Norgestrel

Norgestrel is a synthetic progestogen used in combined oral contraceptives. It is a racemic mix of the stereoisomers dextronorgestrel and levonorgestrel. As dextronorgestrel is biologically inactive, the behavior of norgestrel is identical to that of levonorgestrel.

Tags
Approvals
US FDA-Approved
Related Compounds
Levonorgestrel
norgestrel
MOL

Identifiers

CASRN

6533-00-2

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References

PubChem CID

16051930

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References

  1. PubChem: Norgestrel (View all citations for this reference)

ECHA InfoCard

  • 100.026.758
  • EC / List #: 229-433-5

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References

  1. ECHA: Norgestrel (View all citations for this reference)

DrugBank Accession Number

DB09389

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References

  1. DrugBank: Norgestrel.
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

UNII

3J8Q1747Z2

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References

  1. UNII: Norgestrel (View all citations for this reference)

KEGG Entry Number

D00954

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References

  1. KEGG: Norgestrel (View all citations for this reference)

Wikipedia Entry Name

Norgestrel

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References

  1. Wikipedia: Norgestrel (View all citations for this reference)

ChEBI ID

CHEBI:7630

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References

  1. ChEBI: Norgestrel (View all citations for this reference)

ChemSpider ID

10481953

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References

  1. ChemSpider: Norgestrel (View all citations for this reference)

ATC Code(s)

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References

  1. DrugBank: Norgestrel.
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

Physical & Chemical Properties

Molecular Formula

C21H28O2

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References

Molecular Weight

312.45 g/mol

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References

Appearance

White or almost white crystalline powder

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References

  1. BP 2017: Norgestrel monograph.
    2. (View all citations for this reference)

Solubility

Practically insoluble in water, sparingly soluble in methylene chloride, slightly soluble in alcohol.

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References

  1. BP 2017: Norgestrel monograph.
    2. (View all citations for this reference)

Specific Optical Rotation

BP: +0.05° to -0.05°. 0.5 g in methylene chloride diluted to 10.0 mL
IARC: -0.1 to +0.1° in chloroform

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References

  1. BP 2017: Norgestrel monograph.
    2. (View all citations for this reference)
  2. WHO International Agency for Research on Cancer: IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Volume 91: Combined Estrogen-Progestogen Contraceptives and Combined Estrogen-Progestogen Menopausal Therapy. 2007, Lyon, France. (View all citations for this reference)

Toxicology

GHS Hazard Code(s)

Class Category Code Description
Carcinogenicity 2 H351 Suspected of causing cancer if inhaled
Reproductive Toxicity 1A H360FD May damage fertility. May damage the unborn child
Reproductive Toxicity, Effects On or Via Lactation H362 May cause harm to breast-fed children

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References

  1. ECHA: Norgestrel (View all citations for this reference)

Genotoxicity

Found to affect genetic material of human lymphocyte chromosomes as measured by chromosomal aberrations, sister chromatid exchanges, and cell growth kinetics.

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References

  1. Ahmad, M. E.; Shadab, G.; Azfer, M. A.; Afzal, M. Evaluation of Genotoxic Potential of Synthetic Progestins-Norethindrone and Norgestrel in Human Lymphocytes in Vitro. Mutat. Res. Toxicol. Environ. Mutagen. 2001, 494 (1–2), 13–20. (View all citations for this reference)

Biochemistry & Pharmacology

Progesterone Receptor Activity

Agonist

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References

  1. KEGG: Norgestrel (View all citations for this reference)

Target Pathways

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References

  1. KEGG: Norgestrel (View all citations for this reference)

Serum Protein Binding

Binds to SHBG

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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)

Metabolism

CYP3A4

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References

  1. Nanda, K.; Stuart, G. S.; Robinson, J.; Gray, A. L.; Tepper, N. K.; Gaffield, M. E. Drug Interactions between Hormonal Contraceptives and Antiretrovirals. AIDS 2017, 31 (7), 917–952. (View all citations for this reference)

Clearance

458 L/day

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References

  1. Murugesan, K.; Laumas, K. R. Norethynodrel Binding to Human Plasma Proteins. J. Steroid Biochem. 1975, 6 (11–12), 1495–1499. (View all citations for this reference)

Metabolites

Name
Structure
Notes
4-Dihydro-16-hydroxynorgestrel
structure

D-Homoannulated Norgestrel
structure

2α-Hydroxynorgestrel
structure

1β-Hydroxynorgestrel
structure

16β-Hydroxynorgestrel
structure

View All (11)

Impurities

Name
Structure
CASRN
Other Names & Identifiers
10β-Hydroxynorgestrel
structure

6β-Hydroxynorgestrel
structure

6α-Hydroxynorgestrel
structure

8(14)-Dehydronorgestrel
structure

Norethindrone
structure

68-22-4

  • BP Norethisterone Acetate Impurity A
  • Norethisterone

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US FDA-Approved Products

Name
Formulation
Status
ANDA #
Ovral 28
ETHINYL ESTRADIOL: 0.05 mg
NORGESTREL: 0.5 mg
28 oral tablets

Discontinued

016806

Ovral
ETHINYL ESTRADIOL: 0.05 mg
NORGESTREL: 0.5 mg
21 oral tablets

Discontinued

016672

Ogestrel 0.5/50-28
ETHINYL ESTRADIOL: 0.05 mg
NORGESTREL: 0.5 mg
28 oral tablets

Prescription

075406

Ogestrel 0.5/50-21
ETHINYL ESTRADIOL: 0.05 mg
NORGESTREL: 0.5 mg
21 oral tablets

Discontinued

075406

Norgestrel and Ethinyl Estradiol, #202875
ETHINYL ESTRADIOL: 0.05 mg NORGESTREL: 0.5 mg 28 oral tablets

Discontinued

202875

View All (12)