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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
Structure of DIMETHISTERONE

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

HIDE SMILES / InChI

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Oracon

Approved Use

Birth Control/Contraception

Launch Date

1959
Doses

Doses

DosePopulationAdverse 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)
Soreness breast (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Some biological properties of dimethisterone "secrosteron" a new orally active progestational agent.
1959 Aug
Oral contraceptives and neoplasia.
1984 Jul
Hormonal content and potency of oral contraceptives and breast cancer risk among young women.
2003 Jan 13
Patents

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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:59:25 GMT 2023
Edited
by admin
on Fri Dec 15 14:59:25 GMT 2023
Record UNII
K4MZ02M175
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHISTERONE
JAN   MI   USAN  
USAN  
Official Name English
17β-Hydroxy-6-α-methyl-17-(1-propynyl)androst-4-en-3-one monohydrate
Common Name English
DIMETHISTERONE [JAN]
Common Name English
DIMETHISTERONE MONOHYDRATE [MI]
Common Name English
ANDROST-4-EN-3-ONE, 17-HYDROXY-6-METHYL-17-(1-PROPYNYL)-, MONOHYDRATE, (6.ALPHA.,17.BETA.)-
Common Name English
DIMETHISTERONE [USAN]
Common Name English
5048
Code English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
Code System Code Type Description
SMS_ID
100000082662
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
PUBCHEM
65320
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID30194305
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
WIKIPEDIA
DIMETHISTERONE
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
NCI_THESAURUS
C65404
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
MERCK INDEX
m4510
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY Merck Index
MESH
D004116
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
DRUG CENTRAL
904
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106347
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
FDA UNII
K4MZ02M175
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
CAS
41354-30-7
Created by admin on Fri Dec 15 14:59:25 GMT 2023 , Edited by admin on Fri Dec 15 14:59:25 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY