Dydrogesterone

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Approved, Investigational, Withdrawn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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prevention ofAbortions spontaneous••••••••••••••••••
Adjunct therapy in treatment ofInfertility••••••••••••••••••
Treatment ofMenstrual cramps••••••••••••••••••
Treatment ofPremenstrual syndrome••••••••••••••••••
Prevention ofRecurrent miscarriages••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AProgesterone receptor
agonist
Humans
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.

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Route of elimination

Not Available

Half-life

Dydrogesterone: 5-7 hours, 20-dihydrodydrogesterone (DHD) metabolite: 14-17 hours

Clearance

Not Available

Adverse Effects
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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
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
AbametapirThe serum concentration of Dydrogesterone can be increased when it is combined with Abametapir.
AbciximabDydrogesterone may decrease the anticoagulant activities of Abciximab.
AcenocoumarolDydrogesterone may decrease the anticoagulant activities of Acenocoumarol.
AlteplaseDydrogesterone may decrease the anticoagulant activities of Alteplase.
AmiodaroneThe metabolism of Dydrogesterone can be decreased when combined with Amiodarone.
Food Interactions
Not Available

Products

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International/Other Brands
Dabroston (Abbott) / Dufaston (Abbott) / Duphaston (Abbott) / Terolut (Solvay)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FEMOSTONDydrogesterone (20 mg) + Estradiol (2 mg)TabletOralViatris Healthcare Limited2014-07-082024-01-11Italy flag
FEMOSTONDydrogesterone (5 mg) + Estradiol (1 mg)Tablet, film coatedOralViatris Healthcare Limited2014-07-08Not applicableItaly flag
FEMOSTONDydrogesterone (5 mg) + Estradiol (1 mg)Tablet, film coatedOralViatris Healthcare Limited2014-07-08Not applicableItaly flag
FEMOSTONDydrogesterone (2.5 MG) + Estradiol (0.5 MG)Tablet, coatedOralMylan Ire Healthcare Limited2018-02-21Not applicableItaly flag
FEMOSTONDydrogesterone (10 mg) + Estradiol (1 mg)TabletOralViatris Healthcare Limited2014-07-08Not applicableItaly flag

Categories

ATC Codes
G03FA14 — Dydrogesterone and estrogenG03DB01 — DydrogesteroneG03FB08 — Dydrogesterone and estrogen
Drug Categories
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
  1. Link [Link]
Human Metabolome Database
HMDB0014522
KEGG Drug
D01217
PubChem Compound
9051
PubChem Substance
46506195
ChemSpider
8699
RxNav
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

Pharmacoeconomics

Manufacturers
  • Solvay pharmaceuticals
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
TabletOral5 MG
TabletOral10.000 mg
Tablet, film coatedOral
Tablet, film coatedOral10 MG
TabletOral2.06 mg
Tablet, film coatedOral
Tablet, film coatedOral10 mg
Tablet, coatedOral
Tablet, film coatedOral5 mg
Kit; tablet, film coatedOral
Tablet, coatedOral10 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)168-169Reerink, E.H., Westerhof, P. and Scholer, H.F.L.; U.S. Patent 3,198,792; assigned to North American Philips Company, Inc.
logP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00486 mg/mLALOGPS
logP3.27ALOGPS
logP3.79Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)19.4Chemaxon
pKa (Strongest Basic)-4.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area34.14 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity93.82 m3·mol-1Chemaxon
Polarizability36.39 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.982
Caco-2 permeable+0.7724
P-glycoprotein substrateSubstrate0.5449
P-glycoprotein inhibitor IInhibitor0.8841
P-glycoprotein inhibitor IIInhibitor0.6043
Renal organic cation transporterNon-inhibitor0.6931
CYP450 2C9 substrateNon-substrate0.847
CYP450 2D6 substrateNon-substrate0.8795
CYP450 3A4 substrateSubstrate0.7408
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9533
CYP450 2C19 inhibitorNon-inhibitor0.6514
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8203
Ames testNon AMES toxic0.9626
CarcinogenicityNon-carcinogens0.9151
BiodegradationNot ready biodegradable0.9575
Rat acute toxicity1.8041 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7451
hERG inhibition (predictor II)Non-inhibitor0.7454
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-MSsplash10-0006-1490000000-10de0224e8083d668121
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0089-2910000000-0f3c030b838629088a3b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2920000000-7383353a3b2099383437
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-2966000000-979f386c9d37c0f83d8c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ot-0196000000-b1cfb077f79ca21ea775
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00mk-0960000000-7b1f0945aa58ed5c8a35
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0019000000-7585b393b0d4ff849ccf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-0095000000-f7826b32f9b8648bde9f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kpr-0910000000-a53993439cdaae68c99e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0091000000-256120e30220d6e9314d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-186.1184773
predicted
DarkChem Lite v0.1.0
[M-H]-186.6202773
predicted
DarkChem Lite v0.1.0
[M-H]-178.50243
predicted
DeepCCS 1.0 (2019)
[M+H]+186.1636773
predicted
DarkChem Lite v0.1.0
[M+H]+187.3652773
predicted
DarkChem Lite v0.1.0
[M+H]+180.56108
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.8765773
predicted
DarkChem Lite v0.1.0
[M+Na]+186.8449773
predicted
DarkChem Lite v0.1.0
[M+Na]+186.77002
predicted
DeepCCS 1.0 (2019)

Targets

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insights 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
  1. 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]
  2. 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]
  3. 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]
  4. Okada H: [Metabolism, structure and biological activity of sex steroids]. Nihon Naibunpi Gakkai Zasshi. 1993 Feb 20;69(2):67-79. [Article]
  5. 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]
  6. 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
  1. 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 March 03, 2024 02:24