This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Promestriene is a synthetic estrogen applied topically for the treatment of vulvovaginal atrophic symptoms and to speed wound healing following vulvovaginal surgery or trauma (e.g. post-partum).

Generic Name
Promestriene
DrugBank Accession Number
DB12487
Background

Promestriene (3-propyl ethyl, 17B-methyl estradiol) has been used in trials studying the prevention of Hypospadias. It 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.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 328.496
Monoisotopic: 328.24023027
Chemical Formula
C22H32O2
Synonyms
  • Promestriano
  • Promestriene
  • Promestrieno
  • Promestrienum

Pharmacology

Indication

Not Available

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbciximabPromestriene may increase the thrombogenic activities of Abciximab.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Promestriene.
AdalimumabPromestriene may increase the thrombogenic activities of Adalimumab.
AducanumabPromestriene may increase the thrombogenic activities of Aducanumab.
AlemtuzumabPromestriene may increase the thrombogenic activities of Alemtuzumab.
AlirocumabPromestriene may increase the thrombogenic activities of Alirocumab.
AmivantamabPromestriene may increase the thrombogenic activities of Amivantamab.
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Promestriene.
AnifrolumabPromestriene may increase the thrombogenic activities of Anifrolumab.
AnsuvimabPromestriene may increase the thrombogenic activities of Ansuvimab.
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Food Interactions
Not Available

Products

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International/Other Brands
Colpotrophine

Categories

ATC Codes
G03CA09 — Promestriene
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
GXM4PER6WZ
CAS number
39219-28-8
InChI Key
IUWKNLFTJBHTSD-AANPDWTMSA-N
InChI
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
IUPAC Name
(1S,3aS,3bR,9bS,11aS)-1-methoxy-11a-methyl-7-propoxy-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene
SMILES
[H][C@@]12CC[C@H](OC)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OCCC)C=C3

References

General References
  1. AIFA Product Information: Colpotrophine (promestriene) for vaginal use [Link]
PubChem Substance
347911337
ChemSpider
8059589
RxNav
34625
ChEBI
135402
ChEMBL
CHEMBL2105394
ZINC
ZINC000001999256
Wikipedia
Promestriene

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedSupportive CareAtrophic Vaginitis / Endometrial Hyperplasia / Pelvic Organ Prolapse (POP)1
4TerminatedTreatmentBacterial Vaginosis (BV)1
3CompletedPreventionHypospadias1
3CompletedTreatmentVulvo Vaginal Atrophy1
Not AvailableCompletedNot AvailableVulvo Vaginal Atrophy1
Not AvailableCompletedTreatmentVulvo Vaginal Atrophy1
Not AvailableRecruitingTreatmentBreast Cancer / Vulva; Atrophy / Vulvo Vaginal Atrophy1
Not AvailableRecruitingTreatmentPostmenopausal Vulvovaginal Atrophy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamVaginal1 g
Capsule, liquid filledVaginal10 mg
CapsuleVaginal10 MG
CreamTopical; Vaginal1 g/100g
CreamVaginal1 %
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.81e-06 mg/mLALOGPS
logP5.61ALOGPS
logP5.41ChemAxon
logS-7.6ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.41 m3·mol-1ChemAxon
Polarizability40.9 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created at October 20, 2016 22:34 / Updated at June 02, 2021 20:03