Cas no 6856-28-6 (6a-Hydroxy Norethindrone Acetate)

6a-Hydroxy Norethindrone Acetate is a synthetic steroidal compound derived from norethindrone, featuring a hydroxyl group at the 6a position and an acetate ester modification. This structural alteration enhances its metabolic stability and bioavailability compared to its parent compound. It exhibits potent progestogenic activity, making it valuable in hormonal research and pharmaceutical applications, particularly in the development of contraceptive and hormone replacement therapies. The 6a-hydroxy modification may also influence receptor binding affinity and selectivity, offering potential advantages in tailored therapeutic formulations. Its well-defined chemical properties ensure consistency in preclinical and clinical studies, supporting its use as a reliable reference standard or intermediate in steroid synthesis.
6a-Hydroxy Norethindrone Acetate structure
6856-28-6 structure
Product Name:6a-Hydroxy Norethindrone Acetate
CAS No:6856-28-6
MF:C22H28O4
MW:356.455327033997
CID:1059603
Update Time:2025-06-09

6a-Hydroxy Norethindrone Acetate Chemical and Physical Properties

Names and Identifiers

    • 6α-Hydroxy Norethindrone Acetate
    • 17α-Ethinyl-17β-acetoxy-6β-hydroxy-oestr-4-en-3-on
    • 6A-HYDROXY NORETHINDRONE ACETATE
    • 6-alpha-Hydroxy Norethindrone Acetate
    • 6Alpha-Hydroxy Norethindrone Acetate
    • 6alpha-Hydroxynorethisterone Acetate
    • 6a-Hydroxy Norethindrone Acetate
    • Inchi: 1S/C22H28O4/c1-4-22(26-13(2)23)10-8-19-17-12-20(25)18-11-14(24)5-6-15(18)16(17)7-9-21(19,22)3/h1,11,15-17,19-20,25H,5-10,12H2,2-3H3/t15-,16-,17-,19+,20+,21+,22+/m1/s1
    • InChI Key: NVEXGWVOAPQSMX-OARMXLMKSA-N
    • SMILES: O(C(C)=O)[C@@]1(C#C)CC[C@H]2[C@@H]3C[C@@H](C4=CC(CC[C@@H]4[C@H]3CC[C@@]21C)=O)O

Computed Properties

  • Exact Mass: 356.19900

Experimental Properties

  • PSA: 63.60000
  • LogP: 3.03410

6a-Hydroxy Norethindrone Acetate Pricemore >>

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Additional information on 6a-Hydroxy Norethindrone Acetate

Introduction to 6a-Hydroxy Norethindrone Acetate (CAS No. 6856-28-6)

6a-Hydroxy Norethindrone Acetate, with the CAS number 6856-28-6, is a synthetic progestin derivative that has garnered significant attention in the fields of reproductive health and endocrinology. This compound is a modified form of norethindrone, a widely used progestogen in hormonal contraceptives and other therapeutic applications. The addition of a hydroxyl group at the 6a position and an acetate ester provides unique pharmacological properties that make it a valuable compound in both research and clinical settings.

The chemical structure of 6a-Hydroxy Norethindrone Acetate is characterized by its steroidal backbone, which is common among many progestins. The presence of the hydroxyl group at the 6a position and the acetate ester at the 17β position contributes to its enhanced solubility and stability, making it suitable for various formulations. These structural modifications also influence its binding affinity to progesterone receptors, which is crucial for its biological activity.

In recent years, research on 6a-Hydroxy Norethindrone Acetate has focused on its potential therapeutic applications beyond contraception. Studies have shown that this compound exhibits anti-androgenic properties, which can be beneficial in treating conditions such as hirsutism and acne. Additionally, its progestogenic effects make it a candidate for use in hormone replacement therapy (HRT) for postmenopausal women, where it can help alleviate symptoms such as hot flashes and vaginal dryness while potentially reducing the risk of endometrial hyperplasia.

Clinical trials have demonstrated that 6a-Hydroxy Norethindrone Acetate has a favorable safety profile when used in appropriate doses. Its side effects are generally mild and similar to those observed with other progestins, including breast tenderness, headache, and mood changes. However, these side effects are typically transient and do not significantly impact patient compliance or treatment outcomes.

The pharmacokinetics of 6a-Hydroxy Norethindrone Acetate have been extensively studied to optimize its use in various formulations. It is rapidly absorbed following oral administration and undergoes extensive first-pass metabolism in the liver. The active metabolite, 6a-hydroxy norethindrone, has a longer half-life compared to the parent compound, which contributes to its sustained biological activity. This property makes it suitable for once-daily dosing regimens, enhancing patient convenience and adherence.

In terms of drug interactions, 6a-Hydroxy Norethindrone Acetate can be affected by drugs that induce or inhibit hepatic enzymes involved in its metabolism. For example, co-administration with cytochrome P450 inducers such as rifampin may decrease its plasma levels, while inhibitors like ketoconazole can increase them. Therefore, careful monitoring and dose adjustments may be necessary when using this compound in combination with other medications.

The development of novel delivery systems for 6a-Hydroxy Norethindrone Acetate has also been an area of active research. Transdermal patches and vaginal rings have shown promise in providing sustained release of the compound, potentially reducing systemic side effects and improving patient satisfaction. These delivery methods offer an alternative to oral administration for patients who prefer non-oral routes or have gastrointestinal issues that affect drug absorption.

Beyond its clinical applications, 6a-Hydroxy Norethindrone Acetate has been studied for its potential use in basic research to understand the mechanisms of progestin action at the molecular level. Its unique structural features make it a valuable tool for investigating receptor binding dynamics and signaling pathways involved in reproductive processes. This knowledge can contribute to the development of more targeted therapies for hormonal disorders.

In conclusion, 6a-Hydroxy Norethindrone Acetate (CAS No. 6856-28-6) is a versatile compound with significant potential in both clinical practice and scientific research. Its unique pharmacological properties make it a promising candidate for various therapeutic applications, particularly in reproductive health and endocrinology. Ongoing research continues to explore new avenues for its use, further solidifying its importance in the field of medicinal chemistry.

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