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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H32O2
Molecular Weight 328.4883
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROMESTRIENE

SMILES

CCCOC1=CC2=C(C=C1)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC2)OC

InChI

InChIKey=IUWKNLFTJBHTSD-AANPDWTMSA-N
InChI=1S/C22H32O2/c1-4-13-24-16-6-8-17-15(14-16)5-7-19-18(17)11-12-22(2)20(19)9-10-21(22)23-3/h6,8,14,18-21H,4-5,7,9-13H2,1-3H3/t18-,19-,20+,21+,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H32O2
Molecular Weight 328.4883
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Promestriene (3-propyl ethyl, 17B-methyl estradiol) is a synthetic estrogen analog, which is used in topical estrogen therapy. Promestriene’s potential for treating vaginal atrophy symptoms associated with aromatase inhibitor treatment would be precluded if its minimal absorption leads to estrogen-like effects on cell proliferation and estrogen-responsive gene expression. The concern with absorbed vaginal estrogens or estrogen analogs is that they activate occult sites of residual breast cancer or negate the tumor suppressive effects of aromatase inhibitor adjuvant therapy. Promestriene has been studied in phase IV of the clinical trial on improvement of hormonal cytology, local and systemic climacteric complaints, as well as its endometrial security in patients with vaginitis atrophic pelvic; organ prolapse and endometrial hyperplasia. It has been also studied in phase III of the clinical trial in the post-operative patients with hypospadias. In addition, promestriene was in phase IV of the clinical trial to study its treatment of patients with vaginosis, bacterial, but that studied was terminated.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Colposeptine

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
10 mg 3 times / week multiple, vaginal
Studied dose
Dose: 10 mg, 3 times / week
Route: vaginal
Route: multiple
Dose: 10 mg, 3 times / week
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Urogenital disorders associated with oestrogen deficiency: the role of promestriene as topical oestrogen therapy.
2010-09
[Safety of promestriene capsule used in postmenopausal atrophic vaginitis].
2009-08
Estrogen therapy influence on periurethral vessels in postmenopausal incontinent women using Dopplervelocimetry analysis.
2008-11-20
Atypical squamous cells and low squamous intraepithelial lesions in postmenopausal women: implications for management.
2008-10
Presurgical promestriene therapy in postmenopausal women with stress urinary incontinence.
2007
Patents

Sample Use Guides

Promestriene was given by continuous therapy for 20 days, then maintenance therapy for 8 weeks (1 pill two times per week used). The level of follicle stimulation hormone (FSH) and estradiol (E(2)) in serum was and thickness of endometrium was detected before and after treatment.
Route of Administration: Vaginal
In estrogen sufficient cultures, promestriene exhibited no cell proliferative properties on MCF-7, BT-474, or T47-D tumor cells, even at very high concentrations (up to 100000 pg/mL). However, in estrogen deprivation conditions, low dose promestriene (2 - 10 pg/ml) stimulated GREB1 expression in all cell lines tested to levels equal to or greater than estrogen. In both estrogen replete and depleted cultures of MCF7 cells, 2 pg/ml promestriene stimulated GREB1 expression significantly greater than that seen with estradiol. For BT-474 cells, there was no significant difference in the GREB1 expression stimulated by 2 pg/ml promestriene compared to that induced by estradiol in either estrogen-replete or depleted conditions.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:26:45 GMT 2025
Edited
by admin
on Mon Mar 31 18:26:45 GMT 2025
Record UNII
GXM4PER6WZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COLPOTROPHINE
Preferred Name English
PROMESTRIENE
INN   MART.   WHO-DD  
INN  
Official Name English
PROMESTRIENE [MART.]
Common Name English
promestriene [INN]
Common Name English
Promestriene [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QG03CA09
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
WHO-ATC G03CA09
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
NCI_THESAURUS C483
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
Code System Code Type Description
SMS_ID
100000081126
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
WIKIPEDIA
PROMESTRIENE
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
RXCUI
34625
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
254-361-6
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
DRUG CENTRAL
4023
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
DRUG BANK
DB12487
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
FDA UNII
GXM4PER6WZ
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID2057730
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
ChEMBL
CHEMBL2105394
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
MESH
C013657
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
CAS
39219-28-8
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
INN
3546
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
EVMPD
SUB10087MIG
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
NCI_THESAURUS
C76998
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
PUBCHEM
9883915
Created by admin on Mon Mar 31 18:26:45 GMT 2025 , Edited by admin on Mon Mar 31 18:26:45 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY