Identification
- Summary
Dydrogesterone is a synthetic progesterone for menstrual cycle regulation, infertility treatment, prevention of miscarriage, and other conditions.
- Generic Name
- Dydrogesterone
- DrugBank Accession Number
- DB00378
- Background
A synthetic progestational hormone with no androgenic or estrogenic properties. Unlike many other progestational compounds, dydrogesterone produces no increase in temperature and does not inhibit ovulation.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
Structure for Dydrogesterone (DB00378)
- Weight
- Average: 312.4458
Monoisotopic: 312.20893014 - Chemical Formula
- C21H28O2
- Synonyms
- (9β,10α)-pregna-4,6-diene-3,20-dione
- 10α-Isopregnenone
- 6-Dehydro-retro-progesterone
- 9β,10α-pregna-4,6-diene-3,20-dione
- delta(6)-Retroprogesterone
- delta(sup 6)-Retroprogesterone
- Didrogesterona
- Didrogesterone
- Dydrogesterona
- Dydrogestérone
- Dydrogesterone
- Dydrogesteronum
- Gestatron
- Hydrogesterone
- Hydrogestrone
- Isopregnenone
- Retro-6-dehydroprogesterone
- External IDs
- NSC-92336
Pharmacology
- Indication
Used to treat irregular duration of cycles and irregular occurrence and duration of periods caused by progesterone deficiency. Also used to prevent natural abortion in patients who have a history of habitual abortions.
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 Prevention of Abortions spontaneous •••••••••••• •••••• Adjunct therapy in treatment of Infertility •••••••••••• •••••• Treatment of Menstrual cramps •••••••••••• •••••• Treatment of Premenstrual syndrome •••••••••••• •••••• Prevention of Recurrent miscarriages •••••••••••• •••••• - 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
Dydrogesterone is an orally active progestogen which acts directly on the uterus, producing a complete secretory endometrium in an estrogen-primed uterus. At therapeutic levels, dydrogesterone has no contraceptive effect as it does not inhibit or interfere with ovulation or the corpus luteum. Furthermore, dydrogesterone is non-androgenic, non-estrogenic, non-corticoid, non-anabolic and is not excreted as pregnanediol. Dydrogesterone helps to regulate the healthy growth and normal shedding of the uterus lining. Therefore, it may be useful in the treatment of menstrual disorders such as absent, irregular or painful menstrual periods, infertility, premenstrual syndrome and endometriosis.
- Mechanism of action
Dydrogesterone is a progestogen that works by regulating the healthy growth and normal shedding of the womb lining by acting on progesterone receptors in the uterus.
Target Actions Organism AProgesterone receptor agonistHumans - Absorption
Rapidly absorbed in the gastrointestinal tract with a bioavailability of 28%.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Metabolism is complete to a 20-dihydrodydrogesterone (DHD) metabolite.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Dydrogesterone: 5-7 hours, 20-dihydrodydrogesterone (DHD) metabolite: 14-17 hours
- 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
No serious or unexpected toxicity has been observed with dydrogesterone. In acute toxicity studies, the LD50 doses in rats exceeded 4,640mg/kg for the oral route.
- 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 Dydrogesterone can be increased when it is combined with Abametapir. Abciximab Dydrogesterone may decrease the anticoagulant activities of Abciximab. Acenocoumarol Dydrogesterone may decrease the anticoagulant activities of Acenocoumarol. Alteplase Dydrogesterone may decrease the anticoagulant activities of Alteplase. Amiodarone The metabolism of Dydrogesterone can be decreased when combined with Amiodarone. - 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.- International/Other Brands
- Dabroston (Abbott) / Dufaston (Abbott) / Duphaston (Abbott) / Terolut (Solvay)
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image FEMOSTON Dydrogesterone (20 mg) + Estradiol (2 mg) Tablet Oral Viatris Healthcare Limited 2014-07-08 2024-01-11 Italy 
FEMOSTON Dydrogesterone (5 mg) + Estradiol (1 mg) Tablet, film coated Oral Viatris Healthcare Limited 2014-07-08 Not applicable Italy FEMOSTON Dydrogesterone (5 mg) + Estradiol (1 mg) Tablet, film coated Oral Viatris Healthcare Limited 2014-07-08 Not applicable Italy FEMOSTON Dydrogesterone (2.5 MG) + Estradiol (0.5 MG) Tablet, coated Oral Mylan Ire Healthcare Limited 2018-02-21 Not applicable Italy FEMOSTON Dydrogesterone (10 mg) + Estradiol (1 mg) Tablet Oral Viatris Healthcare Limited 2014-07-08 Not applicable Italy
Categories
- ATC Codes
- G03FA14 — Dydrogesterone and estrogen
- 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
- G03DB — Pregnadien derivatives
- G03D — PROGESTOGENS
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Adrenal Cortex Hormones
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Pregnadien Derivatives
- Pregnadienes
- Pregnanes
- Progestins
- Progestogens and Estrogens, Sequential Preparations
- 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 gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Pregnane steroids
- Direct Parent
- Gluco/mineralocorticoids, progestogins and derivatives
- Alternative Parents
- 20-oxosteroids / 3-oxosteroids / Cyclohexenones / Organic oxides / Hydrocarbon derivatives
- Substituents
- 20-oxosteroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic ketone / Cyclohexenone / Hydrocarbon derivative / Ketone / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3-oxo steroid, 3-oxo Delta(4)-steroid, 20-oxo steroid (CHEBI:31527)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 90I02KLE8K
- CAS number
- 152-62-5
- InChI Key
- JGMOKGBVKVMRFX-HQZYFCCVSA-N
- InChI
- InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1
- IUPAC Name
- (1S,3aS,3bS,9aS,9bR,11aS)-1-acetyl-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
- SMILES
- [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@@]12C
References
- Synthesis Reference
Reerink, E.H., Westerhof, P. and Scholer, H.F.L.; U.S. Patent 3,198,792; assigned to North American Philips Company, Inc.
- General References
- Link [Link]
- External Links
- Human Metabolome Database
- HMDB0014522
- KEGG Drug
- D01217
- PubChem Compound
- 9051
- PubChem Substance
- 46506195
- ChemSpider
- 8699
- 3706
- ChEBI
- 31527
- ChEMBL
- CHEMBL1200853
- ZINC
- ZINC000003875998
- Therapeutic Targets Database
- DAP001205
- PharmGKB
- PA164745443
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Dydrogesterone
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 Active Not Recruiting Treatment Dydrogesterone / Female Infertility / Frozen Embryo Transfer / Hormone Replacement Therapy 1 4 Completed Prevention Threatened Miscarriage 1 4 Completed Treatment Assisted Reproduction / Frozen Embryo / Luteal Phase Defect / Luteal Support / Placenta; Implantation / Pregnancy Loss 1 4 Completed Treatment Dydrogesterone / Female Infertility / Genital Diseases, Female / Genital Diseases, Male / Hormones / Hormones, Hormone Substitutes, and Hormone Antagonists / Infertility / Physiological Effects of Drugs / Progesterone / Progestins 1 4 Completed Treatment Endometrial Polyps 1
Pharmacoeconomics
- Manufacturers
- Solvay pharmaceuticals
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Tablet Oral 5 MG Tablet Oral 10.000 mg Tablet, film coated Oral Tablet, film coated Oral 10 MG Tablet Oral 2.06 mg Tablet, film coated Oral Tablet, film coated Oral 10 mg Tablet, coated Oral Tablet, film coated Oral 5 mg Kit; tablet, film coated Oral Tablet, coated Oral 10 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 168-169 Reerink, E.H., Westerhof, P. and Scholer, H.F.L.; U.S. Patent 3,198,792; assigned to North American Philips Company, Inc. logP 3.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00486 mg/mL ALOGPS logP 3.27 ALOGPS logP 3.79 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 19.4 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 34.14 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 93.82 m3·mol-1 Chemaxon Polarizability 36.39 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
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.982 Caco-2 permeable + 0.7724 P-glycoprotein substrate Substrate 0.5449 P-glycoprotein inhibitor I Inhibitor 0.8841 P-glycoprotein inhibitor II Inhibitor 0.6043 Renal organic cation transporter Non-inhibitor 0.6931 CYP450 2C9 substrate Non-substrate 0.847 CYP450 2D6 substrate Non-substrate 0.8795 CYP450 3A4 substrate Substrate 0.7408 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9533 CYP450 2C19 inhibitor Non-inhibitor 0.6514 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8203 Ames test Non AMES toxic 0.9626 Carcinogenicity Non-carcinogens 0.9151 Biodegradation Not ready biodegradable 0.9575 Rat acute toxicity 1.8041 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7451 hERG inhibition (predictor II) Non-inhibitor 0.7454
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 186.1184773 predictedDarkChem Lite v0.1.0 [M-H]- 186.6202773 predictedDarkChem Lite v0.1.0 [M-H]- 178.50243 predictedDeepCCS 1.0 (2019) [M+H]+ 186.1636773 predictedDarkChem Lite v0.1.0 [M+H]+ 187.3652773 predictedDarkChem Lite v0.1.0 [M+H]+ 180.56108 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.8765773 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.8449773 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.77002 predictedDeepCCS 1.0 (2019)
Targets
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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
- Blois SM, Joachim R, Kandil J, Margni R, Tometten M, Klapp BF, Arck PC: Depletion of CD8+ cells abolishes the pregnancy protective effect of progesterone substitution with dydrogesterone in mice by altering the Th1/Th2 cytokine profile. J Immunol. 2004 May 15;172(10):5893-9. [Article]
- Tamaya T, Tsurusaki T, Ide N, Yamada T, Murakami T, Wada K, Fujimoto Z, Okada H: Nuclear translocation of progesterone receptor--progestogen complex in vitro. Nihon Sanka Fujinka Gakkai Zasshi. 1983 Jan;35(1):77-82. [Article]
- Raghupathy R, Al Mutawa E, Makhseed M, Azizieh F, Szekeres-Bartho J: Modulation of cytokine production by dydrogesterone in lymphocytes from women with recurrent miscarriage. BJOG. 2005 Aug;112(8):1096-101. [Article]
- Okada H: [Metabolism, structure and biological activity of sex steroids]. Nihon Naibunpi Gakkai Zasshi. 1993 Feb 20;69(2):67-79. [Article]
- Tamaya T, Furuta N, Ohono Y, Ide N, Tsurusaki T, Okada H: Chromatin transcription by progesterone-receptor complex in rabbit uterus. Endocrinol Jpn. 1979 Feb;26(1):117-22. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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
- Olbrich M, Weigl K, Kahler E, Mihara K: Dydrogesterone metabolism in human liver by aldo-keto reductases and cytochrome P450 enzymes. Xenobiotica. 2016 Oct;46(10):868-74. doi: 10.3109/00498254.2015.1134852. Epub 2016 Jan 21. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:41