5(6)-Dehydro-4(5)-dihydro D-(-)-Norgestrel
CAS No.:
100021-05-4
M. Wt:
312.44600
M. Fa:
C21H28O2
InChI Key:
LYRBZVWRTAFWPO-XUDSTZEESA-N
Names and Identifiers of 100021-05-4
CAS Number |
100021-05-4 |
|---|---|
IUPAC Name |
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,4,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one |
InChI |
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,5,16-19,23H,3,6-13H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1 |
InChIKey |
LYRBZVWRTAFWPO-XUDSTZEESA-N |
Canonical SMILES |
CCC12CCC3C4CCC(=O)CC4=CCC3C1CCC2(C#C)O |
Isomeric SMILES |
CC[C@]12CC[C@@H]3[C@H]4CCC(=O)CC4=CC[C@H]3[C@@H]1CC[C@]2(C#C)O |
UNII |
QV7HH25Q8V |
Physical and chemical properties of 100021-05-4
Acidity coefficient |
13.10±0.40(Predicted) |
|---|---|
Boiling Point |
451.8±45.0 °C(Predicted) |
Density |
1.13±0.1 g/cm3(Predicted) |
Exact Mass |
312.20900 |
LogP |
3.88260 |
Melting Point |
>189°C (dec.) |
Molecular Formula |
C21H28O2 |
Molecular Weight |
312.44600 |
PSA |
37.30000 |
Solubility |
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
Storage condition |
Amber Vial, -20°C Freezer, Under Inert Atmosphere |
Applications of 100021-05-4
5(6)-Dehydro-4(5)-dihydro D-(-)-Norgestrel is primarily used in:
- Hormonal Contraceptives: It is a key ingredient in various oral contraceptive formulations.
- Hormone Replacement Therapy: The compound may be utilized in therapies aimed at alleviating symptoms associated with menopause.
- Menstrual Disorder Treatments: It is effective in managing conditions like dysmenorrhea and endometriosis.
These applications underscore its significance in women's health.
Interaction Studies of 100021-05-4
Research on interaction studies involving 5(6)-Dehydro-4(5)-dihydro D-(-)-Norgestrel has shown that it can interact with various other drugs:
- Enzyme Inhibitors: Certain medications that inhibit cytochrome P450 enzymes may affect the metabolism of this compound, leading to altered efficacy or increased side effects.
- Antibiotics: Some antibiotics can reduce the effectiveness of hormonal contraceptives, necessitating careful monitoring when co-administered.
Understanding these interactions is vital for optimizing therapeutic regimens involving this progestin.
Biological Activity of 100021-05-4
The primary biological activity of 5(6)-Dehydro-4(5)-dihydro D-(-)-Norgestrel lies in its progestational effects. It mimics the action of progesterone in the body, influencing various physiological processes:
- Endometrial Regulation: It plays a crucial role in preparing the endometrium for potential implantation of an embryo.
- Contraceptive Effects: By inhibiting ovulation and altering cervical mucus, it serves as an effective contraceptive agent.
- Menstrual Cycle Regulation: The compound is also used to manage menstrual disorders by stabilizing hormonal fluctuations.
The potency and efficacy of this compound make it a valuable agent in reproductive health.
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