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Norgestimate

July 24, 2017
Common Name

Norgestimate Description

Norgestimate is only found in individuals that have used or taken this drug. It is a form of progesterone, which is a female hormone important for the regliation of ovliation and menstruation. Norgestimate is used with estradiol to treat the symptoms of menopause.Norgestimate binds to androgen and progestogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Norgestimate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovliatory LH (luteinizing hormone) surge. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetate (ester)ChEBI (17alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oximeChEBI D-13beta-Ethyl-17alpha-ethynyl-17beta-acetoxygon-4-en-3-one oximeChEBI Dexnorgestrel acetimeChEBI NorgestimatoChEBI NorgestimatumChEBI (+)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one oxime acetate (ester)Generator (+)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one oxime acetic acid (ester)Generator (+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetic acid (ester)Generator (+)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one oxime acetate (ester)Generator (+)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one oxime acetic acid (ester)Generator Norgestimic acidGenerator (17a)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oximeGenerator (17α)-17-(acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oximeGenerator D-13b-Ethyl-17a-ethynyl-17b-acetoxygon-4-en-3-one oximeGenerator D-13β-ethyl-17α-ethynyl-17β-acetoxygon-4-en-3-one oximeGenerator Norgestrel oxime acetateMeSH

Chemical Formlia

C23H31NO3 Average Molecliar Weight

369.4971 Monoisotopic Molecliar Weight

369.230393863 IUPAC Name

(1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate Traditional Name

norgestimate CAS Registry Number

35189-28-7 SMILES

[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(C=C3CC[C@@]21[H])=N/O

InChI Identifier

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 Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group. Kingdom

Organic compounds Super Class

Lipids and lipid-like moleclies Class

Steroids and steroid derivatives Sub Class

Steroid esters Direct Parent

Steroid esters Alternative Parents

  • Estrane steroids
  • Delta-4-steroids
  • Ynones
  • Ketoximes
  • Carboxylic acid esters
  • Monocarboxylic acids and derivatives
  • Acetylides
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Steroid ester
  • Estrane-skeleton
  • Delta-4-steroid
  • Ynone
  • Ketoxime
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxime
  • Acetylide
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • terminal acetylenic compound (CHEBI:50815 )
  • steroid ester (CHEBI:50815 )
  • ketoxime (CHEBI:50815 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cell signaling
  • Contraceptives
  • Contraceptives, Oral, Synthetic
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point216 °CNot Available Boiling PointNot AvailableNot Available Water Solubility5.31e-03 g/LNot Available LogP4.8Not Available

    Predicted Properties

    Property Value Source Water Solubility0.0053 mg/mLALOGPS logP3.8ALOGPS logP4.11ChemAxon logS-4.8ALOGPS pKa (Strongest Acidic)11.47ChemAxon pKa (Strongest Basic)3.11ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area58.89 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity105 m3·mol-1ChemAxon Polarizability42.82 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00957

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00957

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00957 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5022837 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Norgestimate NuGOwiki Link

    HMDB15092 Metagene Link

    HMDB15092 METLIN ID

    Not Available PubChem Compound

    6540478 PDB ID

    Not Available ChEBI ID

    50815

    Product: VU 0240552

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in sequence-specific DNA binding transcription factor activity
    Specific function:
    Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
    Gene Name:
    PGR
    Uniprot ID:
    P06401
    Molecular weight:
    98980.0
    References
    1. London RS, Chapdelaine A, Upmalis D, Olson W, Smith J: Comparative contraceptive efficacy and mechanism of action of the norgestimate-containing triphasic oral contraceptive. Acta Obstet Gynecol Scand Suppl. 1992;156:9-14. [PubMed:1324557 ]
    2. Graziottin A: A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. [PubMed:17107221 ]
    3. Kuhnz W, Fritzemeier KH, Hegele-Hartung C, Krattenmacher R: Comparative progestational activity of norgestimate, levonorgestrel-oxime and levonorgestrel in the rat and binding of these compounds to the progesterone receptor. Contraception. 1995 Feb;51(2):131-9. [PubMed:7750291 ]
    4. Juchem M, Pollow K, Elger W, Hoffmann G, Mobus V: Receptor binding of norgestimate–a new orally active synthetic progestational compound. Contraception. 1993 Mar;47(3):283-94. [PubMed:8384965 ]
    5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    General function:
    Involved in sequence-specific DNA binding transcription factor activity
    Specific function:
    Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
    Gene Name:
    ESR1
    Uniprot ID:
    P03372
    Molecular weight:
    66215.4
    References
    1. Pasqualini JR: Differential effects of progestins on breast tissue enzymes. Maturitas. 2003 Dec 10;46 Suppl 1:S45-54. [PubMed:14670645 ]
    2. Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. [PubMed:2175153 ]
    3. Shields-Botella J, Duc I, Duranti E, Puccio F, Bonnet P, Delansorne R, Paris J: An overview of nomegestrol acetate selective receptor binding and lack of estrogenic action on hormone-dependent cancer cells. J Steroid Biochem Mol Biol. 2003 Nov;87(2-3):111-22. [PubMed:14672731 ]

    Transporters

    General function:
    Involved in ATP binding
    Specific function:
    Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
    Gene Name:
    ABCC2
    Uniprot ID:
    Q92887
    Molecular weight:
    174205.6
    References
    1. Lindenmaier H, Becker M, Haefeli WE, Weiss J: Interaction of progestins with the human multidrug resistance-associated protein 2 (MRP2). Drug Metab Dispos. 2005 Nov;33(11):1576-9. Epub 2005 Jul 27. [PubMed:16049127 ]

    PMID: 12699745

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