You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameNorgestimate
Accession NumberDB00957  (APRD00569)
TypeSmall Molecule
GroupsApproved
DescriptionNorgestimate 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
FemynorAmneal Pharmaceuticals Llc
MiliAurobindo Pharma Limited
Mono-linyahNorthstar Rx LLC
MononessaActavis Pharma, Inc
Norgestimate and Ethinyl EstradiolMylan Pharmaceuticals Inc.
Ortho CyclenJanssen Pharmaceuticals, Inc.
Ortho Tri CyclenPhysicians Total Care, Inc.
Ortho Tri Cyclen LoPhysicians Total Care, 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
SprintecRebel Distributors Corp
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-miliAurobindo Pharma Limited
Tri-LO-sprintecTeva Pharmaceuticals USA Inc
Tri-miliAurobindo Pharma Limited
Tri-previfemQualitest Pharmaceuticals
Tri-previfem (21 Day)Novopharm Limited
Tri-previfem (28 Day)Novopharm Limited
Tri-sprintecRebel Distributors Corp
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 KeyKIQQMECNKUGGKA-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
Pharmacology
IndicationFor the prevention of pregnancy
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Progesterone receptorProteinyes
agonist
HumanP06401 details
Estrogen receptorProteinyes
agonist
HumanP03372 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Norgestimate.Approved, Investigational
AcenocoumarolNorgestimate may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norgestimate.Withdrawn
AcitretinThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Adapalene.Approved
AicarThe therapeutic efficacy of Aicar can be decreased when used in combination with Norgestimate.Experimental
AlitretinoinThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Alitretinoin.Approved, Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Norgestimate.Approved
AmobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Amobarbital.Approved, Illicit
AprepitantThe serum concentration of Norgestimate can be decreased when it is combined with Aprepitant.Approved, Investigational
ArtemetherThe serum concentration of Norgestimate can be decreased when it is combined with Artemether.Approved
AtazanavirThe serum concentration of Norgestimate can be increased when it is combined with Atazanavir.Approved, Investigational
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Norgestimate.Investigational
BarbexacloneThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Barbital.Illicit
BexaroteneThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Bexarotene.Approved, Investigational
BexaroteneThe serum concentration of Norgestimate can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe serum concentration of Norgestimate can be increased when it is combined with Boceprevir.Approved
BosentanThe serum concentration of Norgestimate can be decreased when it is combined with Bosentan.Approved, Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Norgestimate.Withdrawn
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Norgestimate.Approved
CarbamazepineThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Carbamazepine.Approved, Investigational
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Norgestimate.Experimental
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Norgestimate.Approved
CholestyramineThe serum concentration of Norgestimate can be decreased when it is combined with Cholestyramine.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Norgestimate.Experimental
ClobazamThe serum concentration of Norgestimate can be decreased when it is combined with Clobazam.Approved, Illicit
CobicistatThe serum concentration of Norgestimate can be increased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Norgestimate can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Norgestimate can be decreased when it is combined with Colestipol.Approved
DabrafenibThe serum concentration of Norgestimate can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe serum concentration of Norgestimate can be decreased when it is combined with Darunavir.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Norgestimate.Investigational
DicoumarolNorgestimate may decrease the anticoagulant activities of Dicoumarol.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Norgestimate.Approved
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.Approved, Investigational
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Norgestimate.Approved
Eslicarbazepine acetateThe serum concentration of Norgestimate can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateNorgestimate may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideThe serum concentration of Norgestimate can be decreased when it is combined with Exenatide.Approved, Investigational
FelbamateThe serum concentration of Norgestimate can be decreased when it is combined with Felbamate.Approved
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Norgestimate.Approved
FluindioneNorgestimate may decrease the anticoagulant activities of Fluindione.Investigational
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Norgestimate resulting in a loss in efficacy.Approved
FosaprepitantThe serum concentration of Norgestimate can be decreased when it is combined with Fosaprepitant.Approved
FosphenytoinThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Fosphenytoin.Approved
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Norgestimate.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Norgestimate.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Norgestimate.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Norgestimate.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Norgestimate.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Norgestimate.Approved
GriseofulvinThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Griseofulvin.Approved, Vet Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Norgestimate.Investigational
HexobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Hexobarbital.Approved
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Norgestimate.Approved, Illicit
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Norgestimate.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Norgestimate.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Norgestimate.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Norgestimate.Approved
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Norgestimate.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Norgestimate.Approved
IsotretinoinThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Isotretinoin.Approved
LamotrigineThe serum concentration of Norgestimate can be decreased when it is combined with Lamotrigine.Approved, Investigational
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Norgestimate.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Norgestimate.Approved
LopinavirThe serum concentration of Norgestimate can be decreased when it is combined with Lopinavir.Approved
LumacaftorThe serum concentration of Norgestimate can be decreased when it is combined with Lumacaftor.Approved
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Norgestimate.Approved
MethohexitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Methylphenobarbital.Approved
MetreleptinThe serum concentration of Norgestimate can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Mifepristone.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Norgestimate.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Norgestimate.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Norgestimate.Approved, Investigational
Mycophenolic acidThe serum concentration of Norgestimate can be decreased when it is combined with Mycophenolic acid.Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Norgestimate.Approved, Investigational
NelfinavirThe serum concentration of Norgestimate can be decreased when it is combined with Nelfinavir.Approved
NevirapineThe serum concentration of Norgestimate can be decreased when it is combined with Nevirapine.Approved
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Norgestimate.Approved
OxcarbazepineThe serum concentration of Norgestimate can be decreased when it is combined with Oxcarbazepine.Approved
PentobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Pentobarbital.Approved, Vet Approved
PerampanelThe serum concentration of Norgestimate can be decreased when it is combined with Perampanel.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Norgestimate.Approved, Withdrawn
PhenindioneNorgestimate may decrease the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Phenobarbital.Approved
PhenprocoumonNorgestimate may decrease the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Norgestimate.Approved, Investigational
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Norgestimate.Approved, Investigational
PrimidoneThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Primidone.Approved, Vet Approved
PrucaloprideThe serum concentration of Norgestimate can be decreased when it is combined with Prucalopride.Approved
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Norgestimate.Approved, Investigational
RifabutinThe serum concentration of Norgestimate can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Norgestimate can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Norgestimate can be decreased when it is combined with Rifapentine.Approved
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Norgestimate.Approved, Investigational
SaquinavirThe serum concentration of Norgestimate can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Norgestimate.Approved
SecobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Norgestimate.Approved, Investigational, Vet Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Norgestimate.Approved, Investigational
St. John's WortThe therapeutic efficacy of Norgestimate can be decreased when used in combination with St. John's Wort.Nutraceutical
SugammadexThe serum concentration of Norgestimate can be decreased when it is combined with Sugammadex.Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Norgestimate.Approved, Investigational
TelaprevirThe serum concentration of Norgestimate can be decreased when it is combined with Telaprevir.Approved
ThalidomideNorgestimate may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiazolidinedioneThe therapeutic efficacy of Thiazolidinedione can be decreased when used in combination with Norgestimate.Investigational
ThiopentalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Thiopental.Approved, Vet Approved
TipranavirThe serum concentration of Norgestimate can be increased when it is combined with Tipranavir.Approved, Investigational
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Norgestimate.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Norgestimate.Approved
TopiramateThe serum concentration of Norgestimate can be decreased when it is combined with Topiramate.Approved
Tranexamic AcidNorgestimate may increase the thrombogenic activities of Tranexamic Acid.Approved
TretinoinThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Norgestimate.Withdrawn
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Norgestimate.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Norgestimate.Approved, Investigational
VoriconazoleThe serum concentration of Norgestimate can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinNorgestimate may decrease the anticoagulant activities of Warfarin.Approved
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.
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesG03AA11G03FA13
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot 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
KitOral
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
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

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
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on December 02, 2016 03:58