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세파피린

Cephapirin

HCID 30699
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
21593-23-7
표준 SMILES
CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CSc3ccncc3)[C@H]2SC1
InChIKey
UQLLWWBDSUHNEB-CZUORRHYSA-N
분자식
C17H17N3O6S2
평균 분자량
423.5 g/mol
단동위원소 질량
423.05587762

개요

Cephapirin is a cephalosporin with acetoxymethyl and 2(pyridin-4-ylsulfanyl)acetamido substituents at positions 3 and 7, respectively, of the cephem skeleton. It is used (as its sodium salt) as an antibiotic, being effective against gram-negative and gram-positive organisms. It has a role as an antibacterial drug. It is a conjugate acid of a cephapirin(1-).

이름 및 식별자

우선 이름
Cephapirin
IUPAC
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
현지명
세파피린
영어명
cefapirin
분자식
C17H17N3O6S2
분자량
423.46

이름 및 동의어

cephapirinCefapirin21593-23-7CephapirineCefaprinCefapirinaCefapirineCefapirinumCEPR(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid7-(2-(4-Pyridylthio)acetamido)cephalosporanic acidCHEBI:554446
이름 더 보기
세파피린C06896CephaprinCefapirin acidCefotiam Impurity 397-[2-(4-Pyridylthio)acetamido]cephalosporanic acid(6R-trans)-3-[(Acetyloxy)Methyl]-8-oxo-7- [[(4-pyridinylthio)acetyl]aMino]-(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(pyridin-4-ylthio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 3-(acetyloxy)methyl-8-oxo-7-(4-pyridinylthio)acetylamino-, (6R,7R)-(6R,7R)-3-[(Acetyloxy)Methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]aMino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
89B59H32VN5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridinylthio)acetyl)amino)-, (6R-trans)-DTXSID90227845-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-, acetate (ester)Cephalosporanic acid, 7-(2-(4-pyridylthio)acetamido)-(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-((acetyloxy)methyl)-8-oxo-7-(2-(pyridin-4-ylsulfanyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-3-(acetoxymethyl)-8-oxo-7-(((pyridin-4-ylsulfanyl)acetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

물성

구조 계산 물성

XLogP
-1.1
극성 표면적
177 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
9
회전 가능 결합 수
8
무거운 원자 수
28
형식 전하
0
복잡도
707

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

LogP · 2건

-0.1

-0.15

Solubility · 3건

SOL IN WATER /CEPHAPIRIN SODIUM/

VERY SOL IN DIL HYDROCHLORIC & GLACIAL ACETIC ACID; INSOL IN CHLOROFORM, ETHER, TOLUENE /CEPHAPIRIN SODIUM/

1.51e-01 g/L

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Physical DescriptionSolid
Stability/Shelf Life · 3건

STABLE DRY STATE FOR 18 MO @ ROOM TEMP /CEPHAPIRIN SODIUM/

Solutions containing cephapirin sodium 50 to 600 mg/ml in water for injection are stable for 12 hr at 25 °C or 10 days at 4 °C. /Cephapirin sodium/

If frozen immediately after reconstitution with sterile water for injection, bacteriostatic water for injection, 0.9% sodium chloride injection, or 5% dextrose injection, solutions retain their potency for up to 60 days at -15 °C (5 °F). After thawing at room temperature, solutions retain their potency for 12 hours at room temperature or for 10 days if refrigerated at 4 °C (39 °F).

Dissociation Constants2.15

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H317 (14.6%): 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 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 2건

REACH registered substance: Cefapirin (EC: 244-466-5)

Cephapirin: 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, 3-[(acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-,(6R-trans)-: Human health tier I assessment
FDA RequirementsTolerances are established for the residues of cephapirin in the milk and edible tissues of dairy cattle.
Hazard Classes and CategoriesSkin Sens. 1 (14.6%)

안전 및 보호

Storage ConditionsPrior to reconstitution, store below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless other wise specified by manufacturer.
Allowable TolerancesA tolerance of 0.02 ppm is established for residues of cephapirin in the milk and 0.1 ppm in the uncooked edible tissue of dairy cattle.

화학 및 산업

약리 정보

ATC Code · 4건

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

QG - Genito urinary system and sex hormones

Pharmacodynamics · 1건

Cephapirin is a first-generation cephalosporin that has a wide spectrum of activity against gram-positive and gram-negative organisms. Cephapirin is more resistant to beta-lactamases than are the penicillins and so is effective against staphylococci, with the exception of methicillin-resistant staphylococci.

Mechanism of Action · 4건

The bactericidal activity of cephapirin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).

... VERY RESISTANT TO ACTION OF PENICILLINASE, FOR WHICH IT IS BOTH COMPETITIVE & NONCOMPETITIVE INHIBITOR ... IT DOES NOT SUPPRESS BREAKDOWN OF PENICILLIN G BY STAPHYLOCOCCAL PENICILLINASE. CEPHALOSPORIN C & ITS SEMISYNTHETIC CONGENERS INDUCE SYNTH OF PENICILLINASE BY B CEREUS & STAPH AUREUS. /CEPHALOSPORIN C/

... ENZYME ACTING SPECIFICALLY ON CEPHALOSPORIN C TO DESTROY ITS ANTIBACTERIAL ACTIVITY. THIS SUBSTANCE, CEPHALOSPORINASE IS ALSO BETA-LACTAMASE. MOST PREPN OF ENZYME ALSO EXHIBIT PENICILLINASE ACTIVITY, & SOME MICROORGANISMS PRODUCE ONE BETA-LACTAMASE THAT ACTS ON BOTH PENICILLIN & CEPHALOSPORINS. /CEPHALOSPORIN C/

Bactericidal; action depends on ability to reach and bind pencillin-binding proteins located in bacterial cytoplasmic membranes; cephalosporins inhibit bacterial septum and cell wall synthesis, probably by acylation of membrane-bound transpeptidase enzymes. This prevents cross-linkage of peptidoglycan chains, which is necessary for bacterial cell wall strength and rigidity. Also, cell division and growth are inhibited, and lysis and elongation of susceptible bacteria frequently occur. Rapidly dividing bacteria are those most susceptible to the action of cephalosporins. /Cephalosporins/

Biological Half-Life · 3건

EIGHT HEALTHY ADULTS RECEIVED 1 G, IV AND IM. BIOLOGICAL HALF-LIFE OF CEPHAPIRIN WAS 43 MIN. ABSORPTION HALF-LIFE OF CEPHAPIRIN FROM IM ADMIN WAS 1.25 HR.

IV SODIUM CEPHAPIRIN SHOWED BIEXPONENTIAL DISPOSITION CHARACTERISTICS IN SERUM & SUBCHONDRAL BONE, REACHING DISTRIBUTION EQUIL WITHIN 20 MIN. RAPIDLY ELIMINATED, WITH BETA HALF-LIFE OF ABOUT 0.3 HR & BODY CLEARANCE OF 400 ML/MIN.

관련 반응

2건
반응 기록 만들기
HRID 614446 반응식
HRID 614446반응물로uspto-grants-1979_03
HRID 1058487 반응식
HRID 1058487반응물로uspto-grants-2003_02

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

데이터베이스 식별자

CAS
21593-23-7
PubChem CID
30699
DTXSID
DTXSID9022784
ChEMBL
CHEMBL1599
ChEBI
CHEBI:554446
UNII
89B59H32VN
EC Number
244-466-5
Nikkaji
J11.255K
Collision Cross Section · 2건

173.05 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

183.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

Other Experimental PropertiesOdorless or with a slight odor. /Cephapirin Sodium/

물리화학적 성질

녹는점
135 °C · >135°C (dec.)
끓는 점
783.9 · 783.9±60.0 °C(Predicted)
밀도
1.4021 · 1.4021 (rough estimate)
굴절률
1.639 · 1.6390 (estimate)
저장 조건
-20 °C · -20°C Freezer, Under Inert Atmosphere
용해도
10 mg/ml · ≤10mg/ml in DMSO;5mg/ml in dimethyl formamide
물리적 상태
결정질 고체
산도 계수 (pKa)
2.67 · 2.67±0.50(Predicted)
색상
White to off-white

화학적 성질

Beige Solid

독성 정보

Body BurdenCephalosporins cross the placenta and are found in low concentrations in milk. /Cephalosporins/
Interactions · 2건

PROBENECID & SULFINPYRAZONE COMPETE WITH URIC ACID @ RENAL TUBULE TRANSPORT SITES. URINARY EXCRETION OF OTHER WEAK ACIDS ALSO CAN BE AFFECTED BY THESE URICOSURIC AGENTS. ... CEPHALOSPORINS ... MAY BE AFFECTED BY CONCURRENT USE OF PROBENECID OR SULFINPYRAZONE. /CEPHALOSPORINS/

The admixture of beta-lactam antibacterials (penicillins and cephalosporins) and aminoglycosides may result in substantial mutual inactivation. If they are administered concurrently, they should be administered in separate sites. Do not mix them in the same intravenous bag or bottle. /Cephalosporins/

Milk ConcentrationsCephalosporins cross the placenta and are found in low concentrations in milk. /Cephalosporins/
Human Toxicity Excerpts · 5건

... ADVERSE REACTIONS ... INCL LOCAL PAIN, INDURATION, STERILE ABSCESS, OR TISSUE SLOUGH AFTER IM INJECTION ... . /IV INFUSION/ IS CONSIDERABLY LESS IRRITATING THAN CEPHALOTHIN TO BLOOD VESSELS ... . REACTIONS ... DURING TREATMENT ARE TRANSIENT ELEVATIONS OF SERUM TRANSAMINASES & ALKALINE PHOSPHATASE, HALLUCINATIONS, NYSTAGMUS ... .

A positive Coombs' reaction appears frequently in patients who receive large doses of a cephalosporin. Hemolysis is not usually associated with this phenomenon, although it has been reported. Cephalosporins have produced rare instances of bone-marrow depression, characterized by granulocytopenia. The cephalosporins have /also/ been implicated as potentially nephrotoxic agents. /Cephalosporins/

TRANSIENT NEUTROPENIA HAS BEEN OBSERVED BETWEEN 10TH & 20TH DAYS OF THERAPY. /SEMISYNTHETIC CEPHALOSPORINS/

... MILD HYPERSENSITIVITY, MANIFESTED MOST FREQUENTLY AS ... LEUKOPENIA, ... TRANSIENT INCR IN SGOT, SGPT, ... BILIRUBIN, & BUN LEVELS. ... FALSE-POSITIVE REACTIONS FOR URINE GLUCOSE MAY BE OBSERVED ... OVERGROWTH OF NONSUSCEPTIBLE ORGANISMS CAN OCCUR AFTER PROLONGED USE.

For more Human Toxicity Excerpts (Complete) data for CEPHAPIRIN (12 total), please visit the HSDB record page.

Drug Induced Liver Injury · 4건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cephapirin

DILI Negative

DOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity Excerpts · 1건

First-generation cephalosporins /including cephapirin/ have the highest degree of activity against most gram-positive bacteria, including beta-lactamase producing Staphylococcus aureus and most streptococci; exceptions include methicillin resistant staphylococci, and penicillin resistant Streptococcus pneumonia. No cephalosporin is effective against Enterococcus faecalis infections. Gram-negative bacteria coverage is generally limited to Escherichia coli, Klebsiella species, and Proteus mirabilis. /Cephalosporins/

Populations at Special Risk · 1건

These medications sould not be used when the following medical problem exists: Previous allergic reaction (anaphylaxis) to penicillins, penicillin derivatives penicillamine, or cephalosporins; Gastrointestinal disease, history of, especially ulcerative colitis, regional enteritis, or antibiotic-associated colitis (cephalosporins may cause pseudomembranous colitis); Hepatic function impairment (cefoperazone is primarily excreted in bile; may also cause elevated SGOT, SGPT, and alkaline phosphatase; it is recommended that patients with both severe liver disease and significant renal disease receive a reduced dosage of cefoperazone. /Cephalosporins/

규제 정보

FDA RequirementsTolerances are established for the residues of cephapirin in the milk and edible tissues of dairy cattle.

안전 데이터

유해 물질 데이터
21593-23-7(Hazardous Substances Data)

Serum half-life is 0.6 hr /From table/

Metabolism/Metabolites · 3건

Major metabolite detected is desacetylcephapirin.

MAJOR METABOLITE OF CEPHAPIRIN IS DEACETYLCEPHAPIRIN, WHICH IS ABOUT ONE HALF OF ANTIMICROBIAL ACTIVITY OF PARENT CMPD; 20% OF ANTIBIOTIC ACTIVITY IN PLASMA IS DUE TO DEACETYLATED CMPD.

Cephapirin is partially metabolized in the plasma, liver and kidneys to diacetyl cephapirin, which has about 50% of the antibacterial activity of the parent cmpd. ... Up to 20% of the antibiotic activity in serum is due to the desacetyl metabolite.

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion · 5건

... PENETRATION OF CEPHALOSPORINS INTO /CEREBROSPINAL FLUID/ IS POOR. /CEPHALOSPORINS/

CLOSE TO 50% OF CEPHAPIRIN IS BOUND TO PLASMA PROTEIN. HALF-LIFE ... IN NORMAL INDIVIDUALS IS ABOUT 40 MIN & IS DEPENDENT ON RENAL FUNCTION. SIGNIFICANT AMT ... PRESENT IN BLOOD IS REMOVED BY HEMODIALYSIS. ... EXCRETED MAINLY BY KIDNEY; ONLY 1% PRESENT IN BILE.

... /CEPHAPIRIN/ NOT ABSORBED FROM GI TRACT. IM INJECTION OF 0.5 G OF CEPHAPIRIN PRODUCES MAX PLASMA CONCN OF ABOUT 10 UG/ML @ 45 MIN; 1 G ABOUT 16 UG/ML. PLASMA CONCN ... EFFECTIVE AGAINST MANY SENSITIVE MICROORGANISMS ARE STILL DETECTABLE 6 HR AFTER SINGLE IM DOSE OF 1 G.

ABOUT 30% OF IM DOSE OF CEPHAPIRIN IS EXCRETED IN URINE IN EACH OF 1ST 2 HR PERIODS AFTER INJECTION.

For more Absorption, Distribution and Excretion (Complete) data for CEPHAPIRIN (8 total), please visit the HSDB record page.

Cellular LocationsCytoplasm

용도 및 제조

UsesMEDICATION
Methods of Manufacturing · 1건

7-AMINOCEPHALOSPORANIC ACID, PREPD FROM NATURAL ANTIBIOTIC CEPHALOSPORIN C ... IS ACYLATED ... IN APPROPRIATE DEHYDROCHLORINATING ENVIRONMENT, & RESULTING CEPHAPIRIN (ACID) IS CONVERTED INTO ITS SODIUM SALT BY INTERACTION WITH SODIUM 2-ETHYLHEXANOATE IN SUITABLE ORG SOLVENT. /CEPHARIRIN SODIUM/

Formulations/PreparationsCefadyl sodium is available in 500 mg, 1g, 2g, 4g, 20g, for IM and IV injection. /Cefadyl sodium/

응용 분야

용도An antimicrobial agent.

상·하류 제품 정보

상류 원료

Aminocephalosporanic acid2-머캅토피리미딘모노브로모초산 브롬화물소듐 2-에틸헥사노에이트중탄산나트륨(중조)

공급사50 곳

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