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QuickView for Rifampin (compound)
PubChem
| Name: | Rifampin |
|---|---|
| PubChem Compound ID: | 5381226 |
| Description: | A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160) |
| Molecular formula: | C43H58N4O12 |
| Molecular weight: | 822.94 g/mol |
| Synonyms: |
Rimactane (TN); Riforal; Rimactane; Rifadin I.V.; 8-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV; Rifagen; AIDS088820; Rimazid; Ramp; Rifoldin.
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Rimactane (TN); Riforal; Rimactane; Rifadin I.V.; 8-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV; Rifagen; AIDS088820; Rimazid; Ramp; Rifoldin; Rifobac; Rifampicinum; Rimactan; 2,7-(epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-1,11(2H)-dione, 21-(acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-[(E)-[(4-methyl-1-piperazinyl)imino]meth; NSC 113926; Rifampicine; 8-[[(4-Methyl-1-piperazinyl)imino]methyl]rifamycin sv; Dione 21-acetate; HSDB 3181; 5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione 21-acetate; 8-[[(4-Methylpiperazinyl)imino]methyl]rifamycin sv; R-Cin; Rifater; Rifampicin (JP15); Rifadin; Rifampicin & EEP; Rifomycin SV, 8-(N-(4-methyl-1-piperazinyl)formidoyl)-; Rifampicin & Propolis; 8CI); Rifampicin; Rf; Sinerdol; 13292-46-1; Doloresum; Fenampicin; AIDS032285; Benemicin; AIDS-007228; 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV; Archidyn; Famcin; Rifampin & CRL8131; NSC113926; Rifadine; Rifampin (USP); Rifa; RMP; 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-[N-(4-methyl-1-piperazinyl)formimidoyl]-, 21-acetate; Ba 41166/E; Rifampicina [INN-Spanish]; Rifampin; 3-(4-Methylpiperazinyliminomethyl)-rifamycin SV; Rifampin [USAN]; 3-[(4-Methyl-1-piperazinyl)iminomethyl]rifamycin SV; Rifadin (TN); Rifoldine; 8-[[(4-Methyl-1-piperazinyl)imino[methyl]rifamycin; Rifampicin SV; 3-([(4-Methyl-1-piperazinyl)imino]methyl)rifamycin SV; Tubocin; Eremfat; Rifcin; AIDS007228; RFP; C06688; Rifamycin, 3-[[(4-methyl-1-piperazinyl)imino]methyl]-; Rifamycin AMP; 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-, 21-acetate (; Rifampicinum [INN-Latin]; Arzide; Rifaprodin; 3-[[(4-Methyl-1-piperazinyl)imino]-methyl]rifamycin; 2,7- (Epoxypentadeca[1,11,13]trienimino)naphtho[2, 1-b]furan-1,11(2H)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2, 4,12,16,18,20, 22-heptamethyl-8-[N-(4-methyl-1-piperazinyl)formimidoyl]-, 21-acetate; yl]-, (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-; Rifaldazine; Arficin; EINECS 236-312-0; Rifamycin, 3-[[ (4-methyl-1-piperazinyl)imino]methyl]-; Rifinah; CCRIS 551; Rimactazid; Rifamor; Rifaldin; D00211; Ba 41166; Rifamycin, 3-(((4-methyl-1-piperazinyl)imino)methyl)-; Rimactizid; Rifampicine [French]; Prestwick_833; 5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-beta)furan-1,11(2H)-dione 21-acetate; DRG-0109; AIDS-088820; 8-(4-Methylpiperazinyliminomethyl) rifamycin SV; Rifomycin sv, 8-[N-(4-Methyl-1-piperazinyl)formidoyl]-; Rifaldazin; RIF; AIDS-032285; Rifam; L-5103 Lepetit; 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-, 21-acetate (8CI); Abrifam; R/AMP
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DrugBank
Identification
| Name: | Rifampin |
|---|---|
| Name (isomeric): | DB01045 |
| Drug Type: | small molecule |
| Description: | A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160) |
| Synonyms: |
RFP
|
| Brand: | Rifaprodin, Riforal, Archidyn, Rifaldazine, Rifadin IV, Rifamycin, Rifadine, Rimactan, Rifoldin, L-5103 Lepetit, Rifaldin, Rifaldazin, Rimactane, R/AMP, Rifagen, RAMP, Tubocin, Rifamycin Amp, Rifoldine, Rifadin, Rifampicin SV, Rifa, Rifampicin, Rofact, Rimactin, Rfamipicin, Rimazid |
| Brand name mixture: | Rifamate(Rifampin + Isoniazid), Rifater(Isoniazid + Pyrazinaamide + Rifampin) |
| Category: | Antibiotics, Antituberculosis Agents, Enzyme Inhibitors, Nucleic Acid Synthesis Inhibitors, Antibiotics, Antitubercular, Leprostatic Agents |
| CAS number: | 13292-46-1 |
Pharmacology
| Indication: | For the treatment of Tuberculosis and Tuberculosis-related mycobacterial infections. |
|---|---|
| Pharmacology: |
Rifampin is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aerugino...
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Rifampin is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aeruginosa) and specifically Mycobacterium tuberculosis. Because of rapid emergence of resistant bacteria, use is restricted to treatment of mycobacterial infections and a few other indications. Rifampin is well absorbed when taken orally and is distributed widely in body tissues and fluids, including the CSF. It is metabolized in the liver and eliminated in bile and, to a much lesser extent, in urine, but dose adjustments are unnecessary with renal insufficiency.
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| Mechanism of Action: | Rifampin acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death. |
| Absorption: | Well absorbed from gastrointestinal tract. |
| Protein binding: | 89% |
| Biotransformation: | Primarily hepatic, rapidly deacetylated. |
| Route of elimination: | Less than 30% of the dose is excreted in the urine as rifampin or metabolites. |
| Half Life: | 3.35 (+/- 0.66) hours |
| Clearance: | 0.19 +/- 0.06 L/hr/kg [300 mg IV] 0.14 +/- 0.03 L/hr/kg [600 mg IV] |
| Toxicity: | LD50=1570 mg/kg (rat), chronic exposure may cause nausea and vomiting and unconsciousness |
| Affected organisms: | Mycobacteria||Various gram-negative and gram-positive eubacteria |
Interactions
| Food interaction: |
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| Drug interaction: |
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Targets
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates
| UniProt ID: | P0A8V2 | |||||
|---|---|---|---|---|---|---|
| Gene: | rpoB | |||||
| Actions: | inhibitor | |||||
| References: |
|
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates
| UniProt ID: | P0A8T7 | |||||
|---|---|---|---|---|---|---|
| Gene: | rpoC | |||||
| Actions: | inhibitor | |||||
| References: |
|
Orphan receptor; its natural ligand is probably pregnane. Binds to a response element in the CYP3A4 and ABCB1/MDR1 genes promoter. Activates its expression in response to a wide variety of endobiotics and xenobiotics
| UniProt ID: | O75469 | ||
|---|---|---|---|
| Gene: | NR1I2 | ||
| Actions: | agonist | ||
| References: |
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Enzymes
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan
| UniProt ID: | P11712 | |||
|---|---|---|---|---|
| Gene: | CYP2C9 | |||
| Actions: | substrate, inducer | |||
| References: |
|
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen
| UniProt ID: | P05177 | |
|---|---|---|
| Gene: | CYP1A2 | |
| Actions: | inducer | |
| References: |
|
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)
| UniProt ID: | P10632 | |||
|---|---|---|---|---|
| Gene: | CYP2C8 | |||
| Actions: | substrate, inhibitor, inducer | |||
| References: |
|
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide
| UniProt ID: | P08684 | ||
|---|---|---|---|
| Gene: | CYP3A4 | ||
| Actions: | substrate, inducer | ||
| References: |
|
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 unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P20813 | |||
|---|---|---|---|---|
| Gene: | CYP2B6 | |||
| Actions: | inducer | |||
| References: |
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UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX- alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate
| UniProt ID: | P22309 | ||
|---|---|---|---|
| Gene: | UGT1A1 | ||
| Actions: | inducer | ||
| References: |
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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 imipramine
| UniProt ID: | P33261 | |
|---|---|---|
| Gene: | CYP2C19 | |
| Actions: | inducer | |
| References: |
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Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase
| UniProt ID: | P11509 | |
|---|---|---|
| Gene: | CYP2A6 | |
| Actions: | substrate, inhibitor, inducer | |
| References: |
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Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms
| UniProt ID: | P05181 | |
|---|---|---|
| Gene: | CYP2E1 | |
| Actions: | inducer | |
| References: |
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Exhibits low testosterone 6-beta-hydroxylase activity
| UniProt ID: | Q9HB55 | |
|---|---|---|
| Gene: | CYP3A43 | |
| Actions: | inducer | |
| References: |
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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 unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P20815 | |
|---|---|---|
| Gene: | CYP3A5 | |
| Actions: | inducer | |
| References: |
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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 unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P24462 | |
|---|---|---|
| Gene: | CYP3A7 | |
| Actions: | inducer | |
| References: |
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Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity towards prostaglandins A1 and E1
| UniProt ID: | Q02928 | |
|---|---|---|
| Gene: | CYP4A11 | |
| Actions: | inducer | |
| References: |
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Transporters
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
| UniProt ID: | P08183 | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Gene: | ABCB1 | ||||||||||
| Actions: | substrate, inhibitor, inducer | ||||||||||
| References: |
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Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
| UniProt ID: | Q9NPD5 | |||
|---|---|---|---|---|
| Gene: | SLCO1B3 | |||
| Actions: | substrate, inhibitor | |||
| References: |
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May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May protect milk against xenobiotics
| UniProt ID: | P33527 | |
|---|---|---|
| Gene: | ABCC1 | |
| Actions: | inhibitor | |
| References: |
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Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
| UniProt ID: | O94956 | |
|---|---|---|
| Gene: | SLCO2B1 | |
| Actions: | inhibitor | |
| References: |
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Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
| UniProt ID: | O95342 | ||||
|---|---|---|---|---|---|
| Gene: | ABCB11 | ||||
| Actions: | inhibitor | ||||
| References: |
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Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity)
| UniProt ID: | P46721 | ||||
|---|---|---|---|---|---|
| Gene: | SLCO1A2 | ||||
| Actions: | inhibitor | ||||
| References: |
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Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
| UniProt ID: | Q9Y694 | |
|---|---|---|
| Gene: | SLC22A7 | |
| Actions: | inhibitor | |
| References: |
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Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
| UniProt ID: | Q9Y6L6 | ||||
|---|---|---|---|---|---|
| Gene: | SLCO1B1 | ||||
| Actions: | inhibitor | ||||
| References: |
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Acts as a multispecific organic anion pump which can transport nucleotide analogs
| UniProt ID: | O15440 | |
|---|---|---|
| Gene: | ABCC5 | |
| Actions: | inducer | |
| References: |
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Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
| UniProt ID: | Q92887 | ||
|---|---|---|---|
| Gene: | ABCC2 | ||
| Actions: | inducer | ||
| References: |
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May act as an inducible transporter in the biliary and intestinal excretion of organic anions
| UniProt ID: | O15438 | |
|---|---|---|
| Gene: | ABCC3 | |
| Actions: | inducer | |
| References: |
|
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