Rifampicin is an antibiotic used to treat several types of mycobacterial infections including Mycobacterium avium complex, leprosy, and in combination with other antibacterials to treat latent or active tuberculosis. Show Brand Names Isonarif, Rifadin, Rifamate, Rifater, Rofact Generic NameRifampicinDrugBank Accession NumberDB01045Background 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) TypeSmall MoleculeGroupsApprovedStructure WeightAverage: 822.9402 Monoisotopic: 822.40512334 Chemical FormulaC43H58N4O12Synonyms
Rifampin is indicated for the treatment of tuberculosis and tuberculosis-related mycobacterial infections. In combination with pyrazinamide and isoniazid, it is used in the initial phase of the short-course treatment of pulmonary tuberculosis.  Reduce drug development failure rates Build, train, & validate machine-learning models with evidence-based and structured datasets. Build, train, & validate predictive machine-learning models with structured datasets. Associated ConditionsAssociated Therapies
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. Mechanism of action Rifampin acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death. TargetActionsOrganismA inhibitor Escherichia coli (strain K12)U agonist HumansAbsorption Well absorbed from gastrointestinal tract. Volume of distribution Not Available Protein binding 89% Metabolism 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
LD50=1570 mg/kg (rat), chronic exposure may cause nausea and vomiting and unconsciousness PathwaysNot AvailablePharmacogenomic Effects/ADRs Not AvailableDrug Interactions 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. DrugInteraction Integrate drug-drug interactions in your software 1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be increased when combined with Rifampicin.AbacavirThe metabolism of Abacavir can be increased when combined with Rifampicin.AbemaciclibThe serum concentration of Abemaciclib can be decreased when it is combined with Rifampicin.AbirateroneThe metabolism of Abiraterone can be increased when combined with Rifampicin.AbrocitinibThe metabolism of Abrocitinib can be increased when combined with Rifampicin.Food Interactions
Drug product information from 10+ global regions Our 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 IngredientUNIICASInChI KeyRifampicin sodiumGPE7477YEK38776-75-9PPGHYTPFGILTSZ-LGIBZRBQSA-MProduct ImagesInternational/Other BrandsRifadine / Rifaldin / Rifoldin / Rimactan / Rimactane / Rofact / TubocinBrand Name Prescription ProductsGeneric Prescription ProductsMixture ProductsATC CodesJ04BA50 — Dapsone and rifampicin
Chemical TaxonomyProvided by ClassyfireDescriptionThis 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.KingdomOrganic compoundsSuper ClassPhenylpropanoids and polyketidesClassMacrolactamsSub ClassNot AvailableDirect ParentMacrolactamsAlternative ParentsNaphthofurans / Naphthols and derivatives / Benzofurans / Coumarans / Aryl alkyl ketones / Hydroquinones / Ketals / N-methylpiperazines / Amino acids and derivatives / Trialkylamines show 13 moreSubstituents1,4-diazinane / 1-naphthol / Acetal / Alcohol / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle show 35 moreMolecular FrameworkAromatic heteropolycyclic compoundsExternal DescriptorsN-methylpiperazine, N-iminopiperazine, rifamycin (CHEBI:28077) / Ansamycins (C06688) Affected organisms
InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/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-26-[(E)-[(4-methylpiperazin-1-yl)imino]methyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate SMILES CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C2=C(O)C(\C=N\N4CCN(C)CC4)=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(O)=C2C(O)=C3C Synthesis Reference Klaus Jurgen, Joachim Seydel, "Combination preparations containing rifampicin and thioacetazon." U.S. Patent US5104875, issued August, 1973. General References
Not Available Packagers
Dosage FormsFormRouteStrengthTabletOralTablet, film coatedOral600 MGTablet, film coatedOralCreamTopicalCreamTopical2 gCapsuleOral50 mg/5mLInjection, powder, lyophilized, for solutionIntravenousCapsuleOral300.000 mgInjection, powder, for solutionIntravenous300 mg/5mlPill450 MGPill600 MGPowder, for solutionParenteral600 MG/10MLSolution / drops1.5 GSuspensionOral2.000 gSyrupOral2.4 gSyrupOral20 MG/MLSuspensionOral100 mg/5mlSuspensionOralCapsuleOralTablet, film coatedOralTablet, solubleOralCapsule, coatedOral150 mgCapsule, coatedOralCapsule, coatedOral300 mgSyrupOral2 gPillCapsuleOral150 mg/1CapsuleOral300 mg/1Capsule, coatedOral300 mg/1Injection, powder, lyophilized, for solutionIntravenous600 mg/10mLInjection, powder, lyophilized, for solutionIntravenous600 mg/1Capsule, gelatin coatedOral150 mgCapsule, gelatin coatedOral300 mgTablet, sugar coatedOralCapsuleOralTablet, sugar coatedOralInjection, powder, for solutionParenteralSyrupOralSuspensionOral2 gTablet, chewableBuccalTablet, delayed releaseOralTablet, chewableOralSyrupOral100 mgTablet, coatedOralKitTablet, coatedOral600 mgTablet, coatedOral450 mgCapsuleOral300 mgCapsuleOral150 mgCapsuleOral450 mgCapsuleOral600 mgTablet, coatedOral300 mgTablet, film coatedOral450 mgTablet, film coatedPowder, for suspensionOral100 mg/5mlPricesUnit descriptionCostUnitRifadin iv 600 mg vial140.9USD vialRifampin iv 600 mg vial136.3USD vialRifampin crystals6.72USD gRifampin powder3.98USD gRifadin 300 mg capsule3.09USD capsuleRifadin 150 mg capsule2.57USD capsuleRifampin 300 mg capsule2.37USD capsuleRimactane 300 mg capsule2.35USD capsuleRifampin 150 mg capsule2.27USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only. PatentsNot AvailableStateSolidExperimental PropertiesPropertyValueSourcemelting point (°C)183 °CNot Availablewater solubility1400 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)logP2.7Not AvailablepKa1.7SANGSTER (2004)Predicted PropertiesPropertyValueSourceWater Solubility0.0413 mg/mLALOGPSlogP3.85ALOGPSlogP2.95ChemaxonlogS-4.3ALOGPSpKa (Strongest Acidic)6.8ChemaxonpKa (Strongest Basic)7.37ChemaxonPhysiological Charge0ChemaxonHydrogen Acceptor Count14ChemaxonHydrogen Donor Count6ChemaxonPolar Surface Area220.15 Å2ChemaxonRotatable Bond Count5ChemaxonRefractivity225.58 m3·mol-1ChemaxonPolarizability86.84 Å3ChemaxonNumber of Rings5ChemaxonBioavailability0ChemaxonRule of FiveNoChemaxonGhose FilterNoChemaxonVeber's RuleNoChemaxonMDDR-like RuleNoChemaxonPredicted ADMET FeaturesPropertyValueProbabilityHuman Intestinal Absorption+0.5553Blood Brain Barrier-0.974Caco-2 permeable-0.7123P-glycoprotein substrateSubstrate0.9308P-glycoprotein inhibitor IInhibitor0.8564P-glycoprotein inhibitor IINon-inhibitor0.6049Renal organic cation transporterNon-inhibitor0.8178CYP450 2C9 substrateNon-substrate0.8508CYP450 2D6 substrateNon-substrate0.9115CYP450 3A4 substrateSubstrate0.7296CYP450 1A2 substrateNon-inhibitor0.9045CYP450 2C9 inhibitorNon-inhibitor0.907CYP450 2D6 inhibitorNon-inhibitor0.9231CYP450 2C19 inhibitorNon-inhibitor0.9025CYP450 3A4 inhibitorNon-inhibitor0.8432CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9099Ames testNon AMES toxic0.5803CarcinogenicityNon-carcinogens0.8493BiodegradationNot ready biodegradable0.9962Rat acute toxicity2.6875 LD50, mol/kg Not applicablehERG inhibition (predictor I)Weak inhibitor0.908hERG inhibition (predictor II)Non-inhibitor0.5486 ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397) Mass Spec (NIST)Not AvailableSpectraSpectrumSpectrum TypeSplash KeyPredicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSPredicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSPredicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSPredicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSPredicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSPredicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MS TargetsBuild, predict & validate machine-learning models Use our structured and evidence-based datasets to unlock new insights and accelerate drug research. Use our structured and evidence-based datasets to unlock new insights and accelerate drug research. KindProteinOrganismEscherichia coli (strain K12)Pharmacological action Yes Actions Inhibitor General FunctionRibonucleoside bindingSpecific FunctionDNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates.Gene NamerpoBUniprot IDP0A8V2Uniprot NameDNA-directed RNA polymerase subunit betaMolecular Weight150631.165 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Agonist General FunctionZinc ion bindingSpecific FunctionNuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...Gene NameNR1I2Uniprot IDO75469Uniprot NameNuclear receptor subfamily 1 group I member 2Molecular Weight49761.245 Da References
EnzymesKindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionSteroid hydroxylase activitySpecific FunctionExhibits 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. Const...Gene NameCYP2A6Uniprot IDP11509Uniprot NameCytochrome P450 2A6Molecular Weight56501.005 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionSteroid hydroxylase activitySpecific FunctionMetabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...Gene NameCYP2E1Uniprot IDP05181Uniprot NameCytochrome P450 2E1Molecular Weight56848.42 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionMonooxygenase activitySpecific FunctionExhibits low testosterone 6-beta-hydroxylase activity.Gene NameCYP3A43Uniprot IDQ9HB55Uniprot NameCytochrome P450 3A43Molecular Weight57669.21 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionOxygen bindingSpecific FunctionCytochromes 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 NameCYP3A7Uniprot IDP24462Uniprot NameCytochrome P450 3A7Molecular Weight57525.03 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inhibitor General FunctionRetinoic acid bindingSpecific FunctionUDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...Gene NameUGT1A9Uniprot IDO60656Uniprot NameUDP-glucuronosyltransferase 1-9Molecular Weight59940.495 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionOxygen bindingSpecific FunctionCytochromes 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 NameCYP3A5Uniprot IDP20815Uniprot NameCytochrome P450 3A5Molecular Weight57108.065 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionVitamin d3 25-hydroxylase activitySpecific FunctionCytochromes 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 NameCYP3A4Uniprot IDP08684Uniprot NameCytochrome P450 3A4Molecular Weight57342.67 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionOxidoreductase 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 oxygenSpecific FunctionCytochromes 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 NameCYP1A2Uniprot IDP05177Uniprot NameCytochrome P450 1A2Molecular Weight58293.76 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inhibitor Inducer General FunctionSteroid hydroxylase activitySpecific FunctionCytochromes 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 NameCYP2C8Uniprot IDP10632Uniprot NameCytochrome P450 2C8Molecular Weight55824.275 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionSteroid bindingSpecific FunctionUDPGT 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...Gene NameUGT1A1Uniprot IDP22309Uniprot NameUDP-glucuronosyltransferase 1-1Molecular Weight59590.91 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionSteroid hydroxylase activitySpecific FunctionCytochromes 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 NameCYP2C9Uniprot IDP11712Uniprot NameCytochrome P450 2C9Molecular Weight55627.365 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionSteroid hydroxylase activitySpecific FunctionCytochromes 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 NameCYP2B6Uniprot IDP20813Uniprot NameCytochrome P450 2B6Molecular Weight56277.81 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionSteroid hydroxylase activitySpecific FunctionResponsible 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 NameCYP2C19Uniprot IDP33261Uniprot NameCytochrome P450 2C19Molecular Weight55930.545 Da References
CarriersKindProteinOrganismHumansPharmacological action Unknown Actions Ligand General FunctionToxic substance bindingSpecific FunctionSerum 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 NameALBUniprot IDP02768Uniprot NameSerum albuminMolecular Weight69365.94 Da References
KindProtein groupOrganismHumansPharmacological action Unknown Actions Ligand General FunctionNot AvailableSpecific FunctionFunctions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in... Components:References
TransportersKindProteinOrganismHumansPharmacological action Unknown Actions Inducer General FunctionXenobiotic-transporting atpase activitySpecific FunctionEnergy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.Gene NameABCB1Uniprot IDP08183Uniprot NameMultidrug resistance protein 1Molecular Weight141477.255 Da References
KindProteinOrganismHumansPharmacological action Unknown Actions Substrate Inhibitor General FunctionSodium-independent organic anion transmembrane transporter activitySpecific FunctionPlays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...Gene NameSLC22A8Uniprot IDQ8TCC7Uniprot NameSolute carrier family 22 member 8Molecular Weight59855.585 Da |
Drug interaction ระหว าง rifampicin ก บ ยาค ม
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