DANAZOL

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC G03XA01
UNII N29QWW3BUO
EPA CompTox DTXSID2022880

Structure

InChI Key POZRVZJJTULAOH-LHZXLZLDSA-N
Smiles 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

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Androgen Receptor agonist AGONIST ISBN PubMed FDA
Protein: Progesterone receptor
Description: Progesterone receptor
Organism : Homo sapiens
P06401 ENSG00000082175
Protein: Androgen Receptor
Description: Androgen receptor
Organism : Homo sapiens
P10275 ENSG00000169083
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
- 1440 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 2740 - - -
Enzyme Hydrolase
- - - - 30
Enzyme
- 12-77 - 20 30
Secreted protein
- - 6 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 81
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 18700-18700 - - -
Assay Description Organism Bioactivity Reference
Inhibition of steroid sulfatase activity of JEG-3 cells by the compound at 20 uM, activity was determined by considering total labeled estrone ([3H]E1) formed from labeled estrone sulfate ([3H]-E1S) None 30.0 %
Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin Homo sapiens 6.31 nM
DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 259.0 nM DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 34.0 nM
DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Mibolerone) Escherichia coli 12.0 nM DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Mibolerone) Escherichia coli 7.99 nM
DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 300.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 80.9 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 95.7 %
Inhibition of CYP2J2 in human liver microsomes using 7 probe cocktail containing phenacetin, paclitaxel, diclofenac, S-mephenytoin, dextromethorphan, astemizole and midazolam after 8 mins by LC-MS/MS analysis Homo sapiens 100.0 nM
Mixed inhibition of recombinant CYP2J2 (unknown origin)-mediated astemizole O-demethylation in presence of NADPH Homo sapiens 20.0 nM
Inhibition of recombinant CYP2J2 (unknown origin)-mediated astemizole O-demethylation preincubated for 30 mins followed by substrate addition in presence of NADPH Homo sapiens 12.0 nM
Inhibition of CYP2J2-mediated astemizole O-demethylation in human liver microsomes after 8 mins by LC-MS/MS analysis Homo sapiens 100.0 nM
Inhibition of recombinant CYP2J2 (unknown origin)-mediated astemizole O-demethylation in presence of NADPH Homo sapiens 19.0 nM
Inhibition of recombinant CYP2J2 (unknown origin)-mediated terfenadine hydroxylation in presence of NADPH Homo sapiens 77.0 nM
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 87.5 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 2.21 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -2.5 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 2.6 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 3.85 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 26.36 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 6.36 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 0.96 %

Cross References

Resources Reference
ChEBI 4315
ChEMBL CHEMBL1479
DrugBank DB01406
DrugCentral 779
FDA SRS N29QWW3BUO
Human Metabolome Database HMDB0002835
Guide to Pharmacology 6942
KEGG C06938
PDB QA1
PharmGKB PA164749056
PubChem 28417
SureChEMBL SCHEMBL21107
ZINC ZINC000003881958
CONTENTS