BUDESONIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1994)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A07EA06
UNII: Q3OKS62Q6X

Structure
InChI Key VOVIALXJUBGFJZ-KWVAZRHASA-N
Smile CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H34O6
Molecular Weight 430.54
AlogP 2.72
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 93.06
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 31.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Glucocorticoid receptor agonist KEGG PubMed PubMed PubMed
Primary Target
Glucocorticoid receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Secreted protein
- 26200-27100 - - 55-70
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 1
2-12 1-4 - 1 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 2
5 14 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 3
- 28 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- 710 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 44-73
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 38
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 46000 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 37000 - - -
Unclassified protein
- 26200 - - 70

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Emphysema 4 D004646 ClinicalTrials
Colitis, Ulcerative 4 D003093 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Eosinophilic Esophagitis 3 D057765 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Bronchopulmonary Dysplasia 3 D001997 ClinicalTrials
Proctitis 3 D011349 ClinicalTrials
Sinusitis 3 D012852 ClinicalTrials
Altitude Sickness 3 D000532 ClinicalTrials
Sleep Apnea, Obstructive 3 D020181 ClinicalTrials
Proctocolitis 3 D011350 ClinicalTrials
Colitis, Collagenous 3 D046729 ClinicalTrials
Colitis, Lymphocytic 3 D046730 ClinicalTrials
Colitis, Microscopic 3 D046728 ClinicalTrials
Liver Cirrhosis, Biliary 3 D008105 ClinicalTrials
Respiratory Tract Diseases 3 D012140 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Respiratory Distress Syndrome 2 D012128 ClinicalTrials
Glomerulonephritis, IGA 2 D005922 ClinicalTrials
Bronchiolitis Obliterans 2 D001989 ClinicalTrials
Esophageal Stenosis 2 D004940 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Lung Neoplasms 2 D008175 ClinicalTrials
Diarrhea 2 D003967 ClinicalTrials
Nasal Polyps 2 D009298 ClinicalTrials
Malnutrition 2 D044342 ClinicalTrials
Status Asthmaticus 2 D013224 ClinicalTrials
Radiation Pneumonitis 2 D017564 ClinicalTrials
Hypersensitivity 2 D006967 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Hepatitis, Autoimmune 2 D019693 ClinicalTrials
Aspergillosis, Allergic Bronchopulmonary 2 D001229 ClinicalTrials
Snoring 1 D012913 ClinicalTrials
Cholangitis, Sclerosing 1 D015209 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Endocrine disorders Cushing's syndrome 47.6
Infections and infestations Respiratory tract infection 38.0
Endocrine disorders Cushingoid 36.6
Infections and infestations Respiratory tract infection
Infections and infestations Respiratory tract infection 35.0
Infections and infestations Respiratory tract infection 34.0
Endocrine disorders Cushing's syndrome 31.0
Nervous system disorders Headache 28.0
Endocrine disorders Cushing's syndrome
Skin and subcutaneous tissue disorders Acne 22.8
Nervous system disorders Headache 21.4
Nervous system disorders Headache
Nervous system disorders Headache 20.6
General disorders and administration site conditions Hyperhidrosis 17.9
Nervous system disorders Headache
Nervous system disorders Headache 17.8
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 16.8
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 16.8
Skin and subcutaneous tissue disorders Acne 14.8
Injury, poisoning and procedural complications Contusion 14.8
Nervous system disorders Headache 14.6
Infections and infestations Respiratory tract infection 13.8
Skin and subcutaneous tissue disorders Acne
Gastrointestinal disorders Nausea 13.1
Infections and infestations Respiratory tract infection 13.1
Nervous system disorders Headache 12.5
Cardiac disorders Dizziness 12.4
Gastrointestinal disorders Nausea 12.4
Ear and labyrinth disorders Otitis media 12.0
Infections and infestations Rhinitis 12.0
Musculoskeletal and connective tissue disorders Back pain 11.7
Gastrointestinal disorders Dyspepsia 11.7
General disorders and administration site conditions Pain 11.7
Gastrointestinal disorders Abdominal pain 11.4
Gastrointestinal disorders Gastrointestinal pain 11.4
Nervous system disorders Headache 11.4
Injury, poisoning and procedural complications Contusion
Nervous system disorders Insomnia 11.0
Gastrointestinal disorders Nausea 11.0
Ear and labyrinth disorders Otitis media
Ear and labyrinth disorders Otitis media 11.0
Infections and infestations Rhinitis 11.0
Endocrine disorders Cushingoid 10.8
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Infections and infestations Respiratory tract infection 10.6
Nervous system disorders Headache
Injury, poisoning and procedural complications Contusion 10.3
Cardiac disorders Dizziness 10.1
Gastrointestinal disorders Diarrhoea 10.0
Musculoskeletal and connective tissue disorders Back pain 9.7
Skin and subcutaneous tissue disorders Acne 9.66
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 9.35
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 9.35
Infections and infestations Nasopharyngitis 9.3
Musculoskeletal and connective tissue disorders Back pain
General disorders and administration site conditions Pain
Infections and infestations Respiratory tract infection
Respiratory, thoracic and mediastinal disorders Cough 9.0
Gastrointestinal disorders Dyspepsia 9.0
Ear and labyrinth disorders Otitis media 9.0
Infections and infestations Rhinitis
Injury, poisoning and procedural complications Contusion 8.97
Musculoskeletal and connective tissue disorders Joint swelling 8.97
Cardiac disorders Oedema peripheral 8.97
Gastrointestinal disorders Dyspepsia 8.96
Infections and infestations Nasopharyngitis
Gastrointestinal disorders Flatulence 8.28
Cardiac disorders Palpitations 8.28
General disorders and administration site conditions Asthenia 8.21
General disorders and administration site conditions Fatigue 8.21
Respiratory, thoracic and mediastinal disorders Cough 8.0
Respiratory, thoracic and mediastinal disorders Epistaxis 8.0
Infections and infestations Sinusitis 8.0
Gastrointestinal disorders Nausea 7.95
General disorders and administration site conditions Asthenia 7.59
General disorders and administration site conditions Fatigue 7.59
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Nausea
Gastrointestinal disorders Vomiting
Musculoskeletal and connective tissue disorders Joint swelling 7.49
Cardiac disorders Oedema peripheral 7.49
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 7.48
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 7.48
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 7.48
General disorders and administration site conditions Pain 7.46
Cardiac disorders Dizziness 7.31
Gastrointestinal disorders Flatulence 7.09
Gastrointestinal disorders Vomiting 7.09
Infections and infestations Rhinitis 7.0
Musculoskeletal and connective tissue disorders Back pain 6.92
Gastrointestinal disorders Vomiting 6.82
Gastrointestinal disorders Abdominal pain 6.72
Gastrointestinal disorders Gastrointestinal pain 6.72
Nervous system disorders Insomnia
Infections and infestations Respiratory tract infection
Infections and infestations Respiratory tract infection 6.54
Psychiatric disorders Affect lability 6.45
Nervous system disorders Insomnia 6.45
Psychiatric disorders Mood swings 6.45
Nervous system disorders Insomnia 6.34
Gastrointestinal disorders Abdominal pain 6.15
Gastrointestinal disorders Gastrointestinal pain 6.15
Musculoskeletal and connective tissue disorders Arthralgia
Skin and subcutaneous tissue disorders Dermatitis
Cardiac disorders Dizziness
Gastrointestinal disorders Flatulence
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Skin and subcutaneous tissue disorders Rash
Immune system disorders Urticaria 6.0
Infections and infestations Viral infection 6.0
Gastrointestinal disorders Dyspepsia 5.96
Gastrointestinal disorders Flatulence 5.77
Musculoskeletal and connective tissue disorders Back pain 5.68
Cardiac disorders Dizziness 5.68
Gastrointestinal disorders Flatulence 5.68
Infections and infestations Respiratory tract infection 5.68
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Flatulence 5.61
Musculoskeletal and connective tissue disorders Joint swelling
Cardiac disorders Oedema peripheral
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 5.61
Gastrointestinal disorders Vomiting 5.58
General disorders and administration site conditions Hyperhidrosis 5.22
Endocrine disorders Hirsutism 5.15
Gastrointestinal disorders Nausea 5.1
Musculoskeletal and connective tissue disorders Arthralgia 5.0
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 5.0
Infections and infestations Ear infection 5.0
Respiratory, thoracic and mediastinal disorders Epistaxis
Gastrointestinal disorders Gastroenteritis 5.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Infections and infestations Viral infection 5.0
Endocrine disorders Cushingoid
Skin and subcutaneous tissue disorders Acne 4.84
Endocrine disorders Cushingoid 4.84
Endocrine disorders Hirsutism 4.84
General disorders and administration site conditions Asthenia 4.81
General disorders and administration site conditions Fatigue 4.81
Gastrointestinal disorders Nausea 4.72
Cardiac disorders Dizziness
Cardiac disorders Dizziness 4.67
General disorders and administration site conditions Pain 4.62
Skin and subcutaneous tissue disorders Acne 4.55
Injury, poisoning and procedural complications Contusion 4.55
Nervous system disorders Insomnia
Musculoskeletal and connective tissue disorders Arthralgia 4.48
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.48
Blood cortisol decreased 4.31
Psychiatric disorders Affect lability
Psychiatric disorders Mood swings
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain 4.14
Musculoskeletal and connective tissue disorders Arthralgia 4.14
Endocrine disorders Cushingoid 4.14
Gastrointestinal disorders Gastrointestinal pain 4.14
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.14
Gastrointestinal disorders Vomiting 4.14
Skin and subcutaneous tissue disorders Dermatitis 4.1
Skin and subcutaneous tissue disorders Rash 4.1
Infections and infestations Candida infection 4.0
Eye disorders Conjunctivitis 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Gastrointestinal disorders Diarrhoea 4.0
Infections and infestations Ear infection
Infections and infestations Ear infection 4.0
Respiratory, thoracic and mediastinal disorders Epistaxis 4.0
Gastrointestinal disorders Gastroenteritis
Musculoskeletal and connective tissue disorders Muscle spasms 4.0
Gastrointestinal disorders Pharyngitis 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Infections and infestations Viral infection 4.0
Gastrointestinal disorders Vomiting 4.0
Psychiatric disorders Affect lability 3.94
Psychiatric disorders Mood swings 3.94
Gastrointestinal disorders Abdominal pain upper 3.92
Endocrine disorders Cushingoid
Gastrointestinal disorders Dyspepsia
Psychiatric disorders Affect lability 3.53
Psychiatric disorders Mood swings 3.53
Injury, poisoning and procedural complications Contusion
Endocrine disorders Hirsutism 3.45
Metabolism and nutrition disorders Lipohypertrophy 3.45
Endocrine disorders Cushingoid 3.41
Gastrointestinal disorders Dyspepsia 3.41
Psychiatric disorders Affect lability
Psychiatric disorders Mood swings
Gastrointestinal disorders Abdominal pain upper 3.15
Gastrointestinal disorders Flatulence 3.15
General disorders and administration site conditions Asthenia 3.14
General disorders and administration site conditions Fatigue 3.14
Nervous system disorders Insomnia
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Hyperhidrosis
Gastrointestinal disorders Abdominal pain 3.0
Infections and infestations Candida infection 3.0
Skin and subcutaneous tissue disorders Dermatitis
Respiratory, thoracic and mediastinal disorders Epistaxis 3.0
Gastrointestinal disorders Gastrointestinal pain 3.0
Gastrointestinal disorders Pharyngitis
Skin and subcutaneous tissue disorders Rash
Infections and infestations Viral infection
Infections and infestations Viral infection 3.0
Eye disorders Vision blurred 3.0
Gastrointestinal disorders Vomiting
Respiratory, thoracic and mediastinal disorders Nasal congestion 2.7
Gastrointestinal disorders Pharyngitis 2.7
Cardiac disorders Palpitations 2.61
Blood cortisol decreased 2.36
Nervous system disorders Insomnia 2.36
Gastrointestinal disorders Abdominal distension 2.35
Skin and subcutaneous tissue disorders Acne 2.35
Gastrointestinal disorders Flatulence 2.35
Nervous system disorders Insomnia 2.35
Endocrine disorders Hirsutism 2.27
Musculoskeletal and connective tissue disorders Joint swelling 2.27
Cardiac disorders Oedema peripheral 2.27
General disorders and administration site conditions Pain 2.27
Skin and subcutaneous tissue disorders Skin striae 2.27
Immune system disorders Rhinitis allergic 2.2
Infections and infestations Viral upper respiratory tract infection 2.2
Skin and subcutaneous tissue disorders Acne
Musculoskeletal and connective tissue disorders Joint swelling
Cardiac disorders Oedema peripheral
Skin and subcutaneous tissue disorders Dermatitis 2.07
Musculoskeletal and connective tissue disorders Joint swelling 2.07
Cardiac disorders Oedema peripheral 2.07
Skin and subcutaneous tissue disorders Rash 2.07
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 2.0
Immune system disorders Bronchospasm 2.0
Infections and infestations Candida infection
Eye disorders Conjunctivitis
Eye disorders Conjunctivitis 2.0
Respiratory, thoracic and mediastinal disorders Cough 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 2.0
Infections and infestations Ear infection 2.0
Respiratory, thoracic and mediastinal disorders Epistaxis 2.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 2.0
Reproductive system and breast disorders Menstrual disorder 2.0
Respiratory, thoracic and mediastinal disorders Nasal discomfort 2.0
Cardiac disorders Palpitations 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Gastrointestinal disorders Vomiting 2.0
Musculoskeletal and connective tissue disorders Arthralgia 1.97
General disorders and administration site conditions Asthenia 1.97
General disorders and administration site conditions Fatigue 1.97
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.97
Musculoskeletal and connective tissue disorders Arthralgia 1.96
Gastrointestinal disorders Constipation 1.96
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.96
Infections and infestations Urinary tract infection 1.96
Gastrointestinal disorders Abdominal pain upper
Skin and subcutaneous tissue disorders Acne
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Flatulence
Endocrine disorders Hirsutism
Metabolism and nutrition disorders Lipohypertrophy
Skin and subcutaneous tissue disorders Skin striae
Gastrointestinal disorders Nausea 1.8
Gastrointestinal disorders Viral diarrhoea 1.8
Gastrointestinal disorders Pharyngitis
Metabolism and nutrition disorders Fluid retention
General disorders and administration site conditions Flushing
Metabolism and nutrition disorders Fluid retention 1.61
General disorders and administration site conditions Flushing 1.61
Gastrointestinal disorders Abdominal distension 1.57
Musculoskeletal and connective tissue disorders Arthralgia
Endocrine disorders Cushingoid
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Metabolism and nutrition disorders Lipohypertrophy 1.41
Infections and infestations Candida infection 1.3
Gastrointestinal disorders Oral candidiasis 1.3
Ear and labyrinth disorders Otitis media 1.3
Immune system disorders Rhinitis allergic
Infections and infestations Viral upper respiratory tract infection
Endocrine disorders Cushingoid 1.18
Metabolism and nutrition disorders Fluid retention 1.18
Metabolism and nutrition disorders Fluid retention
General disorders and administration site conditions Flushing
Metabolism and nutrition disorders Lipohypertrophy 1.14
Immune system disorders Bronchospasm
Eye disorders Conjunctivitis 1.0
Respiratory, thoracic and mediastinal disorders Cough
Skin and subcutaneous tissue disorders Dermatitis 1.0
Respiratory, thoracic and mediastinal disorders Epistaxis
Respiratory, thoracic and mediastinal disorders Nasal discomfort
Skin and subcutaneous tissue disorders Rash 1.0
Skin and subcutaneous tissue disorders Skin striae 0.937
Gastrointestinal disorders Nausea
Ear and labyrinth disorders Otitis media
Skin and subcutaneous tissue disorders Acne 0.787
Metabolism and nutrition disorders Fluid retention 0.784
Gastrointestinal disorders Abdominal distension
Gastrointestinal disorders Constipation
Skin and subcutaneous tissue disorders Skin striae
Endocrine disorders Hirsutism
Metabolism and nutrition disorders Lipohypertrophy 0.69
Infections and infestations Candida infection
Respiratory, thoracic and mediastinal disorders Nasal congestion
Gastrointestinal disorders Oral candidiasis
Gastrointestinal disorders Viral diarrhoea
Gastrointestinal disorders Constipation 0.394
General disorders and administration site conditions Flushing 0.394
Infections and infestations Urinary tract infection 0.394
Endocrine disorders Hirsutism 0.392
Blood cortisol decreased
Infections and infestations Urinary tract infection

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Respiratory, thoracic and mediastinal disorders
17.26
Injury, poisoning and procedural complications
16.19
General disorders and administration site conditions
9.76
Gastrointestinal disorders
7.51
Nervous system disorders
6.22
Cardiac disorders
5.87
Infections and infestations
4.37
Immune system disorders
4.34
Psychiatric disorders
3.95
Product issues
3.6
Musculoskeletal and connective tissue disorders
3.26
Vascular disorders
3.17
Investigations
3.04
Skin and subcutaneous tissue disorders
2.99
Metabolism and nutrition disorders
2.05
Eye disorders
2.03

Cross References

Resources Reference
CAS NUMBER 51333-22-3
ChEBI 3207
ChEMBL CHEMBL1370
DrugBank DB01222
DrugCentral 419
EPA CompTox DTXSID8020202
FDA SRS Q3OKS62Q6X
Human Metabolome Database HMDB0015353
Guide to Pharmacology 7434
KEGG D00246
PubChem 5281004
SureChEMBL SCHEMBL4096
ZINC ZINC04097286
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