Tibolone
G03D - Progestogens
ATC G03DC05
Small molecule
Natural product
JFDA label: LIVIAL TABS
Indications
Off-label
- Breast Neoplasms
- Menopause
- Osteoporosis
- Sexual Dysfunction, Physiological
Pregnancy & Lactation
Pregnancy
Chemistry & Properties
| Formula | C21H28O2 |
|---|---|
| Molecular weight | 312.45 g/mol |
| IUPAC name | (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one |
| CAS | 5630-53-5 |
| PubChem CID | 444008 |
| InChIKey | WZDGZWOAQTVYBX-XOINTXKNSA-N |
| logP | 3.88 (XLogP 2.4) |
| Polar surface area | 37.3 Ų |
| H-bond acceptors / donors | 2 / 1 |
| Drug-likeness (QED) | 0.54 |
| Lipinski violations | 0 |
SMILES
C#C[C@]1(O)CC[C@H]2[C@@H]3[C@H](C)CC4=C(CCC(=O)C4)[C@H]3CC[C@@]21CBiology & Pharmacokinetics
Pharmacokinetics
| BBB penetrant | Yes (logBB 0.4) |
|---|
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP1A2 | Substrate | — |
| CYP2B6 | Inhibitor | — |
| CYP2C19 | Inhibitor | IC₅₀ 3.0000000000000013 µM |
| CYP2C19 | Substrate | — |
| CYP2C8 | Inhibitor | — |
| CYP2C9 | Inhibitor | — |
| CYP3A4 | Substrate | — |
Receptor binding (top 1)
| Target | Action | Affinity |
|---|---|---|
| Estrogen receptor-α (ESR1) | Agonist | pEC50 8.4 |
Transporters
BCRP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)
Registered Products (1)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| LIVIAL TABS | Tablet 2.5 mg | 28 tab | Sabbagh Drug Store | 10.330 |