Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H32O2.H2O |
Molecular Weight | 358.5143 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[H][C@@]12CC[C@@](O)(C#CC)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])C[C@H](C)C4=CC(=O)CC[C@]34C
InChI
InChIKey=REHJTMDOJHAPJV-IVTQUDKZSA-N
InChI=1S/C23H32O2.H2O/c1-5-9-23(25)12-8-19-17-13-15(2)20-14-16(24)6-10-21(20,3)18(17)7-11-22(19,23)4;/h14-15,17-19,25H,6-8,10-13H2,1-4H3;1H2/t15-,17+,18-,19-,21+,22-,23-;/m0./s1
Molecular Formula | C23H32O2 |
Molecular Weight | 340.499 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Dimethisterone (brand name Secrosteron) is an orally active progestational agent. It was developed by the British pharmaceutical company British Drug Houses and was first reported in the literature in 1959 with introduction for medical use as Secrosteron. Relative to ethisterone, it is 12 times as potent orally as a progestogen in animals (Clauberg test). It has an oral LD50 in mice of 7.65 g/kg, no apparent anabolic, androgenic properties and no significant effect on sodium, potassium or water excretion in saline loaded rats. Dimethisterone was introduced in the United States as an oral contraceptive for birth control in combination with ethinylestradiol under the brand name Oracon (25 mg dimethisterone, 100 ug ethinylestradiol) and was produced by Mead Johnson & Company (Evansville, Indiana) in 1974. This preparation was eventually found to be associated with a substantially increased risk of endometrial cancer in women, and is now no longer marketed.
Originator
Approval Year
Doses
Dose | Population | Adverse events |
---|---|---|
25 mg steady, oral Recommended Dose: 25 mg Route: oral Route: steady Dose: 25 mg Co-administed with:: ethinyl estradiol(0.1 mg) Sources: |
healthy, adult n = 22 Health Status: healthy Age Group: adult Sex: F Population Size: 22 Sources: |
Disc. AE: Nausea, Soreness breast... AEs leading to discontinuation/dose reduction: Nausea (2 patients) Sources: Soreness breast (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Soreness breast | 1 patient Disc. AE |
25 mg steady, oral Recommended Dose: 25 mg Route: oral Route: steady Dose: 25 mg Co-administed with:: ethinyl estradiol(0.1 mg) Sources: |
healthy, adult n = 22 Health Status: healthy Age Group: adult Sex: F Population Size: 22 Sources: |
Nausea | 2 patients Disc. AE |
25 mg steady, oral Recommended Dose: 25 mg Route: oral Route: steady Dose: 25 mg Co-administed with:: ethinyl estradiol(0.1 mg) Sources: |
healthy, adult n = 22 Health Status: healthy Age Group: adult Sex: F Population Size: 22 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Some biological properties of dimethisterone "secrosteron" a new orally active progestational agent. | 1959 Aug |
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Oral contraceptives and neoplasia. | 1984 Jul |
|
Hormonal content and potency of oral contraceptives and breast cancer risk among young women. | 2003 Jan 13 |
Patents
Sample Use Guides
One tablet Oragon-28 daily as prescribed (dimethisterone, 25 mg (drug (pink tablets) active ingredients), ethinyl estradiol, 0.1 mg (drug (white and pink tablets) active ingredients). The blister pack contains 16 white estrogen pills, 6 pink combination estrogen and progesterone pills, and 6 green inert pills.
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 14:59:25 GMT 2023
by
admin
on
Fri Dec 15 14:59:25 GMT 2023
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Record UNII |
K4MZ02M175
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Record Status |
Validated (UNII)
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Record Version |
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Code | English |
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NCI_THESAURUS |
C776
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100000082662
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65320
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DTXSID30194305
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DIMETHISTERONE
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C65404
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m4510
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D004116
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41354-30-7
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Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |