GLPBio

Levonorgestrel

Catalog No.: GC14704Purity:>98.00%
COASDSData Sheet
Levonorgestrel ist ein synthetisches Gestagen, das als Wirkstoff in einigen hormonellen VerhÜtungsmitteln verwendet wird.

Die Produkte sind ausschließlich für Forschungszwecke bestimmt. Nicht zur Anwendung am Menschen. Wir verkaufen nicht an Patienten.

Levonorgestrel
Cas No.: 797-63-7
10mM (in 1mL DMSO)In Stock
$23.00
1
100mgIn Stock
$21.00
1
500mgIn Stock
$32.00
1
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Beschreibung (Description)

Levonorgestrel is an effective oral progesterone inhibitor [1]. Levonorgestrel can be used for contraception and can be combined with other drugs. Levonorgestrel has anti-cancer activity and can induce cell apoptosis, and is used in the research of osteoporosis and uterine leiomyoma [2].

In vitro, Levonorgestrel (5-25μg/mL; 72h) can inhibit cell proliferation and promote cell apoptosis in uterine smooth muscle tumor cells in a concentration-dependent manner. It can significantly reduce the expression of Bcl-2 and Survivin, increase the phosphorylation level of p38, and activate caspase 3 [2]. Levonorgestrel (50μM) has a time-dependent inhibitory effect on the proliferation of HESCs and HEGCs, and significantly increases cell apoptosis. Levonorgestrel causes a time-dependent increase in the total Cx43 content, but does not cause changes in Ser368 phosphorylated Cx43, while Ser255 phosphorylated Cx43 shows a nuclear translocation phenomenon [3].

In vivo, after random mating in mice, Levonorgestrel (8mg/kg) isintraperitoneally injected immediately, and the frequency of ciliary beating of the fallopian tubes (CBF) in mice decreases significantly. The average percentage of embryo-tube retention in the Levonorgestrel group is 18.27% [4]. Oral administration of Levonorgestrel (0.67mg/kg/day) and quinestrol for 7 days significantly reduces sperm count in SD rats and decreases androgen receptor and Wilms tumor nuclear protein 1 (WT1) staining. Quinestrolalone or in combination with Levonorgestrel induces low fertility in male rats, primarily by interfering with reproductive cell differentiation [5].

References:
[1] Tellería CM, Carrizo DG, Deis RP. Levonorgestrel inhibits luteinizing hormone-stimulated progesterone production in rat luteal cells. J Steroid Biochem Mol Biol. 1994 Aug;50(3-4):161-6. 
[2] Xu Qing, et al. Levonorgestrel inhibits proliferation and induces apoptosis in uterine leiomyoma cells. Contraception vol. 82,3 (2010): 301-8. 
[3] Zhao X, Tang X, Ma T, et al. Levonorgestrel inhibits human endometrial cell proliferation through the upregulation of gap junctional intercellular communication via the nuclear translocation of Ser255 phosphorylated Cx43[J]. BioMed Research International, 2015, 2015(1): 758684.
[4] Li C, Zhang H Y, Liang Y, et al. Effects of Levonorgestrel and progesterone on Oviductal physiology in mammals[J]. Reproductive Biology and Endocrinology, 2018, 16(1): 59. 
[5] Liu M, Wan X, Yin Y, et al. Subfertile effects of quinestrol and levonorgestrel in male rats[J]. Reproduction, Fertility and Development, 2012, 24(2): 297-308.

Protokoll (Protocol)

Cell experiment [1]:

Cell lines

Human endometrial stromal cells (HESCs) and glandular cells (HEGCs)

Preparation Method

HESCs and HEGCs were placed in 200 μl of culture media per well in a 96-well plate with a density of 2 × 104 cells/mL and incubated overnight to allow the cells to attach to the wells. The cells were then treated with 2 μL of Levonorgestrel in a concentration course manner (1×10−3, 10, 25, or 50μM) and in a time course (24h, 48h, and 72h), with Estradiol (E2) as the opposite control, and DMSO (0.5%) as the negative control. The concentration of Levonorgestrel displaying an inhibitory effect and that of E2 exhibiting a stimulatory effect on cell proliferation (both were 50μM) were adopted as the final treating concentrations during the followed experiments determined according to the preliminary experiments. The concentration of 50μM Levonorgestrel is similar to that in the vivo endometrium in the presence of a mirena with a releasing rate of 20 μg/24 hours of Levonorgestrel. Subsequently, the MTT method was used for detection.

Reaction Conditions

1×10−3, 10, 25, or 50μM ; 24h, 48h and 72h

Applications

50μM Levonorgestrel inhibited the cell proliferation of primary HESCs significantly over time (24h, 48h, and 72h). 
Animal experiment [2]:

Animal models

C57BL/6

Preparation Method

Eight-week-old C57BL/6 J mice were used in this study (Shanghai Research Center for Model Organisms). All animal experiments were approved by the Medical Ethics Committee of Shanghai Research Center for Model Organisms. The mice were housed in a room at 25°C with a 12-h light:12-hdark cycle and 50–60% humidity and were given a standard diet (containing 10% fat) and water. Female mice (6–8 weeks of age) were mated randomly, and vaginal plug-positive mice were immediately injected intraperitoneally with saline, Levonorgestrel (8mg/kg), or Progesterone (8mg/kg). Twelve hours after observation of the vaginal plug, the mice were sacrificed via cervical dislocation to measure the CBF. Embryo-tube transportation assays were conducted as described by Ning et al. Seventy-four hours after observation of the vaginal plug, the oviducts and uterus were ligated. The embryos were flushed from the oviducts or uteri with PBS. We counted the embryos remaining in the oviducts, and the results are expressed as percentages of the total number of embryos.

Dosage form

8mg/kg once; i.p.

Applications

All the mice in the Levonorgestrel group experienced embryo-tube retention, with an average percentage of embryo retention of 18.27%, whereas none of the mice in the saline-treated group experienced embryo-tube retention. Consistently, the same effect was also observed in the Progesterone group, which had an average percentage of embryo retention of 15.37%, compared with the control group, which had an average percentage of 0%.

References:
[1]Zhao X, Tang X, Ma T, et al. Levonorgestrel inhibits human endometrial cell proliferation through the upregulation of gap junctional intercellular communication via the nuclear translocation of Ser255 phosphorylated Cx43[J]. BioMed Research International, 2015, 2015(1): 758684. 
[2]Li C, Zhang H Y, Liang Y, et al. Effects of Levonorgestrel and progesterone on Oviductal physiology in mammals[J]. Reproductive Biology and Endocrinology, 2018, 16(1): 59.

Produktdokumente (Product Documents)

Purity:>98.00%Appearance:A solid
COASDSData Sheet

Chemische Eigenschaften (Chemical Properties)

CAS-Nr.
797-63-7
Chemischer Name
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
SMILES
CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
Summenformel
C21H28O2
Molekulargewicht
312.45
Löslichkeit
≥ 13.8mg/mL in DMSO
Lagerung
Store at 2-8°C
Allgemeine Hinweise
Wählen Sie anhand der Löslichkeitsdaten des Produkts ein geeignetes Lösungsmittel. Aliquotieren Sie die Stammlösung nach der Herstellung, um wiederholte Gefrier-Auftau-Zyklen zu vermeiden.
Verwenden Sie Stammlösungen bei Lagerung bei -80°C innerhalb von 6 Monaten bzw. bei -20°C innerhalb von 1 Monat.
Zur Verbesserung der Löslichkeit das Röhrchen auf 37°C erwärmen und für eine angemessene Dauer beschallen.
Versandbedingungen
Evaluierungsmuster werden mit Kühlakkus versandt. Andere verfügbare Größen werden bei Raumtemperatur oder auf Anfrage mit Kühlakkus versandt.

Rechner (Calculators)Molarität / Verdünnung / Molekulargewicht / Einheitenumrechnung / In-vivo-Formulierung / Löslichkeit

g/mol

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