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Rifaximin

Rifaximin structure

CAS No:
80621-81-4
Formula:
C43H51N3O11
Chemical Name:
Rifaximin
Synonyms:
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,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-;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)]-;(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;L 105;Rifamycin L 105SV;L 105SV;Rifaximin;Rifamycin L 105;L 105 (ansamacrolide antibiotic);refaximin;Xifaxan;Normix;Xifaxanta;(2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,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;126334-60-9;88747-56-2;1229193-76-3
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Rifaximin(Xifaxan) is an orally administered, semi-synthetic, nonsystemic antibiotic derived from rifamycin SV with antibacterial activity.IC50 Value:Target: RNA polymerase; antibacterialRifaximin is a semisynthetic, rifamycin-based non-systemic antibiotic, meaning that very little of the drug will pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It is used in the treatment of traveler's diarrhea and hepatic encephalopat

Rifaximin is a nonabsorbable antibiotic that is used as treatment and prevention of travelers’ diarrhea and, in higher doses, for prevention of hepatic encephalopathy in patients with advanced liver disease and to treat diarrhea in patients with irritable bowel syndrome. Rifaximin has minimal oral absorption and has not been implicated in causing liver test abnormalities or clinically apparent liver injury.|A synthetic rifamycin derivative and anti-bacterial agent that is used for the treatment of GASTROENTERITIS caused by ESCHERICHIA COLI INFECTIONS. It may also be used in the treatment of HEPATIC ENCEPHALOPATHY.

Rifaximin Basic Attributes

Molecular Weight：

785.88

Exact Mass：

785.88

EC Number：

1308068-626-2

DSSTox ID：

DTXSID7045998

ATC Code：

A - Alimentary tract and metabolism|D - Dermatologicals

Characteristics

PSA：

198

XLogP3：

6.29580

Appearance：

dark orange

Density：

1.4±0.1 g/cm3

Melting Point：

200-205 °C (decomp)

Refractive Index：

1.634

Water Solubility：

ethanol: soluble1mg/mL

Storage Conditions：

0-6°C

Toxicity：

LD50 orally in rats: >2000 mg/kg (Borelli, Bertoli)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

RTECS Number：

KD1576000

GHS Classification：

|Warning|H312 (76.92%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P201, P202, P261, P271, P280, P281, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 17 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Hepatotoxicity：

Despite widespread use, there is little evidence that rifaximin when given orally causes liver injury, either in the form of serum enzyme elevations or clinically apparent liver disease.

Drug Information

LiverTox Summary：

Drug Classes：

Antiinfective Agents

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)

MeSH Entry Terms：

4-deoxy-4'-methylpyrido(1',2'-1,2)imidazo(5,4C)rifamycin

Rifaximin Use and Manufacturing

Uses

Non-absorbable semisynthetic Rifamycin antibiotic

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:785.9
XLogP3:6.9
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:3
Exact Mass:785.35235945
Monoisotopic Mass:785.35235945
Topological Polar Surface Area:198
Heavy Atom Count:57
Complexity:1590
Defined Atom Stereocenter Count:9
Undefined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is a derivative of rifamycin and is the first non-aminoglycoside intestinal antibiotic. This product has a strong effect and a broad antibacterial spectrum. It has good antibacterial activity against Staphylococcus aureus, Staphylococcus epidermidis and Streptococcus faecalis among Gram-positive aerobic bacteria, and Salmonella, Escherichia coli, Shigella and Yersinia enterocolitica among Gram-negative aerobic bacteria. This product has high antibacterial activity against Proteus, Clostridium difficile among Gram-positive anaerobic bacteria, and Bacteroides among Gram-negative anaerobic bacteria. When using this product, there is no need to use intestinal antispasmodics (such as lopramamide, etc.) or intestinal adsorbents (such as white clay, pectin, etc.). This product acts quickly, and diarrhea will no longer occur after 2 days, and abdominal cramps, headaches, nausea, and vomiting symptoms will disappear quickly. This product is not absorbed and maintains extremely high concentrations in the intestine, but does not exist in other organs. Features superior to neomycin, streptomycin and other aminoglycoside antibiotics: ① This product does not damage hearing function; ② It does not cause renal damage; ③ Parasitic normal flora, especially non-pathogenic enteric bacteria Escherichia coli, quickly relocate to the intestines to avoid repeated infection; ④ Intestinal mucosal inflammation may tend to disappear. Mucosal inflammation is a contraindication to the use of topical aminoglycosides, because the inflammation may be aggravated after medication.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Rifaximin Tablets
Ingredients	Rifaximin. Chemical name: 4-deoxy-4-methylpyridinium [1,2-1,2] imidazole well [5,4-cyclo] rifamycin SV.
Indication	Less than 1% of an oral dose of rifaximin is absorbed from the gastrointestinal tract, so rifaximin is unlikely to cause systemic problems due to drug interactions.
Specifications	0.1g
Manufacturer	Shandong Zibo Xinda Pharmaceutical Co., Ltd.

Rifaximin Tablets
Ingredients	Rifaximin. Chemical name: 4-deoxy-4-methylpyridinium [1,2-1,2] imidazole well [5,4-cyclo] rifamycin SV.
Indication	Less than 1% of an oral dose of rifaximin is absorbed from the gastrointestinal tract, so rifaximin is unlikely to cause systemic problems due to drug interactions.
Specifications	0.2g
Manufacturer	Nanchang Feihong Pharmaceutical Co., Ltd.

Rifaximin dry suspension
Ingredients	The main ingredient of this product is rifaximin
Indication	Less than 1% of the oral dose of rifaximin is absorbed through the gastrointestinal tract, so it will not cause drug interactions and lead to systemic problems.
Specifications	0.2g
Manufacturer	Shandong Dyne Marine Organism Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

CHEMECA DRUGS PRIVATE LTD

United States
Active
OPTIMUS DRUGS PRIVATE LTD

United States
Active
RAKS PHARMA PVT LTD

United States
Active

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