Banner
targets (2) transporters (1)
for drugs
Identification
Name Norgestimate
Accession Number DB00957 (APRD00569)
Type small molecule
Groups approved
Description

Norgestimate is a form of progesterone, which is a female hormone important for the regulation of ovulation and menstruation. Norgestimate is used with estradiol to treat the symptoms of menopause.

Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Dexnorgestrel Acetime
  • Norgestimato [INN-Spanish]
  • Norgestimatum [INN-Latin]
Brand names
  • Ortho Cyclen-21
  • Ortho Cyclen-28
  • Ortho Tri-Cyclen
  • Ortho-Prefest
Brand name mixtures
  • Tri-Cyclen Tablets - 21-Day (Ethinyl Estradiol + Norgestimate)
  • Tri-Cyclen Tablets - 28-Day (Ethinyl Estradiol + Norgestimate)
Categories
  • Contraceptives
  • Contraceptives, Oral, Synthetic
CAS number 35189-28-7
Weight Average: 369.4971
Monoisotopic: 369.230393863
Chemical Formula C23H31NO3
InChI Key InChIKey=KIQQMECNKUGGKA-NMYWJIRASA-N
InChI
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
Plain Text
IUPAC Name
(1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl acetate
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Alkynes
  • Ethers
  • Imines
  • Cyclohexenes and Derivatives
  • Oximes and Derivatives
Pharmacology
Indication For the prevention of pregnancy
Pharmacodynamics Norgestimate is used as a female contraceptive. Norgestimate is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Norgestimate tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
Mechanism of action 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-ovulatory LH (luteinizing hormone) surge.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism

GI tract/Hepatic

Route of elimination Not Available
Half life 12-30 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Ortho Tri-Cyclen Lo 28 0.18/0.215/0.25 mg-25 mcg tablet Disp Pack 78.06 USD disp
Ortho Tri-Cyclen (28) 28 0.18/0.215/0.25 mg-35 mcg tablet Disp Pack 47.99 USD disp
Ortho-Cyclen (28) 28 0.25-35 mg-mcg tablet Disp Pack 38.99 USD disp
Ortho tri-cyclen lo tablet 2.68 USD tablet
Ortho-prefest tablet 1.36 USD tablet
Ortho-cyclen 28 tablet 1.13 USD tablet
Patents
Country Patent Number Approved Expires
United States 7320970 2000-03-30 2020-03-30
United States 5382573 1995-01-17 2012-01-17
Properties
State solid
Melting point 216 oC
Experimental Properties
Property Value Source
logP 4.8 PhysProp
Predicted Properties
Property Value Source
water solubility 5.31e-03 g/l ALOGPS
logP 3.80 ALOGPS
logP 4.03 ChemAxon Molconvert
logS -4.84 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 58.89 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 105.00 ChemAxon Molconvert
polarizability 42.82 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 6540478 Link_out
PubChem Substance 46507381 Link_out
ChemSpider 5022837 Link_out
ChEBI 50815 Link_out
ChEMBL 50815 Link_out
Therapeutic Targets Database DAP001210 Link_out
PharmGKB PA450655 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic/norgestimest.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Norgestimate Link_out
ATC Codes
  • G03AA11
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.
  • Take at the same time everyday.
  • Take with food.
Targets

1. Progesterone receptor

Pharmacological action: yes
Actions: agonist

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues

Organism class: human
UniProt ID: P06401 Link_out
Gene: PGR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Graziottin A: A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. Pubmed
  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
  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
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Estrogen receptor

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P03372 Link_out
Gene: ESR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Pasqualini JR: Differential effects of progestins on breast tissue enzymes. Maturitas. 2003 Dec 10;46 Suppl 1:S45-54. Pubmed
  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
  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

Transporters

1. Canalicular multispecific organic anion transporter 1

Actions: substrate

Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter

UniProt ID: Q92887 Link_out
Gene: ABCC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:07

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.