基本情報
- CAS
3577-01-3- 標準SMILES
CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1- InChIKey
FUBBGQLTSCSAON-PBFPGSCMSA-N- 分子式
- C18H19N3O6S
- 平均分子量
- 405.4 g/mol
- 単同位体質量
- 405.09945651
概要
Cefaloglycin is a cephalosporin antibiotic containing at the 7beta-position of the cephem skeleton an (R)-amino(phenyl)acetamido group. It has a role as an antimicrobial agent. It is a cephalosporin and a beta-lactam antibiotic allergen.
名称と識別子
- 優先名称
- Cephaloglycin
- IUPAC
- (6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セファログリシン
- 英語名
- cefaloglycin
- 分子式
- C18H19N3O6S
- 分子量
- 405.42
名称と別名
CefaloglycinCEPHALOGLYCINCephaloglycineKafocin3577-01-3Cephaloglycin anhydrousD-CephaloglycineCephaoglycin acidCefaloglycineKefglycinCefaloglicinaCefaloglycinum
名称をさらに表示
カホシン7-(D-α-アミノフェニルアセトアミド)-セファロスポリン酸(6R)-3-[(アセチルオキシ)メチル]-7α-[[(R)-アミノ(フェニル)アセチル]アミノ]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸(6R,7R)-7-[(R)-2-アミノ-2-フェニルアセチルアミノ]-3-(アセトキシメチル)-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸セファログリシン(無水物)(6R)-7α-[(R)-アミノ(フェニル)アセチルアミノ]-3-[(アセトキシ)メチル]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸セファログリシン(6R,7R)-7-[(R)-アミノフェニルアセチルアミノ]-3-(アセトキシメチル)-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸ケフグリシンセファログリシン (JAN)(6R,7R)-3-[(アセチルオキシ)メチル]-7-[(2R)-2-アミノ-2-フェニルアセトアミド]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸Lilly-39435Cephaloglycin(anhydrous)FUBBGQLTSCSAON-PBFPGSCMSA-N
物性
構造計算による物性
- XLogP
- -3
- 極性表面積
- 164 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 8
- 回転可能結合数
- 7
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 718
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP-0.3
Solubility
SLIGHTLY SOL IN WATER; PRACTICALLY INSOL IN MOST ORGANIC SOLVENTS /DIHYDRATE/
1.48e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
DecompositionWhen heated to decomposition it emits toxic fumes of sulfoxides and nitroxides.
Melting Point237 °C
Physical DescriptionSolid
Other Experimental Properties
MP: 223-250 °C, DECOMP; MAX ABSORPTION (2% DIMETHYLFORMAMIDE): 258 NM (E= 166, 1%, 1 CM) /DIHYDRATE/
ISOELECTRIC POINT & PH OF MAX STABILITY: 4.5 /DIHYDRATE/
CRYSTALLINE POWDER /DIHYDRATE/
WHITE TO OFF-WHITE, CRYSTALLINE POWDER /DIHYDRATE/
物理化学的性質
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
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[(aminophenylacetyl)amino]-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Human health tier I assessment
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 ReportsWANG RIH, GARTHWAITE; DRUG THER 6: 103-106, 111-113 (1976). A COMPARISON OF SPECTRUM & THERAPEUTIC USAGES & DOSAGE OF THE CEPHALOSPORIN DERIV IS PRESENTED ALONG WITH METABOLISM AND TOXICITY.
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.
化学と産業
薬理情報
PharmacodynamicsCephaloglycin is an antibiotic related to cephalosporin but no longer in common use. It is an orally absorbed derivative of cephalosporin C.
Mechanism of Action
The bactericidal activity of cephaloglycin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
CEPHALOTHIN & ITS CONGENERS INHIBIT BACTERIAL CELL-WALL SYNTHESIS IN MANNER SIMILAR TO THAT OF PENICILLIN. /CEPHALOTHIN & ITS CONGENERS/
/PENICILLINS & CEPHALOSPORINS/...HAVE SIMILAR MECHANISM OF ANTIBACTERIAL ACTION; BOTH INTERFERE WITH TERMINAL STEP IN BACTERIAL CELL WALL SYNTH BY INACTIVATING TRANSPEPTIDASE, THEREFORE PREVENTING CROSS-LINKAGE OF PEPTIDOGLYCAN CHAINS. /PENICILLINS & CEPHALOSPORINS/
Biological Half-Life
THIS ANTIBIOTIC IS PARTIALLY ABSORBED FROM GI TRACT... PLASMA CONCN REACH PEAK OF ONLY 2-6 UG/ML @ ABOUT 2 HR FOLLOWING SINGLE DOSE OF 0.5 G; DRUG IS NO LONGER DETECTABLE IN PLASMA 8 HR AFTER THIS DOSE. HALF-LIFE...IS ABOUT 4 HR.
PLASMA LEVELS AFTER ORAL ADMIN VARY WIDELY AMONG PT. PEAK LEVEL OF AT LEAST 0.6 UG/ML IS USUALLY ACHIEVED WITH ORAL DOSE OF 500 MG, & IT MAY REACH 6 UG/ML IN FAIR PROP OF CASES. FOOD IN STOMACH INTERFERES WITH ABSORPTION. HALF-LIFE IN PLASMA...ABOUT 3-5 HR, BUT WHEN...SEVERE RENAL IMPAIRMENT...MAY BE 9-20 HR. /DIHYDRATE/
Metabolism/MetabolitesMOST OF CEPHALOGLYCIN THAT IS ABSORBED IS EXCRETED...AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Well absorbed following oral administration.
MOST OF CEPHALOGLYCIN THAT IS ABSORBED IS EXCRETED IN URINE AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE. URINARY CONCN OF METABOLITE AVG 350 UG/ML OVER 8-HR PERIOD FOLLOWING ADMIN OF 500 MG OF CEPHALOGLYCIN...
CEPHALOGLYCIN IS NOT DESTROYED IN GASTRIC ACID, BUT IT GRADUALLY DECOMP IN NEUTRAL & ALKALINE SECRETIONS OF INTESTINES. ONLY 1/4 TO 1/3 IS ABSORBED. /DIHYDRATE/
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