기본 정보
- CAS
50-59-9- 표준 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- 분자식
- C19H17N3O4S2
- 평균 분자량
- 415.5 g/mol
- 단동위원소 질량
- 415.06604838
개요
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.
이름 및 식별자
- 우선 이름
- 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
- 현지명
- 세팔로리딘
- 영어명
- Cephaloridine
- 분자식
- C19H17N3O4S2
- 분자량
- 415.48
이름 및 동의어
cephaloridinecefaloridine50-59-9CephaloridinCephaloridinumCefaloridinCefalorizinCepaloridinCephalomycineLoridineCefaloridinaCeflorin
이름 더 보기
세팔로리딘SefacinCeporanKeflodinKeflordinSch 11527Cephaloridine IICephaloridine USP/EP/BP
CepalorinKefloridinCeporinCefaloridinumGlaxoridinAmpligramCeporineDeflorin
데이터베이스 식별자
- CAS
50-59-9- PubChem CID
- 5773
- DTXSID
DTXSID9022782- ChEMBL
CHEMBL316157- ChEBI
CHEBI:3537- UNII
- LVZ1VC61HB
- EC Number
- 200-052-6
물성
구조 계산 물성
- XLogP
- 1.9
- 극성 표면적
- 147 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 28
- 형식 전하
- 0
- 복잡도
- 687
실험 및 물리화학적 성질
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.
물리화학적 성질
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
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.
유해성 정보
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%)
안전 및 보호
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.
독성 정보
화학 및 산업
약리 정보
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.
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