Rifamycin
Identification
- Summary
Rifamycin is an antibacterial used to treat traveler's diarrhea.
- Brand Names
- Aemcolo
- Generic Name
- Rifamycin
- DrugBank Accession Number
- DB11753
- Background
Rifamycin is the prime member of the rifamycin family which are represented by drugs that are a product of fermentation from the gram-positive bacterium Amycolatopsis mediterranei, also known as Streptomyces mediterranei. The parent compound of rifamycin was rifamycin B which was originally obtained as a main product in the presence of diethylbarburitic acid. Some small modifications where performed in this inactive compound and with the creation of rifamycin SV there was the first antibiotic used intravenously for the treatment of tuberculosis.2
Rifamycin has had several direct derivative products such as rifamycin SV, rifaximin, rifampin and rifamycin CV. All of the derivatives have slight different physicochemical properties when compared to the parent structure.1
Rifamycin was further developed by Cosmo Technologies Ltd and approved in November 16, 2018 by the FDA as a prescription drug after being granted the designation of Qualified Infectious Disease Product which allowed it to have a status a priority review.10 This drug was also sent for review to the EMA in 2015 by Dr. Falk Pharma Gmbh and it was granted a waiver for the tested conditions.11
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 697.778
Monoisotopic: 697.309825957 - Chemical Formula
- C37H47NO12
- Synonyms
- Rifamicina
- Rifamicine SV
- Rifamycin
- Rifamycin SV
- Rifamycine
- Rifamycinum
- Rifomycin SV
- External IDs
- M-14
Pharmacology
- Indication
Rifamycin is indicated for the treatment of adult patients with travelers' diarrhea caused by noninvasive strains of E. coli. The status of the disease should not be complicated by fever or blood in the stool. To prevent drug-resistant bacteria, it is important to mention that the use of rifamycin for this indication should be only done in cases where the infection is proven or strongly suspected to be caused by bacteria.12
Travallers' diarrhea is very common problem affecting 20-60% of the travellers and it is defined as an increase in frequency of bowel movements to three or more loose stools per day during a trip abroad. This condition is rarely life threatening but in severe cases it can produce dehydration and sepsis. The most common cause of travellers' diarrhea is a pathogen and from the pathogens identified, bacteria is the most common cause followed by norovirus, rotavirus and similar viruses.3
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Not complicated by fever, not complicated by bloody stool traveler's diarrhea caused by noninvasive strains of escherichia coli •••••••••••• ••••• ••••••• •••••••• ••••••• Used in combination to treat Susceptible bacterial infections Combination Product in combination with: Lidocaine (DB00281) •••••••••••• •••••••••• ••••••••• •••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Rifamycin is known to be effective against Gram-positive and Gram-negative pathogens and mycobacteria. It is very effective against E. coli reporting a MIC90 of 64-128 mcg/ml without showing cross-resistance with other antimicrobial agents.4
The specific indication of rifamycin is extremely important as ther were previous reports that indicated a high risk factor in the generation of resistant E. coli strains in patients with inflammatory bowel disease.13
In clinical trials, rifamycin was tested in a randomized clinical trial of travellers' coming from Mexico and Guatemala. In this trial, rifamycin was proven to significantly reduce the symptoms of travellers' diarrhea.12
- Mechanism of action
Rifamycins, as well as all the other members of this group, present an antibacterial mechanism of action related to the inhibition of RNA synthesis. This mechanism of action is done by the strong binding to the DNA-dependent RNA polymerase of prokaryotes. The inhibition of the RNA synthesis is thought to be related with the initiation phase of the process and to involve stacking interactions between the naphthalene ring and the aromatic moiety in the polymerase. As well, it has been suggested that the presence of zinc atoms in the polymerase allows for the binding of phenolic -OH groups of the naphthalene ring.9
In eukaryotic cells, the binding is significantly reduced making them at least 100 to 10,000 times less sensitive to the action of rifamycins. The members of the rifamycin family present the same mechanism of action and the structural modifications are usually related to pharmacokinetic properties as well as to the interaction with eukaryotic cells.8
Target Actions Organism ADNA-directed RNA polymerase subunit beta binderEscherichia coli (strain K12) ADNA-directed RNA polymerase subunit alpha binderEscherichia coli (strain K12) ADNA-directed RNA polymerase subunit beta' binderEscherichia coli (strain K12) - Absorption
Rifamycin has a very poor absorption4 and thus, the generation of an oral modified-release formulation using the technology of the multi-matrix structure was required for the generation of the FDA approved product. This preparation allows the delivery of the active ingredient in the distal small bowel and colon without interfering with the flora in the upper gastrointestinal tract.5
The multi-matrix is made by a lipophiic matrix surrounded in a hydrophilic matrix which allows for the protection of the active ingredient from dissolution in the intestinal aqueous fluids before it arrives in the cecum. All this matrix is surrounded by a gastro-resistant polymer that only desintegrate in a pH lower than 7.6
All this administration-customed formulation allows for a bioavailability of <0.1% and the plasma concentrations are reported to be of <2 ng/ml in patients receiving a dose of 400 mg. This confirms that the site of action of rifamycin stays in the small intestine and colon which prevents the need for dose adjustments in special populations as well as systemic drug interactions.6
The reported Cmax, tmax, AUC and mean residence time after a dosage of 250 mg of rifamycin is 36 mg/L, 5 min, 11.84 mg.h/L and 0.49 h respectively.6
- Volume of distribution
The reported volume of distribution after measured after a dosage of 250 mg of rifamycin is 101.8 L.6
- Protein binding
The protein binding of rifamycin is of about 80-95%.7
- Metabolism
When absorbed, rifamycin is mainly metabolzied in hepatocytes and intestinal microsomes to a 25-deacetyl metabolite.6
Hover over products below to view reaction partners
- Route of elimination
From the administered dose, 18%, 50% and 21% is recovered in feces during the first 24, 48 and 72h after administration. This will represent about 90% of the administered dose eliminated by the feces while the urinary secretion is negligible.6
- Half-life
The reported half-life when a dose of 250 mg of rifamycin was administered is 3 h.6
- Clearance
The reported clearance when a dose of 250 mg of rifamycin was administered is 23.3 L/h.6
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
In safety studies with rifamycin, it was reported a potential of hepatotoxicity due to the depletion of glutathione and the generation of reactive oxygen species in liver microsomes. It is important to mention that this effect is mainly observed in the intravenous administration as the oral dosage does not have a significant systemic absorption.7
Rifamycin is not genotoxic in bacterial mutation assays, mouse cell mutation assay or mouse bone marrow micronucleus assay. There is no current information about the effects on fertility, overdosage or carcinogenesis.Label
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The metabolism of 1,2-Benzodiazepine can be increased when combined with Rifamycin. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Rifamycin. Abiraterone The metabolism of Abiraterone can be increased when combined with Rifamycin. Abrocitinib The metabolism of Abrocitinib can be increased when combined with Rifamycin. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Rifamycin. - Food Interactions
- Avoid alcohol.
- Take with a full glass of water.
- Take with or without food.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Rifamycin sodium 32086GS35Z 14897-39-3 YVOFSHPIJOYKSH-NLYBMVFSSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aemcolo Tablet, delayed release 194 mg/1 Oral Aries Pharmaceuticals Inc 2019-02-01 2022-04-01 US Aemcolo Tablet, delayed release 194 mg/1 Oral RedHill Biopharma Ltd 2021-07-01 Not applicable US Aemcolo Tablet, delayed release 194 mg/1 Oral RedHill Biopharma Ltd 2021-07-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image RIF 125 MG 1 AMPUL Rifamycin sodium (125 mg) + Lidocaine hydrochloride (5 mg) Solution Intramuscular KOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş. 2008-04-17 Not applicable Turkey RIF 250 MG 1 AMPUL Rifamycin sodium (250 mg) + Lidocaine hydrochloride (10 mg) Solution Intramuscular KOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş. 2008-04-17 Not applicable Turkey RIF 250 MG AMPUL, 100 ADET Rifamycin sodium (250 mg) + Lidocaine hydrochloride (10 mg) Solution Intramuscular KOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş. 2020-08-14 Not applicable Turkey RIFETEM 125 MG / 1,5 ML AMPUL, 1 ADET Rifamycin (125 mg/1.5ml) + Lidocaine hydrochloride (5 mg/1.5ml) Solution Intramuscular MENARİNİ SAĞLIK VE İLAÇ SAN. VE TİC. A.Ş. 1996-05-03 2021-03-16 Turkey RIFETEM 250 MG / 3 ML AMPUL, 1 ADET Rifamycin (250 mg/3ml) + Lidocaine hydrochloride (10 mg/3ml) Solution Intramuscular İ.E. ULAGAY İLAÇ SAN. TÜRK A.Ş. 1996-05-03 2024-01-23 Turkey
Categories
- ATC Codes
- S01AA16 — RifamycinS02AA12 — RifamycinD06AX15 — Rifamycin
- D06AX — Other antibiotics for topical use
- D06A — ANTIBIOTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- A07AA — Antibiotics
- A07A — INTESTINAL ANTIINFECTIVES
- A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Alimentary Tract and Metabolism
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibiotics for Topical Use
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antiinfectives for Systemic Use
- Antimycobacterials
- Antirheumatic Agents
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strength unknown)
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inducers
- Cytochrome P-450 CYP2C19 Inducers (strong)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Inducers
- Cytochrome P-450 CYP2C8 Inducers (strength unknown)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inducers
- Cytochrome P-450 CYP2C9 Inducers (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inducers (strong)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strong)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Drugs for Treatment of Tuberculosis
- Heterocyclic Compounds, Fused-Ring
- Intestinal Antiinfectives
- Lactams, Macrocyclic
- MATE 1 Inhibitors
- MATE inhibitors
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- Ophthalmologicals
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Otologicals
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Rifamycin Antibacterial
- Rifamycins
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Macrolactams
- Sub Class
- Not Available
- Direct Parent
- Macrolactams
- Alternative Parents
- Naphthofurans / Naphthols and derivatives / Benzofurans / Coumarans / Aryl alkyl ketones / Hydroquinones / 1-hydroxy-2-unsubstituted benzenoids / Ketals / Secondary carboxylic acid amides / Secondary alcohols show 11 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-naphthol / Acetal / Alcohol / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Benzenoid / Benzofuran show 27 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- acetate ester, polyphenol, lactam, macrocycle, cyclic ketal, rifamycin (CHEBI:29673) / Ansamycins and related polyketides (C12044) / Ansamycins and related polyketides (LMPK05000005)
- Affected organisms
- Escherichia coli
Chemical Identifiers
- UNII
- DU69T8ZZPA
- CAS number
- 6998-60-3
- InChI Key
- HJYYPODYNSCCOU-ODRIEIDWSA-N
- InChI
- InChI=1S/C37H47NO12/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/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
- IUPAC Name
- (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
- SMILES
- CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C)C(O)=C4C(O)=C(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C=C(O)C4=C3C2=O
References
- General References
- Lin SW, Lin CJ, Yang JC: Rifamycin SV MMX for the treatment of traveler's diarrhea. Expert Opin Pharmacother. 2017 Aug;18(12):1269-1277. doi: 10.1080/14656566.2017.1353079. Epub 2017 Jul 27. [Article]
- Sensi P: History of the development of rifampin. Rev Infect Dis. 1983 Jul-Aug;5 Suppl 3:S402-6. [Article]
- Barrett J, Brown M: Travellers' diarrhoea. BMJ. 2016 Apr 19;353:i1937. doi: 10.1136/bmj.i1937. [Article]
- Ross AG, Olds GR, Cripps AW, Farrar JJ, McManus DP: Enteropathogens and chronic illness in returning travelers. N Engl J Med. 2013 May 9;368(19):1817-25. doi: 10.1056/NEJMra1207777. [Article]
- Rosette C, Buendia-Laysa F Jr, Patkar S, Moro L, Celasco G, Bozzella R, Ajani M, Gerloni M: Anti-inflammatory and immunomodulatory activities of rifamycin SV. Int J Antimicrob Agents. 2013 Aug;42(2):182-6. doi: 10.1016/j.ijantimicag.2013.04.020. Epub 2013 Jun 5. [Article]
- Di Stefano AF, Rusca A, Loprete L, Droge MJ, Moro L, Assandri A: Systemic absorption of rifamycin SV MMX administered as modified-release tablets in healthy volunteers. Antimicrob Agents Chemother. 2011 May;55(5):2122-8. doi: 10.1128/AAC.01504-10. Epub 2011 Mar 14. [Article]
- Aristoff PA, Garcia GA, Kirchhoff PD, Showalter HD: Rifamycins--obstacles and opportunities. Tuberculosis (Edinb). 2010 Mar;90(2):94-118. doi: 10.1016/j.tube.2010.02.001. Epub 2010 Mar 16. [Article]
- Floss HG, Yu TW: Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev. 2005 Feb;105(2):621-32. doi: 10.1021/cr030112j. [Article]
- Kerr P. (2013). Fighting multidrug resistance with herbal extracts, essential oils and their components. Academic Press.
- FDA approvals [Link]
- EMA approvals [Link]
- FDA news [Link]
- Bentham Science [Link]
- FDA Approved Drug Products: AEMCOLO (rifamycin) delayed-release tablets, for oral use [Link]
- External Links
- KEGG Drug
- D02549
- KEGG Compound
- C12044
- PubChem Substance
- 347911235
- ChemSpider
- 16735998
- BindingDB
- 50391000
- 35616
- ChEBI
- 29673
- ChEMBL
- CHEMBL437765
- ZINC
- ZINC000169633673
- Wikipedia
- Rifamycin
- FDA label
- Download (349 KB)
- MSDS
- Download (23.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Impacted Third Molar Tooth 1 4 Recruiting Treatment Pulmonology 1 3 Completed Treatment Traveler's Diarrhea 2 3 Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) / Human Immunodeficiency Virus (HIV) Infections / Tuberculosis (TB) 1 2 Completed Treatment Cirrhosis of the Liver / Hepatic Encephalopathy (HE) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, delayed release Oral 194 mg/1 Tablet Solution Intramuscular Solution Intramuscular 125 mg Solution Intramuscular 250 mg Injection Intramuscular 125 mg/1.5ml Solution Topical 1 g Solution / drops Ophthalmic 1 % Solution / drops Auricular (otic) 1 % Injection, solution Intramuscular 250 MG/3ML Injection, solution Intravenous 250 MG/10ML Injection, solution Intravenous 500 MG/10ML Injection, solution Intramuscular Solution / drops Ophthalmic 10 mg/5ml Solution / drops Auricular (otic) 100 mg/10ml Tablet 200 MG - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8741948 No 2014-06-03 2025-05-03 US US8263120 No 2012-09-11 2025-05-03 US US8529945 No 2013-09-10 2025-05-03 US US8486446 No 2013-07-16 2025-05-03 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 171 ºC 'MSDS' boiling point (°C) 972.8 ºC at 760 mm Hg 'MSDS' water solubility Insoluble Shu-Wen L., Chun-Jung L. and Jyh-Chin Y. (2017). Expert Opinion in Pharmacotherapy. Vol 18. logP 5 Shu-Wen L., Chun-Jung L. and Jyh-Chin Y. (2017). Expert Opinion in Pharmacotherapy. Vol 18. pKa 1.8 Stefano A., Rusca A., Loprete L., Droge M., Moro L. and Assandri A. (2011). Antimicrob Agents Chemother. - Predicted Properties
Property Value Source Water Solubility 0.0147 mg/mL ALOGPS logP 4.15 ALOGPS logP 4.17 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 7.09 Chemaxon pKa (Strongest Basic) -1.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 201.31 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 187.8 m3·mol-1 Chemaxon Polarizability 72.6 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 264.6304243 predictedDarkChem Lite v0.1.0 [M-H]- 261.33533 predictedDeepCCS 1.0 (2019) [M+H]+ 264.5424243 predictedDarkChem Lite v0.1.0 [M+H]+ 263.17422 predictedDeepCCS 1.0 (2019) [M+Na]+ 264.1724243 predictedDarkChem Lite v0.1.0 [M+Na]+ 269.3163 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Ribonucleoside binding
- Specific Function
- DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates.
- Gene Name
- rpoB
- Uniprot ID
- P0A8V2
- Uniprot Name
- DNA-directed RNA polymerase subunit beta
- Molecular Weight
- 150631.165 Da
References
- Floss HG, Yu TW: Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev. 2005 Feb;105(2):621-32. doi: 10.1021/cr030112j. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Zinc ion binding
- Specific Function
- DNA-dependent RNA polymerase (RNAP) catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. This subunit plays an important role in subunit assembly s...
- Gene Name
- rpoA
- Uniprot ID
- P0A7Z4
- Uniprot Name
- DNA-directed RNA polymerase subunit alpha
- Molecular Weight
- 36511.35 Da
References
- Floss HG, Yu TW: Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev. 2005 Feb;105(2):621-32. doi: 10.1021/cr030112j. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Dna-directed rna polymerase activity
- Specific Function
- DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates.
- Gene Name
- rpoC
- Uniprot ID
- P0A8T7
- Uniprot Name
- DNA-directed RNA polymerase subunit beta'
- Molecular Weight
- 155158.84 Da
References
- Floss HG, Yu TW: Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev. 2005 Feb;105(2):621-32. doi: 10.1021/cr030112j. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- InhibitorInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Pea F, Furlanut M: Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions. Clin Pharmacokinet. 2001;40(11):833-68. doi: 10.2165/00003088-200140110-00004. [Article]
- Edwards RJ, Price RJ, Watts PS, Renwick AB, Tredger JM, Boobis AR, Lake BG: Induction of cytochrome P450 enzymes in cultured precision-cut human liver slices. Drug Metab Dispos. 2003 Mar;31(3):282-8. [Article]
- Ridtitid W, Wongnawa M, Mahatthanatrakul W, Punyo J, Sunbhanich M: Rifampin markedly decreases plasma concentrations of praziquantel in healthy volunteers. Clin Pharmacol Ther. 2002 Nov;72(5):505-13. doi: 10.1067/mcp.2002.129319. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- InhibitorInducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- InhibitorInducer
- Curator comments
- Rifamycin derivatives are inducers of CYP2C9 hepatic enzyme. This enzyme action is based on the drug class of Rifamycin.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Chen Y, Ferguson SS, Negishi M, Goldstein JA: Induction of human CYP2C9 by rifampicin, hyperforin, and phenobarbital is mediated by the pregnane X receptor. J Pharmacol Exp Ther. 2004 Feb;308(2):495-501. Epub 2003 Nov 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Di Stefano AF, Rusca A, Loprete L, Droge MJ, Moro L, Assandri A: Systemic absorption of rifamycin SV MMX administered as modified-release tablets in healthy volunteers. Antimicrob Agents Chemother. 2011 May;55(5):2122-8. doi: 10.1128/AAC.01504-10. Epub 2011 Mar 14. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Hirano M, Maeda K, Shitara Y, Sugiyama Y: Drug-drug interaction between pitavastatin and various drugs via OATP1B1. Drug Metab Dispos. 2006 Jul;34(7):1229-36. doi: 10.1124/dmd.106.009290. Epub 2006 Apr 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Hirano M, Maeda K, Shitara Y, Sugiyama Y: Drug-drug interaction between pitavastatin and various drugs via OATP1B1. Drug Metab Dispos. 2006 Jul;34(7):1229-36. doi: 10.1124/dmd.106.009290. Epub 2006 Apr 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Hirano M, Maeda K, Shitara Y, Sugiyama Y: Drug-drug interaction between pitavastatin and various drugs via OATP1B1. Drug Metab Dispos. 2006 Jul;34(7):1229-36. doi: 10.1124/dmd.106.009290. Epub 2006 Apr 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
- Gene Name
- SLCO2A1
- Uniprot ID
- Q92959
- Uniprot Name
- Solute carrier organic anion transporter family member 2A1
- Molecular Weight
- 70043.33 Da
References
- Hirano M, Maeda K, Shitara Y, Sugiyama Y: Drug-drug interaction between pitavastatin and various drugs via OATP1B1. Drug Metab Dispos. 2006 Jul;34(7):1229-36. doi: 10.1124/dmd.106.009290. Epub 2006 Apr 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- Hirano M, Maeda K, Shitara Y, Sugiyama Y: Drug-drug interaction between pitavastatin and various drugs via OATP1B1. Drug Metab Dispos. 2006 Jul;34(7):1229-36. doi: 10.1124/dmd.106.009290. Epub 2006 Apr 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- Hirano M, Maeda K, Shitara Y, Sugiyama Y: Drug-drug interaction between pitavastatin and various drugs via OATP1B1. Drug Metab Dispos. 2006 Jul;34(7):1229-36. doi: 10.1124/dmd.106.009290. Epub 2006 Apr 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- FDA Approved Drug Products: AEMCOLO (rifamycin) delayed-release tablets, for oral use [Link]
Drug created at October 20, 2016 20:45 / Updated at August 05, 2021 01:52