Norelgestromin

Norelgestromin (NGMN) is a synthetic progestogen used in combined oral contraceptives and in menopausal hormonal therapy. It is the primary metabolite of norgestimate.

Tags
Approvals
US FDA-Approved
Related Compounds
Norgestimate
norelgestromin

Identifiers

Abbreviation

NGMN

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References

Names

  • levonorgestrel 3-oxime
  • 17β-deacetylnorgestimate
  • 17α-ethynyl-18-methyl-19-nortestosterone 3-oxime
  • 17α-ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime
  • 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, oxime, (17α)-
  • 13-ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one oxime

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References

CASRN

53016-31-2

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References

PubChem CID

62930

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UNII

R0TAY3X631

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KEGG Entry Number

D05205

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Wikipedia Entry Name

Norelgestromin

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ChEBI ID

CHEBI:135398

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ChEMBL ID

CHEMBL1200807

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ChemSpider ID

56648

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Physical & Chemical Properties

Molecular Formula

C21H29NO2

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References

Molecular Weight

327.46 g/mol

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References

Specific Optical Rotation

+35° to +41 °, 5 mg/mL in 75:25 alcohol:water

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References

  1. USP 40: Norelgestromin monograph.
  2. (View all citations for this reference)

Ratio of (E)- to (Z)- Isomer

Between 1.3 and 1.6

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References

  1. USP 40: Norelgestromin monograph.
  2. (View all citations for this reference)

Biochemistry & Pharmacology

Elimination Half-Life (t1/2)

  • 29.2 +/- 14.5 h from IV injection of 252 μg norelgestromin and 25 μg ethinyl estradiol.
  • 28.4 +/- 12.8 h from transdermal patch of 150 μg/day norelgestromin and 20 μg/day ethinyl estradiol.

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References

  1. Abrams, L. S.; Skee, D.; Natarajan, J.; Wong, F. A. Pharmacokinetic Overview of Ortho Evra (TM)/Evra (TM). Fertil. Steril. 2002, 77 (2, 2), S3–S12.
  2. (View all citations for this reference)

Serum Protein Binding

>97% bound, primarily to albumin. No binding to SHBG, except as metabolite norgestrel.

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References

  1. Abrams, L. S.; Skee, D.; Natarajan, J.; Wong, F. A. Pharmacokinetic Overview of Ortho Evra (TM)/Evra (TM). Fertil. Steril. 2002, 77 (2, 2), S3–S12.
  2. (View all citations for this reference)
  3. Toxnet: Norgestimate. (View all citations for this reference)
  4. FDA Ortho Evra Information (View all citations for this reference)

Excretion

Via renal and fecal pathways.

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Clearance

7.89 +/- 1.63 L/h from IV injection of 252 μg norelgestromin and 25 μg ethinyl estradiol.

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References

  1. Abrams, L. S.; Skee, D.; Natarajan, J.; Wong, F. A. Pharmacokinetic Overview of Ortho Evra (TM)/Evra (TM). Fertil. Steril. 2002, 77 (2, 2), S3–S12.
  2. (View all citations for this reference)

Metabolites

Name
Structure
Notes
structure

Position of hydroxyl group not specified. Referred to as Met6 in source.

structure

Position of hydroxyl group not specified. Referred to as Met5 in source.

structure

Position of hydroxyl group not specified. Referred to as Met4 in source.

structure

Position of hydroxyl group not specified. Referred to as Met3 in source.

structure

Position of hydroxyl group not specified. Referred to as Met1 in source.

Impurities

Name
Structure
CASRN
Other Names & Identifiers
structure

  • 13-ethyl-17-hydroxy-18,19-dinor-17α-pregn-5(10)-en-20-yn-3-one oxime

structure

  • (E)- and (Z)-Norgestimate

US FDA-Approved Products

Name
Formulation
Status
ANDA #
ETHINYL ESTRADIOL: 0.035 mg/day
NORELGESTROMIN: 0.15 mg/day
Film, extended release; transdermal

Prescription

200910

ETHINYL ESTRADIOL: 0.035 mg/day
NORELGESTROMIN: 0.15 mg/day
Film, extended release; transdermal

Discontinued

021180