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Gestodene (SHB 331; WL 70)

Alias: SH B 331; Gestodene; Gestoden; Gestodenum; Gestodeno; Gestodenum; Gestoden; Gestodene; Gestodene, SHB 331;SHB-331;WL-70; SHB 331; WL 70; SHB331; WL70
Cat No.:V1754 Purity: ≥98%
Gestodene (WL-70, Δ15-norgestrel or 15-dehydronorgestrel; Gestodeno; Gestodenum; Gestoden; Gestodene; Gestodene, SHB 331;SHB-331;WL-70; SHB 331; WL 70; SHB331; WL70) is a potent progestogen hormonal contraceptive.
Gestodene (SHB 331; WL 70)
Gestodene (SHB 331; WL 70) Chemical Structure CAS No.: 60282-87-3
Product category: Estrogenprogestogen Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
250mg
500mg
1g
Other Sizes

Other Forms of Gestodene (SHB 331; WL 70):

  • Gestodene-d6 (SHB 331-d6; WL 70-d6)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Gestodene (WL-70, Δ15-norgestrel or 15-dehydronorgestrel; Gestodeno; Gestodenum; Gestoden; Gestodene; Gestodene, SHB 331; SHB-331;WL-70; SHB 331; WL 70; SHB331; WL70) is a potent progestogen hormonal contraceptive. It is a steroidal progestin of the 19-nortestosterone group related to norgestrel and levonorgestrel that is used in combination with ethinylestradiol as a hormonal contraceptive. Contraceptive pills containing gestodene do not exhibit the androgenic side effects associated with second-generation contraceptive pills.

Biological Activity I Assay Protocols (From Reference)
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
in vitro 99% using 3H=R5020 / in vivo similar to progesterone
Orally administered gestodene is rapidly and completely absorbed.
The absolute bioavailability of gestodene was determined to be 99% of the dose administered.
For gestodene, an apparent volume of distribution of 0.7 L/kg and a metabolic clearance rate from serum of about 0.8 mL/min/kg were determined.
Following ingestion of 0.1 mg gestodene together with 0.03 mg ethinylestradiol (which represents the combination with the highest gestodene content of the tri-step formulation), maximum drug serum levels of about 5.6 ng/mL are reached at 0.5 hour.
For more Absorption, Distribution and Excretion (Complete) data for GESTODENE (8 total), please visit the HSDB record page.
Metabolism / Metabolites
The biotransformation follows the known pathways of steroid metabolism. No pharmacologically active metabolites are known.
Gestodene is metabolized primarily in the liver by CYP 3A4 and is a strong inducer of this enzyme. Although ethinylestradiol is also metabolized by CYP 3A4, gestodene does not appear to inhibit its metabolism. Known metabolites of gestodene include dihydrogestodene, 3,5-tetrahydrogestodene and hydroxygestodene.
There is limited information on the metabolism of levonorgestrel, norethindrone and structurally related contraceptive steroids. Both levonorgestrel and norethindrone undergo extensive reduction of the alpha, beta-unsaturated ketone in ring A. Levonorgestrel also undergoes hydroxylation at carbons 2 and 16. The metabolites of both compounds circulate predominantly as sulfates. In urine, levonorgestrel metabolites are found primarily in the glucuronide form, whereas norethindrone metabolites are present in approximately equal amounts as sulfates and glucuronides. Of the progestogens structurally related to norethindrone, norethindrone acetate, ethynodiol diacetate, norethindrone enanthate, and perhaps lynestrenol, undergo rapid hydrolysis and are converted to the parent compound and its metabolites. There is no convincing evidence that norethynodrel is converted to norethindrone. Of the progestogens structurally related to levonorgestrel, it appears that neither desogestrel nor gestodene are transformed to the parent compound. However, there is evidence that norgestimate can be, at least partly, converted to levonorgestrel. ...
Biological Half-Life
16 to 18 hrs.
Gestodene serum levels decrease in two phases, characterised by half-lives of 0.1 hours and about 18 hours.
The half-life of elimination of gestodene was shown to range from 12 to 14 hr for the three doses studied (0.025, 0.075 or 0.125 mg gestodene).
Gestodene is not excreted in unchanged form but as metabolites, which are eliminated with a half-life of about 1 day.
Toxicity/Toxicokinetics
Interactions
... In a parallel-group study, 15 healthy women using OCs and 15 healthy women without OCs (control subjects) ingested a single dose of 4 mg tizanidine. Plasma and urine concentrations of tizanidine, as well as several of its metabolites (M-3, M-4, M-5, M-9, and M-10), and pharmacodynamic variables were measured until 24 hours after dosing. As a marker of CYP1A2 activity, an oral caffeine test was performed in both groups. The mean area under the plasma concentration-time curve from time 0 to infinity [AUC0-infinity] of tizanidine was 3.9 times greater (P<.001) and the mean peak plasma tizanidine concentration (Cmax) was 3.0 times higher (P<.001) in the OC users than in the control subjects. In 1 OC user the AUC0-infinity of tizanidine exceeded the mean AUC0-infinity of the control subjects by nearly 20 times. There were no significant differences in the elimination half-life or time to peak concentration in plasma of tizanidine between the groups. Tizanidine/metabolite ratios in plasma (M-3 and M-4) and urine (M-3, M-4, M-5, M-9, and M-10) were 2 to 10 times higher in the users of OCs than in the control subjects. In the OC group the excretion of unchanged tizanidine into urine was, on average, 3.8 times greater (P=.008) than in the control subjects. The plasma caffeine/paraxanthine ratio was 2.8 times higher (P<.001) in the OC users than in the control subjects. The caffeine/paraxanthine ratio correlated significantly with the AUC0-infinity and peak concentration of tizanidine in plasma, with its excretion into urine, and with, for example, the tizanidine/M-3 and tizanidine/M-4 area under the plasma concentration-time curve ratios. Both the systolic and diastolic blood pressures were lowered by tizanidine more in the OC users (-29+/- 10 mm Hg and -21+/- 8 mm Hg, respectively) than in the control subjects (-17+/- 9 mm Hg and -13+/- 5 mm Hg, respectively) (P < .01). OCs containing ethinyl estradiol and gestodene increase, to a clinically significant extent, the plasma concentrations and effects of tizanidine, probably mainly by inhibiting its CYP1A2-mediated presystemic metabolism. Care should be exercised when tizanidine is prescribed to OC users.
Non-Human Toxicity Values
LD50 Mouse oral 6 g/kg
References

[1]. Spona, J. and J. Huber, Pharmacological and endocrine profiles of gestodene. Int J Fertil, 1987. 32 Suppl: p. 6-14.

[2]. Lack of binding of gestodene to estrogen receptor in human breast cancer tissue. Eur J Cancer, 1990. 26(5): p. 608-10.

Additional Infomation
Therapeutic Uses
Contraceptives, oral, Synthetic; Progestational hormones, Synthetic
/Triadene is indicated for/ oral contraception and the recognized gynecological indications for such estrogen-progestogen combinations.
Drug Warnings
Some epidemiological studies have suggested an association between the use of combined oral contraceptives (COCs) and an increased risk of arterial and venous thrombotic and thromboembolic diseases such as myocardial infarction, stroke, deep venous thrombosis and pulmonary embolism. These events occur rarely. Full recovery from such disorders does not always occur, and it should be realised that in a few cases they are fatal.
/Contraindications for Triadene include/: Pregnancy; severe disturbances of liver function, jaundice or persistent itching during a previous pregnancy, Dubin-Johnson syndrome, Rotor syndrome, previous or existing liver tumors; history of confirmed venous thromboembolism (VTE). Family history of idiopathic VTE. Other known risk factors for VTE; existing or previous arterial thrombotic or embolic processes, conditions which predispose to them eg disorders of the clotting processes, valvular heart disease and atrial fibrillation; Sickle-cell anemia; mammary or endometrial carcinoma, or a history of these conditions; severe diabetes mellitus with vascular changes; disorders of lipid metabolism; history of herpes gestationis; deterioration of otosclerosis during pregnancy; undiagnosed abnormal vaginal bleeding; hypersensitivity to any of the components of Triadene.
The following conditions require strict medical supervision during medication with oral contraceptives. Deterioration or first appearance of any of these conditions may indicate that use of the oral contraceptive should be discontinued: diabetes mellitus, or a tendency towards diabetes mellitus (eg unexplained glycosuria), hypertension, varicose veins, a history of phlebitis, otosclerosis, multiple sclerosis, epilepsy, porphyria, tetany, disturbed liver function, Sydenham's chorea, renal dysfunction, family history of clotting disorders, obesity, family history of breast cancer and patient history of benign breast disease, history of clinical depression, systemic lupus erythematosus, uterine fibroids and migraine, gall-stones, cardiovascular diseases, chloasma, asthma, an intolerance to contact lenses, or any disease that is prone to worsen during pregnancy.
In rare cases, headaches, gastric upsets, nausea, vomiting, breast tenderness, changes in body weight, changes in libido, depressive moods can occur.
For more Drug Warnings (Complete) data for GESTODENE (44 total), please visit the HSDB record page.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H26O2
Molecular Weight
310.43
Exact Mass
310.193
CAS #
60282-87-3
Related CAS #
Gestodene-d6;1542211-40-4
PubChem CID
3033968
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
462.7±45.0 °C at 760 mmHg
Melting Point
190-192°C
Flash Point
196.9±21.3 °C
Vapour Pressure
0.0±2.6 mmHg at 25°C
Index of Refraction
1.588
LogP
3.65
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
23
Complexity
648
Defined Atom Stereocenter Count
6
SMILES
CC[C@]12CC[C@H]3[C@H]([C@@H]1C=C[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
InChi Key
PCGOZSMTJRCWQF-ZUHHCLADSA-N
InChi Code
InChI=1S/C21H26O2/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/h2,5,10,12,16-19,23H,3,6-9,11,13H2,1H3/t16-,17+,18+,19-,20-,21+/m0/s1
Chemical Name
(17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-5,15-dien-20-yn-3-one
Synonyms
SH B 331; Gestodene; Gestoden; Gestodenum; Gestodeno; Gestodenum; Gestoden; Gestodene; Gestodene, SHB 331;SHB-331;WL-70; SHB 331; WL 70; SHB331; WL70
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO:62 mg/mL (199.7 mM)
Water:<1 mg/mL
Ethanol:8 mg/mL (25.8 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.75 mg/mL (8.86 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 27.5 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: ≥ 2.75 mg/mL (8.86 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 27.5 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.

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Solubility in Formulation 3: ≥ 2.75 mg/mL (8.86 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2213 mL 16.1067 mL 32.2134 mL
5 mM 0.6443 mL 3.2213 mL 6.4427 mL
10 mM 0.3221 mL 1.6107 mL 3.2213 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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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.
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