(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

• ChemBase ID: 262
• Molecular Formular: C21H28O2
• Molecular Mass: 312.44582
• Monoisotopic Mass: 312.20893014
• SMILES: O=C([C@@H]1[C@@]2([C@H]([C@H]3[C@@H](CC2)[C@]2(C(=CC(=O)CC2)C=C3)C)CC1)C)C
• Canonical SMILES: O=C1CC[C@@]2(C(=C1)C=C[C@@H]1[C@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• 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
• InChIKey: JGMOKGBVKVMRFX-HQZYFCCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: dydrogesterone
• Brand Name: Diphaston; Dufaston; Duphaston; Duvaron; Gestatron; Gynorest; Prodel; Retrone; Terolut
• Synonyms: 10alpha-Isopregnenone; Didrogesterone [DCIT]; Dydrogesterona [INN-Spanish]; Dydrogesteronum [INN-Latin]; Hydrogesterone; Hydrogestrone; Isopregnenone; Dydrogesterone

Database IDs

• CAS Number: 152-62-5
• PubChem SID: 46506195; 160963725
• PubChem CID: 9051

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.291891
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.7866828
• LogD (pH = 7.4): 3.7866828
• Log P: 3.7866828
• Molar Refractivity: 93.8219 cm^3
• Polarizability: 36.159924 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.27
• LOG S: -4.81
• Solubility (Water): 4.86e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.4

DETAILS

DrugBank - DB00378

• Drug Groups: approved
• Description: 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. [PubChem]
• 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.
• Pharmacology: 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.
• 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolism is complete to a 20-dihydrodydrogesterone (DHD) metabolite.
• Absorption: Rapidly absorbed in the gastrointestinal tract with a bioavailability of 28%.
• Half Life: Dydrogesterone: 5-7 hours, 20-dihydrodydrogesterone (DHD) metabolite: 14-17 hours
• References: / [Link]
• External Links: Wikipedia

REFERENCES

• Link/