A progestin
Related Products
Active Metabolite(s)
10006318Levonorgestrel 35243Norelgestromin
Labeled Version(s)
31176Norgestimate-d6
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Norgestimate

Item No. 16547

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(17α)-17-(acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime
CAS Number
35189-28-7
Synonyms
  • Dexnorgestrel acetime
  • ORF 10131
  • RWJ 10131
Molecular Formula
C23H31NO3
Formula Weight
369.5
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMF:PBS(pH7.2) (1:2): 0.3 mg/mlDMSO: 14 mg/mlEthanol: 2 mg/ml
λmax
241 nm
SMILES
CC[C@@]12[C@](CC[C@@]2(OC(C)=O)C#C)([H])[C@]3([H])CCC4=C/C(CC[C@]4([H])[C@@]3([H])CC1)=N/O
InChi Code
InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
InChi Key
KIQQMECNKUGGKA-NMYWJIRASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Norgestimate is a progestin and a prodrug form of norelgestromin and levonorgestrel (Item No. 10006318).1,2 It binds to progestin receptors (mean IC50 = 3.48 nM for rabbit uterine receptors) and is selective for progestin over androgen receptors (mean IC50 = 764 nM for rat prostatic receptors) in radioligand binding assays.3 Norgestimate maintains pregnancy in ovariectomized female rats in a dose-dependent manner.1 It inhibits ovulation in 100% of female rats when administered at a dose of 0.5 mg/kg. Norgestimate (2 mg/kg) completely inhibits estrone-induced vaginal cornification in ovariectomized female rats, indicating antiestrogenic activity. Formulations containing norgestimate in combination with ethinyl estradiol have been used as oral contraceptives and in the treatment of acne vulgaris.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hahn, D.W., Allen, G.O., and McGuire, J.L. The pharmacological profile of norgestimate, a new orally active progestin. Contraception 16(5), 541-553 (1977).

    2. Stanczyk, F.Z. All progestins are not created equal. Steroids 68(10-13), 879-890 (2003).

    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).