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
Structure for Promestriene (DB12487)
- Weight
- Average: 328.496
Monoisotopic: 328.24023027 - Chemical Formula
- C22H32O2
- Synonyms
- Promestriano
- Promestriene
- Promestrieno
- Promestrienum
Pharmacology
- Indication
Not Available
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Vulvovaginal atrophy •••••••••••• •••••••• ••••• Treatment of Wound healing delayed •••••••••••• •••••••• ••••• Treatment of Wound healing delayed •••••••••••• •••••••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab Promestriene may increase the thrombogenic activities of Abciximab. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Promestriene. Adalimumab Promestriene may increase the thrombogenic activities of Adalimumab. Aducanumab Promestriene may increase the thrombogenic activities of Aducanumab. Alemtuzumab Promestriene may increase the thrombogenic activities of Alemtuzumab. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Colpotrophine
Categories
- ATC Codes
- G03CA09 — Promestriene
- Drug Categories
- Estradiol Congeners
- Estranes
- Estrenes
- Estrogens
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Natural and Semisynthetic Estrogens, Plain
- Sex Hormones and Modulators of the Genital System
- Steroids
- 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
- AIFA Product Information: Colpotrophine (promestriene) for vaginal use [Link]
- External Links
- PubChem Substance
- 347911337
- ChemSpider
- 8059589
- 34625
- ChEBI
- 135402
- ChEMBL
- CHEMBL2105394
- ZINC
- ZINC000001999256
- Wikipedia
- Promestriene
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Supportive Care Atrophic Vaginitis / Endometrial Hyperplasia / Pelvic Organ Prolapse (POP) 1 4 Not Yet Recruiting Treatment Human Papilloma Virus (HPV) 1 4 Terminated Treatment Bacterial Vaginosis (BV) 1 3 Completed Prevention Hypospadias 1 3 Completed Treatment Vulvo Vaginal Atrophy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Vaginal 1 g Capsule, liquid filled Vaginal 10 mg Capsule Vaginal 10 MG Cream Topical; Vaginal 1 g/100g Cream Vaginal 1 % Insert Vaginal 10.00 mg Ointment Vaginal 1.000 g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 8.81e-06 mg/mL ALOGPS logP 5.61 ALOGPS logP 5.41 Chemaxon logS -7.6 ALOGPS pKa (Strongest Basic) -4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 18.46 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 98.41 m3·mol-1 Chemaxon Polarizability 40.9 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-1009000000-97335205b8bf6ac0e492 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-48460dc93e60547e6116 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-2496000000-999dda671c03fc403c74 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004r-0096000000-746afa23aa209bb3374f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-015i-0091000000-0edeae5a78bdb274e5d0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0309-0940000000-fd74188cfbc6405d97f7 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Drug created at October 20, 2016 22:34 / Updated at June 02, 2021 20:03