Levonorgestrel | CAS#797-63-7 | Hormone

MedKoo Cat#: 318103 | Name: Levonorgestrel

Description:

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

Levonorgestrel 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

CAS#797-63-7 (free)

Theoretical Analysis

MedKoo Cat#: 318103

Name: Levonorgestrel

CAS#: 797-63-7 (free)

Chemical Formula: C21H28O2

Exact Mass: 312.2089

Molecular Weight: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to Ship
200mg	USD 150.00	Ready to Ship
500mg	USD 350.00	Ready to Ship
1g	USD 550.00	Ready to Ship
2g	USD 700.00	Ready to Ship
5g	USD 950.00	Ready to Ship
10g	USD 1,450.00	Ready to Ship

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Related CAS #

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

Synonym

Levonorgestrel, Norgestrel, Microval, Postinor, Mirena, Plan B

IUPAC/Chemical Name

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

InChi Key

WWYNJERNGUHSAO-XUDSTZEESA-N

InChi Code

InChI=1S/C21H28O2/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/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

SMILES Code

CC[C@]12CC[C@H]3[C@@H](CCC4=CC(CC[C@H]34)=O)[C@@H]1CC[C@@]2(O)C#C

Appearance

White to off-white crystalline 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, not in water

Shelf Life

>2 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

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A24T03K28

QC Data

View QC data: current batch, Lot#A24T03K28

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Levonorgestrel is a synthetic progestogen used as an active ingredient in some hormonal contraceptives.

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/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	16.00
	DMSO	45.3	145.03
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.96
	Ethanol	1.1	3.52

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 312.45 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.

1: Jatlaoui TC, Riley H, Curtis KM. Safety data for levonorgestrel, ulipristal acetate and Yuzpe regimens for emergency contraception. Contraception. 2016 Feb;93(2):93-112. doi: 10.1016/j.contraception.2015.11.001. Epub 2015 Nov 3. Review. PubMed PMID: 26546020. 2: Dominick S, Hickey M, Chin J, Su HI. Levonorgestrel intrauterine system for endometrial protection in women with breast cancer on adjuvant tamoxifen. Cochrane Database Syst Rev. 2015 Dec 9;12:CD007245. doi: 10.1002/14651858.CD007245.pub3. Review. PubMed PMID: 26649916. 3: van Dijk MM, van Hanegem N, de Lange ME, Timmermans A. Treatment of Women With an Endometrial Polyp and Heavy Menstrual Bleeding: A Levonorgestrel-Releasing Intrauterine Device or Hysteroscopic Polypectomy? J Minim Invasive Gynecol. 2015 Nov-Dec;22(7):1153-62. doi: 10.1016/j.jmig.2015.06.016. Epub 2015 Jul 4. Review. PubMed PMID: 26151760. 4: Abu Hashim H, Ghayaty E, El Rakhawy M. Levonorgestrel-releasing intrauterine system vs oral progestins for non-atypical endometrial hyperplasia: a systematic review and metaanalysis of randomized trials. Am J Obstet Gynecol. 2015 Oct;213(4):469-78. doi: 10.1016/j.ajog.2015.03.037. Epub 2015 Mar 19. Review. PubMed PMID: 25797236. 5: Liletta--A Third Levonorgestrel-Releasing IUD. Med Lett Drugs Ther. 2015 Jul 6;57(1472):99-100. Review. PubMed PMID: 26147893. 6: Jóźwik M, Jóźwik M, Modzelewska B, Niewińska M, Jóźwik M. [Levonorgestrel-releasing intrauterine system Mirena® (Bayer) for the prevention and treatment of endometrial adenocarcinoma and the incidence of other malignancies in women]. Ginekol Pol. 2015 Apr;86(4):305-10. Review. Polish. PubMed PMID: 26117991. 7: Kahlenborn C, Peck R, Severs WB. Mechanism of action of levonorgestrel emergency contraception. Linacre Q. 2015 Feb;82(1):18-33. doi: 10.1179/2050854914Y.0000000026. Review. PubMed PMID: 25698840; PubMed Central PMCID: PMC4313438. 8: Qiu J, Cheng J, Wang Q, Hua J. Levonorgestrel-releasing intrauterine system versus medical therapy for menorrhagia: a systematic review and meta-analysis. Med Sci Monit. 2014 Sep 23;20:1700-13. doi: 10.12659/MSM.892126. Review. PubMed PMID: 25245843; PubMed Central PMCID: PMC4181308. 9: Jiang W, Shen Q, Chen M, Wang Y, Zhou Q, Zhu X, Zhu X. Levonorgestrel-releasing intrauterine system use in premenopausal women with symptomatic uterine leiomyoma: a systematic review. Steroids. 2014 Aug;86:69-78. doi: 10.1016/j.steroids.2014.05.002. Epub 2014 May 14. Review. PubMed PMID: 24832215. 10: Shohel M, Rahman MM, Zaman A, Uddin MM, Al-Amin MM, Reza HM. A systematic review of effectiveness and safety of different regimens of levonorgestrel oral tablets for emergency contraception. BMC Womens Health. 2014 Apr 4;14:54. doi: 10.1186/1472-6874-14-54. Review. PubMed PMID: 24708837; PubMed Central PMCID: PMC3977662. 11: Gizzo S, Di Gangi S, Bertocco A, Noventa M, Fagherazzi S, Ancona E, Saccardi C, Patrelli TS, D'Antona D, Nardelli GB. Levonorgestrel intrauterine system in adjuvant tamoxifen treatment: balance of breast risks and endometrial benefits--systematic review of literature. Reprod Sci. 2014 Apr;21(4):423-31. doi: 10.1177/1933719113503408. Epub 2013 Sep 23. Review. PubMed PMID: 24060633. 12: Lello S, Cavani A. Ethynilestradiol 20 mcg plus Levonorgestrel 100 mcg: Clinical Pharmacology. Int J Endocrinol. 2014;2014:102184. doi: 10.1155/2014/102184. Epub 2014 Nov 16. Review. PubMed PMID: 25477960; PubMed Central PMCID: PMC4247926. 13: Fu Y, Zhuang Z. Long-term effects of levonorgestrel-releasing intrauterine system on tamoxifen-treated breast cancer patients: a meta-analysis. Int J Clin Exp Pathol. 2014 Sep 15;7(10):6419-29. eCollection 2014. Review. PubMed PMID: 25400720; PubMed Central PMCID: PMC4230119. 14: Imai A, Matsunami K, Takagi H, Ichigo S. Levonorgestrel-releasing intrauterine device used for dysmenorrhea: five-year literature review. Clin Exp Obstet Gynecol. 2014;41(5):495-8. Review. PubMed PMID: 25864246. 15: Luo L, Luo B, Zheng Y, Zhang H, Li J, Sidell N. Levonorgestrel-releasing intrauterine system for atypical endometrial hyperplasia. Cochrane Database Syst Rev. 2013 Jun 5;6:CD009458. doi: 10.1002/14651858.CD009458.pub2. Review. PubMed PMID: 23737032. 16: Bayer LL, Hillard PJ. Use of levonorgestrel intrauterine system for medical indications in adolescents. J Adolesc Health. 2013 Apr;52(4 Suppl):S54-8. doi: 10.1016/j.jadohealth.2012.09.022. Review. PubMed PMID: 23535058. 17: Lowe RF, Prata N. Hemoglobin and serum ferritin levels in women using copper-releasing or levonorgestrel-releasing intrauterine devices: a systematic review. Contraception. 2013 Apr;87(4):486-96. doi: 10.1016/j.contraception.2012.09.025. Epub 2012 Nov 2. Review. PubMed PMID: 23122687. 18: Kim ML, Seong SJ. Clinical applications of levonorgestrel-releasing intrauterine system to gynecologic diseases. Obstet Gynecol Sci. 2013 Mar;56(2):67-75. doi: 10.5468/OGS.2013.56.2.67. Epub 2013 Mar 12. Review. PubMed PMID: 24327984; PubMed Central PMCID: PMC3784091. 19: Fraser IS. Added health benefits of the levonorgestrel contraceptive intrauterine system and other hormonal contraceptive delivery systems. Contraception. 2013 Mar;87(3):273-9. doi: 10.1016/j.contraception.2012.08.039. Epub 2012 Oct 4. Review. PubMed PMID: 23040129. 20: Abou-Setta AM, Houston B, Al-Inany HG, Farquhar C. Levonorgestrel-releasing intrauterine device (LNG-IUD) for symptomatic endometriosis following surgery. Cochrane Database Syst Rev. 2013 Jan 31;1:CD005072. doi: 10.1002/14651858.CD005072.pub3. Review. PubMed PMID: 23440798.