U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[H][C@@]12CC[C@H](OC)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OCCC)C=C4

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
PubMed

PubMed

TitleDatePubMed
[Safety of promestriene capsule used in postmenopausal atrophic vaginitis].
2009 Aug
Urogenital disorders associated with oestrogen deficiency: the role of promestriene as topical oestrogen therapy.
2010 Sep
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 Fri Dec 15 16:23:50 GMT 2023
Edited
by admin
on Fri Dec 15 16:23:50 GMT 2023
Record UNII
GXM4PER6WZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
COLPOTROPHINE
Brand Name English
Classification Tree Code System Code
WHO-VATC QG03CA09
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
WHO-ATC G03CA09
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
NCI_THESAURUS C483
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
Code System Code Type Description
SMS_ID
100000081126
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
WIKIPEDIA
PROMESTRIENE
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
RXCUI
34625
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
254-361-6
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
DRUG CENTRAL
4023
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
DRUG BANK
DB12487
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
FDA UNII
GXM4PER6WZ
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID2057730
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105394
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
MESH
C013657
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
CAS
39219-28-8
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
INN
3546
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
EVMPD
SUB10087MIG
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
NCI_THESAURUS
C76998
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
PUBCHEM
9883915
Created by admin on Fri Dec 15 16:23:50 GMT 2023 , Edited by admin on Fri Dec 15 16:23:50 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY