DANAZOL

Search structure
Trade Names:
Synonyms:
Status: Approved (1976)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: G03XA01
UNII: N29QWW3BUO

Structure
InChI Key POZRVZJJTULAOH-LHZXLZLDSA-N
Smile C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=Cc5oncc5C[C@]4(C)[C@H]3CC[C@@]21C
InChI
InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H27NO2
Molecular Weight 337.46
AlogP 4.22
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 46.26
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 25.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Androgen Receptor agonist
Primary Target
Androgen receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 1950 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 300-1440 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 2740 - - -
Enzyme Hydrolase
- - - -
Enzyme Transferase
- - - - 14.61
Enzyme
- 12-77 - 20 14.61
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -25.28-3.7
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Neurokinin receptor
- 26580 - 8860 -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor
- 14079 - 5715 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- 17747 - 3762 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 17020 - 10574 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- 20449 - 10225 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 8850 - 2528 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
- 11160 - 6309 -
Secreted protein
- - 6.31 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 1
- 17790 - 5083 -
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
- 4314 - 1961 -
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
- 259 - 34 -
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
- 12 - 7.99 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 15420 - 5436 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 80.9
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 18700-18700 - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Infertility 3 D007246 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 2 D016553 ClinicalTrials
Mastodynia 2 D059373 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Purpura, Thrombotic Thrombocytopenic 2 D011697 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 2 D016553 ClinicalTrials
Anemia, Aplastic 1 D000741 ClinicalTrials
Fanconi Anemia 1 D005199 ClinicalTrials
Dyskeratosis Congenita 1 D019871 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Vascular disorders
14.29
Hepatobiliary disorders
11.69
Gastrointestinal disorders
10.39
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
7.79
Investigations
6.49
Skin and subcutaneous tissue disorders
6.49
Nervous system disorders
5.84
Blood and lymphatic system disorders
5.19
General disorders and administration site conditions
5.19
Cardiac disorders
4.55
Infections and infestations
4.55
Immune system disorders
3.9
Musculoskeletal and connective tissue disorders
3.25
Renal and urinary disorders
2.6
Respiratory, thoracic and mediastinal disorders
2.6

Cross References

Resources Reference
CAS NUMBER 17230-88-5
ChEBI 4315
ChEMBL CHEMBL1479
DrugBank DB01406
DrugCentral 779
EPA CompTox DTXSID2022880
FDA SRS N29QWW3BUO
Human Metabolome Database HMDB02835
Guide to Pharmacology 6942
KEGG C06938
PDB QA1
PharmGKB PA164749056
PubChem 28417
SureChEMBL SCHEMBL21107
ZINC ZINC000003881958
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