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Identification
NameRifabutin
Accession NumberDB00615  (APRD00094)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
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
Mycobutin (tn)
Rifabutin
Rifabutina
Rifabutine
Rifabutinum
External Identifiers
  • LM 427
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mycobutincapsule150 mg/1oralPharmacia and Upjohn Company1992-12-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mycobutincapsule150 mgoralPfizer Canada Inc1995-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Mycobutincapsule150 mg/1oralPhysicians Total Care, Inc.1995-03-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Rifabutincapsule150 mg/1oralGreenstone LLC2014-04-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Rifabutincapsule150 mg/1oralLupin Pharmaceuticals, Inc.2014-03-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
AnsatipinPfizer
AnsatipineSERB
RibutinLupin
Brand mixturesNot Available
SaltsNot Available
Categories
UNII1W306TDA6S
CAS number72559-06-9
WeightAverage: 847.0047
Monoisotopic: 846.441508846
Chemical FormulaC46H62N4O11
InChI KeyInChIKey=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[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C2=C(C(O)=C3C)C(=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)=C1NC3(CCN(CC3)CC(C)C)N=C21
Taxonomy
DescriptionThis 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 compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Naphthofuran
  • Macrolactam
  • Naphthalene
  • Azaspirodecane
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzenoid
  • Piperidine
  • Acetate salt
  • Vinylogous amide
  • Vinylogous acid
  • 3-imidazoline
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Lactam
  • Ketone
  • Ketimine
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the prevention of disseminated Mycobacterium avium complex (MAC) disease in patients with advanced HIV infection.
PharmacodynamicsRifabutin 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 actionRifabutin 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.
AbsorptionRifabutin is readily absorbed from the gastrointestinal tract, with an absolute bioavailability averaging 20%.
Volume of distributionNot Available
Protein binding85%
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.

SubstrateEnzymesProduct
Rifabutin
27-O-demethylrifabutinDetails
Rifabutin
Not Available
25-O-desacetyl rifabutinDetails
Rifabutin
Not Available
31-hydroxy rifabutinDetails
Route of eliminationA 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 life45 (± 17) hours
Clearance
  • 0.69 +/- 0.32 L/hr/kg
ToxicityLD50 = 4.8 g/kg (mouse, male)
Affected organisms
  • Enteric bacteria and other eubacteria
  • Mycobacterium tuberculosis
  • Mycobacterium leprae
  • Mycobacterium avium
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Capsuleoral150 mg/1
Capsuleoral150 mg
Prices
Unit descriptionCostUnit
Mycobutin 150 mg capsule13.01USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ04AB04
AHFS Codes
  • 08:16.04
PDB EntriesNot Available
FDA labelDownload (69.5 KB)
MSDSDownload (58.4 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Abiraterone can be decreased when it is combined with Rifabutin.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Rifabutin.
AcetaminophenThe metabolism of Acetaminophen can be increased when combined with Rifabutin.
AlfentanilThe serum concentration of Alfentanil can be decreased when it is combined with Rifabutin.
AmlodipineThe serum concentration of Amlodipine can be decreased when it is combined with Rifabutin.
AmobarbitalThe metabolism of Amobarbital can be increased when combined with Rifabutin.
AmrinoneThe serum concentration of Amrinone can be decreased when it is combined with Rifabutin.
ApixabanThe serum concentration of Apixaban can be decreased when it is combined with Rifabutin.
ApremilastThe serum concentration of Apremilast can be decreased when it is combined with Rifabutin.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Rifabutin.
ArtemetherThe serum concentration of the active metabolites of Artemether can be reduced when Artemether is used in combination with Rifabutin resulting in a loss in efficacy.
AtazanavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Atazanavir.
AtorvastatinThe serum concentration of Atorvastatin can be decreased when it is combined with Rifabutin.
AtovaquoneThe serum concentration of Atovaquone can be decreased when it is combined with Rifabutin.
AxitinibThe serum concentration of Axitinib can be decreased when it is combined with Rifabutin.
BedaquilineThe serum concentration of Bedaquiline can be decreased when it is combined with Rifabutin.
BepridilThe serum concentration of Bepridil can be decreased when it is combined with Rifabutin.
BexaroteneThe serum concentration of Rifabutin can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Boceprevir can be decreased when it is combined with Rifabutin.
BortezomibThe serum concentration of Bortezomib can be decreased when it is combined with Rifabutin.
BosentanThe serum concentration of Rifabutin can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Rifabutin.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Rifabutin.
BrexpiprazoleThe serum concentration of Brexpiprazole can be decreased when it is combined with Rifabutin.
BuspironeThe serum concentration of Buspirone can be decreased when it is combined with Rifabutin.
ButabarbitalThe metabolism of Butabarbital can be increased when combined with Rifabutin.
ButalbitalThe metabolism of Butalbital can be increased when combined with Rifabutin.
ButethalThe metabolism of Butethal can be increased when combined with Rifabutin.
CabozantinibThe serum concentration of Cabozantinib can be decreased when it is combined with Rifabutin.
CaffeineThe metabolism of Caffeine can be increased when combined with Rifabutin.
CannabidiolThe serum concentration of Cannabidiol can be decreased when it is combined with Rifabutin.
CeritinibThe serum concentration of Ceritinib can be decreased when it is combined with Rifabutin.
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Rifabutin.
ClarithromycinThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Rifabutin.
ClopidogrelThe risk or severity of adverse effects can be increased when Rifabutin is combined with Clopidogrel.
ClozapineThe serum concentration of Clozapine can be decreased when it is combined with Rifabutin.
CrizotinibThe serum concentration of Crizotinib can be decreased when it is combined with Rifabutin.
CyclosporineThe metabolism of Cyclosporine can be increased when combined with Rifabutin.
DabrafenibThe serum concentration of Rifabutin can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be decreased when it is combined with Rifabutin.
DapsoneThe metabolism of Dapsone can be increased when combined with Rifabutin.
DarunavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Darunavir.
DasatinibThe serum concentration of Dasatinib can be decreased when it is combined with Rifabutin.
DeferasiroxThe serum concentration of Rifabutin can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Delavirdine can be increased when combined with Rifabutin.
DesogestrelThe serum concentration of Desogestrel can be decreased when it is combined with Rifabutin.
DexamethasoneThe serum concentration of Dexamethasone can be decreased when it is combined with Rifabutin.
DicoumarolThe metabolism of Dicoumarol can be increased when combined with Rifabutin.
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Rifabutin.
DiltiazemThe serum concentration of Diltiazem can be decreased when it is combined with Rifabutin.
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Rifabutin.
DronabinolThe serum concentration of Dronabinol can be decreased when it is combined with Rifabutin.
DronedaroneThe serum concentration of Dronedarone can be decreased when it is combined with Rifabutin.
DrospirenoneThe serum concentration of Drospirenone can be decreased when it is combined with Rifabutin.
EfavirenzThe serum concentration of Rifabutin can be decreased when it is combined with Efavirenz.
EliglustatThe serum concentration of Eliglustat can be decreased when it is combined with Rifabutin.
ElvitegravirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Elvitegravir.
EnzalutamideThe serum concentration of Enzalutamide can be decreased when it is combined with Rifabutin.
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Rifabutin.
ErythromycinThe metabolism of Rifabutin can be decreased when combined with Erythromycin.
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Rifabutin.
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Rifabutin.
EthynodiolThe serum concentration of Ethynodiol can be decreased when it is combined with Rifabutin.
EtonogestrelThe serum concentration of Etonogestrel can be decreased when it is combined with Rifabutin.
EtoposideThe serum concentration of Etoposide can be decreased when it is combined with Rifabutin.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Rifabutin.
EverolimusThe serum concentration of Everolimus can be decreased when it is combined with Rifabutin.
ExemestaneThe serum concentration of Exemestane can be decreased when it is combined with Rifabutin.
FelodipineThe serum concentration of Felodipine can be decreased when it is combined with Rifabutin.
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Rifabutin.
FlibanserinThe serum concentration of Flibanserin can be decreased when it is combined with Rifabutin.
FluconazoleThe serum concentration of Rifabutin can be increased when it is combined with Fluconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be decreased when it is combined with Rifabutin.
FlunarizineThe serum concentration of Flunarizine can be decreased when it is combined with Rifabutin.
FlunisolideThe metabolism of Flunisolide can be increased when combined with Rifabutin.
FluvastatinThe serum concentration of Fluvastatin can be decreased when it is combined with Rifabutin.
FosamprenavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Fosamprenavir.
GabapentinThe serum concentration of Gabapentin can be decreased when it is combined with Rifabutin.
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Rifabutin.
GuanfacineThe serum concentration of Guanfacine can be decreased when it is combined with Rifabutin.
HeptabarbitalThe metabolism of Heptabarbital can be increased when combined with Rifabutin.
HexobarbitalThe metabolism of Hexobarbital can be increased when combined with Rifabutin.
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Rifabutin.
HydrocortisoneThe serum concentration of Hydrocortisone can be decreased when it is combined with Rifabutin.
IbrutinibThe serum concentration of Ibrutinib can be decreased when it is combined with Rifabutin.
IdelalisibThe serum concentration of Idelalisib can be decreased when it is combined with Rifabutin.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Rifabutin.
ImatinibThe serum concentration of Imatinib can be decreased when it is combined with Rifabutin.
IndinavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Indinavir.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Rifabutin resulting in a loss in efficacy.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be reduced when Isavuconazonium is used in combination with Rifabutin resulting in a loss in efficacy.
IsoniazidRifabutin may increase the hepatotoxic activities of Isoniazid.
IsradipineThe serum concentration of Isradipine can be decreased when it is combined with Rifabutin.
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Rifabutin.
IvabradineThe serum concentration of Ivabradine can be decreased when it is combined with Rifabutin.
IvacaftorThe serum concentration of Ivacaftor can be decreased when it is combined with Rifabutin.
IxabepiloneThe serum concentration of Ixabepilone can be decreased when it is combined with Rifabutin.
KetoconazoleThe serum concentration of Rifabutin can be increased when it is combined with Ketoconazole.
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Rifabutin.
LapatinibThe serum concentration of Lapatinib can be decreased when it is combined with Rifabutin.
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Rifabutin.
LercanidipineThe serum concentration of Lercanidipine can be decreased when it is combined with Rifabutin.
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Rifabutin.
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Rifabutin.
LopinavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Lopinavir.
LovastatinThe serum concentration of Lovastatin can be decreased when it is combined with Rifabutin.
LumefantrineThe serum concentration of Lumefantrine can be decreased when it is combined with Rifabutin.
LurasidoneThe serum concentration of Lurasidone can be decreased when it is combined with Rifabutin.
MACITENTANThe serum concentration of MACITENTAN can be decreased when it is combined with Rifabutin.
Magnesium SulfateThe serum concentration of Magnesium Sulfate can be decreased when it is combined with Rifabutin.
MaravirocThe serum concentration of Maraviroc can be decreased when it is combined with Rifabutin.
Medroxyprogesterone AcetateThe serum concentration of Medroxyprogesterone Acetate can be decreased when it is combined with Rifabutin.
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Rifabutin.
MethohexitalThe metabolism of Methohexital can be increased when combined with Rifabutin.
MethylprednisoloneThe serum concentration of Methylprednisolone can be decreased when it is combined with Rifabutin.
MifepristoneThe serum concentration of Mifepristone can be decreased when it is combined with Rifabutin.
MitotaneThe serum concentration of Rifabutin can be decreased when it is combined with Mitotane.
MorphineThe serum concentration of Morphine can be decreased when it is combined with Rifabutin.
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Rifabutin.
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Rifabutin.
NaloxegolThe serum concentration of Naloxegol can be decreased when it is combined with Rifabutin.
NelfinavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Nelfinavir.
NetupitantThe serum concentration of Netupitant can be decreased when it is combined with Rifabutin.
NevirapineThe serum concentration of Nevirapine can be decreased when it is combined with Rifabutin.
NicardipineThe serum concentration of Nicardipine can be decreased when it is combined with Rifabutin.
NifedipineThe serum concentration of Nifedipine can be decreased when it is combined with Rifabutin.
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Rifabutin.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Rifabutin.
NisoldipineThe serum concentration of Nisoldipine can be decreased when it is combined with Rifabutin.
NitrendipineThe serum concentration of Nitrendipine can be decreased when it is combined with Rifabutin.
NorethindroneThe serum concentration of Norethindrone can be decreased when it is combined with Rifabutin.
NorgestimateThe serum concentration of Norgestimate can be decreased when it is combined with Rifabutin.
OlaparibThe serum concentration of Olaparib can be decreased when it is combined with Rifabutin.
PalbociclibThe serum concentration of Palbociclib can be decreased when it is combined with Rifabutin.
PanobinostatThe serum concentration of Panobinostat can be decreased when it is combined with Rifabutin.
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Rifabutin.
PentobarbitalThe metabolism of Pentobarbital can be increased when combined with Rifabutin.
PerampanelThe serum concentration of Perampanel can be decreased when it is combined with Rifabutin.
PerhexilineThe serum concentration of Perhexiline can be decreased when it is combined with Rifabutin.
PhenobarbitalThe metabolism of Phenobarbital can be increased when combined with Rifabutin.
PhenytoinThe metabolism of Rifabutin can be increased when combined with Phenytoin.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Rifabutin.
PonatinibThe serum concentration of Ponatinib can be decreased when it is combined with Rifabutin.
PosaconazoleThe serum concentration of Rifabutin can be increased when it is combined with Posaconazole.
PravastatinThe serum concentration of Pravastatin can be decreased when it is combined with Rifabutin.
PraziquantelThe serum concentration of Praziquantel can be decreased when it is combined with Rifabutin.
PrednisoloneThe serum concentration of Prednisolone can be decreased when it is combined with Rifabutin.
PrednisoneThe serum concentration of Prednisone can be decreased when it is combined with Rifabutin.
PrenylamineThe serum concentration of Prenylamine can be decreased when it is combined with Rifabutin.
PrimidoneThe metabolism of Primidone can be increased when combined with Rifabutin.
ProguanilThe serum concentration of Proguanil can be decreased when it is combined with Rifabutin.
PropafenoneThe serum concentration of Propafenone can be decreased when it is combined with Rifabutin.
QuetiapineThe serum concentration of Quetiapine can be decreased when it is combined with Rifabutin.
QuinidineThe serum concentration of Quinidine can be decreased when it is combined with Rifabutin.
RaltegravirThe serum concentration of Raltegravir can be decreased when it is combined with Rifabutin.
RamelteonThe metabolism of Ramelteon can be increased when combined with Rifabutin.
RanolazineThe serum concentration of Ranolazine can be decreased when it is combined with Rifabutin.
RegorafenibThe serum concentration of Regorafenib can be decreased when it is combined with Rifabutin.
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Rifabutin.
RisedronateThe serum concentration of Risedronate can be decreased when it is combined with Rifabutin.
RitonavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Ritonavir.
RivaroxabanThe serum concentration of Rivaroxaban can be decreased when it is combined with Rifabutin.
RoflumilastThe serum concentration of Roflumilast can be decreased when it is combined with Rifabutin.
RolapitantThe serum concentration of Rolapitant can be decreased when it is combined with Rifabutin.
RomidepsinThe serum concentration of Romidepsin can be decreased when it is combined with Rifabutin.
SaquinavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Saquinavir.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Rifabutin.
SecobarbitalThe metabolism of Secobarbital can be increased when combined with Rifabutin.
SiltuximabThe serum concentration of Rifabutin can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be decreased when it is combined with Rifabutin.
SimvastatinThe serum concentration of Simvastatin can be decreased when it is combined with Rifabutin.
Sodium picosulfateThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Rifabutin.
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Rifabutin.
SonidegibThe serum concentration of Sonidegib can be decreased when it is combined with Rifabutin.
SorafenibThe serum concentration of Sorafenib can be decreased when it is combined with Rifabutin.
St. John's WortThe serum concentration of Rifabutin can be decreased when it is combined with St. John's Wort.
SulfisoxazoleThe metabolism of Rifabutin can be decreased when combined with Sulfisoxazole.
SunitinibThe serum concentration of Sunitinib can be decreased when it is combined with Rifabutin.
SuvorexantThe serum concentration of Suvorexant can be decreased when it is combined with Rifabutin.
TacrolimusThe serum concentration of Tacrolimus can be decreased when it is combined with Rifabutin.
TadalafilThe serum concentration of Tadalafil can be decreased when it is combined with Rifabutin.
TamoxifenThe metabolism of Tamoxifen can be increased when combined with Rifabutin.
TasimelteonThe serum concentration of Tasimelteon can be decreased when it is combined with Rifabutin.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Rifabutin.
TelithromycinThe metabolism of Rifabutin can be decreased when combined with Telithromycin.
TemsirolimusThe serum concentration of Temsirolimus can be decreased when it is combined with Rifabutin.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Rifabutin resulting in a loss in efficacy.
TipranavirThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Tipranavir.
TocilizumabThe serum concentration of Rifabutin can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be decreased when it is combined with Rifabutin.
TolvaptanThe serum concentration of Tolvaptan can be decreased when it is combined with Rifabutin.
ToremifeneThe serum concentration of Toremifene can be decreased when it is combined with Rifabutin.
TrabectedinThe serum concentration of Trabectedin can be decreased when it is combined with Rifabutin.
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Rifabutin.
VandetanibThe serum concentration of Vandetanib can be decreased when it is combined with Rifabutin.
VemurafenibThe serum concentration of Vemurafenib can be decreased when it is combined with Rifabutin.
VerapamilThe serum concentration of Verapamil can be decreased when it is combined with Rifabutin.
VilazodoneThe serum concentration of Vilazodone can be decreased when it is combined with Rifabutin.
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Rifabutin.
VorapaxarThe serum concentration of Vorapaxar can be decreased when it is combined with Rifabutin.
VoriconazoleThe serum concentration of Rifabutin can be increased when it is combined with Voriconazole.
VortioxetineThe serum concentration of Vortioxetine can be decreased when it is combined with Rifabutin.
WarfarinThe metabolism of Warfarin can be increased when combined with Rifabutin.
ZaleplonThe serum concentration of Zaleplon can be decreased when it is combined with Rifabutin.
ZolpidemThe serum concentration of Zolpidem can be decreased when it is combined with Rifabutin.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be decreased when it is combined with Rifabutin.
Food Interactions
  • High-fat meals slow the rate of absorption.
  • Take with food to reduce irritation.

Targets

1. DNA-directed RNA polymerase subunit alpha

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
DNA-directed RNA polymerase subunit alpha P0A7Z4 Details

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
  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
  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

2. DNA-directed RNA polymerase subunit beta

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
DNA-directed RNA polymerase subunit beta P0A8V2 Details

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

3. DNA-directed RNA polymerase subunit beta'

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
DNA-directed RNA polymerase subunit beta' P0A8T7 Details

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

4. Heat shock protein HSP 90-alpha

Kind: Protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Heat shock protein HSP 90-alpha P07900 Details

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
  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
  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
  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
  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

5. Endoplasmin

Kind: Protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Endoplasmin P14625 Details

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
  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
  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

Enzymes

1. Cytochrome P450 3A4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. 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

2. Cytochrome P450 1A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 20, 2014 11:32