Molecule Details
| InChIKey | RGLYKWWBQGJZGM-ISLYRVAYSA-N |
|---|---|
| Compound Name | Diethylstilbestrol |
| Canonical SMILES | CC/C(=C(/CC)c1ccc(O)cc1)c1ccc(O)cc1 |
| Clinical Status | Clinical Multi-Target |
| Targets (Human+Pathogen) | 8 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 7.99 |
| Source | ChEMBL;BindingDB;TTD_MultiTarget |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00255 |
|---|---|
| Drug Name | Diethylstilbestrol |
| CAS Number | 56-53-1 |
| Groups | approved withdrawn |
| ATC Codes | L02AA04 L02AA01 G03CC05 G03CB02 |
| Description | A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11... |
Categories: Adrenal Cortex Hormones Antineoplastic Agents, Hormonal Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Inhibitors BSEP/ABCB11 Substrates Benzene Derivatives Benzylidene Compounds COMT Substrates Carcinogens Contraceptive Agents, Female Contraceptive Agents, Male Contraceptives, Postcoital Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (strong) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Endocrine Therapy Estrogen Contraceptives Estrogens Estrogens, Non-Steroidal Genito Urinary System and Sex Hormones Hormonal Contraceptives for Systemic Use Hormones Hormones and Related Agents Hormones, Hormone Substitutes, and Hormone Antagonists Noxae OATP1B1/SLCO1B1 Inhibitors OATP2B1/SLCO2B1 substrates P-glycoprotein substrates Sex Hormones and Modulators of the Genital System Stilbenes Stilbestrols Synthetic Estrogens, Plain Thyroxine-binding globulin inducers Toxic Actions
Cross-references: BindingDB: 20625 ChEBI: 41922 CHEMBL411 ChemSpider: 395306 Drugs Product Database (DPD): 7384 C07620 D00577 PDB: DES PharmGKB: PA449307 PubChem:3054 PubChem:46507453 RxCUI: 3390 Therapeutic Targets Database: DAP001011 Wikipedia: Diethylstilbestrol ZINC: ZINC000000001290
Target Activities (8)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P18505 | GABRB1 | Homo sapiens | Human | PF02931 PF02932 | 10.7 | pIC50 | TTD_MultiTarget |
| P03372 | ESR1 | Homo sapiens | Human | PF12743 PF00104 PF02159 PF00105 | 9.4 | IC50 | ChEMBL;BindingDB |
| Q92731 | ESR2 | Homo sapiens | Human | PF12497 PF00104 PF00105 | 8.4 | IC50 | ChEMBL;BindingDB |
| Q06278 | AOX1 | Homo sapiens | Human | PF01315 PF03450 PF00941 PF00111 PF01799 PF02738 PF20256 | 6.3 | IC50 | ChEMBL;BindingDB |
| Q9UNQ0 | ABCG2 | Homo sapiens | Human | PF01061 PF19055 PF00005 | 6.3 | IC50 | ChEMBL;BindingDB |
| Q01959 | SLC6A3 | Homo sapiens | Human | PF00209 | 6.1 | Ki | ChEMBL |
| P41143 | OPRD1 | Homo sapiens | Human | PF00001 | 6.0 | Ki | ChEMBL |
| Q96WX4 | erg6 | Pneumocystis carinii (strain B80) | Pathogen | PF08241 PF08498 | 10.7 | pIC50 | TTD_MultiTarget |
DrugBank Target Actions (23)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P02766 | TTR | Transthyretin | binder | carriers |
| P05181 | CYP2E1 | Cytochrome P450 2E1 | inhibitor | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | inhibitor | enzymes |
| P10632 | CYP2C8 | Cytochrome P450 2C8 | inhibitor | enzymes |
| P11511 | CYP19A1 | Aromatase | inhibitor | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | inhibitor | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10632 | CYP2C8 | Cytochrome P450 2C8 | substrate | enzymes |
| P21964 | COMT | Catechol O-methyltransferase | substrate | enzymes |
| P03372 | ESR1 | Estrogen receptor | agonist | targets |
| P62508 | ESRRG | Estrogen-related receptor gamma | agonist | targets |
| Q92731 | ESR2 | Estrogen receptor beta | agonist | targets |
| P10275 | AR | Androgen receptor | antagonist | targets |
| O75469 | NR1I2 | Nuclear receptor subfamily 1 group I member 2 | binder | targets |
| O95718 | ESRRB | Steroid hormone receptor ERR2 | binder | targets |
| P04278 | SHBG | Sex hormone-binding globulin | binder | targets |
| P11474 | ESRRA | Steroid hormone receptor ERR1 | binder | targets |
| Q15596 | NCOA2 | Nuclear receptor coactivator 2 | binder | targets |
| Q9UNQ0 | ABCG2 | Broad substrate specificity ATP-binding cassette transporter ABCG2 | inhibitor | transporters |
| Q9Y6L6 | SLCO1B1 | Solute carrier organic anion transporter family member 1B1 | inhibitor | transporters |
| O94956 | SLCO2B1 | Solute carrier organic anion transporter family member 2B1 | substrate | transporters |
| O95342 | ABCB11 | Bile salt export pump | substrate | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |