Identification

Name
Budesonide
Accession Number
DB01222  (APRD00442)
Type
Small Molecule
Groups
Approved
Description

Budesonide is a glucocorticoid used in the management of asthma, the treatment of various skin disorders, and allergic rhinitis. [PubChem] The extended release oral tablet, marketed as Uceris, was FDA approved on January 14, 2013 for the management of ulcerative colitis. Budesonide is provided as a mixture of two epimers (22R and 22S). Interestingly, the 22R form is two times more active than the 22S epimer. The two forms do not interconvert.

Structure
Thumb
Synonyms
  • (11beta,16alpha)-16,17-(Butylidenebis(oxy))-11,21-dihydroxypregna-1,4-diene-3,20-dione
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BudesonideSpray, metered32 ug/1NasalAstra Zeneca Lp2014-05-132018-02-28Us
BudesonideCapsule3 mg/1OralPaddock Laboratories, Inc.2018-06-29Not applicableUs
CortimentTablet, extended release9 mgOralFerring Pharmaceuticals2016-07-25Not applicableCanada
EntocortCapsule, extended release3 mgOralTillotts Pharma Gmbh1997-01-30Not applicableCanada
Entocort ECCapsule3 mg/1OralPrometheus Laboratories2001-10-29Not applicableUs
Entocort ECCapsule3 mg/1OralAstra Zeneca Lp2001-10-022019-01-31Us
Entocort ECCapsule3 mg/1OralPhysicians Total Care, Inc.2006-05-22Not applicableUs65483 0702 10 nlmimage10 f6387b33
Entocort ECCapsule3 mg/1OralPaddock Laboratories, Inc.2001-10-29Not applicableUs
Pulmicort FlexhalerAerosol, powder180 ug/1Respiratory (inhalation)A-S Medication Solutions2007-03-19Not applicableUs
Pulmicort FlexhalerAerosol, powder90 ug/1Respiratory (inhalation)Rebel Distributors2010-07-30Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BudesonideCapsule3 mg/1OralRising Pharmaceuticals, Inc.2017-08-30Not applicableUs
BudesonideSuspension0.5 mg/2mLRespiratory (inhalation)Sandoz2015-07-24Not applicableUs
BudesonideInhalant0.25 mg/2mLRespiratory (inhalation)Nephron Sc Inc.2013-10-01Not applicableUs
BudesonideInhalant0.5 mg/2mLRespiratory (inhalation)Preferreed Pharmaceuticals Inc.2017-01-20Not applicableUs
BudesonideSuspension1 mg/2mLRespiratory (inhalation)Teva Pharmaceuticals USA, Inc.2016-03-11Not applicableUs
BudesonideSuspension0.5 mg/2mLRespiratory (inhalation)Preferreed Pharmaceuticals Inc.2009-02-04Not applicableUs
BudesonideSuspension0.25 mg/2mLRespiratory (inhalation)Apotex Corporation2009-03-30Not applicableUs
BudesonideCapsule3 mg/1OralAppco Pharma Llc2017-06-01Not applicableUs
BudesonideSuspension0.25 mg/2mLRespiratory (inhalation)Preferreed Pharmaceuticals Inc.2017-10-11Not applicableUs
BudesonideSuspension0.5 mg/2mLRespiratory (inhalation)Physicians Total Care, Inc.2009-02-04Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BudesonideSpray, metered32 ug/1NasalApotex Corporation2016-04-19Not applicableUs
BudesonideSpray, metered32 ug/1NasalWalgreens2016-04-11Not applicableUs
BudesonideSpray, metered32 ug/1NasalSafeway2016-09-15Not applicableUs
BudesonideSpray, metered32 ug/1NasalAmerisource Bergen2016-09-15Not applicableUs
BudesonideSpray, metered32 ug/1NasalRugby2016-07-13Not applicableUs
BudesonideSpray, metered32 ug/1NasalApotex Corporation2018-04-26Not applicableUs
BudesonideSpray, metered32 ug/1NasalWalmart2016-08-22Not applicableUs
BudesonideSpray, metered32 ug/1NasalTopco Associates2016-08-31Not applicableUs
BudesonideSpray, metered32 ug/1NasalCVS Health2016-04-09Not applicableUs
BudesonideSpray, metered32 ug/1NasalRite Aid2016-07-13Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Entocort EnemaBudesonide (2.3 mg) + Sodium Chloride (115 ml)Enema; Kit; TabletRectalTillotts Pharma Gmbh1994-12-31Not applicableCanada
SymbicortBudesonide (80 ug/1) + Formoterol fumarate (4.5 ug/1)AerosolRespiratory (inhalation)Astra Zeneca Lp2007-05-29Not applicableUs
SymbicortBudesonide (160 ug/1) + Formoterol fumarate (4.5 ug/1)AerosolRespiratory (inhalation)Remedy Repack2016-04-042016-04-05Us
SymbicortBudesonide (160 ug/1) + Formoterol fumarate (4.5 ug/1)AerosolRespiratory (inhalation)Astra Zeneca Lp2007-05-29Not applicableUs
SymbicortBudesonide (160 ug/1) + Formoterol fumarate (4.5 ug/1)AerosolRespiratory (inhalation)A-S Medication Solutions2007-05-29Not applicableUs
Symbicort 100 TurbuhalerBudesonide (100 mcg) + Formoterol fumarate (6 mcg)PowderRespiratory (inhalation)Astra Zeneca2002-02-08Not applicableCanada
Symbicort 200 TurbuhalerBudesonide (200 mcg) + Formoterol fumarate (6 mcg)PowderRespiratory (inhalation)Astra Zeneca2002-02-08Not applicableCanada
Symbicort Forte TurbuhalerBudesonide (400 mcg) + Formoterol fumarate (12 mcg)PowderRespiratory (inhalation)Astra ZenecaNot applicableNot applicableCanada
T.R.U.E. Test Thin-Layer Rapid Use Patch TestBudesonide (0.8 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bromothalonil (4 ug/48h) + Bronopol (203 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamaldehyde (41 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb Zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Eugenol (41 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Geraniol (81 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Isoeugenol (17 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylchloroisothiazolinone (3 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + P-Tert-Butylphenol-Formaldehyde Resin (Low Molecular Weight) (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc Dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h)KitSmartPractice Denmark ApS2012-03-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Budesonide/formoterol TevaBudesonide (160 μg / dose) + Formoterol fumarate (4.5 μg / dose)Respiratory (inhalation)Teva Pharma B.V.2014-11-192017-01-31Eu
Budesonide/formoterol TevaBudesonide (320 μg / dose) + Formoterol fumarate (9 μg / dose)Respiratory (inhalation)Teva Pharma B.V.2014-11-192017-01-31Eu
International/Other Brands
Bidien / Budeson / Budicort / ENTOCORT / Noex (Eurofarma) / Pulmicort (AstraZeneca) / Rhinocort (AstraZeneca) / Rhinosol / Spirocort
Categories
UNII
Q3OKS62Q6X
CAS number
51333-22-3
Weight
Average: 430.5339
Monoisotopic: 430.23553882
Chemical Formula
C25H34O6
InChI Key
VOVIALXJUBGFJZ-KWVAZRHASA-N
InChI
InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1
IUPAC Name
(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one
SMILES
[H][C@@]12C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

Pharmacology

Indication

The oral capsule is used for the treatment of mild to moderate active Crohn's disease. The oral tablet is used for induction of remission in patients with active, mild to moderate ulcerative colitis. The oral inhalation formulation is used for the treatment of asthma, non-infectious rhinitis (including hay fever and other allergies), and for treatment and prevention of nasal polyposis.

Associated Conditions
Pharmacodynamics

Budesonide has a high glucocorticoid effect and a weak mineralocorticoid effect. It binds to the glucocorticoid receptor with a higher binding affinity than cortisol and prednisolone. When budesonide is systemically administered, suppression of endogenous cortisol concentrations and an impairment of the hypothalamus-pituitary-adrenal (HPA) axis function has been observed. Furthermore, a decrease in airway reactivity to histamine and other entities has been observed with the inhaled formulation. Generally, the inhaled formulation has a rapid onset action and improvement in asthma control can occur within 24 hours of initiation of treatment.

Mechanism of action

Budesonide is an anti-inflammatory corticosteroid that exhibits potent glucocorticoid activity and weak mineralocorticoid activity. The precise mechanism of corticosteroid actions on inflammation in asthma, Crohn's disease, or ulcerative colitis is not known. Inflammation is an important component in the pathogenesis of asthma. Corticosteroids have been shown to have a wide range of inhibitory activities against multiple cell types (eg, mast cells, eosinophils, neutrophils, macrophages, and lymphocytes) and mediators (eg, histamine, eicosanoids, leukotrienes, and cytokines) involved in allergic and non-allergic-mediated inflammation. These anti-inflammatory actions of corticosteroids may contribute to their efficacy in the aforementioned diseases. Because budesonide undergoes significant first-pass elimination, the both oral preparations are formulated as an extended release tablet. As a result, budesonide release is delyaed until exposure to a pH ≥ 7 in the small intestine.

TargetActionsOrganism
AGlucocorticoid receptor
antagonist
Human
Absorption

Absorption is complete following oral administration. The pharmacokinetic parameters of the inhaled powder formulation are as follows: Tmax = 30 minutes; Absolute systemic availability = 39%. When a single oral administration of 9 mg of Uceris are given, the pharmacokinetic parameters are as follows: Tmax = 13.3 ± 5.9 hours; Cmax = 1.35 ± 0.96 ng/mL; AUC = 16.43 ± 10.52 ng·hr/mL. It is important to note that the parameters have a high degree of variability. When a single oral administration of Entocort EC are given, the pharmacokinetic parameters are as follows: Tmax = 3- 600 minutes; Cmax = 5 nmol/L; AUC = 30 nmol•hr/L.

Volume of distribution

Tablet and capsule, healthy subjects and patients = 2.2 - 3.9 L/kg; Powder, metered = 3 L/kg

Protein binding

85-90% protein bound.

Metabolism

Following absorption, budesonide is subject to high first pass metabolism (80-90%). Budesonide is rapidly and extensively biotransformed, mainly by CYP3A4, to its 2 major metabolites, 6b-hydroxybudesonide and 16a- hydroxyprednisolone. The glucocorticoid activity of these metabolites is negligible (<1/100) in relation to that of the parent compound.

Route of elimination

Budesonide is excreted in urine and feces in the form of metabolites. Approximately 60% of an intravenous radiolabelled dose was recovered in the urine. No unchanged budesonide was detected in the urine.

Half life

Following IV administration of budesonide, the elimination half-life is 2.0 to 3.6 hours. This value does not differ between healthy adults and patients with Crohn’s disease.

Clearance

Plasma clearance, tablet = 0.9 - 1.8 L/min; Systemic clearance, powder, 22R = 1.4 L/min; Systemic clearance, powder, 22S = 1.0 L/min; 0.5 L/min [Athmatic children 4 to 6 years of age]

Toxicity

Single oral doses of 200 and 400 mg/kg were lethal in female and male mice, respectively. The signs of acute toxicity were decreased motor activity, piloerection and generalized edema.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
T-box transcription factor TBX21---(C;G)CG allele (heterozygotes)Effect Directly StudiedThe presence of this polymorphism in TBX21 may be associated with improved responsiveness to budenoside for the treatment of asthma.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Budesonide can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Budesonide can be decreased when combined with (S)-Warfarin.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Budesonide.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Budesonide.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Budesonide.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Budesonide.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Budesonide.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Budesonide is combined with 2-Methoxyethanol.
3,5-diiodothyropropionic acidThe metabolism of Budesonide can be decreased when combined with 3,5-diiodothyropropionic acid.
4-HydroxytestosteroneThe risk or severity of edema formation can be increased when 4-Hydroxytestosterone is combined with Budesonide.
Food Interactions
  • A mean delay in time to peak concentration of 2.5 hours is observed with the intake of a high-fat meal, with no significant differences in AUC.

References

Synthesis Reference

Peter Gruber, Hans Joachim Lach, Norbert Otterbeck, "Budesonide pellets with a controlled released pattern and process for producing the same." U.S. Patent US5932249, issued May, 1991.

US5932249
General References
Not Available
External Links
Human Metabolome Database
HMDB0015353
KEGG Drug
D00246
PubChem Compound
5281004
PubChem Substance
46504869
ChemSpider
4444479
BindingDB
50354850
ChEBI
3207
ChEMBL
CHEMBL1370
Therapeutic Targets Database
DAP000320
PharmGKB
PA448681
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Budesonide
ATC Codes
R03AK07 — Formoterol and budesonideA07EA06 — BudesonideR03BA02 — BudesonideD07AC09 — BudesonideR03AK12 — Salmeterol and budesonideR01AD05 — Budesonide
AHFS Codes
  • 68:04.00 — Adrenals
  • 52:08.00 — Anti-inflammatory Agents
  • 52:08.08 — Corticosteroids
FDA label
Download (52.3 KB)
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceAsthma Bronchial1
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedPreventionAcute Chest Syndrome / Asthma Bronchial / Sickle Cell Disorders1
1CompletedTreatmentAllergies1
1CompletedTreatmentAsthma Bronchial6
1CompletedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)2
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentGraft Versus Host Disease (GVHD) / Transplantation, Stem Cell1
1CompletedTreatmentLiver Cirrhosis, Biliary / Sclerosing Cholangitis1
1CompletedTreatmentSnoring1
1, 2CompletedPreventionBronchopulmonary Dysplasia (BPD)1
1, 2CompletedTreatmentAsthma Bronchial1
2Active Not RecruitingTreatmentOesophagitis, Eosinophilic1
2CompletedNot AvailableAsthma Bronchial1
2CompletedPreventionAcute Respiratory Distress Syndrome (ARDS)1
2CompletedPreventionLung Cancers2
2CompletedTreatmentAllergic Rhinitis (AR)1
2CompletedTreatmentAllogeneic Stem Cell Transplantation / Obliterative Bronchiolitis1
2CompletedTreatmentAsthma Bronchial5
2CompletedTreatmentBronchial Asthma1
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)4
2CompletedTreatmentCopd Bronchitis1
2CompletedTreatmentCrohn's Disease (CD)1
2CompletedTreatmentEosinophilic Esophagitis (EoE)1
2CompletedTreatmentExercised Induced Asthma1
2CompletedTreatmentIgA Nephropathy1
2CompletedTreatmentMalignant Melanoma1
2CompletedTreatmentObstructive Airway Disease1
2CompletedTreatmentOesophagitis, Eosinophilic3
2CompletedTreatmentSeasonal Allergic Rhinitis (SAR)3
2CompletedTreatmentStable Asthma1
2CompletedTreatmentUlcerative Colitis (UC)1
2RecruitingTreatmentAcute Cellular Graft Rejection / New Onset Diabetes After Transplant1
2RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2RecruitingTreatmentCrohn's Disease (CD)1
2RecruitingTreatmentDiarrhea1
2RecruitingTreatmentEarly Stage HER2+ Breast Cancer1
2RecruitingTreatmentEsophageal Strictures1
2TerminatedPreventionCryptogenic Organizing Pneumonia / Lung Diseases, Interstitial / Obliterative Bronchiolitis / Respiratory Tract Infections (RTI)1
2TerminatedPreventionProphylaxis of Radiation proctitis1
2TerminatedTreatmentInflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
2Unknown StatusPreventionChronic Lung Disease of Prematurity1
2Unknown StatusTreatmentTransient Tachypnea of the Newborn1
2WithdrawnTreatmentGraft Versus Host Disease, Acute / Intestinal Graft Versus Host Disease1
2WithdrawnTreatmentOlfaction Disorders / Paranasal Sinus Diseases / Sinusitis1
2, 3CompletedTreatmentAllergies1
2, 3CompletedTreatmentEE / Gastro-esophageal Reflux Disease (GERD) / Gastroesophageal Reflux Disease / Oesophagitis, Eosinophilic1
2, 3CompletedTreatmentHepatitis, Autoimmune1
2, 3CompletedTreatmentPolyps, Nasal1
2, 3CompletedTreatmentSinusitis1
2, 3CompletedTreatmentStatus Asthmaticus1
2, 3Not Yet RecruitingTreatmentChronic Rhinosinusitis / Chronic Sinus Congestion / Chronic Sinus Infection / Chronic Sinusitis - Ethmoidal, Posterior1
2, 3TerminatedTreatmentDiarrhea / Lymphocytic Colitis1
3Active Not RecruitingTreatmentAcute maxillary sinusitis caused by M. catarrhalis1
3Active Not RecruitingTreatmentEosinophilic Esophagitis (EoE) / Eosinophilic Esophagitis (EoE) Dysphagia1
3CompletedNot AvailableAsthma Bronchial1
3CompletedPreventionChronic Lung Disease of Prematurity1
3CompletedPreventionGraft Versus Host Disease (GVHD) / Leukemias1
3CompletedPreventionOther and unspecified effects of high altitude1
3CompletedTreatmentAllergic Rhinitis (AR)1
3CompletedTreatmentAsthma Bronchial44
3CompletedTreatmentAsthma Bronchial / Chronic Lung Diseases1
3CompletedTreatmentBronchial Asthma1
3CompletedTreatmentCOPD Patients1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)7
3CompletedTreatmentChronic Obstructive Pulmonary Disorder2
3CompletedTreatmentChronic Rhinosinusitis With Polyposis1
3CompletedTreatmentChronic / Chronic Rhinosinusitis / Polyposis / Sinusitis1
3CompletedTreatmentCollagenous Colitis2
3CompletedTreatmentCrohn's Disease (CD)4
3CompletedTreatmentGraft Versus Host Disease (GVHD)1
3CompletedTreatmentInduction and Maintaining Remission of Collagenous Colitis1
3CompletedTreatmentLymphocytic Colitis1
3CompletedTreatmentMicroscopic Colitis1
3CompletedTreatmentMild or Moderate Asthma1
3CompletedTreatmentOesophagitis, Eosinophilic1
3CompletedTreatmentOral Chronic Graft vs Host Disease1
3CompletedTreatmentProctitis / Proctosigmoiditis2
3CompletedTreatmentPulmonary Disease, Chronic Obstructive1
3CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
3CompletedTreatmentUlcerative Colitis (UC)4
3Not Yet RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
3Not Yet RecruitingTreatmentRhinitis, Allergic, Perennial2
3RecruitingTreatmentAcute maxillary sinusitis caused by M. catarrhalis / Chronic Polyposis1
3RecruitingTreatmentAsthma Bronchial1
3RecruitingTreatmentAsthma Bronchial / Bioequivalence1
3RecruitingTreatmentAsthma, Allergic1
3RecruitingTreatmentBronchial Asthma1
3RecruitingTreatmentChronic Rhinosinusitis (Diagnosis), Nasal Polyposis1
3RecruitingTreatmentChronic Rhinosinusitis With Nasal Polyps1
3RecruitingTreatmentEosinophilic Esophagitis (EoE)1
3RecruitingTreatmentEosinophilic Esophagitis (EoE) / Oesophagitis, Eosinophilic1
3TerminatedTreatmentPrimary Biliary Cirrhosis (PBC)1
3Unknown StatusTreatmentBronchial Asthma1
3Unknown StatusTreatmentCollagenous Colitis1
3Unknown StatusTreatmentEmphysema / Poor Sleeping Quality1
3WithdrawnPreventionAltitude Sickness1
4Active Not RecruitingTreatmentOesophagitis, Eosinophilic1
4Active Not RecruitingTreatmentPulmonary Disease, Chronic Obstructive2
4CompletedNot AvailableAsthma Bronchial1
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
4CompletedBasic ScienceMild Asthma1
4CompletedSupportive CareAsthma Bronchial1
4CompletedTreatmentAcute maxillary sinusitis caused by M. catarrhalis / Allergic Rhinosinusitis / Chronic Eosinophilic Rhinosinusitis1
4CompletedTreatmentAllergic Rhinitis (AR)1
4CompletedTreatmentAsthma Acute / Asthma Bronchial / Reactive Airway Exacerbation1
4CompletedTreatmentAsthma Bronchial12
4CompletedTreatmentBronchial Asthma1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)10
4CompletedTreatmentCrohn's Disease (CD)1
4CompletedTreatmentObstructive Sleep Apnea Syndrome (OSAS)1
4CompletedTreatmentOesophagitis, Eosinophilic1
4CompletedTreatmentPerennial Allergic Rhinitis (PAR)2
4CompletedTreatmentPulmonary Disease, Chronic Obstructive1
4Not Yet RecruitingPreventionChronic Lung Disease of Prematurity / Respiratory Distress Syndrome (RDS)1
4Not Yet RecruitingPreventionChronic Obstructive Pulmonary Disease (COPD) / Lung Cancers / Post Operative Complication, Pulmonary1
4Not Yet RecruitingPreventionExposure to Pollution / Glucocorticoid Resistance1
4Not Yet RecruitingTreatmentAsthma Bronchial1
4RecruitingNot AvailableAsthma Bronchial1
4RecruitingPreventionChronic Lung Disease of Prematurity / Infants, Premature / Respiratory Distress Syndrome (RDS)1
4RecruitingTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease / Chronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentAsthma Bronchial1
4RecruitingTreatmentAsthma Bronchial / Pediatric ALL1
4RecruitingTreatmentAsthma-chronic obstructive pulmonary disease overlap syndrome / Pulmonary Disease, Chronic Obstructive / Quality of Life / Small Airway Disease1
4RecruitingTreatmentBronchial Asthma1
4RecruitingTreatmentBronchiectasis / Chronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentExercise / Lung Function Decreased / Pulmonary Disease, Chronic Obstructive / Quality of Life1
4RecruitingTreatmentPulmonary Disease,Chronic Obstructive1
4RecruitingTreatmentSevere IgE-mediated Asthma1
4TerminatedTreatmentAsthma Bronchial1
4TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
4TerminatedTreatmentExercised Induced Asthma1
4Unknown StatusPreventionChronic Lung Disease of Prematurity / Respiratory Distress Syndrome (RDS)1
4Unknown StatusTreatmentAsthma Bronchial1
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4Unknown StatusTreatmentObstructive Sleep Apnea (OSA)1
4WithdrawnNot AvailableBone destruction1
4WithdrawnBasic ScienceAsthma Bronchial1
4WithdrawnTreatmentAcute Cellular Graft Rejection / Liver Transplant Rejection1
4WithdrawnTreatmentAsthma Bronchial2
Not AvailableActive Not RecruitingNot AvailableCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD)1
Not AvailableActive Not RecruitingBasic ScienceAsthma Bronchial1
Not AvailableActive Not RecruitingTreatmentAsthma Bronchial1
Not AvailableCompletedNot AvailableAsthma Bronchial3
Not AvailableCompletedNot AvailableAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailablePerception of Physicians & Patients of AMD1
Not AvailableCompletedNot AvailableUlcerative Colitis (UC)1
Not AvailableCompletedBasic ScienceAsthma Bronchial2
Not AvailableCompletedDiagnosticAsthma Bronchial1
Not AvailableCompletedHealth Services ResearchAsthma Bronchial1
Not AvailableCompletedTreatmentAsthma Bronchial1
Not AvailableCompletedTreatmentAsthma Bronchial / Chronic Lung Diseases1
Not AvailableCompletedTreatmentChronic Rhinosinusitis / Nasal Polyposis1
Not AvailableCompletedTreatmentPolyps, Nasal / Sinusitis1
Not AvailableCompletedTreatmentRespiratory Distress Syndrome (RDS)1
Not AvailableRecruitingNot AvailableAsthma Bronchial2
Not AvailableRecruitingPreventionAcute Exacerbation of Chronic Obstructive Pulmonary Disease / Air Pollution1
Not AvailableTerminatedTreatmentAsthma Bronchial1
Not AvailableTerminatedTreatmentChronic Rhinosinusitis1
Not AvailableTerminatedTreatmentColitis1
Not AvailableUnknown StatusNot AvailableAllergic Rhinitis (AR) / Asthma Bronchial1
Not AvailableUnknown StatusNot AvailableFocus of Study is to Improve Asthma Control Based on Phenotype, NO and Sputum Cell Count1
Not AvailableUnknown StatusPreventionRespiratory Sounds2
Not AvailableUnknown StatusTreatmentAsthma Bronchial2
Not AvailableUnknown StatusTreatmentStridor1
Not AvailableWithdrawnTreatmentHepatitis, Autoimmune / Primary Biliary Cirrhosis (PBC)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • 3M Health Care
  • A-S Medication Solutions LLC
  • Astra Pharma Inc.
  • AstraZeneca Inc.
  • Dispensing Solutions
  • Galderma Laboratories
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Physicians Total Care Inc.
  • Prometheus Laboratories Inc.
  • Redpharm Drug
  • Spectrum Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
Capsule, coated pelletsOral3 mg/1
Capsule, gelatin coatedOral3 mg/1
InhalantRespiratory (inhalation)0.25 mg/2mL
InhalantRespiratory (inhalation)0.5 mg/2mL
SuspensionRespiratory (inhalation)1 mg/2mL
Tablet, extended releaseOral9 mg/1
Tablet, film coated, extended releaseOral9 mg/1
Capsule, delayed release pelletsOral3 mg/1
InhalantOral0.25 mg/2mL
InhalantOral0.5 mg/2mL
InhalantOral1 mg/2mL
Tablet, extended releaseOral9 mg
Capsule, extended releaseOral3 mg
CapsuleOral3 mg/1
Enema; kit; tabletRectal
Spray, meteredNasal100 mcg
Spray, meteredNasal64 mcg
Aerosol, powderRespiratory (inhalation)180 ug/1
Aerosol, powderRespiratory (inhalation)90 ug/1
SuspensionRespiratory (inhalation)0.125 mg
SuspensionRespiratory (inhalation)0.25 mg
SuspensionRespiratory (inhalation)0.5 mg
SuspensionRespiratory (inhalation)0.25 mg/2mL
SuspensionRespiratory (inhalation)0.5 mg/2mL
Powder, meteredRespiratory (inhalation)200 ug/1
Aerosol, metered; powderRespiratory (inhalation)100 mcg
Aerosol, metered; powderRespiratory (inhalation)200 mcg
Aerosol, metered; powderRespiratory (inhalation)400 mcg
Spray, meteredNasal32 ug/1
Aerosol, meteredNasal100 mcg
PowderNasal; Respiratory (inhalation)100 mcg
AerosolRespiratory (inhalation)
PowderRespiratory (inhalation)
Kit
Aerosol, foamRectal28 mg/1
Prices
Unit descriptionCostUnit
Budesonide micronized powder346.5USD g
DesOwen Lot w/Cetaphil Cream 0.05% Kit Box255.84USD box
Desowen 0.05% ointment kit217.2USD kit
Desowen 0.05% cream kit212.4USD kit
DesOwen 0.05% Lotion 118ml Bottle183.17USD bottle
Pulmicort Flexhaler 180 mcg/act Aerosol Inhaler163.34USD inhaler
Pulmicort 180 mcg flexhaler157.06USD inhaler
DesOwen 0.05% Lotion 59ml Bottle123.38USD bottle
Pulmicort Flexhaler 90 mcg/act Aerosol Inhaler121.98USD inhaler
Pulmicort 90 mcg flexhaler117.29USD inhaler
Rhinocort Aqua 32 mcg/act 8.6 gm Bottle111.96USD bottle
Rhinocort aqua nasal spray13.93USD g
Entocort EC 3 mg 24 Hour Capsule13.86USD capsule
Entocort ec 3 mg capsule12.22USD capsule
Budesonide 0.5 mg/2ml Suspension 2ml Plastic Container9.73USD plastic
Pulmicort 0.5 mg/2ml Suspension 2ml Plastic Container9.24USD plastic
Budesonide 0.25 mg/2ml Suspension 2ml Plastic Container9.07USD plastic
Entocort (115 Ml) 2.3 mg/enm Enema8.93USD enema
Pulmicort 1 mg/2 ml respule8.89USD ml
Pulmicort 0.25 mg/2ml Suspension 2ml Plastic Container7.85USD plastic
Pulmicort 0.5 mg/2 ml respule4.45USD ml
Pulmicort 0.25 mg/2 ml respul3.78USD ml
Desowen 0.05% cream2.43USD g
Pulmicort Nebuamp 0.5 mg/ml Suspension0.93USD ml
Pulmicort Turbuhaler 400 mcg/dose Metered Inhalation Powder0.62USD dose
Pulmicort Nebuamp 0.25 mg/ml Suspension0.46USD ml
Pulmicort Turbuhaler 200 mcg/dose Metered Inhalation Powder0.34USD dose
Pulmicort Nebuamp 0.125 mg/ml Suspension0.23USD ml
Pulmicort Turbuhaler 100 mcg/dose Metered Inhalation Powder0.17USD dose
Rhinocort Turbuhaler 100 mcg/dose Metered Dose Aerosol0.13USD dose
Mylan-Budesonide Aq 100 mcg/dose Metered Dose Spray0.1USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6423340No1993-11-152010-11-15Us
CA2071518No2002-11-122010-11-15Canada
US6598603Yes1999-06-232019-06-23Us
US6899099Yes1999-06-232019-06-23Us
US7524834Yes1999-05-112019-05-11Us
US7759328Yes2003-07-292023-07-29Us
US7897646Yes1999-03-092019-03-09Us
US8143239Yes2003-07-292023-07-29Us
US8461211Yes1999-03-092019-03-09Us
US8575137Yes2003-07-292023-07-29Us
US6123924No1997-09-262017-09-26Us
US7967011Yes2002-02-112022-02-11Us
US8616196Yes2009-10-072029-10-07Us
US8387615Yes2005-05-102025-05-10Us
US7587988Yes2006-10-102026-10-10Us
US7367333Yes1999-05-112019-05-11Us
US8528545Yes2009-04-162029-04-16Us
US8875699Yes2005-05-102025-05-10Us
US6027714No1998-01-092018-01-09Us
US7143764No1998-03-132018-03-13Us
US6142145No1998-05-082018-05-08Us
US6287540No1998-01-092018-01-09Us
US9320716No2000-06-092020-06-09Us
US9192581No2011-09-072031-09-07Us
US7410651No2000-06-092020-06-09Us
USRE43799No2000-06-092020-06-09Us
US8895064No2011-09-072031-09-07Us
US7431943No2000-06-092020-06-09Us
US9132093No2011-09-072031-09-07Us
US8784888No2000-06-092020-06-09Us
US8293273No2000-06-092020-06-09Us
US5914122No1995-12-192015-12-19Us
US9532954No2000-06-092020-06-09Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)226°CPhysProp
water solubilityinsolubleNot Available
logP1.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0457 mg/mLALOGPS
logP2.42ALOGPS
logP2.73ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.74ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.11 m3·mol-1ChemAxon
Polarizability47.11 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9872
Blood Brain Barrier+0.9533
Caco-2 permeable-0.6097
P-glycoprotein substrateSubstrate0.804
P-glycoprotein inhibitor INon-inhibitor0.5881
P-glycoprotein inhibitor IINon-inhibitor0.5911
Renal organic cation transporterNon-inhibitor0.7867
CYP450 2C9 substrateNon-substrate0.8488
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7337
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9075
CYP450 2D6 inhibitorNon-inhibitor0.9441
CYP450 2C19 inhibitorNon-inhibitor0.939
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8886
Ames testNon AMES toxic0.9117
CarcinogenicityNon-carcinogens0.9466
BiodegradationNot ready biodegradable0.9759
Rat acute toxicity2.1601 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9483
hERG inhibition (predictor II)Non-inhibitor0.5627
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03k9-1794300000-d4cdef973973a6b24ba4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dj-3950000000-8e98d604876730f53851

Taxonomy

Description
This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 3-oxo delta-1,4-steroids / 11-beta-hydroxysteroids / Delta-1,4-steroids / Alpha-hydroxy ketones / 1,3-dioxolanes / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives
show 5 more
Substituents
Progestogin-skeleton / 21-hydroxysteroid / Pregnane-skeleton / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 11-hydroxysteroid / 11-beta-hydroxysteroid / Oxosteroid / Delta-1,4-steroid
show 17 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
11beta-hydroxy steroid, glucocorticoid, cyclic acetal, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (CHEBI:3207)

Targets

Details
1. Glucocorticoid receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Zhang X, Moilanen E, Kankaanranta H: Enhancement of human eosinophil apoptosis by fluticasone propionate, budesonide, and beclomethasone. Eur J Pharmacol. 2000 Oct 20;406(3):325-32. [PubMed:11040338]
  2. Henriksson G, Norlander T, Forsgren J, Stierna P: Effects of topical budesonide treatment on glucocorticoid receptor mRNA down-regulation and cytokine patterns in nasal polyps. Am J Rhinol. 2001 Jan-Feb;15(1):1-8. [PubMed:11258648]
  3. Zhang X, Moilanen E, Kankaanranta H: Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis. Eur J Pharmacol. 2001 Nov 23;431(3):365-71. [PubMed:11730731]
  4. Kompella UB, Bandi N, Ayalasomayajula SP: Subconjunctival nano- and microparticles sustain retinal delivery of budesonide, a corticosteroid capable of inhibiting VEGF expression. Invest Ophthalmol Vis Sci. 2003 Mar;44(3):1192-201. [PubMed:12601049]
  5. Kunz S, Sandoval R, Carlsson P, Carlstedt-Duke J, Bloom JW, Miesfeld RL: Identification of a novel glucocorticoid receptor mutation in budesonide-resistant human bronchial epithelial cells. Mol Endocrinol. 2003 Dec;17(12):2566-82. Epub 2003 Aug 14. [PubMed:12920235]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

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. Jonsson G, Astrom A, Andersson P: Budesonide is metabolized by cytochrome P450 3A (CYP3A) enzymes in human liver. Drug Metab Dispos. 1995 Jan;23(1):137-42. [PubMed:7720517]
  3. 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
Oxygen binding
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
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 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]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2018 20:30