This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Summary
Lynestrenol is a progestin used for contraception and in the treatment of menstrual disorders.
- Generic Name
- Lynestrenol
- DrugBank Accession Number
- DB12474
- Background
Lynestrenol is a progestin and prodrug of norethisterone.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Lynestrenol (DB12474)
- Weight
- Average: 284.443
Monoisotopic: 284.214015522 - Chemical Formula
- C20H28O
- Synonyms
- Lynestrenol
- External IDs
- NSC-37725
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 Treatment of Endometrial carcinoma •••••••••••• •••••• Prevention of Endometrial hyperplasia •••••••••••• •••••• Treatment of Endometriosis •••••••••••• •••••• Treatment of Hypermenorrhea •••••••••••• •••••• Treatment of Menstrual cramps •••••••••••• •••••• - 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 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 Lynestrenol can be increased when it is combined with Abametapir. Abatacept The metabolism of Lynestrenol can be increased when combined with Abatacept. Abciximab The risk or severity of adverse effects can be increased when Lynestrenol is combined with Abciximab. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Lynestrenol. Acenocoumarol The risk or severity of adverse effects can be increased when Lynestrenol is combined with Acenocoumarol. - 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.
Categories
- ATC Codes
- G03AB02 — Lynestrenol and ethinylestradiol
- G03AB — Progestogens and estrogens, sequential preparations
- G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- 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
- G03DC — Estren derivatives
- G03D — PROGESTOGENS
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G03FB — Progestogens and estrogens, sequential preparations
- 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, Hormonal
- Contraceptives, Oral, Synthetic
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Estren Derivatives
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Hormonal Contraceptives for Systemic Use
- Norpregnanes
- Norpregnenes
- Norsteroids
- Progestin Contraceptives
- Progestins
- Progestogens and Estrogens, Sequential Preparations
- Reproductive Control Agents
- Sex Hormones and Modulators of the Genital System
- Steroids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Estrane steroids
- Direct Parent
- Estrane steroids
- Alternative Parents
- 17-hydroxysteroids / Delta-4-steroids / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Hydrocarbon derivatives
- Substituents
- 17-hydroxysteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Delta-4-steroid / Estrane-skeleton / Hydrocarbon derivative / Hydroxysteroid / Organic oxygen compound
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- steroid (CHEBI:31790) / C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C13037) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030127)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- N2Z8ALG4U5
- CAS number
- 52-76-6
- InChI Key
- YNVGQYHLRCDXFQ-XGXHKTLJSA-N
- InChI
- InChI=1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,6,15-18,21H,4-5,7-13H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
- IUPAC Name
- (1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
- SMILES
- C[C@]12CC[C@H]3[C@@H](CCC4=CCCC[C@H]34)[C@@H]1CC[C@@]2(O)C#C
References
- General References
- External Links
- KEGG Compound
- C13037
- PubChem Compound
- 5857
- PubChem Substance
- 347828712
- ChemSpider
- 5648
- 6529
- ChEBI
- 31790
- ChEMBL
- CHEMBL2107431
- ZINC
- ZINC000003875355
- Wikipedia
- Lynestrenol
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 Basic Science Transsexualism 1 4 Unknown Status Basic Science Gender Dysphoria 1 1 Completed Treatment Infertility 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 0.5 MG Tablet, delayed release Oral 0.5 mg Tablet Oral Tablet Oral 5 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00366 mg/mL ALOGPS logP 4 ALOGPS logP 4.04 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 17.59 Chemaxon pKa (Strongest Basic) -1.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 86.81 m3·mol-1 Chemaxon Polarizability 34.69 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No 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 splash10-000i-0090000000-c0c43efa7aa7d77f6f64 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0090000000-54ebf6593cac47f5bab3 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-1690000000-493b0de92cce9a2ea635 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0090000000-af5f6b5503620dd5658d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0090000000-fdfa3a374897fa53f553 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000t-7900000000-9ace315e35dda052218a 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]- 181.3926 predictedDeepCCS 1.0 (2019) [M+H]+ 183.75058 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.69296 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- 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
- Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
Drug created at October 20, 2016 22:31 / Updated at May 27, 2021 02:58