MedKoo Cat#: 598733 | Name: Levonorgestrel hexanoate

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 hexanoate
CAS#13635-16-0 (hexanoate)

Theoretical Analysis

MedKoo Cat#: 598733

Name: Levonorgestrel hexanoate

CAS#: 13635-16-0 (hexanoate)

Chemical Formula: C27H38O3

Exact Mass: 410.2821

Molecular Weight: 410.60

Elemental Analysis: C, 78.98; H, 9.33; O, 11.69

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.
Bulk Inquiry
Synonym
Levonorgestrel hexanoate; Plan B;
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 hexanoate
InChi Key
MQEMIBNIYXQPDK-VGSPSRCMSA-N
InChi Code
InChI=1S/C27H38O3/c1-4-7-8-9-25(29)30-27(6-3)17-15-24-23-12-10-19-18-20(28)11-13-21(19)22(23)14-16-26(24,27)5-2/h3,18,21-24H,4-5,7-17H2,1-2H3/t21-,22+,23+,24-,26-,27+/m0/s1
SMILES Code
C#C[C@@]1(OC(CCCCC)=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
Biological target:
Levonorgestrel hexanoate 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 410.60 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.

Recalculate based on batch purity %
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:
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.
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.
1: Wood MH, Clarke SM. (S)-(-)-1-Phenyl-ethanaminium hexa-noate. Acta Crystallogr Sect E Struct Rep Online. 2012 Dec 1;68(Pt 12):o3335. doi: 10.1107/S1600536812045746. Epub 2012 Nov 10. PubMed PMID: 23476173; PubMed Central PMCID: PMC3588937. 2: Dorwin EL, Shaw AA, Hom K, Bethel P, Sheltar MD. Photoexchange products of cytosine and 5-methylcytosine with N alpha-acetyl-L-lysine and L-lysine. J Photochem Photobiol B. 1988 Sep;2(2):265-78. PubMed PMID: 3149993. 3: D'Agnolo G, Rosenfeld IS, Vagelos PR. Beta-Ketoacyl-acyl carrier protein synthetase. Characterization of the acyl-enzyme intermediate. J Biol Chem. 1975 Jul 25;250(14):5283-8. PubMed PMID: 237913. 4: Legrand D, Mazurier J, Elass A, Rochard E, Vergoten G, Maes P, Montreuil J, Spik G. Molecular interactions between human lactotransferrin and the phytohemagglutinin-activated human lymphocyte lactotransferrin receptor lie in two loop-containing regions of the N-terminal domain I of human lactotransferrin. Biochemistry. 1992 Sep 29;31(38):9243-51. PubMed PMID: 1327110.