Identification

Name
Rifabutin
Accession Number
DB00615
Description

A broad-spectrum antibiotic that is being used as prophylaxis against disseminated Mycobacterium avium complex infection in HIV-positive patients.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 847.0047
Monoisotopic: 846.441508846
Chemical Formula
C46H62N4O11
Synonyms
  • 1,4-Dihydro-1-deoxy-1',4-didehydro-5'-(2-methylpropyl)-1-oxorifamycin XIV
  • 4-Deoxo-3,4-(2-spiro(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo)-rifamycin S
  • 4-N-isobutylspiropiperidylrifamycin S
  • Ansamicin
  • Ansamycin
  • Rifabutin
  • Rifabutina
  • Rifabutine
  • Rifabutinum
External IDs
  • LM 427
  • LM-427

Pharmacology

Indication

For the prevention of disseminated Mycobacterium avium complex (MAC) disease in patients with advanced HIV infection.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Rifabutin 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. Rifabutin 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

Rifabutin acts via the inhibition of DNA-dependent RNA polymerase in gram-positive and some gram-negative bacteria, leading to a suppression of RNA synthesis and cell death.

TargetActionsOrganism
ADNA-directed RNA polymerase subunit alpha
inhibitor
Escherichia coli (strain K12)
ADNA-directed RNA polymerase subunit beta
inhibitor
Escherichia coli (strain K12)
ADNA-directed RNA polymerase subunit beta'
inhibitor
Escherichia coli (strain K12)
NHeat shock protein HSP 90-alpha
other/unknown
Humans
NEndoplasmin
other/unknown
Humans
Absorption

Rifabutin is readily absorbed from the gastrointestinal tract, with an absolute bioavailability averaging 20%.

Volume of distribution
Not Available
Protein binding

85%

Metabolism

Hepatic. Of the five metabolites that have been identified, 25-O-desacetyl and 31-hydroxy are the most predominant. The former metabolite has an activity equal to the parent drug and contributes up to 10% to the total antimicrobial activity.

Hover over products below to view reaction partners

Route of elimination

A mass-balance study in three healthy adult volunteers with 14C-labeled rifabutin showed that 53% of the oral dose was excreted in the urine, primarily as metabolites. About 30% of the dose is excreted in the feces.

Half-life

45 (± 17) hours

Clearance
  • 0.69 +/- 0.32 L/hr/kg
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

LD50 = 4.8 g/kg (mouse, male)

Affected organisms
  • Enteric bacteria and other eubacteria
  • Mycobacterium tuberculosis
  • Mycobacterium leprae
  • Mycobacterium avium
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug 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
AbametapirThe serum concentration of Rifabutin can be increased when it is combined with Abametapir.
AbirateroneThe metabolism of Abiraterone can be increased when combined with Rifabutin.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Rifabutin.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Rifabutin.
AlbendazoleThe metabolism of Albendazole can be increased when combined with Rifabutin.
AlectinibThe metabolism of Alectinib can be increased when combined with Rifabutin.
AlmotriptanThe metabolism of Almotriptan can be increased when combined with Rifabutin.
AlpelisibThe metabolism of Alpelisib can be increased when combined with Rifabutin.
AminophenazoneThe metabolism of Aminophenazone can be increased when combined with Rifabutin.
AminophyllineThe metabolism of Aminophylline can be increased when combined with Rifabutin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Take with or without food. For those patients with propensity to nausea, vomiting, or other gastrointestinal upset, taking with food may be useful.

Products

Product Images
International/Other Brands
Ansatipin (Pfizer) / Ansatipine (SERB) / Ributin (Lupin)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MycobutinCapsule150 mg/1OralDepartment Of State Health Services, Pharmacy Branch1992-12-23Not applicableUS flag
MycobutinCapsule150 mgOralPfizer Canada Ulc1995-12-31Not applicableCanada flag
MycobutinCapsule150 mg/1OralPhysicians Total Care, Inc.1995-03-15Not applicableUS flag54868 284120180907 15195 rzy2l0
MycobutinCapsule150 mg/1OralPharmacia and Upjohn Company LLC1992-12-23Not applicableUS flag00013 5301 17 nlmimage10 691e34b1
RifabutinCapsule150 mg/1OralGreenstone, Llc2014-04-07Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RifabutinCapsule150 mg/1OralAmerican Health Packaging2016-06-082021-01-31US flag
RifabutinCapsule150 mg/1OralLupin Pharmaceuticals, Inc.2014-03-26Not applicableUS flag
RifabutinCapsule150 mg/1OralAvera McKennan Hospital2016-03-032017-05-24US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
TaliciaRifabutin (12.5 mg/1) + Amoxycillin trihydrate (250 mg/1) + Omeprazole magnesium (10 mg/1)Capsule, delayed releaseOralRedHill Biopharma Ltd2020-03-09Not applicableUS flag

Categories

ATC Codes
J04AB04 — Rifabutin
Drug Categories
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 / Azaspirodecane derivatives / Naphthalenes / Benzofurans / Coumarans / Aryl alkyl ketones / Ketals / Piperidines / Vinylogous amides / Vinylogous acids
show 19 more
Substituents
3-imidazoline / Acetal / Alcohol / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azaspirodecane
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
rifamycin (CHEBI:45367)

Chemical Identifiers

UNII
1W306TDA6S
CAS number
72559-06-9
InChI Key
ATEBXHFBFRCZMA-VXTBVIBXSA-N
InChI
InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14-/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1
IUPAC Name
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23,32-trioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1⁴,⁷.0⁵,³¹.0²⁶,³⁰]tritriacontane-28,4'-piperidin]-1(31),2,4,9,19,21,25,29-octaen-13-yl acetate
SMILES
CO[[email protected]]1\C=C\O[[email protected]@]2(C)OC3=C(C2=O)C2=C(C(O)=C3C)C(=O)C(NC(=O)\C(C)=C/C=C/[[email protected]](C)[[email protected]](O)[[email protected]@H](C)[[email protected]@H](O)[[email protected]@H](C)[[email protected]](OC(C)=O)[[email protected]@H]1C)=C1NC3(CCN(CC3)CC(C)C)N=C21

References

General References
  1. FDA Approved Drug Products: Talicia Amoxicillin, Omeprazole, and Rifabutin Oral Delayed Release Capsules [Link]
Human Metabolome Database
HMDB14753
KEGG Drug
D00424
KEGG Compound
C07235
PubChem Compound
6323490
PubChem Substance
46506468
ChemSpider
10482168
BindingDB
50237607
RxNav
55672
ChEBI
45367
ChEMBL
CHEMBL444633
ZINC
ZINC000169621215
Therapeutic Targets Database
DAP000656
PharmGKB
PA451249
PDBe Ligand
RBT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Rifabutin
AHFS Codes
  • 08:16.04 — Antituberculosis Agents
PDB Entries
2a68 / 4cp3 / 6bec
FDA label
Download (69.5 KB)
MSDS
Download (58.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis (TB)1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Unknown StatusTreatmentMycobacterium avium complex infection1
4Unknown StatusTreatmentMycobacterium Avium Complex Lung Disease1
4Unknown StatusTreatmentReinfection Pulmonary Tuberculosis1
4WithdrawnTreatmentCrohn's Disease (CD)1
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Dyspepsia1
3CompletedTreatmentCrohn's Disease (CD)1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
  • CQ International Co. Inc.
  • Kaiser Foundation Hospital
  • Pfizer Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
Dosage Forms
FormRouteStrength
CapsuleOral150 MG
CapsuleOral150 mg/1
Capsule150 mg
Capsule, coatedOral150 mg
Capsule, delayed releaseOral
Prices
Unit descriptionCostUnit
Mycobutin 150 mg capsule13.01USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9603806No2017-03-282034-02-12US flag
US9498445No2016-11-222034-02-12US flag
US9050263No2015-06-092034-02-12US flag
US10238606No2019-03-262034-02-12US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityMinimally soluble (0.19 mg/mL)Not Available
logP4.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 mg/mLALOGPS
logP4.25ALOGPS
logP4.19ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.93ChemAxon
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area205.55 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity232.64 m3·mol-1ChemAxon
Polarizability90.72 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5507
Blood Brain Barrier-0.9921
Caco-2 permeable-0.7072
P-glycoprotein substrateSubstrate0.9612
P-glycoprotein inhibitor IInhibitor0.5415
P-glycoprotein inhibitor IIInhibitor0.6516
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.819
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.745
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8909
Ames testNon AMES toxic0.6724
CarcinogenicityNon-carcinogens0.9195
BiodegradationNot ready biodegradable0.9687
Rat acute toxicity2.5143 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.946
hERG inhibition (predictor II)Inhibitor0.5416
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Maddix DS, Tallian KB, Mead PS: Rifabutin: a review with emphasis on its role in the prevention of disseminated Mycobacterium avium complex infection. Ann Pharmacother. 1994 Nov;28(11):1250-4. [PubMed:7849340]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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
  1. Maddix DS, Tallian KB, Mead PS: Rifabutin: a review with emphasis on its role in the prevention of disseminated Mycobacterium avium complex infection. Ann Pharmacother. 1994 Nov;28(11):1250-4. [PubMed:7849340]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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
  1. Maddix DS, Tallian KB, Mead PS: Rifabutin: a review with emphasis on its role in the prevention of disseminated Mycobacterium avium complex infection. Ann Pharmacother. 1994 Nov;28(11):1250-4. [PubMed:7849340]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Other/unknown
General Function
Tpr domain binding
Specific Function
Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
Gene Name
HSP90AA1
Uniprot ID
P07900
Uniprot Name
Heat shock protein HSP 90-alpha
Molecular Weight
84659.015 Da
References
  1. Schnaider T, Somogyi J, Csermely P, Szamel M: The Hsp90-specific inhibitor geldanamycin selectively disrupts kinase-mediated signaling events of T-lymphocyte activation. Cell Stress Chaperones. 2000 Jan;5(1):52-61. [PubMed:10701840]
  2. Neckers L, Schulte TW, Mimnaugh E: Geldanamycin as a potential anti-cancer agent: its molecular target and biochemical activity. Invest New Drugs. 1999;17(4):361-73. [PubMed:10759403]
  3. Srethapakdi M, Liu F, Tavorath R, Rosen N: Inhibition of Hsp90 function by ansamycins causes retinoblastoma gene product-dependent G1 arrest. Cancer Res. 2000 Jul 15;60(14):3940-6. [PubMed:10919672]
  4. Munster PN, Srethapakdi M, Moasser MM, Rosen N: Inhibition of heat shock protein 90 function by ansamycins causes the morphological and functional differentiation of breast cancer cells. Cancer Res. 2001 Apr 1;61(7):2945-52. [PubMed:11306472]
  5. Yang J, Yang JM, Iannone M, Shih WJ, Lin Y, Hait WN: Disruption of the EF-2 kinase/Hsp90 protein complex: a possible mechanism to inhibit glioblastoma by geldanamycin. Cancer Res. 2001 May 15;61(10):4010-6. [PubMed:11358819]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Other/unknown
General Function
Virion binding
Specific Function
Molecular chaperone that functions in the processing and transport of secreted proteins. When associated with CNPY3, required for proper folding of Toll-like receptors (By similarity). Functions in...
Gene Name
HSP90B1
Uniprot ID
P14625
Uniprot Name
Endoplasmin
Molecular Weight
92468.06 Da
References
  1. Barzilay E, Ben-Califa N, Supino-Rosin L, Kashman Y, Hirschberg K, Elazar Z, Neumann D: Geldanamycin-associated inhibition of intracellular trafficking is attributed to a co-purified activity. J Biol Chem. 2004 Feb 20;279(8):6847-52. Epub 2003 Dec 1. [PubMed:14660597]
  2. Chavany C, Mimnaugh E, Miller P, Bitton R, Nguyen P, Trepel J, Whitesell L, Schnur R, Moyer J, Neckers L: p185erbB2 binds to GRP94 in vivo. Dissociation of the p185erbB2/GRP94 heterocomplex by benzoquinone ansamycins precedes depletion of p185erbB2. J Biol Chem. 1996 Mar 1;271(9):4974-7. [PubMed:8617772]
  3. Lawson B, Brewer JW, Hendershot LM: Geldanamycin, an hsp90/GRP94-binding drug, induces increased transcription of endoplasmic reticulum (ER) chaperones via the ER stress pathway. J Cell Physiol. 1998 Feb;174(2):170-8. [PubMed:9428803]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
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
  1. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933]
  2. Vourvahis M, Davis J, Wang R, Layton G, Choo HW, Chong CL, Tawadrous M: Effect of rifampin and rifabutin on the pharmacokinetics of lersivirine and effect of lersivirine on the pharmacokinetics of rifabutin and 25-O-desacetyl-rifabutin in healthy subjects. Antimicrob Agents Chemother. 2012 Aug;56(8):4303-9. doi: 10.1128/AAC.06282-11. Epub 2012 May 29. [PubMed:22644026]
  3. Sousa M, Pozniak A, Boffito M: Pharmacokinetics and pharmacodynamics of drug interactions involving rifampicin, rifabutin and antimalarial drugs. J Antimicrob Chemother. 2008 Nov;62(5):872-8. doi: 10.1093/jac/dkn330. Epub 2008 Aug 18. [PubMed:18713760]
  4. Flockhart Table of Drug Interactions [Link]
  5. Mycobutin (Rifabutin) FDA Label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
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
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
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
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
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
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  2. Pharmacists' Letter/Prescribers' Letter: Cytochrome P450 Drug Interactions [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
Curator comments
This drug is a member of the rifamycin derivative drug class, which are known to induce CYP2C9.
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
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  2. Chen J, Raymond K: Roles of rifampicin in drug-drug interactions: underlying molecular mechanisms involving the nuclear pregnane X receptor. Ann Clin Microbiol Antimicrob. 2006 Feb 15;5:3. [PubMed:16480505]
  3. Finch CK, Chrisman CR, Baciewicz AM, Self TH: Rifampin and rifabutin drug interactions: an update. Arch Intern Med. 2002 May 13;162(9):985-92. [PubMed:11996607]
  4. Lutz JD, Kirby BJ, Wang L, Song Q, Ling J, Massetto B, Worth A, Kearney BP, Mathias A: Cytochrome P450 3A Induction Predicts P-glycoprotein Induction; Part 2: Prediction of Decreased Substrate Exposure After Rifabutin or Carbamazepine. Clin Pharmacol Ther. 2018 Mar 23. doi: 10.1002/cpt.1072. [PubMed:29569712]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
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
  1. Baciewicz AM, Chrisman CR, Finch CK, Self TH: Update on rifampin, rifabutin, and rifapentine drug interactions. Curr Med Res Opin. 2013 Jan;29(1):1-12. doi: 10.1185/03007995.2012.747952. Epub 2012 Nov 30. [PubMed:23136913]
  2. Lutz JD, Kirby BJ, Wang L, Song Q, Ling J, Massetto B, Worth A, Kearney BP, Mathias A: Cytochrome P450 3A Induction Predicts P-glycoprotein Induction; Part 2: Prediction of Decreased Substrate Exposure After Rifabutin or Carbamazepine. Clin Pharmacol Ther. 2018 Mar 23. doi: 10.1002/cpt.1072. [PubMed:29569712]
  3. Vourvahis M, Davis J, Wang R, Layton G, Choo HW, Chong CL, Tawadrous M: Effect of rifampin and rifabutin on the pharmacokinetics of lersivirine and effect of lersivirine on the pharmacokinetics of rifabutin and 25-O-desacetyl-rifabutin in healthy subjects. Antimicrob Agents Chemother. 2012 Aug;56(8):4303-9. doi: 10.1128/AAC.06282-11. Epub 2012 May 29. [PubMed:22644026]

Drug created on June 13, 2005 07:24 / Updated on September 27, 2020 08:17

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates