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Structure Database (LMSD)

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Common Name

Norgestrel

Systematic Name

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

Synonyms

WY-3707

LM ID

LMST02030119

Formula

C₂₁H₂₈O₂

Exact Mass

Calculate m/z

312.20893

Sum Composition

ST 21:4;O2

Status

Curated

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Classification

Biological Context

Levonorgestrel is a synthetic progestin and the biologically active component of norgestrel .¹ In vivo, levonorgestrel (60 μg/day) suppresses estrus and pregnancy in female cats.² Post-coital insertion of subdermal levonorgestrel (5 mg pellet) implants prevents uterine implantation of embryos in mice.³ Formulations containing levonorgestrel have been used as contraceptives.

This information has been provided by Cayman Chemical

References

1. Jones, R.C., Singer, A.C., and Edgren, R.A. The biological activities of norgestrel and its enantiomers. Int. J. Fertil. 24(1), 39-43 (1979).

2. Shirley, B., Bundren, J.C., and McKinney, S. Levonorgestrel as a postcoital contraceptive. Contraception 52(2), 277-281 (1995).

3. Baldwin, C.J., Peter, A.T., Bosu, W.T., et al. The contraceptive effects of levonorgestrel in the domestic cat. Lab. Anim. Sci. 44(3), 261-269 (1994).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Wy 3707, a totally synthesized progestogen for contraception.,
Int J Fertil, 1966

Pubmed ID: 5970362

String Representations

InChiKey (Click to copy)

WWYNJERNGUHSAO-XUDSTZEESA-N

InChi (Click to copy)

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 (Click to copy)

[C@]12(CC)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]3([H])[C@]1([H])CC[C@@]2(O)C#C