Identification
- Summary
Norgestimate is a progesterone used as a contraceptive and to treat acne vulgaris.
- Brand Names
- Estarylla 28 Day, Femynor 28 Day, Mili 28 Day, Mono-linyah 28 Day, Mononessa 28 Day, Nymyo 28 Day, Ortho Tri-cyclen 28 Day, Ortho Tri-cyclen Lo 28 Day, Prefest 30 Day, Previfem 28 Day, Sprintec 28 Day, Tri Femynor 28 Day, Tri-LO- Estarylla 28 Day, Tri-LO-marzia 28-day, Tri-LO-mili, Tri-Lo-Sprintec, Tri-estarylla 28 Day, Tri-linyah, Tri-mili 28 Day, Tri-nymyo 28 Day Pack, Tri-previfem 28 Day, Tri-sprintec 28 Day, Tri-vylibra 28 Day, Tri-vylibra Lo 28 Day, Trinessa 28 Day, Trinessa Lo 28 Day, Vylibra 28 Day
- Generic Name
- Norgestimate
- DrugBank Accession Number
- DB00957
- Background
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
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Norgestimate (DB00957)
- Weight
- Average: 369.4971
Monoisotopic: 369.230393863 - Chemical Formula
- C23H31NO3
- 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
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Dysmenorrhea Combination Product in combination with: Ethinylestradiol (DB00977) ••• ••••• Used in combination to treat Hirsutism Combination Product in combination with: Ethinylestradiol (DB00977) ••• ••••• Used in combination to treat Menorrhagia Combination Product in combination with: Ethinylestradiol (DB00977) ••• ••••• Used in combination to prevent Osteoporosis, postmenopausal Combination Product in combination with: Estradiol (DB00783) •••••••••••• Used in combination to treat Moderate acne vulgaris Combination Product in combination with: Ethinylestradiol (DB00977) •••••••••••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Target Actions Organism AProgesterone receptor agonistHumans AEstrogen receptor alpha agonistHumans UAndrogen receptor partial agonistHumans - 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
Hover over products below to view reaction partners
- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Norgestimate can be increased when it is combined with Abametapir. Abatacept The metabolism of Norgestimate can be increased when combined with Abatacept. Abciximab The risk or severity of adverse effects can be increased when Norgestimate is combined with Abciximab. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Norgestimate. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Norgestimate. - Food Interactions
- Take at the same time every day.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Norelgestromin prodrug R0TAY3X631 53016-31-2 ISHXLNHNDMZNMC-XUDSTZEESA-N - Product Images
- International/Other Brands
- Ortho-Prefest
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Centrisa 21 Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) Tablet Oral Patriot A Division Of Janssen Inc Not applicable Not applicable Canada 
Centrisa 21 Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) Tablet Oral Patriot A Division Of Janssen Inc Not applicable Not applicable Canada Centrisa 21 Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) Tablet Oral Patriot A Division Of Janssen Inc Not applicable Not applicable Canada Centrisa 28 Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) Tablet Oral Patriot A Division Of Janssen Inc Not applicable Not applicable Canada Centrisa 28 Norgestimate (0.180 mg) + Norgestimate (0.215 mg) + Norgestimate (0.250 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) + Ethinylestradiol (0.035 mg) Tablet Oral Patriot A Division Of Janssen Inc Not applicable Not applicable Canada
Categories
- ATC Codes
- G03AA11 — Norgestimate and ethinylestradiol
- G03AA — Progestogens and estrogens, fixed combinations
- G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G03FA — Progestogens and estrogens, fixed combinations
- G03F — PROGESTOGENS AND ESTROGENS IN COMBINATION
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Adrenal Cortex Hormones
- Combination Contraceptives (with Estrogen and derivatives)
- Contraceptive Agents, Female
- Contraceptive Agents, Hormonal
- Contraceptives, Oral
- Contraceptives, Oral, Synthetic
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Hormonal Contraceptives for Systemic Use
- Hyperglycemia-Associated Agents
- Norpregnanes
- Norpregnenes
- Norsteroids
- P-glycoprotein inhibitors
- Progestin Contraceptives
- Progestins
- Progestogens and Estrogens, Sequential Preparations
- Reproductive Control Agents
- Sex Hormones and Modulators of the Genital System
- Steroids
- UGT1A1 Substrates
- Chemical TaxonomyProvided by Classyfire
- 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
- Acetylide / Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Delta-4-steroid / Estrane-skeleton / Hydrocarbon derivative / Ketoxime / Monocarboxylic acid or derivatives
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- terminal acetylenic compound, steroid ester, ketoxime (CHEBI:50815)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- NKX8DN6TY9
- CAS number
- 35189-28-7
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Cooper DB, Mahdy H: Oral Contraceptive Pills . [Article]
- 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. [Article]
- FDA Approved Drug Products: Ortho Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets (Discontinued) [Link]
- FDA Approved Drug Products: Ortho Tri-Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
- 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
- 31994
- ChEBI
- 50815
- ChEMBL
- CHEMBL1200934
- ZINC
- ZINC000003938695
- Therapeutic Targets Database
- DAP001210
- PharmGKB
- PA164744346
- RxList
- RxList Drug Page
- Wikipedia
- Norgestimate
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Other Birth Control Compliance 1 4 Completed Prevention Cardiovascular Disease (CVD) / Obesity / Resistance, Insulin / Syndrome, Metabolic 1 4 Completed Screening Cardiovascular Risk / Insulin Sensitivity / Perimenopausal Disorder 1 4 Completed Treatment Acne Vulgaris 1 4 Completed Treatment Contraception 1
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
Form Route Strength Tablet Oral Kit; tablet Oral Kit; tablet, coated Oral Kit Oral Kit; tablet, film coated Oral - Prices
Unit description Cost Unit Ortho Tri-Cyclen Lo 28 0.18/0.215/0.25 mg-25 mcg tablet Disp Pack 78.06USD disp Ortho Tri-Cyclen (28) 28 0.18/0.215/0.25 mg-35 mcg tablet Disp Pack 47.99USD disp Ortho-Cyclen (28) 28 0.25-35 mg-mcg tablet Disp Pack 38.99USD disp Ortho tri-cyclen lo tablet 2.68USD tablet Ortho-prefest tablet 1.36USD tablet Ortho-cyclen 28 tablet 1.13USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5382573 No 1995-01-17 2012-01-17 US 
US6747019 No 2004-06-08 2020-03-20 US US7320970 No 2008-01-22 2020-03-30 US US6214815 Yes 2001-04-10 2019-12-09 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 216 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.00531 mg/mL ALOGPS logP 3.8 ALOGPS logP 4.11 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 11.47 Chemaxon pKa (Strongest Basic) 3.11 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 58.89 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 105 m3·mol-1 Chemaxon Polarizability 42.79 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9896 Blood Brain Barrier + 0.9307 Caco-2 permeable - 0.5125 P-glycoprotein substrate Substrate 0.5877 P-glycoprotein inhibitor I Inhibitor 0.6103 P-glycoprotein inhibitor II Non-inhibitor 0.7485 Renal organic cation transporter Non-inhibitor 0.6733 CYP450 2C9 substrate Non-substrate 0.7842 CYP450 2D6 substrate Non-substrate 0.8374 CYP450 3A4 substrate Substrate 0.736 CYP450 1A2 substrate Non-inhibitor 0.7596 CYP450 2C9 inhibitor Non-inhibitor 0.6541 CYP450 2D6 inhibitor Non-inhibitor 0.8829 CYP450 2C19 inhibitor Non-inhibitor 0.6215 CYP450 3A4 inhibitor Non-inhibitor 0.7716 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7175 Ames test Non AMES toxic 0.5404 Carcinogenicity Non-carcinogens 0.8389 Biodegradation Not ready biodegradable 0.9929 Rat acute toxicity 2.4561 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9075 hERG inhibition (predictor II) Non-inhibitor 0.7999
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-2698000000-7e02d6124cbf30e8be87 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0009000000-9dfa39a926fb72890ae6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0pb9-6009000000-fa9635b56e9489f65323 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-01x0-2194000000-eba1fd77827014a60cbf Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-3029000000-97af2a535b7d0df3d45b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0adi-0920000000-5f616f3511c4df4d996f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0536-8029000000-85f6b1ec0e0069c24e52 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 205.4828471 predictedDarkChem Lite v0.1.0 [M-H]- 205.4763471 predictedDarkChem Lite v0.1.0 [M-H]- 190.10234 predictedDeepCCS 1.0 (2019) [M+H]+ 206.8220471 predictedDarkChem Lite v0.1.0 [M+H]+ 207.0097471 predictedDarkChem Lite v0.1.0 [M+H]+ 191.99776 predictedDeepCCS 1.0 (2019) [M+Na]+ 206.2609471 predictedDarkChem Lite v0.1.0 [M+Na]+ 205.6488471 predictedDarkChem Lite v0.1.0 [M+Na]+ 197.66808 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- 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. [Article]
- Graziottin A: A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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
- Pasqualini JR: Differential effects of progestins on breast tissue enzymes. Maturitas. 2003 Dec 10;46 Suppl 1:S45-54. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- 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
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
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
- 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. [Article]
- FDA Approved Drug Products: Ortho Tri-Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
- 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
- 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. [Article]
- FDA Approved Drug Products: Ortho Tri-Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
- 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
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:46