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Structure Database (LMSD)

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Common Name

Desogestrel

Systematic Name

13-ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17α-ol

Synonyms

LM ID

LMST02030104

Formula

C₂₂H₃₀O

Exact Mass

Calculate m/z

310.229665

Sum Composition

ST 22:4;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Desogestrel is a synthetic progestogen.¹ It inhibits ovulation and prevents fertilization in rabbits and mice. Desogestrel inhibits rhodamine 123 efflux, a measure of P-glycoprotein activity, ex vivo in human lymphocytes and CD8+ T cells in a dose-dependent manner.² Formulations containing desogestrel have been used as oral contraceptives and for the treatment of polycystic ovary syndrome.

This information has been provided by Cayman Chemical

References

1. Fröhlich, M., Albermann, N., Sauer, A., et al. In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins. Biochem. Pharmacol. 68(12), 2409-2416 (2004).

2. van der Vies, J., and de Visser, J. Endocrinological studies with desogestrel. Arzneimittelforschung 33(2), 231-236 (1983).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Desogestrel: Review of Pharmacology and Clinical Trials,
Female Contraception., 1988

DOI: 10.1007/978-3-642-73790-9_14

String Representations

InChiKey (Click to copy)

RPLCPCMSCLEKRS-BPIQYHPVSA-N

InChi (Click to copy)

InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

SMILES (Click to copy)

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