기본 정보
- CAS
50370-12-2- 표준 SMILES
CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1- InChIKey
BOEGTKLJZSQCCD-UEKVPHQBSA-N- 분자식
- C16H17N3O5S
- 평균 분자량
- 363.4 g/mol
- 단동위원소 질량
- 363.08889182
개요
Cefadroxil is a cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a role as an antibacterial drug. It is a conjugate acid of a cefadroxil(1-).
이름 및 식별자
- 우선 이름
- Cefadroxil
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 현지명
- 세파드록실
- 영어명
- CEFADROXIL
- 분자식
- C16H17N3O5S
- 분자량
- 363.39
이름 및 동의어
cefadroxil50370-12-2CephadroxilCefadroxil anhydrousCefadroxiloCefadroxilumD-CefadroxilDuricefUltracefAnhydrous cefadroxilCefadropsDuracef
이름 더 보기
세파드록실cdx(6R,7R)-7-[[(R)-Amino(p-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidRoxilEvacefNeucefNSC438
DTXSID8022749BL-S578S-578(6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidQ525PA8JJBCHEBI:3479S 578NSC-756664
데이터베이스 식별자
- CAS
50370-12-2、66592-87-8- PubChem CID
- 47965
- DTXSID
DTXSID8022749- ChEMBL
CHEMBL1644- ChEBI
CHEBI:3479- UNII
- Q525PA8JJB
- EC Number
물성
구조 계산 물성
- XLogP
- -2.1
- 극성 표면적
- 158 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 7
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 25
- 형식 전하
- 0
- 복잡도
- 629
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics (Cefalosporins)
LogP-0.4
Solubility3.99e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredient
Melting Point197 °C
Physical DescriptionSolid
Collision Cross Section
182.13 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
183.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
187.7 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
183.31 Ų [M-H]-
물리화학적 성질
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 65 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory InformationCefadroxil anhydrous: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[amino(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Human health tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
독성 정보
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefadroxil
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Cefadroxil
23.3
화학 및 산업
약리 정보
ATC Code
J01DB05
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingBinding rates of cefadroxil were 28.1% by U.F. method
PharmacodynamicsCefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.
Mechanism of Action
Like all beta-lactam antibiotics, cefadroxil binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefadroxil interferes with an autolysin inhibitor.
Biological Half-Life1.5 hours
FDA Pharmacological Classification
Q525PA8JJB
CEFADROXIL ANHYDROUS
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefadroxil anhydrous is a Cephalosporin Antibacterial.
CEFADROXIL
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.
Over 90% of the drug is excreted unchanged in the urine within 24 hours. Cefadroxil was detected in the placenta and breast milk.
Cellular LocationsMembrane
관련 반응
17건
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