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5α-Dihydrolevonorgestrel

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(Redirected from 5α-dihydrolevonorgestrel) Chemical compound Pharmaceutical compound
5α-Dihydrolevonorgestrel
Clinical data
Other names5α-Dihydrolevonorgestrel; 5α-DHLNG; 5α-LNG
Identifiers
IUPAC name
  • (5S,8R,9R,10S,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol
3D model (JSmol)
SMILES
  • CC12CC3(1CC2(C#C)O)CC43CCC(=O)C4
InChI
  • InChI=1S/C21H30O2/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/h2,14,16-19,23H,3,5-13H2,1H3/t14-,16-,17+,18+,19-,20-,21-/m0/s1
  • Key:BMVIRDJAPBCAPQ-WQGSDSCCSA-N

5α-Dihydrolevonorgestrel (5α-DHLNG) is an active metabolite of the progestin levonorgestrel which is formed by 5α-reductase. It has about one-third of the affinity of levonorgestrel for the progesterone receptor. In contrast to levonorgestrel, the compound has both progestogenic and antiprogestogenic activity, and hence has a selective progesterone receptor modulator-like profile of activity. This is analogous to the case of norethisterone and 5α-dihydronorethisterone. In addition to the progesterone receptor, 5α-DHLNG interacts with the androgen receptor. It has similar affinity for the androgen receptor relative to levonorgestrel (34.3% of that of metribolone for levonorgestrel and 38.0% of that of metribolone for 5α-DHLNG), and has androgenic effects similarly to levonorgestrel and testosterone. 5α-DHLNG is further transformed into 3α,5α- and 3β,5α-THLNG, which bind weakly to the estrogen receptor (0.4 to 2.4% of the RBA of E2Tooltip estradiol (medication)) and have weak estrogenic activity. These metabolites are considered to be responsible for the weak estrogenic activity of high doses of levonorgestrel.

Relative affinities (%) of levonorgestrel and metabolites
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin CBGTooltip Corticosteroid binding globulin
Levonorgestrel 150–162 34, 45 0 1–8 17–75 50 0
5α-Dihydrolevonorgestrel 50 38 0 ? ? ? ?
3α,5α-Tetrahydrolevonorgestrel ? ? 0.4 ? ? ? ?
3β,5α-Tetrahydrolevonorgestrel ? ? 2.4 ? ? ? ?
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PRTooltip progesterone receptor, metribolone ( = mibolerone) for the ARTooltip androgen receptor, E2 for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, DHTTooltip dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip Corticosteroid-binding globulin. Sources: See template.

See also

References

  1. ^ Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (2008). "Classification and pharmacology of progestins". Maturitas. 61 (1–2): 171–80. doi:10.1016/j.maturitas.2008.11.013. PMID 19434889.
  3. ^ Vij U, Murugesan K, Kalita JC, Farooq A (February 1989). "Interaction of antiprogestins with progesterone receptors in rat uterus". J. Steroid Biochem. 32 (2): 279–82. doi:10.1016/0022-4731(89)90264-1. PMID 2921869.
  4. ^ García-Becerra R, Borja-Cacho E, Cooney AJ, Jackson KJ, Lemus AE, Pérez-Palacios G, Larrea F (November 2002). "The intrinsic transcriptional estrogenic activity of a non-phenolic derivative of levonorgestrel is mediated via the estrogen receptor-alpha". J. Steroid Biochem. Mol. Biol. 82 (4–5): 333–41. doi:10.1016/s0960-0760(02)00192-9. PMID 12589940. S2CID 24204715.
  5. Chu YH, Li QA, Zhao ZF, Zhou YP, Cao DC (1985). "". Zhongguo Yao Li Xue Bao (in Chinese). 6 (2): 125–9. PMID 2934946.
  6. ^ Cabeza M, Vilchis F, Lemus AE, Díaz de León L, Pérez-Palacios G (September 1995). "Molecular interactions of levonorgestrel and its 5 alpha-reduced derivative with androgen receptors in hamster flanking organs". Steroids. 60 (9): 630–5. doi:10.1016/0039-128X(95)00075-2. PMID 8545853. S2CID 20869899.
  7. Khan FS, Fotherby K (April 1979). "In vitro metabolism of 17 alpha-ethynylsteroids". J. Steroid Biochem. 10 (4): 437–42. doi:10.1016/0022-4731(79)90332-7. PMID 449320.
  8. ^ Santillán R, Pérez-Palacios G, Reyes M, Damián-Matsumura P, García GA, Grillasca I, Lemus AE (September 2001). "Assessment of the oestrogenic activity of the contraceptive progestin levonorgestrel and its non-phenolic metabolites". Eur. J. Pharmacol. 427 (2): 167–74. doi:10.1016/S0014-2999(01)01263-8. PMID 11557270.


Androgen receptor modulators
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids
Estrogen receptor modulators
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
  • Coregulator-binding modulators: ERX-11
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens


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