Lynestrenol
G03D - Progestogens
ATC G03DC03
Small molecule
Natural product
Withdrawn
Black-box warning
JFDA label: ORGAMETRIL TABS
⚠ Black-Box Warning
- Withdrawn: carcinogenicity — ChEMBL drug_warning (Withdrawn) | Australia | dose-related incidence of mammary tumours in the beagle bitch
Pregnancy & Lactation
Pregnancy
Chemistry & Properties
| Formula | C20H28O |
|---|---|
| Molecular weight | 284.44 g/mol |
| IUPAC name | (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol |
| CAS | 52-76-6 |
| PubChem CID | 5857 |
| InChIKey | YNVGQYHLRCDXFQ-XGXHKTLJSA-N |
| logP | 4.31 (XLogP 4.5) |
| Polar surface area | 20.23 Ų |
| H-bond acceptors / donors | 1 / 1 |
| Drug-likeness (QED) | 0.52 |
| Lipinski violations | 0 |
SMILES
C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3CC[C@@]21CBiology & Pharmacokinetics
Pharmacokinetics predicted
| Bioavailability | 70.0% |
|---|---|
| Half-life | 2.09 h |
| Volume of distribution | 2.88 L/kg |
| Protein binding | 96.3% |
| BBB penetrant | Yes |
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP1A2 | Substrate | — |
| CYP2B6 | Inhibitor | — |
| CYP2C19 | Inhibitor | — |
| CYP2C19 | Substrate | — |
| CYP2C8 | Inhibitor | — |
| CYP3A4 | Inhibitor | — |
| CYP3A4 | Substrate | — |
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) |
|---|---|---|---|---|
| ORGAMETRIL TABS | Tablet 5 mg | 30 tab | Sabbagh Drug Store | 2.420 |