[(7S,11S,12R,13S,14R,16R,17S,18S)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate

Base Information

• Chemical Name: [(7S,11S,12R,13S,14R,16R,17S,18S)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate
• CAS No.: 80621-81-4
• Molecular Formula: C43H51N3O11
• Molecular Weight: 785.891
• NCI Thesaurus Code: C61926
• RXCUI: 35619
• Wikipedia: Rifaximin
• Mol file: 80621-81-4.mol

Synonyms:Rifaximin;Spectrum2_000020;Spectrum3_001945;SPBio_000059;KBio3_002831

Chemical Property of [(7S,11S,12R,13S,14R,16R,17S,18S)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate

Chemical Property:

• Appearance/Colour: Red-orange crystalline powder
• Melting Point: 200-205 °C(dec)
• Refractive Index: 1.633
• PKA: 2.83±0.70(Predicted)
• PSA: 198.38000
• Density: 1.366 g/cm³
• LogP: 6.29580
• Storage Temp.: 0-6°C
• Solubility.: ethanol: soluble1mg/mL
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 785.35235945
• Heavy Atom Count: 57
• Complexity: 1590

Purity/Quality:

97%, ^*data from raw suppliers

Rifaximin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: CC1C=CC=C(C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)OC(C4=O)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)C
• Isomeric SMILES: C[C@H]1C=CC=C(C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)O[C@@](C4=O)(OC=C[C@@H]([C@H]([C@H]([C@@H](C([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)C
• Recent ClinicalTrials: Rifaximin as a Prophylaxis of Spontaneous Bacterial Peritonitis in Comparison With Ciprofloxacin
• Recent EU Clinical Trials: Interventional post-marketing study to evaluate i3.1 efficacy on SIBO (Small Intestinal Bacterial Overgrowth)reduction in IBS (Irritable bowel syndrom) patients
• Recent NIPH Clinical Trials: Studies on the Efficacy of rifaximin for covert hepatic encephalopathy
• 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.
• Uses: Rifaximin is a non-absorbable semisynthetic Rifamycin antibiotic. antibacterial, RNA synthesis inhibitor Muscle Relaxant Non-absorbable semisynthetic Rifamycin antibiotic
• 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.
• Drug interactions: Potentially hazardous interactions with other drugs Ciclosporin: concentration increased by ciclosporin.

Technology Process of [(7S,11S,12R,13S,14R,16R,17S,18S)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate

There total 3 articles about [(7S,11S,12R,13S,14R,16R,17S,18S)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-Amino-4-methylpyridine (695-34-1) → rifaximin (80621-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: CHCl₃ / 2 h / Ambient temperature

2: ascorbic acid

With ascorbic acid; In chloroform;

DOI:10.1021/jm00145a020

Reference yield:

3-bromorifamycin S (57375-25-4) → rifaximin (80621-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: CHCl₃ / 2 h / Ambient temperature

2: ascorbic acid

With ascorbic acid; In chloroform;

DOI:10.1021/jm00145a020

Reference yield:

C43H50N3O11(1+)*Br(1-) → rifaximin (80621-81-4)

Guidance literature:

With ascorbic acid;

DOI:10.1021/jm00145a020

upstream raw materials:

2-Amino-4-methylpyridine

3-bromorifamycin S

Refernces