| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
Norelgestromin inhibits estrone sulfatase, an enzyme that converts sulfated steroid precursors to estrogens. It also has agonistic binding affinities for progesterone and estrogen receptors, similar to its parent compound norgestimate.
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| ln Vitro |
In vitro, norelgestromin inhibits estrone sulfatase activity, thereby reducing the local production of estrogens from sulfated precursors. This action is relevant for both its contraceptive effects and potential applications in estrogen-sensitive conditions like breast cancer.
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| ln Vivo |
In vivo, the combination of norelgestromin and ethinyl estradiol suppresses follicular development, induces changes to the endometrium that decrease implantation chances, and thickens cervical mucus to impede sperm motility. These actions collectively contribute to its contraceptive efficacy.
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| Enzyme Assay |
The estrone sulfatase inhibition assay is performed using cell-free systems containing the recombinant enzyme and a fluorogenic substrate. Norelgestromin is incubated with the enzyme, and the decrease in fluorescent product formation is measured to determine its inhibitory potency and IC50 value.
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| Cell Assay |
In vitro cellular assays are conducted using human breast cancer cell lines (e.g., MCF-7) to evaluate the compound's effect on estrone sulfatase activity and cell proliferation. Cells are treated with norelgestromin, and sulfatase activity is measured using radiolabeled or fluorogenic substrates.
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| Animal Protocol |
In vivo efficacy is typically assessed in female animal models (e.g., rats or rabbits) where norelgestromin is administered via transdermal patches or oral gavage. Parameters such as ovulation inhibition, endometrial thickness, and cervical mucus viscosity are measured to evaluate its contraceptive effects and hormonal activity.
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| ADME/Pharmacokinetics |
Norelgestromin (C21H29NO2) is formulated for transdermal delivery as a patch or in combination with ethinyl estradiol as a vaginal ring. Its pharmacokinetics are characterized by absorption through the skin, leading to sustained systemic levels suitable for once-weekly or monthly administration regimens.
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| Toxicity/Toxicokinetics |
The toxicity profile of norelgestromin is derived from its clinical use as a hormonal contraceptive. Common side effects include those associated with progestin therapy, such as mood changes, weight gain, and breast tenderness. Long-term safety data are available from post-marketing surveillance of norgestimate and its metabolites.
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| Additional Infomation |
Norelgestromin is a steroid. It is derived from the hydrogenation of estradiol.
See also: Norelgestromin (note moved to). Norelgestromin is a progestin used for the prevention of pregnancy. It may potentially be used in breast cancer treatment due to its inhibitory effect on estrone sulfatase. It is marketed under brand names such as Evra, Xulane, and Zafemy. Its chemical formula is C21H29NO2, with a UNII ID of R0TAY3X631. |
| Exact Mass |
327.22
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|---|---|
| CAS # |
53016-31-2
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| Related CAS # |
Norgestimate metabolite norelgestromin-d6;1263184-13-9
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| PubChem CID |
9568628
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| Appearance |
White to off-white solid powder
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| Density |
1.23g/cm3
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| Boiling Point |
491.9ºC at 760mmHg
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| Melting Point |
107-109ºC
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| Flash Point |
327.1ºC
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| Index of Refraction |
1.633
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| LogP |
4.143
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
24
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| Complexity |
642
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| Defined Atom Stereocenter Count |
6
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| SMILES |
O/N=C1CC[C@@]2([H])C(CC[C@]3([H])[C@]2([H])CC[C@@]4(CC)[C@@]3([H])CC[C@]4(C#C)O)=C\1
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| InChi Key |
ISHXLNHNDMZNMC-VTKCIJPMSA-N
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| InChi Code |
InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3/b22-15+/t16-,17+,18+,19-,20-,21-/m0/s1
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| Chemical Name |
(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
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| Synonyms |
Norelgestromin NorelgestromineLevonorgestrel oximeNorplant 3-oximeD-Norgestrel 3-oxime
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~20 mg/mL (~61.08 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2 mg/mL (6.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT00320580 | COMPLETED | Drug: norelgestromin/ethinyl estradiol | Metrorrhagia | McNeil Consumer & Specialty Pharmaceuticals, a Division of McNeil-PPC, Inc | 2003-03 | Phase 2 |
| NCT00261482 | COMPLETED | Drug: norelgestromin + ethinyl estradiol | Contraception Female Contraception |
Janssen Pharmaceutica N.V., Belgium | 2003-07 | Phase 4 |
| NCT00653016 | COMPLETED | Drug: norelgestromin; ethinyl estradiol | Female Contraception | Janssen-Ortho Inc., Canada | 2002-10 | Phase 4 |
| NCT00236769 | COMPLETED | Drug: norelgestromin + ethinyl estradiol | Contraception Female Contraception |
Johnson & Johnson Pharmaceutical Research & Development, L.L.C | 1997-11 | Phase 3 |
| NCT00236795 | COMPLETED | Drug: norelgestromin + ethinyl estradiol; triphasil. | Contraception Female Contraception |
Johnson & Johnson Pharmaceutical Research & Development, L.L.C | 1997-01 | Phase 3 |
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