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암피실린 무수산염

6-((2-Amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid

HCID 2174
새 노트새 반응견적 요청하기
인쇄 미리보기

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

기본 정보

CAS
69-53-4
표준 SMILES
CC1(C)SC2C(NC(=O)C(N)c3ccccc3)C(=O)N2C1C(=O)O
InChIKey
AVKUERGKIZMTKX-UHFFFAOYSA-N
분자식
C16H19N3O4S
평균 분자량
349.4 g/mol
단동위원소 질량
349.10962709

개요

6-[(2-amino-1-oxo-2-phenylethyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is a penicillin.

이름 및 식별자

우선 이름
6-((2-Amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
IUPAC
6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
현지명
암피실린 무수산염
영어명
Ampicillin
분자식
C16H19N3O4S
분자량
349.4

이름 및 동의어

DTXSID208590776-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid856649-99-56-((2-Amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidRefChem:1073645DTXCID80196632AlpenGuicitrineAmpicinWypicil6-{[amino(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidAmpen
이름 더 보기
암피실린무수산염암피실린무수산염Nonane-1,9-diamineAmpicillin SulbactamWymoxUnasynpenbritinprincipenviccillinpolycillinaminobenzylpenicillinp-50
Semicillin RMFCD00005175AB-PC SolAB-PCHI 63D-(-)-.alpha.-AminobenzylpenicillinAmpipenin, nt3AY 6108

물성

구조 계산 물성보충 중

XLogP
-1.1
극성 표면적
138 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
6
회전 가능 결합 수
4
무거운 원자 수
24
형식 전하
0
복잡도
562

물리화학적 성질

녹는점
198 · 198-200 °C (dec.)(lit.)
끓는 점
201.8 °C · 201.8°C (rough estimate)
밀도
1.2794 · 1.2794 (rough estimate)
굴절률
1.632 · 1.6320 (estimate)
저장 조건
2 · 2-8°C
용해도
4 OH · NH4OH 1 M: 50 mg/mL, 투명, 무색
물리적 상태
고체
색상
흰색에서 연한 노란색
산도 계수 (pKa)
2.5 · 2.5 (COOH)(at 25℃)
생물학적 소스
microbial
수용성
13.9 g/L · 13.9g/L(25℃)
JECFA Number
85 · 85
Merck
13 · 13,591
BRN
1090925 · 1090925
안정성
안정적이지만 습기에 민감할 수 있습니다. 강한 산화제와 호환되지 않습니다.
주요 응용
임상 시험
InChI
1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChIKey
AVKUERGKIZMTKX-NJBDSQKTSA-N

안전 및 규제

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

안전 데이터

wgk
2
rtecs
XH8425000
독성
LD50 oral in mouse: > 5gm/kg
HS 번호
29212900
risk_code
36/37/38-42/43-61
hazard_code
Xn,T
safety_code
22-26-36/37-45-53
기존화학 물질
KE-01538
F 고인화성물질
10-23
자연 발화 온도
301°C
Hazard Classifications
Resp. Sens. 1Skin Sens. 1
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
69-53-4(Hazardous Substances Data)

화학 및 산업

응용 분야 · 3건

개요Ampicillin is an antibacterial antibiotic from the α-aminobenzyl penicillin group, which differs from penicillin by the presence of an amino group that facilitates penetration through the outer membrane of some gram-negative bacteria. Ampicillin is Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. Ampicillin acts by interfering directly with the biosynthesis of peptidoglycan, which constitutes the major component of the bacterial cell wall, leading to structural instability and death of bacteria. Ampicillin is a β-lactam antibiotic within the penicillin family. As a member of this family, Ampicillin is susceptible to β-lactamase, which hydrolyzes the β-lactam ring. This broad spectrum antibiotic is effective against gram-positive, gram-negative bacteria and anaerobic bacteria. Ampicillin is widely used in cell culture as a selective agent. As an antibiotic, Ampicillin binds to penicillin binding proteins (PBPs) on a susceptible organism and Inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. After binding to the PBPs, Ampicilin acts as a structural analogue of acyl-D-alanyl-D-alanine, acylates the transpeptidase enzyme and thereby prevents the cross-linking of the peptidoglycan of the cell wall necessary for the growth of the bacterium. Ampicillin sodium can be used as a selective agent in several types of isolation media. Ampicillin sodium is routinely used to select for cells containing the pcDNA3.1 and pEAK10 resistance plasmids in cell line A904L at an effective concentration of 50 μg/ml.

용도Labelled Ampicillin. Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.

일반 설명Ampicillin was synthesized by Beecham Research Laboratories in 1961 and evaluated for its anti-gram-negative activity by Rolinson et al.. It was the first semisynthetic penicillin showing strong activity against gramnegative bacilli. Although it is hydrolyzed by bacterial penicillinase, it is active against Escherichia coli, Shigella, Proteus mirabilis, and Haemophilus influenzae and is used very widely as an oral antibiotic. Ampicillin also is used by injection for serious infections.

상·하류 제품 정보

상류 원료

Penicillin G

관련 반응

21건
반응 기록 만들기
HRID 87276 반응식
HRID 87276반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 136097 반응식
HRID 136097생성물로반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 188878 반응식
HRID 188878생성물로반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 208463 반응식
HRID 208463반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 281919 반응식
HRID 281919반응물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 291676 반응식
HRID 291676반응물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 301584 반응식
HRID 301584반응물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 665278 반응식
HRID 665278반응물로Training data from https://doi.org/10.1039/C8SC04228D (3/10)
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화합물 노트

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데이터베이스 식별자

CAS
69-53-4、856649-99-5
PubChem CID
2174
DTXSID
DTXSID20859077
ChEMBL
CHEMBL1617921
ChEBI
CHEBI:94334
Nikkaji
J281.525G
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c3ccccc3)C(O)=O
EPA
Ampicillin (69-53-4)

화학적 성질

Ampicillin in anhydrous form occurs as crystals.

바륨 클로라이드 디하이드레이트
4-아미노벤조산
플루오르화칼륨
탄산 칼륨
트리에틸아민
피발로일 클로라이드
염산
수산화나트륨
알파-아미노벤제네아세틸클로라이드
염화칼륨
(R)-알파-아마노벤젠아세트산
벤질 클로로탄소산
수소
클로로포름산에틸

하류 제품

6-아미노페니실란 산디칼륨 헥사플루오로티타늄산염과산화모노황산 칼륨 황산브로민화 칼륨불화붕산 칼륨플루오르화칼륨브로민산 칼륨인산 칼륨 이염기성중크롬산 칼륨제일인산칼륨크롬산 칼륨육불화황과망간산칼륨불화 칼륨 지르코늄이불화 칼륨염화칼륨

추가 설명

정의ChEBI: A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.