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Identification
NameNorgestimate
Accession NumberDB00957  (APRD00569)
TypeSmall Molecule
GroupsApproved
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
Synonyms
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetate (ester)
(17alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime
D-13beta-Ethyl-17alpha-ethynyl-17beta-acetoxygon-4-en-3-one oxime
Dexnorgestrel Acetime
Norgestimato
Norgestimatum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Ortho-PrefestNot Available
Brand mixtures
NameLabellerIngredients
Centrisa 21Patriot A Division Of Janssen Inc
Centrisa 28Patriot A Division Of Janssen Inc
Centrisa Lo 21Patriot A Division Of Janssen Inc
Centrisa Lo 28Patriot A Division Of Janssen Inc
Cyclen Tablets (21 Day)Janssen Inc
Cyclen Tablets (28 Day)Janssen Inc
EstaryllaSandoz Inc
Mono-linyahNorthstar Rx LLC
MononessaActavis Pharma, Inc
Norgestimate and Ethinyl EstradiolMylan Pharmaceuticals Inc.
Ortho CyclenJanssen Pharmaceuticals, Inc.
Ortho Tri CyclenJanssen Pharmaceuticals, Inc.
Ortho Tri Cyclen LoJanssen Pharmaceuticals, Inc.
PrefestaSearchlight Pharma Inc
PrevifemQualitest Pharmaceuticals
Previfem (21day)Novopharm Limited
Previfem (28day)Novopharm Limited
Sarensis 21Patriot A Division Of Janssen Inc
Sarensis 28Patriot A Division Of Janssen Inc
SprintecBarr Laboratories Inc.
Tri-cyclen Lo (-21 Day)Janssen Inc
Tri-cyclen Lo (28 Day)Janssen Inc
Tri-cyclen Tablets - 21-dayJanssen Inc
Tri-cyclen Tablets - 28-dayJanssen Inc
Tri-estaryllaSandoz Inc
Tri-lena 21Actavis Pharma Company
Tri-lena 28Actavis Pharma Company
Tri-lena Lo 21Actavis Pharma Company
Tri-lena Lo 28Actavis Pharma Company
Tri-linyahNorthstar Rx LLC
Tri-LO- EstaryllaSandoz Inc
Tri-LO-marziaLupin Pharmaceuticals, Inc.
Tri-LO-sprintecTeva Pharmaceuticals USA Inc
Tri-previfemQualitest Pharmaceuticals
Tri-previfem (21 Day)Novopharm Limited
Tri-previfem (28 Day)Novopharm Limited
Tri-sprintecBarr Laboratories Inc.
Tricira LoApotex Inc
TrinessaRebel Distributors Corp
Trinessa LoActavis Pharma, Inc.
SaltsNot Available
Categories
UNIIC291HFX4DY
CAS number35189-28-7
WeightAverage: 369.4971
Monoisotopic: 369.230393863
Chemical FormulaC23H31NO3
InChI KeyInChIKey=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
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
SMILES
[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CC\C(C=C3CC[C@@]21[H])=N/O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Estrane-skeleton
  • Delta-4-steroid
  • Ynone
  • Acetate salt
  • Carboxylic acid ester
  • Oxime
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the prevention of pregnancy
PharmacodynamicsNorgestimate 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 actionNorgestimate 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

GI tract/Hepatic

Route of eliminationNot Available
Half life12-30 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9896
Blood Brain Barrier+0.9307
Caco-2 permeable-0.5125
P-glycoprotein substrateSubstrate0.5877
P-glycoprotein inhibitor IInhibitor0.6103
P-glycoprotein inhibitor IINon-inhibitor0.7485
Renal organic cation transporterNon-inhibitor0.6733
CYP450 2C9 substrateNon-substrate0.7842
CYP450 2D6 substrateNon-substrate0.8374
CYP450 3A4 substrateSubstrate0.736
CYP450 1A2 substrateNon-inhibitor0.7596
CYP450 2C9 inhibitorNon-inhibitor0.6541
CYP450 2D6 inhibitorNon-inhibitor0.8829
CYP450 2C19 inhibitorNon-inhibitor0.6215
CYP450 3A4 inhibitorNon-inhibitor0.7716
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7175
Ames testNon AMES toxic0.5404
CarcinogenicityNon-carcinogens0.8389
BiodegradationNot ready biodegradable0.9929
Rat acute toxicity2.4561 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9075
hERG inhibition (predictor II)Non-inhibitor0.7999
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Kit
Prices
Unit descriptionCostUnit
Ortho Tri-Cyclen Lo 28 0.18/0.215/0.25 mg-25 mcg tablet Disp Pack78.06USD disp
Ortho Tri-Cyclen (28) 28 0.18/0.215/0.25 mg-35 mcg tablet Disp Pack47.99USD disp
Ortho-Cyclen (28) 28 0.25-35 mg-mcg tablet Disp Pack38.99USD disp
Ortho tri-cyclen lo tablet2.68USD tablet
Ortho-prefest tablet1.36USD tablet
Ortho-cyclen 28 tablet1.13USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5382573 No1995-01-172012-01-17Us
US6214815 Yes1999-12-092019-12-09Us
US6747019 No2000-03-202020-03-20Us
US7320970 No2000-03-302020-03-30Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point216 °CPhysProp
logP4.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00531 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesG03AA11G03FA13
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabNorgestimate may decrease the anticoagulant activities of Abciximab.
AcenocoumarolNorgestimate may decrease the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norgestimate.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Norgestimate.
Anthrax immune globulin humanNorgestimate may increase the thrombogenic activities of Anthrax immune globulin.
BexaroteneThe serum concentration of Norgestimate can be decreased when it is combined with Bexarotene.
ButabarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Butabarbital.
ButethalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Butethal.
C1 Esterase Inhibitor (Human)Norgestimate may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Norgestimate.
CapromabNorgestimate may decrease effectiveness of Capromab as a diagnostic agent.
CarbamazepineThe metabolism of Norgestimate can be increased when combined with Carbamazepine.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Norgestimate.
Citric AcidNorgestimate may decrease the anticoagulant activities of Citric Acid.
ColesevelamThe serum concentration of Norgestimate can be decreased when it is combined with Colesevelam.
Cyproterone acetateThe serum concentration of Norgestimate can be decreased when it is combined with Cyproterone acetate.
DalteparinNorgestimate may decrease the anticoagulant activities of Dalteparin.
DicoumarolNorgestimate may decrease the anticoagulant activities of Dicoumarol.
Edetic AcidNorgestimate may decrease the anticoagulant activities of Edetic Acid.
EfavirenzThe serum concentration of the active metabolites of Norgestimate can be reduced when Norgestimate is used in combination with Efavirenz resulting in a loss in efficacy.
EnoxaparinNorgestimate may decrease the anticoagulant activities of Enoxaparin.
Eslicarbazepine acetateThe serum concentration of Norgestimate can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateNorgestimate may decrease the anticoagulant activities of Ethyl biscoumacetate.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Norgestimate.
Fondaparinux sodiumNorgestimate may decrease the anticoagulant activities of Fondaparinux sodium.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Norgestimate.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Norgestimate.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Norgestimate.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Norgestimate.
HeparinNorgestimate may decrease the anticoagulant activities of Heparin.
HeptabarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Heptabarbital.
HexobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Hexobarbital.
IcosapentIcosapent may increase the thrombogenic activities of Norgestimate.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Norgestimate.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Norgestimate.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Norgestimate.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Norgestimate.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Norgestimate.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Norgestimate.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Norgestimate.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Norgestimate.
LumacaftorThe serum concentration of Norgestimate can be decreased when it is combined with Lumacaftor.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Norgestimate.
MethohexitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Methohexital.
PentobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Pentobarbital.
PhenindioneNorgestimate may decrease the anticoagulant activities of Phenindione.
PhenprocoumonNorgestimate may decrease the anticoagulant activities of Phenprocoumon.
PhenytoinThe metabolism of Norgestimate can be increased when combined with Phenytoin.
PrimidoneThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Primidone.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Norgestimate.
RifabutinThe serum concentration of Norgestimate can be decreased when it is combined with Rifabutin.
SaquinavirThe serum concentration of Norgestimate can be increased when it is combined with Saquinavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Norgestimate.
SecobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Secobarbital.
St. John's WortThe therapeutic efficacy of Norgestimate can be decreased when used in combination with St. John's Wort.
SulodexideNorgestimate may decrease the anticoagulant activities of Sulodexide.
TesmilifeneThe serum concentration of Norgestimate can be decreased when it is combined with Tesmilifene.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Norgestimate.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Norgestimate.
TreprostinilNorgestimate may decrease the anticoagulant activities of Treprostinil.
VerapamilThe serum concentration of Norgestimate can be increased when it is combined with Verapamil.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Norgestimate.
Vitamin CThe serum concentration of Norgestimate can be increased when it is combined with Vitamin C.
WarfarinNorgestimate may decrease the anticoagulant activities of Warfarin.
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

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
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. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
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

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 03:05