Rifamycin S

한글명:Rifamycin S

카스 번호13553-79-2

상품명:Rifamycin S

CBNumberCB1187968

분자식C37H45NO12

포뮬러 무게695.75

MOL 파일13553-79-2.mol

화학적 성질

녹는점	179-181°C (dec.)
알파	D20 +476° (c = 0.1 in methanol)
끓는 점	700.89°C (rough estimate)
밀도	1.2387 (rough estimate)
굴절률	1.6630 (estimate)
저장 조건	-20°C Freezer
용해도	벤젠(약간 용해됨), 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa)	3.85±0.70(Predicted)
색상	주황색에서 진한 주황색까지
최대 파장(λmax)	390nm(MeOH)(lit.)
Merck	14,8217
InChIKey	BTVYFIMKUHNOBZ-ODRIEIDWSA-N

위험 및 안전 성명

RTECS 번호

KD1925000

HS 번호

2941.90.1050

독성

LD50 in mice (mg/kg): 122 i.v.; 258 i.p.; 3000 orally (Sensi, 1964)

NFPA 704:

	0
1		0

그림문자(GHS)

Rifamycin S 화학적 특성, 용도, 생산

용도
Rifamycin S (Rifaximin EP Impurity E) is a semi-synthetic antibiotic.
Clinical Use
The rifamycins are a group of chemically related antibioticsobtained by fermentation from cultures of Streptomycesmediterranei. They belong to a class of antibiotics called theansamycins that contain a macrocyclic ring bridged acrosstwo nonadjacent positions of an aromatic nucleus. The termansa means “handle,” describing well the topography of thestructure. The rifamycins and many of their semisynthetic derivativeshave a broad spectrum of antimicrobial activity.They are most notably active against Gram-positive bacteriaand M. tuberculosis. However, they are also active againstsome Gram-negative bacteria and many viruses. Rifampin, asemisynthetic derivative of rifamycin B, was released as anantitubercular agent in the United States in 1971. A secondsemisynthetic derivative, rifabutin, was approved in 1992 forthe treatment of atypical mycobacterial infections.
The chemistry of rifamycins and other ansamycins hasbeen reviewed. All of the rifamycins (A, B, C, D, and E) arebiologically active. Some of the semisynthetic derivatives ofrifamycin B are the most potent known inhibitors of DNAdirectedRNA polymerase in bacteria, and their action isbactericidal. They have no activity against the mammalianenzyme. The mechanism of action of rifamycins as inhibitorsof viral replication appears to differ from that for their bactericidalaction. Their net effect is to inhibit the formation of thevirus particle, apparently by preventing a specific polypeptideconversion.77 Rifamycins bind to the β subunit of bacterialDNA-dependent RNA polymerases to prevent chain initiation.78 Bacterial resistance to rifampin has been associatedwith mutations leading to amino acid substitution in the subunit.78 A high level of cross-resistance between variousrifamycins has been observed.

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