Dydrogesterone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Dydrogesterone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Dydrogesterone?

The molecule Dydrogesterone presents a molecular formula of C21H28O2 and its IUPAC name is (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one.

Dydrogesterone, also known as 11-beta-progesterone or simply progesterone, is a naturally occurring progestogen and a potent progestational hormone. It is produced in the ovaries, placenta, and adrenal glands, and is the major progestogen in the human body. Dydrogesterone has a variety of effects in the body, including regulation of the menstrual cycle, pregnancy, and embryogenesis. It also has neuroprotective and anti-inflammatory effects..

Dydrogesterone is structurally similar to other progestogens, such as progesterone, 17-alpha-hydroxyprogesterone, and 17-beta-hydroxyprogesterone. However, it differs from these compounds in several important ways. First, dydrogesterone is a C11 steroid, while progesterone and 17-alpha-hydroxyprogesterone are C21 steroids. Second, dydrogesterone has a double bond between C4 and C5, while progesterone has a single bond between these carbons. Finally, dydrogesterone has a hydroxyl group at C3, while progesterone has a ketone group at this position. These structural differences give dydrogesterone different biological activity than progesterone..

Dydrogesterone is a potent progestogen, with a binding affinity for the progesterone receptor that is similar to that of progesterone. It has both agonist and antagonist activity at the receptor, depending on the tissue in which it is acting. In the uterus, dydrogesterone is a full agonist, while in the breast it is a mixed agonist/antagonist. Dydrogesterone has weak androgenic activity, and does not bind to the androgen receptor..

Dydrogesterone is used as a medication in a number of countries. In Europe, it exists under the brand names Duphaston and Utrogestan. In Australia, it is marketed as Crinone and Prochieve. In the United States, it is not currently approved for use, but exists as an investigational new drug..

Dydrogesterone is generally well-tolerated, with the most common side effects being gastrointestinal upset, headaches, and dizziness. Rare side effects include blood clots, strokes, and heart attacks. Dydrogesterone should not be used in women with a history of thromboembolic disease..

3D structure

Cartesian coordinates

Geometry of Dydrogesterone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Dydrogesterone JGMOKGBVKVMRFX-HQZYFCCVSA-N chemical compound 2D structure molecule svg
Dydrogesterone

 

Molecule descriptors

 
IUPAC name(8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
InChI codeInChI=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
InChI KeyJGMOKGBVKVMRFX-HQZYFCCVSA-N
SMILESCC(=O)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@@]4(C)[C@@H]3CC[C@]12C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (1R,2S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one
  • (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
  • (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-8,9,10,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
  • (9-beta,10-alpha)-Pregna-4,6-diene-3,20-dione
  • (9?,10?)-Pregna-4,6-diene-3,20-dione
  • (9beta,10alpha)-pregna-4,6-diene-3,20-dione
  • .DELTA.6-Retroprogesterone
  • 10alpha-Isopregnenone
  • 152-62-5
  • 152D625
  • 6-Dehydro-9.beta.,10.alpha.-progesterone
  • 6-Dehydro-9beta,10alpha-progesterone
  • 6-Dehydro-retro-progesterone
  • 6-Dehydroretroprogesterone
  • 9-.beta.,6-diene-3,20-dione
  • 9-beta,10-alpha-Pregna-4,6-diene-3,20-dione
  • 9-beta,10alpha-Pregna-4,6-diene-3,20-dione
  • 9.beta.,10.alpha.-Pregna-4,6-diene-3,20-dione
  • 9.beta.,6-diene-3,20-dione
  • 90I02KLE8K
  • 9beta,10alpha-Pregna-4,6-diene-3,20-dione
  • AB00513884
  • AB00513884_04
  • AMY23414
  • BCP12878
  • BPBio1_000839
  • BSPBio_000761
  • CCG-220671
  • CCRIS 9069
  • D01217
  • DB00378
  • DSSTox_CID_2974
  • DSSTox_GSID_22974
  • DSSTox_RID_76812
  • Didrogesterone
  • Diphaston
  • Dufaston
  • Duphaston
  • Duvaron
  • Dydrogesterona
  • Dydrogesterone
  • Dydrogesterone (JP17/USP/INN)
  • Dydrogesteronum
  • GS-6735
  • GTPL2878
  • Gestatron
  • Gynorest
  • H10151
  • HMS1570G03
  • HMS2097G03
  • HMS2230C10
  • HMS3714G03
  • HSDB 3321
  • HY-B0257A
  • Hydrogesterone
  • Hydrogestrone
  • Isopregnenone
  • MLS002153947
  • MLS002695106
  • NCGC00016413-01
  • NCGC00179445-01
  • NCGC00179445-03
  • NCGC00179445-04
  • NSC 92336
  • NSC-92336
  • NSC92336
  • PREGNA-4,6-DIENE-3,20-DIONE, (9.BETA.,10.ALPHA.)
  • Pregna-4,20-dione, (9.beta.,10.alpha.)-
  • Pregna-4,6-diene-3,20-dione, (9-beta,10-alpha)-
  • Pregna-4,6-diene-3,20-dione, (9b,10a)-
  • Pregna-4,6-diene-3,20-dione, (9beta,10alpha)-
  • Prestwick0_000671
  • Prestwick1_000671
  • Prestwick2_000671
  • Prestwick3_000671
  • Prodel
  • Q4161380
  • Retro-6-dehydroprogesterone
  • Retrone
  • Retroprogesterone, 6-dehydro-
  • SMR001233286
  • SR-01000841256
  • SR-01000841256-2
  • Terolut
  • W-108050
  • delta(6)-Retroprogesterone
  • delta(sup 6)-Retroprogesterone
  • didrogesterona
  • dydrogesterone
  • s4097

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3875998
  • CAS-152-62-5
  • UNII-90I02KLE8K
  • AKOS015895532
  • BRD-K68620903-001-03-1
  • BRD-K68620903-001-11-4
  • DTXSID1022974
  • CHEMBL1200853
  • CHEBI:31527
  • Tox21_110429
  • Tox21_110429_1
  • EINECS 205-806-8
  • SPBio_002682
  • SCHEMBL37703

Physico-Chemical properties

IUPAC name(8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Molecular formulaC21H28O2
Molecular weight312.446
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity93.54
LogP4.5
Topological polar surface area34.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.