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
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 IDs
ORF 10131 / RWJ 10131
Product Images
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PrefestKitTeva Women's Health2006-05-30Not applicableUs51285 06320180113 27003 1iz3t98
International/Other Brands
Ortho-Prefest
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Centrisa 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 28Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 28Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 28Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg) + Ethinyl Estradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa Lo 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.025 mg) + Ethinyl Estradiol (0.025 mg) + Ethinyl Estradiol (0.025 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa Lo 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.025 mg) + Ethinyl Estradiol (0.025 mg) + Ethinyl Estradiol (0.025 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa Lo 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.025 mg) + Ethinyl Estradiol (0.025 mg) + Ethinyl Estradiol (0.025 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa Lo 28Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinyl Estradiol (0.025 mg) + Ethinyl Estradiol (0.025 mg) + Ethinyl Estradiol (0.025 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Categories
UNII
C291HFX4DY
CAS number
35189-28-7
Weight
Average: 369.4971
Monoisotopic: 369.230393863
Chemical Formula
C23H31NO3
InChI Key
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][[email protected]@]12CC[[email protected]@](OC(C)=O)(C#C)[[email protected]@]1(CC)CC[[email protected]]1([H])[[email protected]@]3([H])CC\C(C=C3CC[[email protected]@]21[H])=N/O

Pharmacology

Indication

For the prevention of pregnancy

Structured Indications
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.

TargetActionsOrganism
AProgesterone receptor
agonist
Human
AEstrogen receptor alpha
agonist
Human
UAndrogen receptor
partial agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Norgestimate.Investigational
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.Investigational, 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
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Norgestimate.Experimental, Investigational
AlitretinoinThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Alitretinoin.Approved, Investigational
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Norgestimate.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
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Norgestimate.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
Bempedoic acidThe therapeutic efficacy of Bempedoic acid can be decreased when used in combination with Norgestimate.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, Withdrawn
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.Investigational, 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
CarbutamideThe therapeutic efficacy of Carbutamide can be decreased when used in combination with Norgestimate.Experimental
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
ClorindioneNorgestimate may decrease the anticoagulant activities of Clorindione.Experimental
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
DiphenadioneNorgestimate may decrease the anticoagulant activities of Diphenadione.Experimental
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.Investigational, 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, Investigational
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Norgestimate.Approved
GriseofulvinThe serum concentration of Norgestimate can be decreased when it is combined 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
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 HumanThe therapeutic efficacy of Insulin Human can be decreased when used in combination with Norgestimate.Approved, Investigational
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
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, Investigational, Withdrawn
PhenindioneNorgestimate may decrease the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Phenobarbital.Approved
PhenprocoumonNorgestimate may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
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
RifaximinThe serum concentration of Norgestimate can be decreased when it is combined with Rifaximin.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Norgestimate.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 serum concentration of Saxagliptin can be decreased when it is combined 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
SotagliflozinThe therapeutic efficacy of Sotagliflozin can be decreased when used in combination with Norgestimate.Investigational
St. John's WortThe therapeutic efficacy of Norgestimate can be decreased when used in combination with St. John's Wort.Investigational, 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, Withdrawn
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
ThiopentalThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Thiopental.Approved, Vet Approved
TioclomarolNorgestimate may decrease the anticoagulant activities of Tioclomarol.Experimental
TipiracilThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Tipiracil.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 AcidTranexamic Acid may increase the thrombogenic activities of Norgestimate.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.Investigational, 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

General References
Not Available
External Links
Human Metabolome Database
HMDB15092
KEGG Drug
D05209
PubChem Compound
6540478
PubChem Substance
46507381
ChemSpider
5022837
ChEBI
50815
ChEMBL
CHEMBL1200934
Therapeutic Targets Database
DAP001210
PharmGKB
PA164744346
RxList
RxList Drug Page
Wikipedia
Norgestimate
ATC Codes
G03AA11 — Norgestimate and ethinylestradiolG03FA13 — Norgestimate and estrogen

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceHIV-infection/Aids1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentMajor Depressive Disorder (MDD)1
1TerminatedNot AvailableCystic Fibrosis Exacerbations While on and Off Hormonal Contraception1
3CompletedTreatmentContraception1
3RecruitingTreatmentPrimary Ovarian Insufficiency1
4Active Not RecruitingBasic ScienceCardiovascular Risks / Insulin Sensitivity / Perimenopausal Disorder1
4Active Not RecruitingPreventionBMI >30 kg/m2 / Cardiovascular Disease (CVD) / Insulin Resistance / Metabolic Syndromes1
Not AvailableCompletedTreatmentThrombosis, Venous1
Not AvailableTerminatedBasic ScienceContraception1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral
KitOral
Kit
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)
US5382573No1995-01-172012-01-17Us
US6747019No2000-03-202020-03-20Us
US7320970No2000-03-302020-03-30Us
US6214815Yes1999-12-092019-12-09Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)216 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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 molecules
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
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, steroid ester, ketoxime (CHEBI:50815)

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 ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Paris F, Rabeolina F, Balaguer P, Bacquet A, Sultan C: Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line. Gynecol Endocrinol. 2007 Apr;23(4):193-7. [PubMed:17505938]
  2. Prifti S, Lelle I, Strowitzki T, Rabe T: Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells. Gynecol Endocrinol. 2004 Jul;19(1):18-21. [PubMed:15625768]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da

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
Uniprot Name
Canalicular multispecific organic anion transporter 1
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]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:45