RifamycinS

Modify Date: 2025-08-25 13:39:37

RifamycinS structure	Common Name	RifamycinS
	CAS Number	13553-79-2	Molecular Weight	695.753
	Density	1.3±0.1 g/cm3	Boiling Point	917.4±65.0 °C at 760 mmHg
	Molecular Formula	C₃₇H₄₅NO₁₂	Melting Point	179-181ºC (dec.)
	MSDS	N/A	Flash Point	508.6±34.3 °C

Use of RifamycinS

Rifamycin S is a quinone and an antibiotic agnet against Gram-positive bacteria (including MRSA). Rifamycin S is the oxidized forms of a reversible oxidation-reduction system involving two electrons. Rifamycin S generates reactive oxygen species (ROS) and inhibits microsomal lipid peroxidation. Rifamycin S can be used for tuberculosis and leprosy[1][2][3].

Name	Rifamycin S
Synonym	More Synonyms

Description	Rifamycin S is a quinone and an antibiotic agnet against Gram-positive bacteria (including MRSA). Rifamycin S is the oxidized forms of a reversible oxidation-reduction system involving two electrons. Rifamycin S generates reactive oxygen species (ROS) and inhibits microsomal lipid peroxidation. Rifamycin S can be used for tuberculosis and leprosy[1][2][3].
Related Catalog	Research Areas >> Infection Signaling Pathways >> Anti-infection >> Bacterial
Target	Gram-positive bacteria[3] Reactive oxygen species (ROS)[1]
In Vitro	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 Mn2+, Cu2+, and Co2+. The most effective metal ion is Mn2+[2].
In Vivo	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[1].
References	[1]. Rao DN, et al. A comparative study of the redox-cycling of a quinone (rifamycin S) and a quinonimine (rifabutin) antibiotic by rat liver microsomes. Free Radic Biol Med. 1997;22(3):439-46. [2]. Kono Y. Oxygen Enhancement of bactericidal activity of rifamycin SV on Escherichia coli and aerobic oxidation of rifamycin SV to rifamycin S catalyzed by manganous ions: the role of superoxide. J Biochem. 1982 Jan;91(1):381-95. [3]. Huang H, et al. Rifamycin S and its geometric isomer produced by a newly found actinomycete, Micromonospora rifamycinica. Antonie Van Leeuwenhoek. 2009 Feb;95(2):143-8.

Density	1.3±0.1 g/cm3
Boiling Point	917.4±65.0 °C at 760 mmHg
Melting Point	179-181ºC (dec.)
Molecular Formula	C₃₇H₄₅NO₁₂
Molecular Weight	695.753
Flash Point	508.6±34.3 °C
Exact Mass	695.294189
PSA	194.99000
LogP	2.87
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.605
InChIKey	BTVYFIMKUHNOBZ-PZCBORFTSA-N
SMILES	COC1C=COC2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)C(C)=CC=CC(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C1C)C4=O
Storage condition	2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KD1925000

CHEMICAL NAME :: 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b) furan-1,6,9,11(2H)-te trone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22 -heptamethyl-, 21-acetate

CAS REGISTRY NUMBER :: 13553-79-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C37-H45-N-O12

MOLECULAR WEIGHT :: 695.83

WISWESSER LINE NOTATION :: T C6 B65-24- A D E 2BC G& AV DV GV LO NO F&VM OU B&U D&U MHT&&TJ IQ J1 M1 QO1 R1 SOV1 T1 UQ V

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 16,412,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 258 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,865,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 122 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,865,1978

RTECS	KD1925000
HS Code	2941903000

rifamycin B

CAS#:13929-35-6

~92%

RifamycinS

CAS#:13553-79-2

Literature: Seong, Baik Lin; Han, Moon Hi Chemistry Letters, 1982 , p. 627 - 628

Rifamycin O

CAS#:14487-05-9

RifamycinS

CAS#:13553-79-2

Literature: Journal of the Chemical Society, Chemical Communications, , p. 395 - 396

Halomicin B

CAS#:54356-09-1

RifamycinS

CAS#:13553-79-2

Literature: Journal of the Chemical Society, Chemical Communications, , p. 395 - 396

Precursor 3
CAS#:13929-35-6 rifamycin B CAS#:14487-05-9 Rifamycin O CAS#:54356-09-1 Halomicin B
DownStream 2
CAS#:72428-95-6 Rifamycin verde CAS#:59232-88-1 Rifamycin Q

HS Code	2941903000

Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Nat. Prod. Rep. 31(4) , 504-13, (2014)

Despite the longstanding importance of polyketide natural products in human medicine, nearly all commercial polyketide-based drugs are prepared through fermentation or semi-synthesis. The paucity of m...

Synthesis and structure-activity relationships of novel substituted 8-amino, 8-thio, and 1,8-pyrazole congeners of antitubercular rifamycin S and rifampin.

Bioorg. Med. Chem. Lett. 21 , 6094-9, (2011)

A series of rifamycin S and rifampin analogues incorporating substituted 8-amino, 8-thio, and 1,8-pyrazole substituents has been synthesized. The compounds were made by activation of the C-8 phenol as...

Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

J. Am. Chem. Soc. 133(32) , 12795-800, (2011)

Under the conditions of transfer hydrogenation employing the cyclometalated iridium catalyst (R)-I derived from [Ir(cod)Cl](2), allyl acetate, 4-cyano-3-nitrobenzoic acid, and the chiral phosphine lig...

Name: Antibacterial activity against Staphylococcus aureus 2999
Source: ChEMBL
Target: Staphylococcus aureus
External Id: CHEMBL998299

Name: Antibacterial activity against Escherichia coli 1074
Source: ChEMBL
Target: Escherichia coli
External Id: CHEMBL998304

Name: Antibacterial activity against Haemophilus influenzae
Source: ChEMBL
Target: Haemophilus influenzae
External Id: CHEMBL998302

Name: Antibacterial activity against Neisseria gonorrhoeae
Source: ChEMBL
Target: Neisseria gonorrhoeae
External Id: CHEMBL998303

Name: Antibacterial activity against Streptococcus pneumoniae
Source: ChEMBL
Target: Streptococcus pneumoniae
External Id: CHEMBL998300

Name: HIV Cellular Data
Source: NIAID
Target: N/A
External Id: HIV Cellular Data

Name: Antibacterial activity against Streptococcus faecalis 1362/3
Source: ChEMBL
Target: Enterococcus faecalis
External Id: CHEMBL998301

Name: Antimicrobial activity against Escherichia coli EC2880 mutant after 16 to 20 hrs
Source: ChEMBL
Target: Escherichia coli
External Id: CHEMBL1914230

Name: Antimicrobial activity against wild type Escherichia coli DH5[alpha] after 16 to 20 h...
Source: ChEMBL
Target: Escherichia coli
External Id: CHEMBL1914229

Name: Antibacterial activity against rifamycin-sensitive Staphylococcus aureus CB190 ATCC 2...
Source: ChEMBL
Target: Staphylococcus aureus
External Id: CHEMBL899818

Total 17, Current Page 1 of 2

Rifamycin,1,4-dideoxy-1,4-dihydro-1,4-dioxo

UNII-PI53N820JV

rifomycin-S

rifamycin-S

(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-Trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1.0]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate

NCI 144-130

(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

EINECS 236-938-4

(12S,3E,5S,13E,15Z)-7t-acetoxy-15,9c,11t-trihydroxy-5r-methoxy-12,4,6t,8c,10c,12t,16-heptamethyl-2-oxa-18-aza-1(2,7)-naphtho[2,1-b]furana-cyclooctadecaphane-3,13,15-triene-11,6,9,17-tetraone

rifaximin S

O1,O4-didehydro-rifamycin

1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin

RifamycinS

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Henan Tianfu Chemical Co., Ltd.
China
Product Name: 1,4-Dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
Price: $Inquiry/1kg $Inquiry/25kg $Inquiry/1000kg $Inquiry/10ton
Purity: 99.0%
Delivery: Inquiry
Contact: Anson
Email: info@tianfuchem.com

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Price: ￥990/10 mM * 1 mL in DMSO

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RifamycinS

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CHEMICAL IDENTIFICATION

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ACUTE TOXICITY DATA

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RifamycinSBioassay

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