Levonorgestrel

  • CAT Number: A000355
  • CAS Number: 797-63-7
  • Molecular Formula: C21H28O2
  • Molecular Weight: 312.5
  • Purity: ≥95%
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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.

Catalog Number A000355
CAS Number 797-63-7
Molecular Formula

C21H28O2

Purity 95%
Target Estrogen/progestogen Receptor
Solubility >13.8mg/mL in DMSO
Storage -20°C
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
InChIKey WWYNJERNGUHSAO-XUDSTZEESA-N
SMILES CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
Reference

1: Shaaban OM, Abbas AM, Mahmoud HR, Yones EM, Hassen SG, Zakherah MS. Counseling
and in-advance provision of levonorgestrel emergency contraceptive pills decrease
the rate of unplanned pregnancy during breastfeeding: a randomized controlled
trial. J Matern Fetal Neonatal Med. 2017 Nov 8:1-111. doi:
10.1080/14767058.2017.1403580. [Epub ahead of print] PubMed PMID: 29117764.
<br>

2: Alegre-Del Rey EJ, Fénix-Caballero S, Díaz-Navarro J. [Controversies about the
mechanism of postcoital levonorgestrel: evidences according to the decrease of
pregnancies]. Farm Hosp. 2017 Nov 1;41(6):696-697. doi: 10.7399/fh.10811.
Spanish. PubMed PMID: 29112497.
<br>

3: Cardoso PG, Loganimoce EM, Neuparth T, Rocha MJ, Rocha E, Arenas F.
Interactive effects of increased temperature, pCO(2) and the synthetic progestin
levonorgestrel on the fitness and breeding of the amphipod Gammarus locusta.
Environ Pollut. 2017 Oct 25. pii: S0269-7491(17)32868-3. doi:
10.1016/j.envpol.2017.10.065. [Epub ahead of print] PubMed PMID: 29102173.

<br>
4: Bahamondes L, Fernandes A, Bahamondes MV, Juliato CT, Ali M, Monteiro I.
Pregnancy outcomes associated with extended use of the 52-mg 20μg/day
levonorgestrel-releasing intrauterine system beyond 60months: A chart review of
776 women in Brazil. Contraception. 2017 Oct 18. pii: S0010-7824(17)30495-X. doi:
10.1016/j.contraception.2017.10.007. [Epub ahead of print] PubMed PMID: 29055780.
<br>

5: Yao G, Quan G, Lin S, Peng T, Wang Q, Ran H, Chen H, Zhang Q, Wang L, Pan X,
Wu C. Novel dissolving microneedles for enhanced transdermal delivery of
levonorgestrel: In vitro and in vivo characterization. Int J Pharm. 2017 Oct
16;534(1-2):378-386. doi: 10.1016/j.ijpharm.2017.10.035. [Epub ahead of print]
PubMed PMID: 29051119.
<br>

6: Nappi RE, Lobo Abascal P, Hsieh J, Micheletti MC. Cycle control with an
extended-regimen oral contraceptive combining levonorgestrel and ethinyl
estradiol that includes continuous low-dose ethinyl estradiol instead of the
traditional hormone-free interval. Int J Womens Health. 2017 Oct 5;9:739-747.
doi: 10.2147/IJWH.S142078. eCollection 2017. PubMed PMID: 29042818; PubMed
Central PMCID: PMC5633331.
<br>

7: Darney PD, Stuart GS, Thomas MA, Cwiak C, Olariu A, Creinin MD. Amenorrhea
rates and predictors during 1 year of levonorgestrel 52 mg intrauterine system
use. Contraception. 2017 Oct 13. pii: S0010-7824(17)30482-1. doi:
10.1016/j.contraception.2017.10.005. [Epub ahead of print] PubMed PMID: 29038072.

<br>
8: Pandey S. Re: Immediate versus delayed initiation of the
levonorgestrel-releasing intrauterine system following medical termination of
pregnancy – 1-year continuation rates: a randomised controlled trial:
Levonorgestrel-releasing intrauterine system following medical termination of
pregnancy: a randomised controlled trial. BJOG. 2017 Oct 5. doi:
10.1111/1471-0528.14901. [Epub ahead of print] PubMed PMID: 28980385.
<br>

9: Amiri M, Nahidi F, Khalili D, Bidhendi-Yarandi R, Ramezani Tehrani F.
Comparing the Effects of Oral Contraceptives Containing Levonorgestrel With
Products Containing Antiandrogenic Progestins on Clinical, Hormonal, and
Metabolic Parameters and Quality of Life in Women With Polycystic Ovary Syndrome:
Crossover Randomized Controlled Trial Protocol. JMIR Res Protoc. 2017 Sep
29;6(9):e191. doi: 10.2196/resprot.8631. PubMed PMID: 28963092; PubMed Central
PMCID: PMC5640820.
<br>

10: Ashraf MN, Habib-Ur-Rehman A, Shehzad Z, AlSharari SD, Murtaza G. Clinical
efficacy of levonorgestrel and norethisterone for the treatment of chronic
abnormal uterine bleeding. J Pak Med Assoc. 2017 Sep;67(9):1331-1338. PubMed
PMID: 28924270.

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