Norethindrone enanthate
Star0
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Summary
Norethindrone enanthate is a synthetic progestogen indicated for contraceptive therapy.
- Generic Name
- Norethindrone enanthate
- DrugBank Accession Number
- DB14678
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 410.598
Monoisotopic: 410.282095084 - Chemical Formula
- C27H38O3
- Synonyms
- Norethisterone enanthate
- Norethisterone oenanthate
- External IDs
- LG 202
- SH 393
- SH-8.0393
- ZK-5410
Pharmacology
- Indication
Not Available
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 prevent Pregnancy Combination Product in combination with: Estradiol valerate (DB13956) •••••••••••• ••••• •••••••••• ••••••••• •••••••• - 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
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- 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
Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Norethindrone enanthate can be increased when it is combined with Abametapir. Abciximab The risk or severity of adverse effects can be increased when Norethindrone enanthate is combined with Abciximab. Acenocoumarol The risk or severity of adverse effects can be increased when Norethindrone enanthate is combined with Acenocoumarol. Acetaminophen The metabolism of Norethindrone enanthate can be increased when combined with Acetaminophen. Acetazolamide The metabolism of Norethindrone enanthate can be increased when combined with Acetazolamide. - Food Interactions
- Not Available
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 Norethisterone prodrug T18F433X4S 68-22-4 VIKNJXKGJWUCNN-XGXHKTLJSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image MESIGYNA 5 MG+50 MG/1 ML ENJEKSIYONLUK COZELTI ICEREN KULLANIMA HAZIR ENJEKTÖR Norethindrone enanthate (50 mg/ml) + Estradiol valerate (5 mg/ml) Injection, solution Intramuscular BAYER TÜRK KİMYA SAN. LTD. ŞTİ. 1999-08-06 Not applicable Turkey MESIGYNA® Norethindrone enanthate (50 mg) + Estradiol valerate (5 mg) Solution Intramuscular Bayer Ag 2006-11-10 2021-04-01 Colombia
Categories
- Drug Categories
- Adrenal Cortex Hormones
- Contraceptive Agents, Female
- Contraceptive Agents, Hormonal
- Contraceptives, Oral
- Contraceptives, Oral, Synthetic
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Hormonal Contraceptives for Systemic Use
- Norpregnanes
- Norpregnenes
- Norsteroids
- Progesterone Congeners
- Progestins
- Reproductive Control Agents
- Steroids
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- HY3S2K0J0F
- CAS number
- 3836-23-5
- InChI Key
- APTGJECXMIKIET-WOSSHHRXSA-N
- InChI
- InChI=1S/C27H38O3/c1-4-6-7-8-9-25(29)30-27(5-2)17-15-24-23-12-10-19-18-20(28)11-13-21(19)22(23)14-16-26(24,27)3/h2,18,21-24H,4,6-17H2,1,3H3/t21-,22+,23+,24-,26-,27-/m0/s1
- IUPAC Name
- (1R,3aS,3bR,9aR,9bS,11aS)-1-ethynyl-11a-methyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl heptanoate
- SMILES
- [H][C@@]12CC[C@@](OC(=O)CCCCCC)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
References
- General References
- NPRA Product Information: NORISTERAT (norethindrone enanthate) intramuscular injection [Link]
- External Links
- KEGG Compound
- C14486
- ChemSpider
- 199613
- 31984
- ChEBI
- 34894
- ChEMBL
- CHEMBL3187229
- ZINC
- ZINC000004217172
- Wikipedia
- Norethisterone_enanthate
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Contraceptive 1 somestatus stop reason just information to hide Not Available Unknown Status Health Services Research Contraception Behavior / Contraceptive Usage 1 somestatus stop reason just information to hide 4 Completed Prevention Bacterial Vaginosis (BV) / Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide 1 Completed Basic Science Pharmacokinetics 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intramuscular 200 mg Injection Intramuscular 200 mg/ml Injection, solution Intramuscular Solution Intramuscular; Parenteral Solution Parenteral Solution Intramuscular 50 mg Solution Intramuscular Solution Parenteral 200.000 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00148 mg/mL ALOGPS logP 5.43 ALOGPS logP 6.14 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 18.25 Chemaxon pKa (Strongest Basic) -4.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 43.37 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 119.61 m3·mol-1 Chemaxon Polarizability 49.66 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001a-2090100000-cbaaef1cad38452bee69 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0bt9-0710900000-41c0fd8ec0548c9354eb Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-08gl-8790000000-afc6dfb2eb7d99215090 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001j-3290000000-94586e403689e504a480 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0pbc-9210000000-1626bc1d7d768f107acd Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-9010000000-d4725436adbf90d73401 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]- 216.5123271 predictedDarkChem Lite v0.1.0 [M-H]- 204.39027 predictedDeepCCS 1.0 (2019) [M+H]+ 215.8657271 predictedDarkChem Lite v0.1.0 [M+H]+ 207.68788 predictedDeepCCS 1.0 (2019) [M+Na]+ 216.0223271 predictedDarkChem Lite v0.1.0 [M+Na]+ 215.00453 predictedDeepCCS 1.0 (2019)
Enzymes
1. DetailsCytochrome P450 3A4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Zhang N, Shon J, Kim MJ, Yu C, Zhang L, Huang SM, Lee L, Tran D, Li L: Role of CYP3A in Oral Contraceptives Clearance. Clin Transl Sci. 2018 May;11(3):251-260. doi: 10.1111/cts.12499. Epub 2017 Oct 6. [Article]
Drug created at September 05, 2018 17:00 / Updated at May 14, 2021 01:07