ChemicalBook > CAS DataBase List > Rifaximin

Rifaximin

Product Name
Rifaximin
CAS No.
80621-81-4
Chemical Name
Rifaximin
Synonyms
XIFAXAN;RIFAMIXIN;l105;normix;l105sv;Riimim;RIFACOL;Rifaxin;Ritacol;RIFAXIMIN
CBNumber
CB5244184
Molecular Formula
C43H51N3O11
Formula Weight
785.89
MOL File
80621-81-4.mol
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Rifaximin Property

Melting point:
200-2050C (dec)
Density 
1.36±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
ethanol: soluble1mg/mL
form 
powder
pka
2.83±0.70(Predicted)
color 
dark orange
Merck 
14,8220
Stability:
Hygroscopic
InChIKey
NZCRJKRKKOLAOJ-XRCRFVBUSA-N
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Safety

WGK Germany 
2
RTECS 
KD1576000
HS Code 
2941.90.3000
Toxicity
LD50 orally in rats: >2000 mg/kg (Borelli, Bertoli)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H312Harmful in contact with skin

H332Harmful if inhaled

H335May cause respiratory irritation

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
R9904
Product name
Rifaximin
Packaging
1g
Price
$157
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR1946
Product name
Rifaximin
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
300mg
Price
$214
Updated
2024/03/01
Sigma-Aldrich
Product number
33999
Product name
Rifaximin
Purity
VETRANAL?, analytical standard
Packaging
100mg
Price
$119
Updated
2024/03/01
TCI Chemical
Product number
R0101
Product name
Rifaximin
Purity
>97.0%(HPLC)(N)
Packaging
1g
Price
$127
Updated
2024/03/01
TCI Chemical
Product number
R0101
Product name
Rifaximin
Purity
>97.0%(HPLC)(N)
Packaging
5g
Price
$461
Updated
2024/03/01
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Rifaximin Chemical Properties,Usage,Production

Description

Rifaximin is an antibiotic structurally related to rifamycin. It is reported to be efficacious in the treatment of gastrointestinal infections and hepatic encephalopathy, being highly active against Gram-positive and -negative aerobic and anaerobic bacteria. Due to poor systemic absorption, rifaximin is effective in presurgical sterilization of the GI tract.It displays good activity against a wide spectrum of bacteria, including Salmonella spp., S. aureus, and E. coli.

Chemical Properties

Red-Orange Crystalline Powder

Originator

Alfa (Italy)

Uses

antibacterial, RNA synthesis inhibitor

Uses

Muscle Relaxant

Uses

Rifaximin is a non-absorbable semisynthetic Rifamycin antibiotic.

Definition

ChEBI: A semisynthetic member of the class of rifamycins and non-systemic gastrointestinal site-specific broad spectrum antibiotic. Used in the treatment of traveller's diarrhoea, hepatic encephalopathy and irritable bowel syndrome.

brand name

Xifaxan (Salix);Normix.

Antimicrobial activity

The in-vitro activity is slightly inferior to that of rifampicin. The MIC90 for Gram-positive cocci is well below 1 mg/L, with the exception of enterococci (MIC 2–8 mg/L). Among intestinal pathogens C. difficile is sensitive (MIC90 0.8 mg/L), Esch. coli, Salmonella spp. and Shigella spp. are inhibited by 4–8 mg/L. Campylobacter jejuni is mostly insensitive.

Pharmaceutical Applications

A semisynthetic derivative of rifamycin S formulated for oral administration. It is poorly absorbed from the gastrointestinal tract, where its high concentrations are effective against a variety of gastrointestinal pathogens.

Mechanism of action

The mechanism of action of pyrazinamide is unknown, but recent findings suggest that pyrazinamide may be active either totally or in part as a pro-drug. Susceptible organisms produce pyrazinamidase, which is responsible for conversion of pyrazinamide to pyrazinoic acid intracellularly. Mutation in the pyrazinamidase gene (pncA) results in resistant strains of M . tuberculosis. Pyrazinoic acid has been shown to possess biological activity at a pH 5.4 or lower, in contract in vitro tests that show pyrazinoic acid is 8- to 16-fold less active than pyrazinamide . Pyrazinoic acid may lower the pH in the immediate surroundings of the M . tuberculosis to such an extent that the organism is unable to grow, but this physicochemical property appears to account for only some of the activity. The protonated pyrazinoic acid also can permeate the mycobacterial membrane to lower the pH of the cytoplasm. Recent evidence suggests that pyrazinoic acid decreases membrane potential in older, nonreplicating bacilli, thus decreasing membrane transport, and interferes with the energetics of the membrane.

Pharmacokinetics

Oral absorption is very low. However, a fraction of the dose may be absorbed and rapidly eliminated through the bile. A 400 mg oral dose produces a maximum plasma concentration of 3.8 mg/L after 1.2 h. The plasma half-life is 5.8 h. Up to 90% of the administered dose is concentrated in the gut, less than 0.2% in the liver and kidney, and less than 0.01% in other tissues.

Clinical Use

It is used for a variety of gastrointestinal diseases, including the treatment of traveler’s diarrhea. Preliminary results suggest clinical efficacy in the therapy of hepatic encephalopathy and of C. difficile infections.

Side effects

Oral doses up to 100 mg/kg for 6 months produced no significant signs of toxicity to rats. Teratogenic effects in rats and rabbits have been reported (pregnancy category C).
Very few adverse effects were reported during human treatment, mostly gastrointestinal discomfort. Prolonged therapy was associated with infrequent urticarial skin reactions.

in vitro

rifaximin, a gut-specific ligand for the human nuclear receptor pregnane-x receptor (pxr), contributes to the maintenance of the intestinal immune homeostasis. rifaximin abrogates the binding of nf-κb caused by lps. in human colon biopsies from inflammatory bowel diseases patients, exposure of rifaximin (100 μm) reduced mrna levels of il-8, rantes, mip-3α and tnfα induced by lps stimulation [1]. rifaximin acted on the β subunit of the deoxyribonucleic acid (dna)-dependent ribonucleic acid (rna) polymerase enzyme of bacteria to inhibit bacterial rna synthesis. the susceptibility of gram-positive organisms to rifaximin was greater than that of gram-negative organisms [2]. in the dpx2 cell line transfected with stable recombinant human pxr expression, hpxr was significantly activated at rifax concentrations over 1 μm and the ec50 was about 20 μm[3].

in vivo

in the small intestine of hpxr mice treated with rifaximin, several pxr target genes such as cyp3a11, gsta1, mrp2, and oatp2 were up-regulated. rifaximin treatment demonstrated no significant effect on hepatic pxr target genes in wild-type, pxr-null, and hpxr mice [3]. in pxr-humanized mice, long-term administration of rifaximin for 6 months on the liver up-regulated the expression of hepatic genes related to triglyceride synthesis and lipid accumulation [4].

Drug interactions

Potentially hazardous interactions with other drugs
Ciclosporin: concentration increased by ciclosporin.

Metabolism

Pyrazinamide is readily absorbed after oral administration, but little of the intact molecule is excreted unchanged. The major metabolic route consists of hydrolysis by hepatic microsomal pyrazinamidase to pyrazinoic acid, which may then be oxidized by xanthine oxidase to 5-hydroxypyrazinoic acid. The latter compound may appear in the urine either free or as a conjugate with glycine.

storage

-20°C

References

[1]. mencarelli a, renga b, palladino g, et al. inhibition of nf-κb by a pxr-dependent pathway mediates counter-regulatory activities of rifaximin on innate immunity in intestinal epithelial cells[j]. european journal of pharmacology, 2011, 668(1): 317-324.
[2]. gillis j c, brogden r n. rifaximin[j]. drugs, 1995, 49(3): 467-484.
[3]. ma x, shah y m, guo g l, et al. rifaximin is a gut-specific human pregnane x receptor activator[j]. journal of pharmacology and experimental therapeutics, 2007, 322(1): 391-398.
[4]. cheng j, krausz k, tanaka n, et al. chronic exposure to rifaximin causes hepatic steatosis in pregnane x receptor-humanized mice[j]. toxicological sciences, 2012: kfs211.
[5]. bass n m, mullen k d, sanyal a, et al. rifaximin treatment in hepatic encephalopathy[j]. new england journal of medicine, 2010, 362(12): 1071-1081.
[6]. pimentel m, lembo a, chey w d, et al. rifaximin therapy for patients with irritable bowel syndrome without constipation[j]. new england journal of medicine, 2011, 364(1): 22-32.
[7]. sharara a i, aoun e, abdul-baki h, et al. a randomized double-blind placebo-controlled trial of rifaximin in patients with abdominal bloating and flatulence[j]. the american journal of gastroenterology, 2006, 101(2): 326-333.

Rifaximin Preparation Products And Raw materials

Raw materials

Preparation Products

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Rifaximin Suppliers

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View Lastest Price from Rifaximin manufacturers

Henan Suikang Pharmaceutical Co.,Ltd.
Product
Rifaximin 80621-81-4
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99.0%
Supply Ability
10tons
Release date
2024-04-26
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Rifaximin 80621-81-4
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
500 KGS
Release date
2024-07-16
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Rifaximin 80621-81-4
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-11-06

80621-81-4, RifaximinRelated Search:

2-Methoxyethanol 1,6-Dihydroxynaphthalene 2-Naphthaleneethanol 1-NAPHTHYLGLYOXAL HYDRATE 6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one PHENYLGLYOXAL MONOHYDRATE 6-METHOXY-1-NAPHTHOL 2-METHOXY-1-NAPHTHALDEHYDE 3,3-Dimethoxybutan-2-one 1,3-DIHYDROXYNAPHTHALENE RIFAMYCIN SV 1H-NAPHTH[1,2-D]IMIDAZOLE 2-Methyl-1H-benzimidazol-7-amine AKOS BBS-00001299 7-METHYL-1-NAPHTHOL Rifaximin Methoxy Rifaximin,Traveller'SDiarrhea

  • 2s-acetyloxy-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11, 16,20,22,24,26-octamethyl-2,7-(epoxypentoeleca(1,11,13)trienimino)benzofuro[4,5-e]pyride[1,2-a]benzimidazole-1,15(2h)-dione
  • XIFAXAN
  • normix
  • ole-1,15(2h)-dione,25-(acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16
  • rifamycinl105
  • rifamycinl105sv
  • rifaxidin
  • RIFAXIMIN
  • RIFACOL
  • 4-DEOXY-4'-METHYLPYRIDO[1',2'-1,2]IMIDAZO[5,4-C]RIFAMYCIN SV
  • 4-Deoxy-4methylpyridol[121,2]imidazo[5,4-c]rifamycin SV
  • 2,7-(Epoxypentadeca1,11,13trienimino)benzofuro4,5-epyrido1,2-abenzimidazole-1,15(2H)-dione, 25-(acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-, (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-
  • RIFAMIXIN
  • Earthworm extract / Earthworm Protein
  • ,20,22,24,26-octamethyl-,(2s-(2r*,16z,18e,20r*,21r*,22s*,23s*,24s*,25r*,26s*,
  • 2,7-(epoxypentadeca(1,11,13)trienimino)benzofuro(4,5-e)pyrido(1,2-a)benzimidaz
  • 28e))-27r
  • fatroximin
  • l105
  • l105(ansamacrolideantibiotic)
  • l105sv
  • Rifacol, 4-Deoxy-4μ-methylpyrido[1μ,2μ-1,2]imidazo[5,4-c]rifamycin SV
  • (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26S,27S,28E)-5,6,21,23,25 Pentahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca(1,11,13)trienimino)benzofuro(4,5-e)pyrido(1,2-a)benzimidazole-1,15(2H)-dione, 25-acetate
  • 2,7-(Epoxypentadeca(1,11,13)trienimino)benzofuro(4,5-e)pyrido(1,2-a)benzimidazole-1,15(2H)- dione, 25-(acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-, (2S-(2R*,16Z,18E,20R*,21R*,22S*,23S*,24S*,25R*,26S*,27R*,28E))
  • CILIFRUITEXTRACT
  • RifaxiMin(Xifaxan)
  • Earthworm Extract
  • (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-25-(acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(Epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1-15(2H)-dione
  • The earthworm extract
  • Rifaximin(Rifacol)
  • Extract of dragon's Dragon
  • (English name): Rifaximin
  • Rifaximinn
  • Riimim
  • Rifaximin for system suitability CRS
  • Rifaximin &gt
  • Rifaximin CRS
  • Rifaximin Standard
  • Ground dragon extract
  • Rifaximin USP/EP/BP
  • Rifaximin (10mM in DMSO)
  • Rifaximin (Y0001074)
  • Rifaximin D6Q: What is Rifaximin D6 Q: What is the CAS Number of Rifaximin D6 Q: What is the storage condition of Rifaximin D6 Q: What are the applications of Rifaximin D6
  • Rifaximin System suitability(Y0001075)
  • RifaximinQ: What is Rifaximin Q: What is the CAS Number of Rifaximin Q: What is the storage condition of Rifaximin Q: What are the applications of Rifaximin
  • Rifaximin (RFX) extrapure, 98%
  • Refaximin
  • Pork medicinal herbs
  • BRN 3584528
  • Rifaxin
  • Ritacol
  • Rifaximin/Rifaxiamine
  • Rifaximin in methanol
  • 80621-81-4
  • C43H51N3O11
  • XIFAXAN
  • Intermediates & Fine Chemicals
  • Pharmaceuticals