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테리스로마이신

테리스로마이신
테리스로마이신 구조식 이미지
카스 번호:
191114-48-4
한글명:
테리스로마이신
동의어(한글):
테리스로마이신
상품명:
Telithromycin
동의어(영문):
KETEK;RU 66647;HMR 3647;TELITHROMYCIN;TelithroMycin 90%;(1R,2R,4R,6S,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-Dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-6-methoxy-2,4,6,8,10,14-hexamethyl-17-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone;2H-Oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)-tetrone,4-ethyloctahydro-11-Methoxy-3a,7,9,11,13,15-hexaMethyl-1-[4-[4-(3-pyridinyl)-1H-iMidazol-1-yl]butyl]-10-[[3,4,6-trideoxy-3-(diMethylaMino)-b-D-xylo-hexopyranosyl]oxy]-,(3aS,4R,7R,9R,10R,11R,1;(3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-Ethyloctahydro-11-Methoxy-3a,7,9,11,13,15-hexaMethyl-1-[4-[4-(3-pyridinyl)-1H-iMidazol-1-yl]butyl]-10-[[3,4,6-trideoxy-3-(diMethylaMino)-β-D-xylo-hexopyranosyl]oxy]-2H-oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)tetrone
CBNumber:
CB1482102
분자식:
C43H65N5O10
포뮬러 무게:
812
MOL 파일:
191114-48-4.mol

테리스로마이신 속성

녹는점
176-188 C
끓는 점
966℃
RTECS 번호
KF4674500
인화점
>110°(230°F)
저장 조건
-20?C Freezer
수용성
Sparingly soluble in water
CAS 데이터베이스
191114-48-4(CAS DataBase Reference)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 36/37/38
안전지침서 26-36
위험 등급 9
유해 물질 데이터 191114-48-4(Hazardous Substances Data)
그림문자(GHS):
신호 어:
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H400 수생생물에 매우 유독함 수생 환경유해성 물질 - 급성 구분 1 경고 P273, P391, P501
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 P273, P391, P501
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.

테리스로마이신 C화학적 특성, 용도, 생산

개요

Telithromycin was first launched in Germany as a once-daily oral treatment for respiratory infections including community-acquired pneumonia, acute bacterial exacerbations of chronic bronchitis, acute sinusitis and tonsillitis/pharyngitis. This semisynthetic derivative of the natural macrolide erythromycin is the first marketed ketolide, a new class of antibiotics featuring a C3-ketone instead of the L-cladinose group. The 14-membered ring antibacterial agent prevents bacterial protein synthesis by binding to two domains of the 50S subunit of bacterial ribosomes. It shows potent in vitro activity against common respiratory pathogens including Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pyogenes as well as other atypical pathogens. The 3-keto group confers increased acidic stability and reduced induction of macrolide-lincosamide-streptogramin B resistance that is frequently observed with macrolides. The substituted C11-C12 carbamate residue appears not only to increase affinity for the ribosomal binding site but also to stabilize the compound against esterase hydrolysis and avoid resistance due to elimination of macrolides from the cell by an efflux pump encoded by the mef gene in certain pathogens. Telithromycin is both a competitive inhibitor and a substrate of CYP3A4. However, unlike several macrolides such as troleandomycin, it does not form a stable inhibitory CYP P-450 Fe2+-nitrosoalkane metabolite complex which is potentially hepatotoxic. The drug is well tolerated and well distributed into pulmonary tissues, bronchial secretions, tonsils and saliva. It turns out to be highly concentrated in azurophil granules of polymorphonuclear neutrophils thereby facilitating its delivery to the phagocytosed bacteria.

화학적 성질

Pale Beige Solid

Originator

Aventis (France)

용도

Telithromycin represents the first member of the current generation of erythromycin descendants, belonging to the ketolide class. The ketolides are characterised by the hydrolysis of the cladinose sugar and subsequent oxidation of the alcohol to a ketone. Telithromycin is acid stabile and has good activity against erythromycin-resistant S. aureus, and improved pharmacokinetics.

용도

A ketolide antibiotic, used to treat respiratory infections

상표명

Ketek (Sanofi Aventis).

Antimicrobial activity

The spectrum covers Gram-positive and Gramnegative cocci, Gram-positive bacilli, fastidious Gram-negative bacilli, atypical mycobacteria, M. leprae, H. pylori, anaerobes, T. pallidum, intracellular pathogens and atypical organisms.
It exhibits bactericidal activity in vitro against isolates of Str. pneumoniae regardless of the underlying resistance to penicillin G, erythromycin A and other agents. It is 2–4 times more active than clarithromycin against erythromycin A-susceptible isolates of Str. pneumoniae and other streptococci. Against H. influenzae the MIC range is 1–4 mg/L. It also exhibits good in-vitro activity against Coxiella burnetii (MIC 1 mg/L) and various Gram-positive species, including viridans streptococci (MIC ≤0.015–0.25 mg/L), C. diphtheriae (MIC 0.004–0.008 mg/L) and Listeria spp. (MIC 0.03–0.25 mg/L).

원료

It retains activity against isolates resistant to erythromycin A. Str. pneumoniae and Str. pyogenes isolates for which the MIC of telithromycin is above the resistance breakpoint of 2 mg/L are presently rare. It is not active against Staph. aureus isolates that owe their resistance to erythromycin to constitutive methylation of adenine 2058 on domain V of the peptidyl transferase loop.

일반 설명

Telithromycin (Ketek) is an orally bioavailable macrolide.The antibiotic is semisynthetic. Telithromycin is classifiedas a ketolide, and it differs chemically from the macrolidegroup of antibacterials by the lack of α-L-cladinose at 3-position of the erythronolide A ring, resulting in a 3-ketofunction. It is further characterized by imidazolyl andpyridyl rings inked to the macrolide nucleus through a butylchain. The mechanism of action of telithromycin is the sameas that of the macrolide class.
Telithromycin causes a blockade of protein synthesis bybinding to domains II and V of 23S rRNA of the 50S ribosomalsubunit. Because telithromycin binds at domain II,activity against Gram-positive cocci is retained in the presenceof resistance mediated by methylases that alter thedomain V binding site. The antibiotic is also believed to inhibitthe assembly of ribosomes. Resistance to telithromycinoccurs because of riboprotein mutations.

Pharmaceutical Applications

A 14-membered-ring ketolide, obtained by semisynthesis from erythromycin A. Formulated for oral administration.

Pharmacokinetics

Oral absorption :90%
Cmax 800 mg oral :1.9–2.27 mg/L (steady state after 2–3 days)
Plasma half-life: 10–12 h
Volume of distribution :210 L
Plasma protein binding:60–70%
After oral administration the absolute bioavailability is 57% in both young and elderly subjects. The rate and extent of absorption are not influenced by food. In a study of ascending doses administered to healthy volunteers, peak plasma concentration ranged from 0.8 mg/L (400 mg dose) to 6 mg/L (2400 mg dose). The peak plasma concentration was reached after 1–2 h. The apparent elimination half-lives ranged from 10 to 14 h, with an AUC of 2.6 mg.h/L (400 mg dose) to 43.3 mg.h/L (2400 mg dose). After repeated oral doses the ratios between day 1 and day 10 ranged from 1.3 to 1.5. After once-daily oral dosing with 800 mg, the AUC is 8.25 mg.h/L.

부작용

It is generally well tolerated. The main adverse event is diarrhea.

테리스로마이신 준비 용품 및 원자재

원자재

준비 용품


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shchemsky@sina.com China 32392 50
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