Identification

Name
Norgestimate
Accession Number
DB00957  (APRD00569)
Type
Small Molecule
Groups
Approved, Investigational
Description

Norgestimate was first described in the literature in 1977.5 It was developed by Ortho Pharmaceutical Corporation as part of an effort to develop new hormonal contraceptives with reduced adverse effects.5 It is commonly formulated with ethinylestradiol as a combined oral contraceptive that can also be used to treat moderate acne vulgaris.10,11

Norgestimate was granted FDA approval on 29 December 1989.9

Structure
Thumb
Synonyms
  • (+)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one oxime acetate (ester)
  • (17α)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime
  • d-13β-Ethyl-17α-ethynyl-17β-acetoxygon-4-en-3-one oxime
  • Dexnorgestrel Acetime
  • Norgestimate
  • Norgestimato
  • Norgestimatum
External IDs
ORF 10131 / RWJ 10131
Active Moieties
NameKindUNIICASInChI Key
NorelgestrominprodrugR0TAY3X63153016-31-2ISHXLNHNDMZNMC-XUDSTZEESA-N
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Centrisa 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 21Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 28Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 28Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Centrisa 28Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (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) + Ethinylestradiol (0.025 mg) + Ethinylestradiol (0.025 mg) + Ethinylestradiol (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) + Ethinylestradiol (0.025 mg) + Ethinylestradiol (0.025 mg) + Ethinylestradiol (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) + Ethinylestradiol (0.025 mg) + Ethinylestradiol (0.025 mg) + Ethinylestradiol (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) + Ethinylestradiol (0.025 mg) + Ethinylestradiol (0.025 mg) + Ethinylestradiol (0.025 mg)TabletOralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
International/Other Brands
Ortho-Prefest
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
(1R,3aS,3bR,7E,9aR,9bS,11aS)-11a-ethyl-1-ethynyl-7-(hydroxyimino)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-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

Indication

Norgestimate is formulated with ethinylestradiol as a combined oral contraceptive.10,11 It can also be given with low dose ethinylestradiol for contraception as well as the treatment of moderate acne vulgaris in women ≥15 years old.11

Associated Conditions
Associated Therapies
Pharmacodynamics

Norgestimate is a progestin that suppresses ovulation for contraception and reduces free testosterone to treat moderate acne vulgaris.7,10,11 The therapeutic index is wide as overdoses are rare.10,11 Patients should be counselled regarding the risk of vascular problems, liver disease, hypertension, metabolic effects, headaches, and bleeding irregularities.10,11

Mechanism of action

Progesterone analogs like norgestimate decrease the frequency of gonadotropin releasing hormone pulses from the hypothalamus, decreasing follicle stimulating hormone and luteinizing hormone.7 These actions prevent ovulation.10,11

Norgestimate suppresses the hypothalamo-pituitary-axis, reducing androgen synthesis.4 It also induces production of sex hormone binding globulin, which decreases free testosterone.4 These actions together result in less testosterone being available to stimulate sebaceous glands, resulting in effective treatment of some forms of acne.4

TargetActionsOrganism
AProgesterone receptor
agonist
Humans
UAndrogen receptor
partial agonist
Humans
AEstrogen receptor alpha
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Oral norgestimate has a Tmax of 0.5-2h.1

On day 21 of cycle 3, 17-desacetylnorgestimate reaches a Cmax of 1.82ng/mL, with a Tmax of 1.5h, and an AUC of 16.1h*ng/mL.11 At the same time, norgestrel reaches a Cmax of 2.79ng/mL, with a Tmax of 1.7h, and an AUC of 49.9h*ng/mL.11

Volume of distribution

Data regarding the volume of distribution of norgestimate are not readily available.10,11

Protein binding

17-desacetylnorgestimate is 97.2% bound to albumin and Norgestrel is >97% protein bound, including 92.5% bound to sex hormone binding globulin.3,10,11

Metabolism

Norgestimate is rapidly deacetylated to the active 17-desacetylnorgestimate, which is deoximated to the active norgestrel.1,2 17-desacetylnorgestimate is metabolized to a number of undefined hydroxylated metabolites, mainly by CYP3A4 and to a lesser extend by CYP2B6 and CYP2C9.2 Norgestrel is O-glucuronidated by UGT1A1 or oxidized to a number of undefined hydroxylated metabolites by CYP3A4.2

Route of elimination

Norgestimate is 45-49% eliminated in urine and 16-49% eliminated in feces.10 Unchanged norgestimate is not detected in urine.10

Half life

Norgestimate is rapidly deacetylated.1,2 The active metabolites of norgestimate, 17-desacetyl norgestimate, has a half life of 12-30h,1 while norgestrel has a half life of 36.4±10.2h.11

Clearance

Data regarding the clearance of norgestimate is not readily available.10,11

Toxicity

Data regarding overdoses of norgestimate are rare.10,11 However, the majority of patients overdosing on oral contraceptives do not become seriously ill.6 Treat overdoses with symptomatic and supportive care.6,10,11

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Norgestimate.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Norgestimate.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Norgestimate.
4-OxoretinolThe therapeutic efficacy of Norgestimate can be decreased when used in combination with 4-Oxoretinol.
7-NitroindazoleThe metabolism of Norgestimate can be increased when combined with 7-Nitroindazole.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be increased when combined with Norgestimate.
AbciximabNorgestimate may decrease the anticoagulant activities of Abciximab.
AbirateroneThe metabolism of Abiraterone can be increased when combined with Norgestimate.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Norgestimate.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Norgestimate.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take at the same time every day.
  • Take with or without food.

References

General References
  1. Saxena A, Gupta AK, Kumar VP, Nainar MS, Bob M, Kasibhatta R: Quantification of 17-desacetyl norgestimate in human plasma by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and its application to bioequivalence study. J Pharm Anal. 2015 Apr;5(2):93-100. doi: 10.1016/j.jpha.2014.09.004. Epub 2014 Sep 22. [PubMed:29403920]
  2. Ahire D, Sinha S, Brock B, Iyer R, Mandlekar S, Subramanian M: Metabolite Identification, Reaction Phenotyping, and Retrospective Drug-Drug Interaction Predictions of 17-Deacetylnorgestimate, the Active Component of the Oral Contraceptive Norgestimate. Drug Metab Dispos. 2017 Jun;45(6):676-685. doi: 10.1124/dmd.116.073940. Epub 2017 Mar 10. [PubMed:28283499]
  3. Hammond GL, Abrams LS, Creasy GW, Natarajan J, Allen JG, Siiteri PK: Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. Contraception. 2003 Feb;67(2):93-9. [PubMed:12586319]
  4. 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]
  5. Hahn DW, Allen GO, McGuire JL: The pharmacological profile of norgestimate, a new orally active progestin. Contraception. 1977 Nov;16(5):541-53. doi: 10.1016/0010-7824(77)90077-4. [PubMed:201429]
  6. Weerasinghe M, Konradsen F, Eddleston M, Pearson M, Agampodi T, Storm F, Agampodi S: Overdose of oral contraceptive pills as a means of intentional self-poisoning amongst young women in Sri Lanka: considerations for family planning. J Fam Plann Reprod Health Care. 2017 Apr;43(2):147-150. doi: 10.1136/jfprhc-2015-101171. Epub 2016 Mar 22. [PubMed:27006385]
  7. Cooper DB, Mahdy H: Oral Contraceptive Pills . [PubMed:28613632]
  8. Frohlich M, Albermann N, Sauer A, Walter-Sack I, Haefeli WE, Weiss J: In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins. Biochem Pharmacol. 2004 Dec 15;68(12):2409-16. doi: 10.1016/j.bcp.2004.08.026. [PubMed:15548387]
  9. FDA Approved Drug Products: Ortho Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets (Discontinued) [Link]
  10. FDA Approved Drug Products: Ortho Tri-Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
  11. FDA Approved Drug Products: Ortho Tri-Cyclen Lo Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
External Links
Human Metabolome Database
HMDB0015092
KEGG Drug
D05209
PubChem Compound
6540478
PubChem Substance
46507381
ChemSpider
5022837
RxNav
31994
ChEBI
50815
ChEMBL
CHEMBL1200934
ZINC
ZINC000003938695
Therapeutic Targets Database
DAP001210
PharmGKB
PA164744346
RxList
RxList Drug Page
Wikipedia
Norgestimate
ATC Codes
G03AA11 — Norgestimate and ethinylestradiolG03FA13 — Norgestimate and estrogenG03AB09 — Norgestimate and ethinylestradiol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableChronic Hepatitis C Virus (HCV) Infection1
1CompletedNot AvailableHepatitis C Virus (HCV) Infection1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections2
1CompletedNot AvailablePharmacokinetics1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedBasic ScienceMigraine1
1CompletedBasic ScienceNASH - Nonalcoholic Steatohepatitis1
1CompletedOtherHealthy Volunteers1
1CompletedPreventionContraception / Drug Drug Interaction (DDI) / Pharmacokinetics1
1CompletedPreventionContraception / Female Contraception / Pharmacokinetics / Therapeutic Equivalency1
1CompletedPreventionDrug Drug Interaction (DDI) / Healthy Volunteers / Pharmacokinetics1
1CompletedPreventionOral Contraception / Pharmacokinetics / Therapeutic Equivalency1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHepatitis C Virus (HCV) Infection1
1CompletedTreatmentMajor Depressive Disorder (MDD)1
1CompletedTreatmentType 2 Diabetes Mellitus1
1SuspendedNot AvailablePharmacokinetics1
1TerminatedNot AvailableCystic Fibrosis Exacerbations While on and Off Hormonal Contraception1
2CompletedTreatmentMetrorrhagia1
2CompletedTreatmentOsteoporosis1
2Unknown StatusTreatmentContraception1
3CompletedTreatmentContraception1
3WithdrawnTreatmentPrimary Ovarian Insufficiency1
4CompletedNot AvailableBirth Control Compliance1
4CompletedPreventionBMI >30 kg/m2 / Cardiovascular Heart Disease / Insulin Resistance / Metabolic Syndromes1
4CompletedScreeningCardiovascular Risk / Insulin Sensitivity / Perimenopausal Disorder1
4CompletedTreatmentAcne Vulgaris1
4CompletedTreatmentContraception1
Not AvailableCompletedNot AvailableContraception / Female Contraception1
Not AvailableCompletedTreatmentThrombosis, Venous1
Not AvailableTerminatedBasic ScienceContraception1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Barr Pharmaceuticals
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Duramed
  • Fielding Pharmaceutical Co.
  • Innovative Manufacturing and Distribution Services Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral
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)
US5382573No1995-01-172012-01-17Us
US6747019No2004-06-082020-03-20Us
US7320970No2008-01-222020-03-30Us
US6214815Yes2001-04-102019-12-09Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)216 °CPhysProp
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
Polarizability42.79 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
Humans
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
Humans
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. 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]
Kind
Protein
Organism
Humans
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. doi: 10.1016/0002-9378(90)90559-p. [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]
  4. Paris F, Balaguer P, Rimbault F, Gaspari L, Sultan C: Molecular action of norgestimate: new developments. Gynecol Endocrinol. 2015 Jun;31(6):487-90. doi: 10.3109/09513590.2015.1016904. Epub 2015 May 13. [PubMed:25970022]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
References
  1. Ahire D, Sinha S, Brock B, Iyer R, Mandlekar S, Subramanian M: Metabolite Identification, Reaction Phenotyping, and Retrospective Drug-Drug Interaction Predictions of 17-Deacetylnorgestimate, the Active Component of the Oral Contraceptive Norgestimate. Drug Metab Dispos. 2017 Jun;45(6):676-685. doi: 10.1124/dmd.116.073940. Epub 2017 Mar 10. [PubMed:28283499]
  2. Saxena A, Gupta AK, Kumar VP, Nainar MS, Bob M, Kasibhatta R: Quantification of 17-desacetyl norgestimate in human plasma by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and its application to bioequivalence study. J Pharm Anal. 2015 Apr;5(2):93-100. doi: 10.1016/j.jpha.2014.09.004. Epub 2014 Sep 22. [PubMed:29403920]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Ahire D, Sinha S, Brock B, Iyer R, Mandlekar S, Subramanian M: Metabolite Identification, Reaction Phenotyping, and Retrospective Drug-Drug Interaction Predictions of 17-Deacetylnorgestimate, the Active Component of the Oral Contraceptive Norgestimate. Drug Metab Dispos. 2017 Jun;45(6):676-685. doi: 10.1124/dmd.116.073940. Epub 2017 Mar 10. [PubMed:28283499]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Ahire D, Sinha S, Brock B, Iyer R, Mandlekar S, Subramanian M: Metabolite Identification, Reaction Phenotyping, and Retrospective Drug-Drug Interaction Predictions of 17-Deacetylnorgestimate, the Active Component of the Oral Contraceptive Norgestimate. Drug Metab Dispos. 2017 Jun;45(6):676-685. doi: 10.1124/dmd.116.073940. Epub 2017 Mar 10. [PubMed:28283499]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Ahire D, Sinha S, Brock B, Iyer R, Mandlekar S, Subramanian M: Metabolite Identification, Reaction Phenotyping, and Retrospective Drug-Drug Interaction Predictions of 17-Deacetylnorgestimate, the Active Component of the Oral Contraceptive Norgestimate. Drug Metab Dispos. 2017 Jun;45(6):676-685. doi: 10.1124/dmd.116.073940. Epub 2017 Mar 10. [PubMed:28283499]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Hammond GL, Abrams LS, Creasy GW, Natarajan J, Allen JG, Siiteri PK: Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. Contraception. 2003 Feb;67(2):93-9. [PubMed:12586319]
  2. FDA Approved Drug Products: Ortho Tri-Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
  3. FDA Approved Drug Products: Ortho Tri-Cyclen Lo Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hammond GL, Abrams LS, Creasy GW, Natarajan J, Allen JG, Siiteri PK: Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. Contraception. 2003 Feb;67(2):93-9. [PubMed:12586319]
  2. FDA Approved Drug Products: Ortho Tri-Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
  3. FDA Approved Drug Products: Ortho Tri-Cyclen Lo Norgestimate and Ethinyl Estradiol Oral Tablets [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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]
  2. Frohlich M, Albermann N, Sauer A, Walter-Sack I, Haefeli WE, Weiss J: In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins. Biochem Pharmacol. 2004 Dec 15;68(12):2409-16. doi: 10.1016/j.bcp.2004.08.026. [PubMed:15548387]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 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]
  2. Frohlich M, Albermann N, Sauer A, Walter-Sack I, Haefeli WE, Weiss J: In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins. Biochem Pharmacol. 2004 Dec 15;68(12):2409-16. doi: 10.1016/j.bcp.2004.08.026. [PubMed:15548387]

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51

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