Identification

Name
Rifabutin
Accession Number
DB00615  (APRD00094)
Type
Small Molecule
Groups
Approved, Investigational
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 IDs
LM 427 / LM-427
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MycobutinCapsule150 mgOralPfizer1995-12-31Not applicableCanada
MycobutinCapsule150 mg/1OralDepartment Of State Health Services, Pharmacy Branch1992-12-23Not applicableUs
MycobutinCapsule150 mg/1OralPhysicians Total Care, Inc.1995-03-15Not applicableUs54868 284120180907 15195 rzy2l0
MycobutinCapsule150 mg/1OralPharmacia & Upjohn Inc1992-12-23Not applicableUs00013 5301 17 nlmimage10 691e34b1
RifabutinCapsule150 mg/1OralGreenstone, Llc2014-04-07Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
RifabutinCapsule150 mg/1OralAmerincan Health Packaging2016-07-01Not applicableUs
RifabutinCapsule150 mg/1OralLupin Pharmaceuticals, Inc.2014-03-26Not applicableUs
RifabutinCapsule150 mg/1OralAvera McKennan Hospital2016-03-032018-06-11Us
International/Other Brands
Ansatipin (Pfizer) / Ansatipine (SERB) / Ributin (Lupin)
Categories
UNII
1W306TDA6S
CAS number
72559-06-9
Weight
Average: 847.0047
Monoisotopic: 846.441508846
Chemical Formula
C46H62N4O11
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[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

Pharmacology

Indication

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

Associated Conditions
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
Human
NEndoplasmin
other/unknown
Human
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.

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
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
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Rifabutin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Rifabutin is combined with (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Rifabutin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Rifabutin.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be increased when combined with Rifabutin.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Rifabutin.
6-Deoxyerythronolide BThe metabolism of Rifabutin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Rifabutin.
7-ethyl-10-hydroxycamptothecinThe metabolism of Rifabutin can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be increased when combined with Rifabutin.
Food Interactions
  • High-fat meals slow the rate of absorption.
  • Take with food to reduce irritation.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB14753
KEGG Drug
D00424
KEGG Compound
C07235
PubChem Compound
6323490
PubChem Substance
46506468
ChemSpider
10482168
ChEBI
45367
ChEMBL
CHEMBL444633
Therapeutic Targets Database
DAP000656
PharmGKB
PA451249
HET
RBT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Rifabutin
ATC Codes
J04AB04 — 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
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I / Mycobacterium avium complex infection1
1CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedTreatmentAntivirals/HIV1
1CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Opioid Dependency1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
1CompletedTreatmentTuberculosis Infection1
1Not Yet RecruitingTreatmentHIV-1-infection1
1TerminatedTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis Infection1
1Unknown StatusTreatmentChildren With Confirmed HIV Infection / Receiving ART Regimen Containing 2 NRTIs + LPV/RTV at Standard Dose / Successfully Completed TB Treatment in the Past 2 to 6 Weeks of Enrollment1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2RecruitingOtherHuman Immunodeficiency Virus (HIV) / Tuberculosis Infection1
2RecruitingTreatmentChlamydophila Pneumoniae Infections / Coronary Heart Disease (CHD)1
2RecruitingTreatmentPulmonary Tuberculosis (TB)1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Staphylococcus Aureus1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis Infection1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3Active Not RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Indigestion1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare3
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare / Mycoses1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
4Unknown StatusTreatmentCrohn's Disease (CD)1
4Unknown StatusTreatmentMycobacterium Avium Complex Lung Disease1
4Unknown StatusTreatmentMycobacterium avium complex infection1
4Unknown StatusTreatmentReinfection Pulmonary Tuberculosis1
Not AvailableCompletedNot AvailableInhibition of Disseminated Mycobacterium Avium Complex (MAC) Disease Associated With HIV Infections / Inhibition of Disseminated Mycobacterium Avium Complex Disease Associated With HIV Infections / Non-tuberculous Mycobacterial Diseases / Non-tuberculous Mycobacterial Diseases (Including MAC Disease) / Tuberculosis Infection1
Not AvailableCompletedNot AvailableNon-tuberculous Mycobacterial Diseases (Including MAC Disease) / Tuberculosis Infection1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare5
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
Not AvailableRecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Pulmonary Tuberculosis (TB)1
Not AvailableRecruitingTreatmentDrug-resistant Tuberculosis / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1

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
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
Not Available

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

Taxonomy

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
Naphthofuran / Macrolactam / Azaspirodecane / Naphthalene / Benzofuran / Coumaran / Aryl ketone / Aryl alkyl ketone / Ketal / Piperidine
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
rifamycin (CHEBI:45367)

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
Human
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
Human
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
Human
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  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:10490933]
Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Agrawal A, Agarwal SK, Kaleekal T, Gupta YK: Rifampicin and anti-hypertensive drugs in chronic kidney disease: Pharmacokinetic interactions and their clinical impact. Indian J Nephrol. 2016 Sep;26(5):322-328. doi: 10.4103/0971-4065.176145. [PubMed:27795624]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 09:09