIUM) LINE (WATER, 1.25%)
Stability/Shelf LifeAQ SOLN (20% WT/VOL) ARE STABLE FOR 4 WK @ 4 °C IN DARK
Other Experimental Properties
EXPOSURE TO SUNLIGHT CAUSES DISCOLORATION
Aqueous solutions (20% w/v) are stable for four weeks at 4 °C in the dark.
物理化学的性質
- 融点
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。
GHS分類
GHS Classification
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory InformationChemical: Pyridinium, 1-[[(6R,7R)-2-carboxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, inner salt
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Special ReportsWHO; Environmental Health Criteria 119: Principles and Methods for the Assessment of Nephrotoxicity Associated with Exposure to Chemicals (1991)
Hazard Classes and CategoriesSkin Sens. 1 (100%)
安全と保護具
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
毒性情報
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of Action
CEPHALOTHIN & ITS CONGENERS INHIBIT BACTERIAL CELL-WALL SYNTHESIS IN MANNER SIMILAR TO THAT OF PENICILLIN. /CEPHALOSPORINS/
Cephaloglycin and cephaloridine are acutely toxic to the proximal renal tubule, in part because of their cellular uptake by a contraluminal anionic secretory carrier and in part through their intracellular attack on the mitochondrial transport and oxidation of tricarboxylic acid (TCA) cycle anionic substrates. Preliminary studies with cephaloglycin have provided evidence of a role of fatty acid (FA) metabolism in its nephrotoxicity, and work with cephaloridine has shown it to be a potent inhibitor of renal tubular cell and mitochondrial carnitine (Carn) transport.
Biological Half-Life
.../CEPHALORIDINE/ PEAK PLASMA CONCN ARE REACHED ABOUT 30 MIN AFTER DRUG IS INJECTED... WHILE ITS T/2 (60 TO 90 MIN)...ONLY SMALL AMT ARE DETECTABLE AFTER 8 HR.
/IN RATS/ RATIOS OF BONE TO SERUM CONCN AVG...1:7 FOR CEPHALORIDINE...DURING 0.25-4 HR AFTER /ORAL OR SC/ DOSING. DESPITE DIFFERENCES IN CONCN, T/2 IN BONE & SERUM WERE SIMILAR.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Renal.
.../CEPHALORIDINE/ POORLY ABSORBED FROM GI TRACT. PEAK PLASMA CONCN ARE REACHED ABOUT 30 MIN AFTER DRUG IS INJECTED; 10 TO 20% OF PLASMA CEPHALORIDINE IS BOUND TO PROTEIN.
IM INJECTIONS OF 0.5 & 1 G YIELD PEAK PLASMA CONCN OF 15 & 30 UG/ML, RESPECTIVELY. APPROX 75% OF GIVEN DOSE IS EXCRETED IN URINE, MAINLY BY GLOMERULAR FILTRATION. CEPHALORIDINE ACCUM IN BLOOD OF PATIENTS WITH DECR RENAL FUNCTION, & IN AZOTEMIC PATIENTS PLASMA CONCN ARE VERY HIGH...
PLACENTAL DRUG TRANSFER- CEPHALORIDINE: TIME TO APPEAR IN FETUS 30 MIN; TIME TO FETAL/MATERNAL CONCN EQUIL 5 HR. /FROM TABLE/
.../CEPHALORIDINE/ READILY PENETRATE NORMAL EYE FOLLOWING SYSTEMIC OR SUBCONJUNCTIVAL ADMIN...
...CEPHALORIDINE...SHOWN...TO PENETRATE INTO BONE TO VERY LIMITED EXTENT AFTER SC OR ORAL DOSES TO RATS. RATIOS OF BONE TO SERUM CONCN AVG...1:7 FOR CEPHALORIDINE...DURING 0.25-4 HR AFTER DOSING.
関連反応
1 件
化合物ノート
読み込み中…