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[CAS NO. 797-63-7] Levonorgestrel

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Catalog:	HY-B0257
Brand:	MCE
CAS:	797-63-7

Overview

MDL	-
Molecular Weight	312.45
Molecular Formula	C21H28O2
SMILES	O=C1CC[C@]2([H])[C@@]3([H])CC[C@]4(CC)[C@@](C#C)(O)CC[C@@]4([H])[C@]3([H])CCC2=C1

For research use only. We do not sell to patients.

Summary

Levonorgestrel is a synthetic progestogen used as an active ingredient in some hormonal contraceptives. Target: Progesterone Receptor A synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Levonorgestrel is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Triphasil, and Min-Ovral [1].

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT04972396	Altimmune, Inc.	NASH - Nonalcoholic Steatohepatitis	October 5, 2021	Phase 1
NCT02357368	Lisa Haddad\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)\|Emory University	HIV\|Contraception	February 2015	Phase 4
NCT00360490	Bayer	Menorrhagia	July 2006	Phase 3
NCT01833793	Bayer	Female Contraception	February 2013
NCT04142762	Assembly Biosciences	Chronic Hepatitis B	October 18, 2019	Phase 1
NCT00551616	HRA Pharma	Contraception	April 2007	Phase 3
NCT01623466	Agile Therapeutics	Healthy	July 2012	Phase 1\|Phase 2
NCT01414140	Bayer	Contraception	May 2007
NCT01320917	University of Sao Paulo	Contraception Desired\|Obesity	February 2009	Phase 4
NCT01873170	University of Pittsburgh	HIV\|Immune Cells (Mucosal and Systemic)\|Contraception	August 2013
NCT02531321	University of Southern California	Contraception\|HIV	August 2015	Phase 4
NCT01508858	Novo Nordisk A+S	Diabetes\|Diabetes Mellitus, Type 2	November 2006	Phase 1
NCT02173808	Health Decisions\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	Contraceptive Usage	May 2011	Phase 1
NCT01096485	Bayer	Contraception\|Contraception, Postcoital	February 2009	Phase 1
NCT01240811	Sharon Achilles\|University of Pittsburgh	Genital Tract Mucosal Immunity\|Genital Tract Microflora	November 2010	Not Applicable
NCT02159131	ViiV Healthcare	Infections, Human Immunodeficiency Virus and Hepatitis	August 2014	Phase 1
NCT01230242	Rebecca Hunt\|MaineHealth	Estimating Rates of Expulsion	September 7, 2010	Not Applicable
NCT00781456	Duramed Research\|Teva Branded Pharmaceutical Products R&D, Inc.	Migraine	January 2009	Phase 2
NCT00204451	University of Saskatchewan\|Canadian Institutes of Health Research (CIHR)	Contraception	July 2005	Phase 4
NCT01963962	University of Utah	Emergency Contraception	July 2013
NCT00868153	Bayer	Idiopathic Menorrhagia	August 2004
NCT01595022	Bayer	Contraception	January 2010	Phase 1
NCT04897217	Wake Forest University Health Sciences\|National Cancer Institute (NCI)	Endometrial Hyperplasia	January 2023	Phase 3
NCT01297348	Pfizer\|Boston Collaborative Drug Surveillance Program	Venous Thrombosis\|Pulmonary Embolism\|Sinus Thrombosis, Intracranial	July 2007
NCT00924560	Duramed Research\|Teva Branded Pharmaceutical Products R&D, Inc.	Bone Mineral Density	June 2009	Phase 2
NCT05444582	University of Utah\|Planned Parenthood Federation of America	Contraception	November 15, 2022
NCT02002260	Women and Infants Hospital of Rhode Island	Abnormal Uterine Bleeding\|Abnormal Uterine Bleeding, Ovulatory Dysfunction\|Abnormal Uterine Bleeding, Endometrial Hemostatic Dysfunction	February 2013	Not Applicable
NCT00864136	Bayer	Menorrhagia	November 2008
NCT01085487	Bayer	Idiopathic Menorrhagia	April 2009
NCT03353012	Chulalongkorn University	Breastfeeding\|Post Partum	January 1, 2018	Phase 4
NCT03819114	AIDS Clinical Trials Group\|National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections\|Tuberculosis	May 6, 2019	Phase 2
NCT02021097	Regenex Pharmaceutical, China	Oral Contraceptive	February 2012	Phase 3
NCT03455075	Health Decisions\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)\|Lundquist Institute for Biomedical Innovation at Harbor-UCLA Medical Center\|University of Washington	Healthy\|Men\|Male Contraception	April 16, 2018	Phase 2
NCT00922233	FHI 360	Healthy	January 2010	Phase 3
NCT02957292	Fundació Institut de Recerca de l´Hospital de la Santa Creu i Sant Pau\|Bayer	Contraception	June 1, 2016	Phase 4
NCT00445887	Gynecologic Oncology Group\|National Cancer Institute (NCI)\|GOG Foundation	Ovarian Carcinoma	March 10, 2008	Phase 2
NCT04785950	Bayer	Hormonal Intrauterine Contraception	February 25, 2021
NCT00621543	Boston University\|University of Utah	Intrauterine Device Expulsion\|Medical Abortion\|Induced Abortion	March 2006	Not Applicable
NCT01539720	Planned Parenthood of the St. Louis Region and Southwest Missouri\|William and Flora Hewlett Foundation\|University of Colorado, Denver\|Planned Parenthood Federation of America\|University of Rochester	Pregnancy, Unplanned\|Pregnancy; Accident	December 2012	Not Applicable
NCT01789879	University of Nebraska\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)\|Makerere University\|University of Liverpool	HIV\|Contraception	June 2013	Phase 2
NCT01328184	Boehringer Ingelheim	Healthy	April 2011	Phase 1
NCT02104609	University of Southern California\|Society of Family Planning	Obesity	April 2013
NCT00271583	University of Pittsburgh\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	Emergency Contraception	September 1999	Phase 2\|Phase 3
NCT01291004	Teva Branded Pharmaceutical Products R&D, Inc.	Follicle Development\|Ovarian Follicle\|Follicle Count\|Follicle Size\|Oral Contraceptive	January 31, 2011	Phase 1
NCT00455845	Mahidol University	Endometriosis\|Pelvic Pain\|Dysmenorrhea	April 2007	Phase 3
NCT03359057	Galeno Desenvolvimento de Pesquisas Clínicas\|Biolab Sanus Farmaceutica	Contraception	February 26, 2013	Phase 3
NCT01731132	Bayer	Contraception	July 2012
NCT00931827	Bayer	Contraception	January 2008
NCT00131885	University of Utah\|National Center for Complementary and Integrative Health (NCCIH)	Contraception	August 2005	Phase 4
NCT04676776	Gynuity Health Projects\|Cuidado Integral de la Mujer, Gineclinic, S.C.	Missed Menstrual Period	January 25, 2021	Phase 2
NCT01250210	Agile Therapeutics	Ovulation Suppression	September 2007	Phase 2
NCT02475356	Bayer	Menorrhagia, Dysmenorrhea	August 4, 2015
NCT03537768	Health Decisions\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	Contraception	July 12, 2018	Phase 4
NCT01590537	Bayer	Contraception	September 2011
NCT01686126	Queensland Centre for Gynaecological Cancer\|The University of Queensland\|Queensland University of Technology	Complex Endometrial Hyperplasia With Atypia\|Grade 1 Endometrial Endometrioid Adenocarcinoma	December 2012	Phase 2
NCT00669396	University of Utah	Pregnancy	April 2008	Not Applicable
NCT02574715	Bayer	Quality of Life	September 18, 2015
NCT05044962	University of Washington\|Moi Teaching and Referral Hospital\|Indiana University\|University of Nebraska\|National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections\|Contraception\|Drug-drug Interaction	November 26, 2021	Not Applicable
NCT01721798	FHI 360\|University of Cape Town\|City University of New York, School of Public Health	HIV	November 10, 2013	Not Applicable
NCT01252186	Teva Women´s Health\|Teva Branded Pharmaceutical Products R&D, Inc.	Hemostasis\|Oral Contraceptive	November 2010	Phase 2
NCT01166412	Health Decisions\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	Contraception	December 2010	Phase 1\|Phase 2
NCT00520455	University of Washington\|Centers for Disease Control and Prevention	Pregnancy	January 2004	Not Applicable
NCT02362373	Columbia University\|Bayer	Epilepsy\|Contraception	August 2011	Phase 4
NCT00570440	FHI 360\|La Asociación Pro Bienestar de la Familia de Guatemala (APROFAM)	Pregnancy Prevention	August 2007	Phase 4
NCT01044056	Organon and Co	Contraception	March 2004	Phase 4
NCT00511355	Organon and Co	Contraception	October 2006	Phase 3
NCT02403401	Bayer	Contraception	May 15, 2015	Phase 3
NCT04230070	Laboratorios Andromaco S.A.	Bioequivalence	October 24, 2020	Phase 1
NCT00490087	IRCCS Burlo Garofolo	Atypical Endometrial Polyps\|Atypical Endometrial Hyperplasia	January 1999	Phase 3
NCT00237042	University of Washington\|National Institute of Dental and Craniofacial Research (NIDCR)	Temporomandibular Joint Disorders	October 2005	Not Applicable
NCT01990703	University of Utah\|Society of Family Planning\|University of New Mexico	Contraception	January 2014	Phase 4
NCT04872244	Gaziosmanpasa Research and Education Hospital	Isthmocele\|Post-menstrual Spotting Bleeding\|Pelvic Pain	November 3, 2019	Not Applicable
NCT04385667	Zagazig University	Atypical Endometrial Hyperplasia	May 20, 2020	Phase 2\|Phase 3
NCT04194905	Laboratorios Andromaco S.A.	Bioequivalence	November 21, 2020	Phase 1
NCT03249402	Janssen-Cilag International NV	Healthy	August 14, 2017	Phase 1
NCT01074892	University Hospital of North Norway\|Helse Nord\|Norwegian Cancer Society	Endometrial Hyperplasia	May 2005	Phase 4
NCT04814927	Eastern Virginia Medical School\|CONRAD\|Kenya Medical Research Institute\|United States Agency for International Development (USAID)	Mucosal Inflammation\|Contraceptive; Complications, Intrauterine	March 1, 2021	Phase 4
NCT02903888	Bayer	Intrauterine Devices, Medicated	September 8, 2016
NCT02556411	University of Cagliari	Adenomyosis\|Chronic Pelvic Pain	June 1, 2021	Not Applicable
NCT01165307	Abimbola Famuyide\|Hologic, Inc.\|Mayo Clinic	Menorrhagia	August 2009	Phase 4
NCT01501448	IVI Madrid	Infertility	January 2012	Phase 4
NCT03642210	Medicines360	Menorrhagia	January 17, 2019	Phase 3
NCT00185380	Bayer	Contraception	April 2005	Phase 2
NCT05343546	Makerere University\|Karolinska Institutet	Incomplete Abortion\|Intrauterine Contraception\|Misoprostol	June 2022	Not Applicable
NCT00433004	University of Pennsylvania	Post Partum	February 2007	Phase 4
NCT03660046	Emory University\|National Institutes of Health (NIH)\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	Hormonal Contraception	December 7, 2018
NCT01088178	United States Naval Medical Center, Portsmouth	Contraception	November 2009	Not Applicable
NCT02577601	Oregon Health and Science University\|Society of Family Planning	Contraception	September 8, 2015	Phase 4
NCT01594476	Oregon Health and Science University\|Society of Family Planning	Contraception	March 2012	Phase 4
NCT01570244	Boehringer Ingelheim	Hepatitis C, Chronic	April 2012	Phase 1
NCT00161226	University of Medicine and Dentistry of New Jersey\|Rutgers, The State University of New Jersey	Endometrial Cancer	February 2004
NCT01073904	Bayer	Contraceptives, Postcoital	September 2009	Phase 1
NCT04058873	Camber Collective\|Population Council\|Marie Stopes International\|Bill and Melinda Gates Foundation\|The Children´s Investment Fund Foundation	Pregnancy Related	October 1, 2019
NCT01157754	IVI Madrid	Infertility	June 2009	Not Applicable
NCT03074045	Bayer	Contraception	March 13, 2017	Phase 3
NCT00874653	Bayer	Menorrhagia	April 2008
NCT02121067	University of North Carolina, Chapel Hill\|Society of Family Planning	Contraception\|Malposition of Intrauterine Contraceptive Device	September 2014	Phase 4
NCT02846142	Proteostasis Therapeutics, Inc.	Healthy Volunteer	June 2016	Phase 1
NCT00248963	Wyeth is now a wholly owned subsidiary of Pfizer	Oral Contraceptive		Phase 3
NCT00393198	Bayer	Contraception\|Menorrhagia	October 2006	Phase 4
NCT01096498	Bayer	Contraception\|Contraception, Postcoital	February 2009	Phase 1
NCT00245921	Wyeth is now a wholly owned subsidiary of Pfizer	Contraception	February 2003	Phase 3
NCT00909857	Bayer	Primary Dysmenorrhea	April 2009	Phase 3
NCT02722421	University of Nebraska\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)\|Infectious Diseases Institute, Uganda\|University of Liverpool\|Northwestern University Feinberg School of Medicine	HIV\|Contraception	April 6, 2017	Phase 2
NCT02599077	Fundación Santa Fe de Bogota	Endometriosis	November 2015	Phase 2\|Phase 3
NCT02203331	Bayer	Endometriosis	October 16, 2014	Phase 2
NCT02480647	University of Campinas, Brazil	Endometriosis	May 2016	Phase 4
NCT02985541	Bayer	Contraception	December 22, 2016	Phase 3
NCT00302848	Center for Epidemiology and Health Research, Germany\|Bayer Healthcare Pharmaceuticals, Inc.+Bayer Schering Pharma	Contraception	November 2000
NCT00254189	Wyeth is now a wholly owned subsidiary of Pfizer	Ovulation	December 2002	Phase 2
NCT00884260	Bayer	Contraception	April 2009	Phase 3
NCT01286948	Population Council	Female Contraception	January 2011	Phase 1
NCT03317795	Shannon K. Laughlin-Tommaso\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)\|Mayo Clinic	Heavy Menstrual Bleeding\|Menorrhagia\|Uterine Fibroids	November 14, 2017	Phase 4
NCT01254292	Bayer	Contraception	January 6, 2011	Phase 3
NCT00475228	University of Pittsburgh	Contraceptive Usage	March 2007	Phase 4
NCT03614494	Dr. Hang Wun Raymond Li\|The Family Planning Association of Hong Kong\|The University of Hong Kong	Emergency Contraception	August 20, 2018	Phase 2\|Phase 3
NCT02158845	University of Sao Paulo\|Fundação de Amparo à Pesquisa do Estado de São Paulo\|Conselho Nacional de Desenvolvimento Científico e Tecnológico	Endometriosis	February 2010	Phase 4
NCT02545452	Bayer	Endometriosis	September 15, 2015	Phase 1
NCT02349815	Bayer\|Karolinska Institutet, Stockholm, Sweden	Contraception	January 1, 2017
NCT01958684	Bayer	Contraception	October 2013
NCT03305081	Tulane University School of Medicine\|Tulane University	Contraception	October 22, 2014	Not Applicable
NCT05282940	Laboratorios Andromaco S.A.	Therapeutic Equivalency	February 26, 2022	Phase 1
NCT00662454	Oregon Health and Science University\|National Institutes of Health (NIH)\|Oregon Clinical and Translational Research Institute	Contraception\|Body Weight	January 2006	Phase 4
NCT03589027	Makerere University\|University of Nebraska\|University of Pittsburgh\|University of Liverpool	HIV-1-infection\|Contraception	August 7, 2018	Phase 2
NCT00685906	AstraZeneca	Healthy	April 2008	Phase 1
NCT04143659	Health Decisions\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	Healthy Women\|Female Contraception	March 3, 2020	Phase 1
NCT03104309	Assiut University	Adenomyosis	June 2015	Not Applicable
NCT04910711	Botswana Harvard AIDS Institute Partnership\|University of Liverpool	Human Immunodeficiency Virus\|Contraception\|ART	October 21, 2021	Phase 4
NCT00883662	Bayer	Contraception\|Menorrhagia\|Endometrial Hyperplasia\|Estrogen Replacement Therapy	May 2009
NCT00966771	University of Utah\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)\|Society of Family Planning	Pregnancy	October 2009
NCT02175030	University of Utah	Contraception	August 2016	Phase 4
NCT03778359	Taipei Veterans General Hospital, Taiwan	Endometriosis\|Adenomyosis	January 1, 2005
NCT05093205	Pfizer	Healthy Adults	October 25, 2021	Phase 1

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 100 mg/mL ( 320.05 mM ; ultrasonic and warming and heat to 60°C)

H ₂ O : < 0.1 mg/mL (insoluble)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	3.2005 mL	16.0026 mL	32.0051 mL
5 mM	0.6401 mL	3.2005 mL	6.4010 mL
10 mM	0.3201 mL	1.6003 mL	3.2005 mL

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)

Solubility: ≥ 2.5 mg/mL (8.00 mM); Clear solution

* All of the co-solvents are available by MCE.

References

[1] Gallos, I.D., et al., Oral progestogens vs levonorgestrel-releasing intrauterine system for endometrial hyperplasia: a systematic review and metaanalysis. Am J Obstet Gynecol, 2010. 203(6): p. 547 e1-10.

Synonyms

18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17α)-

18,19-Dinor-17α-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-

(17α)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one

13-Ethyl-17α-ethynylgon-4-en-17β-ol-3-one

13β-Ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-one

19-Nortestosterone, 17-ethynyl-18-methyl-

17β-Hydroxy-18-methyl-19-nor-17α-pregn-4-en-20-yn-3-one

18-Methyl-17α-ethynyl-19-nortestosterone

17α-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one

17α-Ethynyl-18-methyl-19-nortestosterone

13-Ethyl-17α-ethynyl-17-hydroxygon-4-en-3-one

13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one

17α-Ethynyl-18-homo-19-nortestosterone

13-Ethyl-17-ethynyl-17β-hydroxy-4-gonen-3-one

17α-Ethynyl-13β-ethyl-3-oxo-4-estren-17β-ol

Levonorgestrel

17α-Ethynyl-13-ethyl-19-nortestosterone

Norplant

Follistrel

D-(-)-Norgestrel

Norplant 2

18-Methylnorethindrone

Microluton

(-)-Norgestrel

D-Norgestrel

Norplant II

Levonova

Jadelle

Norlevo

Mirena

Norgestrelem

Wy 5104

Microlut

Norgeston

Dexnorgestrel

Microval

Postinor 2

Lng-IUS

d-(17α)-17-Hydroxy-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one

Femilis

Femilis Slim

Sino-implant (II)

Plan B One-Step

Skyla

Jaydess

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