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4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin

Rifamycin S

CAS: 13553-79-2

Molecular Formula: C37H45NO12

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4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin - Names and Identifiers

Name Rifamycin S
Synonyms NSC 144130
BRN 0604802
RIFAMYCIN S
NCI 144-130
Rifamycin S
Rifomycin S
RIFAMPICIN S
UNII-PI53N820JV
Rifamycin EP Impurity B
Rifaximin EP Impurity E (Rifamycin S)
4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin
1,4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
1,4-Dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
Rifamycin, 1,4-dideoxy-1,4-dihydro-1,4-dioxo-
2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,6,9,11(2h)-tetron
2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,6,9,11(2H)-tetrone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate
2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate (7CI,8CI)
5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate
(14E,24E)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate
(2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate
CAS 13553-79-2
EINECS 236-938-4
InChI InChI=1/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
InChIKey BTVYFIMKUHNOBZ-ODRIEIDWSA-N

4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin - Physico-chemical Properties

Molecular FormulaC37H45NO12
Molar Mass695.75
Density1.2387 (rough estimate)
Melting Point179-181°C (dec.)
Boling Point700.89°C (rough estimate)
Specific Rotation(α)D20 +476° (c = 0.1 in methanol)
Flash Point508.615°C
Solubility Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
Vapor Presure0mmHg at 25°C
Appearanceneat
ColorOrange to Dark Orange
Maximum wavelength(λmax)['390nm(MeOH)(lit.)']
Merck14,8217
pKa3.85±0.70(Predicted)
Storage Condition-20°C Freezer
Refractive Index1.6630 (estimate)
UseUsed as a pharmaceutical Intermediate
In vitro study The inhibition of bacterial growth by Rifamycin SV is due to the production of active species of oxygen resulting from the oxidation-reduction cycle of Rifamycin SV in the cells. The aerobic oxidation of Rifamycin SV to Rifamycin S is induced by metal ions, such as Mn 2+ , Cu 2+ , and Co 2+ . The most effective metal ion is Mn 2+ .
In vivo study Rat liver sub-mitochondrial particles also generated hydroxyl radical in the presence of NADH and Rifamycin S. NADH dehydrogenase (complex I) as the major component involved in the reduction of Rifamycin S. Compared to NADPH, NADH is almost as effective (Rifamycin S) in catalyzing the interactions of these antibiotics with rat liver microsomes. Rifamycin S is shown to be readily reduced to Rifamycin SV, the corresponding hydroquinone by Fe(II). Rifamycin S forms a detectable Fe(II)-(Rifamycin S)3 complex. The Fe:ATP induced lipid peroxidation is completely inhibited by Rifamycin S. Rifamycin S can interact with rat liver microsomes to undergo redox-cycling, with the subsequent production of hydroxyl radicals when iron complexes are present.

4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin - Risk and Safety

RTECSKD1925000
ToxicityLD50 in mice (mg/kg): 122 i.v.; 258 i.p.; 3000 orally (Sensi, 1964)

4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin - Reference Information

rifamycin compounds rifamycin compounds are a class of antibiotics with broad-spectrum antibacterial activity, it has a strong antagonistic effect on Gram-positive bacteria such as Mycobacterium tuberculosis, Mycobacterium leprae, streptococcus and Pneumonia coccus, especially on drug-resistant Staphylococcus aureus, and also has an effect on some Gram-negative bacteria. Rifampicin, rifapentine, rifabutin and other drugs, which were semi-synthesized by natural products rifamycin SV or rifamycin B, entered the list of basic drugs World Health Organization (WHO), and saved tens of thousands of TB patients' lives as first-line anti-TB drugs. The biosynthetic pathway of rifamycin has been a hot topic for biochemists since it was first discovered in1957. Although the use of isotope labeling and gene knockout (knock-in) and other methods have elucidated most of the links in the biosynthetic pathway, but the key link in how rifamycin SV is converted to rifamycin B has long plagued the scientific community. Recently, the enzyme engineering research group, led by Li Shengying, a researcher at the Qingdao Institute of Bioenergy and Bioprocess, Chinese Academy of Sciences, together with Zhao Guoping and Xiao Youli's research group at the Institute of Plant Physiology and Ecology, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, as well as a number of scholars from the Tang phago team at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, for the first time in the world to clarify the detailed biosynthetic pathway and enzyme-catalyzed reaction mechanism of rifamycin SV into rifamycin B, the results have been published online in the newly published journal Nature Communications.
rifamycin sodium rifamycin sodium is the third generation product of rifamycin drugs, which has a broad spectrum of antibacterial activity, it has high sensitivity to a variety of clinical common drug-resistant bacteria. Rifamycin B undergoes oxidation, reduction and hydrolysis to form rifamycin sodium. Its characteristics of Staphylococcus aureus (including penicillin resistant and new penicillin resistant strains), Mycobacterium tuberculosis has a strong antibacterial effect. The mechanism of action is to inhibit the activity of bacterial RNA polymerase. Hinder bacterial RNA synthesis, eventually blocking the synthesis of bacteria required protein, resulting in bacterial death, showing bactericidal effect.
biological activity Rifamycin S is a quinone and antibiotic against gram-positive bacteria, including MRSA. Rifamycin S is an oxidized form of a reversible redox system involving two electrons. Rifamycin S can produce reactive oxygen species (ROS) and inhibit microsomal lipid peroxidation, and can be used in the study of tuberculosis and leprosy.
Target Gram-positive bacteria Reactive oxygen species (ROS)
Use is useful as a pharmaceutical intermediate.
Last Update：2024-04-09 19:55:45
4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
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