TRIAMCINOLONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1957)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A01AC01
UNII: 1ZK20VI6TY

Structure
InChI Key GFNANZIMVAIWHM-OBYCQNJPSA-N
Smile C[C@]12C[C@H](O)[C@@]3(F)[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1C[C@@H](O)[C@]2(O)C(=O)CO
InChI
InChI=1S/C21H27FO6/c1-18-6-5-12(24)7-11(18)3-4-13-14-8-15(25)21(28,17(27)10-23)19(14,2)9-16(26)20(13,18)22/h5-7,13-16,23,25-26,28H,3-4,8-10H2,1-2H3/t13-,14-,15+,16-,18-,19-,20-,21-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H27FO6
Molecular Weight 394.44
AlogP 0.62
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 2.0
Polar Surface Area 115.06
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Glucocorticoid receptor agonist PubMed PubMed PubMed
Primary Target
Glucocorticoid receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 49100 - - -
Enzyme Hydrolase
- - - - 94
Enzyme
- 49100 - - 94
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 71

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Rhinitis, Allergic, Seasonal 3 D006255 ClinicalTrials
Keloid 3 D007627 ClinicalTrials
Retinal Vein Occlusion 3 D012170 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Rhinitis, Allergic, Perennial 3 D012221 ClinicalTrials
Pancreatitis, Chronic 3 D050500 ClinicalTrials
Macular Edema 3 D008269 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 3 D029424 ClinicalTrials
Radiculopathy 3 D011843 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Shoulder Pain 2 D020069 ClinicalTrials
Vascular Diseases 2 D014652 ClinicalTrials
Acneiform Eruptions 2 D017486 ClinicalTrials
Dermatitis, Atopic 2 D003876 ClinicalTrials
Abdominal Pain 2 D015746 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Alopecia Areata 2 D000506 ClinicalTrials
Melanosis 2 D008548 ClinicalTrials
Wet Macular Degeneration 2 D057135 ClinicalTrials
Vitiligo 2 D014820 ClinicalTrials
Osteoarthritis, Knee 2 D020370 ClinicalTrials
Rotator Cuff Injuries 1 D000070636 ClinicalTrials
Macular Degeneration 1 D008268 ClinicalTrials
Optic Neuropathy, Ischemic 1 D018917 ClinicalTrials
Diabetic Retinopathy 1 D003930 ClinicalTrials
Lichen Planus, Oral 1 D017676 ClinicalTrials
Nasal Polyps 1 D009298 ClinicalTrials
Sinusitis 0 D012852 ClinicalTrials
Psoriasis 0 D011565 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 51.0
Nervous system disorders Headache 44.3
Nervous system disorders Headache
Respiratory, thoracic and mediastinal disorders Epistaxis 19.4
Gastrointestinal disorders Pharyngitis
Respiratory, thoracic and mediastinal disorders Sneezing 15.9
Nervous system disorders Headache 15.4
Nervous system disorders Headache
Respiratory, thoracic and mediastinal disorders Sneezing 14.0
Respiratory, thoracic and mediastinal disorders Sneezing 13.8
Gastrointestinal disorders Pharyngitis 13.7
Nervous system disorders Headache
Infections and infestations Rhinitis 11.6
Respiratory, thoracic and mediastinal disorders Sneezing 11.5
Gastrointestinal disorders Pharyngitis
Respiratory, thoracic and mediastinal disorders Epistaxis 11.0
Nervous system disorders Headache
Nervous system disorders Headache 10.3
Gastrointestinal disorders Pharyngitis 10.3
Nervous system disorders Headache 10.1
Infections and infestations Rhinitis 10.1
Respiratory, thoracic and mediastinal disorders Cough 9.4
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Epistaxis
Infections and infestations Sinusitis 9.0
Infections and infestations Influenza 8.94
Infections and infestations Rhinitis
Infections and infestations Influenza 8.9
Infections and infestations Sinusitis
Respiratory, thoracic and mediastinal disorders Cough 8.4
Respiratory, thoracic and mediastinal disorders Cough 8.38
Infections and infestations Rhinitis 8.37
Nervous system disorders Headache
Respiratory, thoracic and mediastinal disorders Nasal discomfort 7.96
Infections and infestations Sinusitis
Investigations Body temperature increased 7.9
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Pharyngitis 7.82
Musculoskeletal and connective tissue disorders Back pain 7.8
Gastrointestinal disorders Dysgeusia 7.8
Gastrointestinal disorders Pharyngitis 7.8
Investigations Body temperature increased 7.69
Gastrointestinal disorders Pharyngitis 7.69
Respiratory, thoracic and mediastinal disorders Nasal discomfort 7.5
Respiratory, thoracic and mediastinal disorders Nasal discomfort 7.48
Nervous system disorders Headache 7.44
Infections and infestations Infection 7.44
Gastrointestinal disorders Pharyngitis 7.44
Infections and infestations Infection
Infections and infestations Influenza
Infections and infestations Influenza
Infections and infestations Infection 7.26
Respiratory, thoracic and mediastinal disorders Nasal discomfort 7.21
Respiratory, thoracic and mediastinal disorders Sneezing
Respiratory, thoracic and mediastinal disorders Sneezing
Nervous system disorders Headache
Gastrointestinal disorders Pharyngitis
Nervous system disorders Headache 7.0
Gastrointestinal disorders Pharyngitis 7.0
Respiratory, thoracic and mediastinal disorders Cough 6.98
Respiratory, thoracic and mediastinal disorders Epistaxis
Nervous system disorders Headache 6.8
Respiratory, thoracic and mediastinal disorders Cough
Gastrointestinal disorders Pharyngitis
Respiratory, thoracic and mediastinal disorders Cough
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Nausea 6.3
Nervous system disorders Headache 6.2
Respiratory, thoracic and mediastinal disorders Nasal discomfort 6.2
Respiratory, thoracic and mediastinal disorders Nasal discomfort 6.19
Investigations Body temperature increased
Investigations Body temperature increased 5.58
Nervous system disorders Headache 5.5
Respiratory, thoracic and mediastinal disorders Laryngeal pain 5.5
Gastrointestinal disorders Oropharyngeal discomfort 5.5
Gastrointestinal disorders Oropharyngeal pain 5.5
Investigations Body temperature increased
Immune system disorders Asthma 5.4
Gastrointestinal disorders Oropharyngeal discomfort
Gastrointestinal disorders Oropharyngeal pain
Respiratory, thoracic and mediastinal disorders Epistaxis
Respiratory, thoracic and mediastinal disorders Epistaxis 5.1
Infections and infestations Nasopharyngitis 5.1
Gastrointestinal disorders Pharyngitis 5.1
Gastrointestinal disorders Dysgeusia 5.0
Respiratory, thoracic and mediastinal disorders Epistaxis
Gastrointestinal disorders Dyspepsia 4.9
Musculoskeletal and connective tissue disorders Back pain 4.7
Gastrointestinal disorders Dyspepsia 4.7
Infections and infestations Ear infection 4.7
General disorders and administration site conditions Pain 4.7
Infections and infestations Rhinitis 4.7
Respiratory, thoracic and mediastinal disorders Epistaxis 4.65
Investigations Body temperature increased 4.47
Respiratory, thoracic and mediastinal disorders Epistaxis 4.47
Eye disorders Conjunctivitis 4.4
Immune system disorders Asthma 4.3
Nervous system disorders Headache
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Musculoskeletal and connective tissue disorders Back pain 4.0
Infections and infestations Influenza 4.0
Infections and infestations Sinusitis 3.91
Respiratory, thoracic and mediastinal disorders Epistaxis 3.85
Infections and infestations Nasopharyngitis
Infections and infestations Ear infection
Respiratory, thoracic and mediastinal disorders Nasal discomfort
Gastrointestinal disorders Pharyngitis
Infections and infestations Sinusitis
Musculoskeletal and connective tissue disorders Back pain
Infections and infestations Influenza
Musculoskeletal and connective tissue disorders Back pain
Infections and infestations Rhinitis 3.5
Infections and infestations Bronchitis 3.4
Gastrointestinal disorders Dyspepsia 3.4
Gastrointestinal disorders Tooth disorder 3.4
Respiratory, thoracic and mediastinal disorders Epistaxis 3.35
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.3
Musculoskeletal and connective tissue disorders Myalgia 3.3
Infections and infestations Sinusitis 3.26
Respiratory, thoracic and mediastinal disorders Epistaxis 3.21
Respiratory, thoracic and mediastinal disorders Epistaxis 3.1
Gastrointestinal disorders Nausea
Gastrointestinal disorders Diarrhoea 3.0
Gastrointestinal disorders Nausea 3.0
Infections and infestations Rhinitis 3.0
Infections and infestations Influenza
Immune system disorders Asthma
Gastrointestinal disorders Dysgeusia
Respiratory, thoracic and mediastinal disorders Nasal discomfort
Respiratory, thoracic and mediastinal disorders Cough 2.7
Gastrointestinal disorders Dyspepsia 2.7
Respiratory, thoracic and mediastinal disorders Epistaxis 2.7
Gastrointestinal disorders Vomiting 2.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Immune system disorders Asthma 2.5
Skin and subcutaneous tissue disorders Dermatitis 2.5
Excoriation 2.5
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.5
Musculoskeletal and connective tissue disorders Myalgia 2.5
Skin and subcutaneous tissue disorders Rash 2.5
Respiratory, thoracic and mediastinal disorders Cough
Gastrointestinal disorders Dyspepsia
Immune system disorders Asthma
Respiratory, thoracic and mediastinal disorders Cough 2.1
Infections and infestations Nasopharyngitis 2.1
Respiratory, thoracic and mediastinal disorders Rhinorrhoea 2.1
Respiratory, thoracic and mediastinal disorders Cough 2.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Nausea 2.0
Respiratory, thoracic and mediastinal disorders Epistaxis 1.9
Respiratory, thoracic and mediastinal disorders Epistaxis 1.87
Infections and infestations Influenza 1.86
Musculoskeletal and connective tissue disorders Back pain
Respiratory, thoracic and mediastinal disorders Epistaxis
Respiratory, thoracic and mediastinal disorders Epistaxis 1.8
Nervous system disorders Headache 1.8
Infections and infestations Rhinitis
Respiratory, thoracic and mediastinal disorders Epistaxis 1.77
Infections and infestations Influenza
Infections and infestations Sinusitis
Skin and subcutaneous tissue disorders Dermatitis
Infections and infestations Nasopharyngitis
Skin and subcutaneous tissue disorders Rash
Respiratory, thoracic and mediastinal disorders Rhinorrhoea
Respiratory, thoracic and mediastinal disorders Epistaxis 1.59
Eye disorders Conjunctivitis
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Epistaxis 1.5
Infections and infestations Rhinitis 1.5
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 1.5
Infections and infestations Rhinitis 1.4
Eye disorders Conjunctivitis 1.3
Gastrointestinal disorders Diarrhoea
Nervous system disorders Headache 1.2
Respiratory, thoracic and mediastinal disorders Nasal discomfort 1.07
Respiratory, thoracic and mediastinal disorders Sneezing 1.07
Infections and infestations Bronchitis
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Tooth disorder
Gastrointestinal disorders Oropharyngeal discomfort
Gastrointestinal disorders Oropharyngeal pain
Respiratory, thoracic and mediastinal disorders Sneezing
Respiratory, thoracic and mediastinal disorders Epistaxis
Gastrointestinal disorders Oropharyngeal discomfort
Gastrointestinal disorders Oropharyngeal pain
Respiratory, thoracic and mediastinal disorders Epistaxis 0.885
Respiratory, thoracic and mediastinal disorders Sinus congestion 0.885
Respiratory, thoracic and mediastinal disorders Nasal discomfort 0.843
Respiratory, thoracic and mediastinal disorders Epistaxis
General disorders and administration site conditions Pain
Nervous system disorders Headache 0.7
Respiratory, thoracic and mediastinal disorders Sinus congestion 0.601
Gastrointestinal disorders Nausea
Gastrointestinal disorders Oropharyngeal discomfort
Gastrointestinal disorders Oropharyngeal pain
Respiratory, thoracic and mediastinal disorders Sneezing
Gastrointestinal disorders Oropharyngeal discomfort 0.559
Gastrointestinal disorders Oropharyngeal pain 0.559
Respiratory, thoracic and mediastinal disorders Sinus congestion 0.559
Gastrointestinal disorders Oropharyngeal discomfort 0.535
Gastrointestinal disorders Oropharyngeal pain 0.535
Respiratory, thoracic and mediastinal disorders Sinus congestion 0.535
Respiratory, thoracic and mediastinal disorders Epistaxis
Respiratory, thoracic and mediastinal disorders Nasal discomfort
Gastrointestinal disorders Pharyngitis 0.3
Gastrointestinal disorders Oropharyngeal discomfort 0.281
Gastrointestinal disorders Oropharyngeal pain 0.281
Respiratory, thoracic and mediastinal disorders Sinus congestion 0.187
Respiratory, thoracic and mediastinal disorders Sneezing 0.187
Respiratory, thoracic and mediastinal disorders Sinus congestion

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Endocrine disorders
18.18
Metabolism and nutrition disorders
18.18
Vascular disorders
18.18
Psychiatric disorders
13.64
Gastrointestinal disorders
9.09
General disorders and administration site conditions
4.55
Immune system disorders
4.55
Infections and infestations
4.55
Injury, poisoning and procedural complications
4.55
Respiratory, thoracic and mediastinal disorders
4.55

Cross References

Resources Reference
CAS NUMBER 124-94-7
ChEBI 9667
ChEMBL CHEMBL1451
DrugBank DB00620
DrugCentral 2725
EPA CompTox DTXSID1040742
FDA SRS 1ZK20VI6TY
Human Metabolome Database HMDB0014758
Guide to Pharmacology 2870
PharmGKB PA451749
PubChem 31307
SureChEMBL SCHEMBL4447
ZINC ZINC000003882036
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