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Compound Detail

CHEMBL1479

DANAZOL
💊 Approved Drug
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💊 Approved Drug
C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=Cc5oncc5C[C@]4(C)[C@H]3CC[C@@]21C

Basic Information

ChEMBL ID CHEMBL1479
Name DANAZOL
Phase Approved
Structure Type MOL
InChI Key POZRVZJJTULAOH-LHZXLZLDSA-N
Therapeutic ✓ Yes

Known Names

Danazol Danocrine NSC-270916 WIN 17,757 WIN-17757
32
Targets
72
Activities
3
Assay Types
2
PK Parameters
20
Publications
5
Known Names
12
Indications
2
Mechanisms

Molecular Properties

337.5
MW (Da)
4.22
ALogP
3
HBA
1
HBD
46.3
PSA (Ų)
0.72
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1976
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1968

Extended Properties

Molecular Formula C22H27NO2
MW 337.46
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness 1.18

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Progesterone receptor agonist AGONIST Progesterone receptor
Androgen Receptor agonist AGONIST Androgen receptor

Indications

Endometriosis Fibrocystic Breast Disease Infertility Endometrial Neoplasms Mastodynia Myelodysplastic Syndromes Purpura, Thrombocytopenic, Idiopathic Purpura, Thrombocytopenic, Idiopathic Purpura, Thrombotic Thrombocytopenic Anemia, Aplastic Dyskeratosis Congenita Fanconi Anemia

ATC Classification

G03XA01
danazol
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Drug Warnings

Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
vascular toxicity
Country: United States
Black Box Warning
carcinogenicity
Country: United States

Activity Summary

IC50 46 meas. best 7.92
Ki 25 meas. best 8.1
Kd 1 meas. best 8.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sex hormone-binding globulin
CHEMBL3305
Kd 8.2 8.2 6.3 1
Androgen receptor
CHEMBL3072
Ki 8.1 8.1 8.0 1
Androgen receptor
CHEMBL3072
IC50 7.92 7.92 12.0 1
Cytochrome P450 2J2
CHEMBL3491
IC50 7.92 7.5833 12.0 3
Cytochrome P450 2J2
CHEMBL3491
Ki 7.7 7.7 20.0 1
Progesterone receptor
CHEMBL1909044
Ki 7.47 7.47 34.0 1
Liver
CHEMBL613642
IC50 7.06 7.06 87.5 1
Progesterone receptor
CHEMBL1909044
IC50 6.59 6.59 259.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 6.52 6.18 300.0 2
Cytochrome P450 2C8
CHEMBL3721
IC50 5.71 5.71 1950.0 1
Glucocorticoid receptor
CHEMBL2034
Ki 5.71 5.71 1961.0 1
Unchecked
CHEMBL612545
IC50 5.6 4.96 2535.0 6
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.6 5.6 2528.0 1
Unchecked
CHEMBL612545
Ki 5.57 4.91 2670.0 5
Cytochrome P450 2D6
CHEMBL289
IC50 5.56 5.56 2740.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 5.46 5.46 3451.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.42 5.42 3762.0 1
Glucocorticoid receptor
CHEMBL2034
IC50 5.37 5.37 4314.0 1
Estrogen receptor
CHEMBL206
Ki 5.29 5.29 5083.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.26 5.26 5436.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.25 5.25 5651.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.24 5.24 5698.0 1
Mu-type opioid receptor
CHEMBL233
Ki 5.24 5.24 5715.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.21 5.21 6207.0 1
Adenosine receptor A3
CHEMBL256
Ki 5.2 5.2 6309.0 1
Trypanosoma cruzi
CHEMBL368
IC50 5.2 5.2 6250.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.17 5.17 6842.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.16 5.16 6873.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.1 4.95 7943.3 7
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.09 5.09 8193.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 5.05 5.05 8850.0 1
Substance-K receptor
CHEMBL2327
Ki 5.05 5.05 8860.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.01 5.01 9800.0 1
Leishmania donovani
CHEMBL367
IC50 4.99 4.99 10160.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 4.99 4.99 10225.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 4.98 4.98 10574.0 1
Adenosine receptor A3
CHEMBL256
IC50 4.95 4.95 11160.0 1
Beta-3 adrenergic receptor
CHEMBL246
Ki 4.89 4.89 12765.0 1
Mu-type opioid receptor
CHEMBL233
IC50 4.85 4.85 14079.0 1
Kappa-type opioid receptor
CHEMBL237
IC50 4.81 4.81 15518.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 4.81 4.81 15420.0 1
Beta-3 adrenergic receptor
CHEMBL246
IC50 4.77 4.77 17020.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 4.75 4.75 17747.0 1
Estrogen receptor
CHEMBL206
IC50 4.75 4.75 17790.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 4.74 4.74 18328.0 1
Bile salt export pump
CHEMBL6020
IC50 4.73 4.73 18700.0 2
D(1A) dopamine receptor
CHEMBL2056
IC50 4.69 4.69 20449.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 4.63 4.63 23163.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 4.62 4.62 23752.0 1
Substance-K receptor
CHEMBL2327
IC50 4.58 4.58 26580.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1850.63 ng.hr.mL-1 Homo sapiens
Cmax 750.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sex hormone-binding globulin Kd = 6.31 nM 8.2 Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding gl... 18330978
Androgen receptor Ki = 7.99 nM 8.1 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Androgen receptor IC50 = 12.0 nM 7.92 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Cytochrome P450 2J2 IC50 = 12.0 nM 7.92 Inhibition of recombinant CYP2J2 (unknown origin)-mediated astemizole O-demethyl... 22328583
Cytochrome P450 2J2 IC50 = 19.0 nM 7.72 Inhibition of recombinant CYP2J2 (unknown origin)-mediated astemizole O-demethyl... 22328583
Cytochrome P450 2J2 Ki = 20.0 nM 7.7 Mixed inhibition of recombinant CYP2J2 (unknown origin)-mediated astemizole O-de... 22328583
Progesterone receptor Ki = 34.0 nM 7.47 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Cytochrome P450 2J2 IC50 = 77.0 nM 7.11 Inhibition of recombinant CYP2J2 (unknown origin)-mediated terfenadine hydroxyla... 22328583
Liver IC50 = 87.5 nM 7.06 Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria ... 24799086
Progesterone receptor IC50 = 259.0 nM 6.59 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Cytochrome P450 2C9 IC50 = 300.0 nM 6.52 DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Cytochrome P450 2C9 IC50 = 1440.0 nM 5.84 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate aft... 22328583
Cytochrome P450 2C8 IC50 = 1950.0 nM 5.71 Inhibition of CYP2C8 in human liver microsomes using paclitaxel as substrate aft... 22328583
Glucocorticoid receptor Ki = 1961.0 nM 5.71 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Unchecked IC50 = 2535.0 nM 5.6 DRUGMATRIX: Phosphodiesterase PDE3 enzyme inhibition (substrate: [3H]cAMP + cAMP... -
5-hydroxytryptamine receptor 2A Ki = 2528.0 nM 5.6 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Unchecked Ki = 2670.0 nM 5.57 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Cytochrome P450 2D6 IC50 = 2740.0 nM 5.56 Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substra... 22328583
Unchecked IC50 = 2978.0 nM 5.53 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Alpha-2C adrenergic receptor Ki = 3451.0 nM 5.46 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1379
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
- 10.5281/zenodo.13943903 ADMET 49
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
22328583 10.1124/dmd.111.043505 Cytochrome P450 2J2 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
403283 10.1021/jm00213a007 Rattus norvegicus 5
403283 10.1021/jm00213a007 Homo sapiens 4
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
18066055 10.1038/nchembio.2007.53 HeLa 2
22931300 10.1021/tx300075j Liver microsomes 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL3392926 Leishmania donovani 2

Data from ChEMBL 36 via Core Engine