An active metabolite of norgestimate
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Pro-drug Form(s)
16547Norgestimate
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Norelgestromin

Item No. 35243

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13-ethyl-17α-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one, oxime
CAS Number
53016-31-2
Synonyms
  • BRN 4202099
  • Levonorgestrel oxime
  • 17-desacetyl Norgestimate
  • RWJ 10553
Molecular Formula
C21H29NO2
Formula Weight
327.5
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 11 mg/mlDMSO: 10 mg/mlEthanol: 12 mg/mlPBS (pH 7.2): 0.25 mg/ml
λmax
242 nm
SMILES
CC[C@@]12[C@](CC[C@@]2(O)C#C)([H])[C@]3([H])CCC4=C/C(CC[C@]4([H])[C@@]3([H])CC1)=N/O
InChi Code
InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3/b22-15+/t16-,17+,18+,19-,20-,21-/m0/s1
InChi Key
ISHXLNHNDMZNMC-VTKCIJPMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    Cayman Chemical
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    Product Description

    Norelgestromin is an active metabolite of the progestin norgestimate (Item No. 16547).1 Norelgestromin is formed from norgestimate via deacetylation in human liver microsomes. It is an agonist of the progesterone receptor and estrogen receptor α (ERα; EC50s = 11.1 and 43.4 nM, respectively) and an antagonist of the glucocorticoid and mineralocorticoid receptors (IC50s = 255 nM and 83.7 nM, respectively).2 Norelgestromin selectively binds to progestin receptors (IC50 = 4.61 nM for rabbit uterine receptors) over androgen receptors (IC50 = 222 nM for rat prostatic receptors) in radioligand binding assays.3 However, norelgestromin (1 nM) activates the androgen receptor in a transactivation assay in MDA-MB-231 breast cancer cells expressing the human receptor.4 Formulations containing norelgestromin in combination with ethynyl estradiol have been used as contraceptives and in the treatment of acne vulgaris in women.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Madden, S., and Back, D.J. Metabolism of norgestimate by human gastrointestinal mucosa and liver microsomes in vitro. J. Steroid Biochem. Mol. Biol. 38(4), 497-503 (1991).

    2. Paris, F., Balaguer, P., Rimbault, F., et al. Molecular action of norgestimate: New developments. Gynecol. Endocrinol. 31(6), 487-490 (2015).

    3. Phillips, A., Demarest, K., Hahn, D.W., et al. Progestational and androgenic receptor binding affinities and in vivo activities of norgestimate and other progestins. Contraception 41(4), 399-410 (1990).

    4. Prifti, S., Lelle, I., Strowitzki, T., et al. Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells. Gynecol. Endocrinol. 19(1), 18-21 (2004).