Levonorgestrel butyrate | CAS#86679-33-6 | birth control

MedKoo Cat#: 598734 | Name: Levonorgestrel butyrate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levonorgestrel butyrate is a manufactured hormone used in a number of birth control methods. In pill form, it is useful within 120 hours as emergency birth control. It becomes less effective the longer after sex and only works before pregnancy has occurred. It is also combined with an estrogen to make combined oral birth control pill. Within an IUD, it is effective for long term prevention of pregnancy. An implantable form of levonorgestrel is also marketed in some countries.

Chemical Structure

Levonorgestrel butyrate

CAS#86679-33-6 (butyrate)

Theoretical Analysis

MedKoo Cat#: 598734

Name: Levonorgestrel butyrate

CAS#: 86679-33-6 (butyrate)

Chemical Formula: C25H34O3

Exact Mass: 382.2508

Molecular Weight: 382.54

Elemental Analysis: C, 78.49; H, 8.96; O, 12.55

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

797-63-7 (free) 13635-16-0 (hexanoate) 86679-33-6 (butyrate)

Synonym

Levonorgestrel butyrate;

IUPAC/Chemical Name

(8R,9S,10R,13S,14S,17S)-13-ethyl-17-ethynyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl butyrate

InChi Key

GPKLGCALNRZIDS-KRTHDRFRSA-N

InChi Code

InChI=1S/C25H34O3/c1-4-7-23(27)28-25(6-3)15-13-22-21-10-8-17-16-18(26)9-11-19(17)20(21)12-14-24(22,25)5-2/h3,16,19-22H,4-5,7-15H2,1-2H3/t19-,20+,21+,22-,24-,25+/m0/s1

SMILES Code

C#C[C@@]1(OC(CCC)=O)CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4([H])[C@@]3([H])CC[C@]12CC)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Levonorgestrel butyrate is a manufactured hormone used in a number of birth control methods.

In vitro activity:

The effects of the synthetic progestin levonorgestrel (LNG) on basal and LH-stimulated progesterone production were studied in collagenase-dispersed luteal cells obtained from 9-day pregnant rats. Luteal cells responded to ovine LH (oLH) with an increase in progesterone output which was maximal at a dose of 100 ng/ml. On the other hand, a dose of 10 microM LNG suppressed the stimulation of progesterone secretion induced by oLH, dibutyryl-cAMP and pregnenolone. Reference: J Steroid Biochem Mol Biol. 1994 Aug;50(3-4):161-6. https://pubmed.ncbi.nlm.nih.gov/8049144/

In vivo activity:

The effects of levonorgestrel (LNG) on serum levels of reproductive hormones and their receptor mRNA expression in the ovary and uterus of Mongolian gerbils were examined. The results show that serum follicle-stimulating hormone (FSH) and luteinizing hormone (LH) increased, whereas serum estradiol (E2) and progesterone (P4) decreased profoundly after LNG treatment. The findings suggest that LNG impairs reproductive hormone receptor expression at the molecular level in Mongolian gerbils. Reference: Exp Anim. 2011;60(4):363-71. https://pubmed.ncbi.nlm.nih.gov/21791876/

Preparing Stock Solutions

The following data is based on the product molecular weight 382.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Lira-Albarrán S, Larrea-Schiavon MF, González L, Durand M, Rangel C, Larrea F. The effects of levonorgestrel on FSH-stimulated primary rat granulosa cell cultures through gene expression profiling are associated to hormone and folliculogenesis processes. Mol Cell Endocrinol. 2017 Jan 5;439:337-345. doi: 10.1016/j.mce.2016.09.020. Epub 2016 Sep 20. PMID: 27663078. 2. 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. doi: 10.1016/0960-0760(94)90023-x. PMID: 8049144. 3. Lv XH, Shi DZ. Effects of levonorgestrel on reproductive hormone levels and their receptor expression in Mongolian gerbils (Meriones unguiculatus). Exp Anim. 2011;60(4):363-71. doi: 10.1538/expanim.60.363. PMID: 21791876. 4. Herkert O, Kuhl H, Busse R, Schini-Kerth VB. The progestin levonorgestrel induces endothelium-independent relaxation of rabbit jugular vein via inhibition of calcium entry and protein kinase C: role of cyclic AMP. Br J Pharmacol. 2000 Aug;130(8):1911-8. doi: 10.1038/sj.bjp.0703524. PMID: 10952682; PMCID: PMC1572279.

In vitro protocol:

In vivo protocol:

1. Lv XH, Shi DZ. Effects of levonorgestrel on reproductive hormone levels and their receptor expression in Mongolian gerbils (Meriones unguiculatus). Exp Anim. 2011;60(4):363-71. doi: 10.1538/expanim.60.363. PMID: 21791876. 2. Herkert O, Kuhl H, Busse R, Schini-Kerth VB. The progestin levonorgestrel induces endothelium-independent relaxation of rabbit jugular vein via inhibition of calcium entry and protein kinase C: role of cyclic AMP. Br J Pharmacol. 2000 Aug;130(8):1911-8. doi: 10.1038/sj.bjp.0703524. PMID: 10952682; PMCID: PMC1572279.

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