Identification
Name Eflornithine Accession Number DB06243 Description
Eflornithine is a prescription drug indicated in the treatment of facial hirsutism (excessive hair growth). Eflornithine hydrochloride cream for topical application is intended for use in women suffering from facial hirsutism and is sold by Allergan, Inc. under the brand name Vaniqa. Eflornithine for injection against sleeping sickness was manufactured by Sanofi Aventis and sold under the brand name Ornidyl in the USA. It is now discontinued. Eflornithine is on the World Health Organization’s List of Essential Medicines.
Type Small Molecule Groups Approved, Withdrawn Structure
Similar Structures
Structure for Eflornithine (DB06243)
×
Weight Average: 182.171
Monoisotopic: 182.08668396 Chemical Formula C6H12F2N2O2 Synonyms
- (RS)-2,5-diamino-2-(difluoromethyl)pentanoic acid
- 2-(difluoromethyl)ornithine
- alpha-difluoromethylornithine
- DFMO
- Eflornithine
- α-difluoromethylornithine
External IDs
- BRN 2250529
- HSDB 7923
- MDL 71782
- RFI 7178
- RMI 71782
Pharmacology
Indication
Eflornithine is indicated in the treatment of facial hirsutism (excessive hair growth).
Associated Conditions
- Meningoencephalitic stage Trypanosoma brucei gambiense infection
Associated Therapies
- Hair removal therapy
Contraindications & Blackbox Warnings
Pharmacodynamics Not Available Mechanism of action
Eflornithine prevents hair growth by inhibiting the anagen phase of hair production. This occurs by eflornithine irreversibly binding (also called suicide inhibition) to ornithine decarboxylase (ODC) and physically preventing the natural substrate ornithine from accessing the active site.
| Target | Actions | Organism |
|---|---|---|
| AOrnithine decarboxylase |
antagonist
blocker
|
Humans |
Absorption Not Available Volume of distribution Not Available Protein binding Not Available Metabolism
Not metabolized
Route of elimination
Renal
Half-life
8 hours
Clearance Not Available Adverse Effects
Toxicity Not Available Affected organisms
- Humans and other mammals
- Yeast, Molds, Trypanosomes
- Trypanosoma brucei gambiense
Pathways Not Available Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
Not Available Food Interactions No interactions found.
Products
Product Ingredients
| Ingredient | UNII | CAS | InChI Key |
|---|---|---|---|
| Eflornithine hydrochloride | 4NH22NDW9H | 96020-91-6 | FJPAMFNRCFEGSD-UHFFFAOYSA-N |
Brand Name Prescription Products
| Name | Dosage | Strength | Route | Labeller | Marketing Start | Marketing End | Region | Image |
|---|---|---|---|---|---|---|---|---|
| Vaniqa | Cream | 139 mg/1g | Topical | Physicians Total Care, Inc. | 2004-07-26 | Not applicable | US |
|
| Vaniqa | Cream | 11.5 % | Cutaneous | Almirall, S.A. | 2020-12-23 | Not applicable | EU |
|
| Vaniqa | Cream | 139 mg/1g | Topical | Allergan | 2013-06-01 | Not applicable | US |
|
| Vaniqa | Cream | 11.5 % | Cutaneous | Almirall, S.A. | 2020-12-23 | Not applicable | EU |
|
| Vaniqa | Cream | 139 mg/1g | Topical | SkinMedica Pharmaceuticals, Inc. | 2000-08-01 | 2014-08-01 | US |
|
| Vaniqa | Cream | 13.9 % | Topical | Cipher Pharmaceuticals Inc. | 2005-11-01 | Not applicable | Canada |
|
| Vaniqa | Cream | 11.5 % | Cutaneous | Almirall, S.A. | 2020-12-23 | Not applicable | EU |
Categories
ATC Codes P01CX03 — Eflornithine
- P01CX – Sonstige Mittel gegen Leishmaniose und Trypanosomiasis
- P01C – Mittel gegen Leishmaniose und Trypanosomiasis
- P01 – ANTIPROTOZOALE
- P – ANTIPARASITISCHE PRODUKTE, INSECTIZIDEN UND REPELLENTEN
D11AX16 – Eflornithin
- D11AX – Andere dermatologische Mittel
- D11A – ANDERE DERMATOLOGISCHE ZUBEREITUNGEN
- D11 – ANDERE DERMATOLOGISCHE ZUBEREITUNGEN
- D – DERMATOLOGISCHE ZUBEREITUNGEN
Drug Categories Chemical TaxonomyProvided by Classyfire Beschreibung Diese Verbindung gehört zur Klasse der organischen Verbindungen, die als Alpha-Aminosäuren bekannt sind. Das sind Aminosäuren, bei denen die Aminogruppe an das Kohlenstoffatom unmittelbar neben der Carboxylatgruppe (Alpha-Kohlenstoff) gebunden ist. Königreich Organische Verbindungen Oberklasse Organische Säuren und Derivate Klasse Carboxylsäuren und Derivate Unterklasse Aminosäuren, Peptide, und Analoge Direkte Eltern Alpha-Aminosäuren Alternative Eltern Halogenierte Fettsäuren / Verzweigte Fettsäuren / Aminosäuren / Monocarbonsäuren und Derivate / Carbonsäuren / Organopnictogene Verbindungen / Organofluoride / Organische Oxide / Monoalkylamine / Kohlenwasserstoffderivate / Carbonylverbindungen / Alkylfluoride zeigen 2 weitere Substituenten Aliphatische azyklische Verbindung / Alkylfluorid / Alkylhalogenid / Alpha-Aminsäure / Amin / Aminosäure / Verzweigte Fettsäure / Carbonylgruppe / Carbonsäure / Fettsäure / Fettacyl / Halogenierte Fettsäure / Kohlenwasserstoffderivat / Monocarbonsäure oder Derivate / Organische Stickstoffverbindung / Organisches Oxid / Organische Sauerstoffverbindung / Organofluorid / Halogenorganische Verbindung / Organische Stickstoffverbindung / Organische Sauerstoffverbindung / Organopnictogene Verbindung / Primäres aliphatisches Amin / Primäres Amin 14 weitere anzeigen Molekulares Gerüst Aliphatische acyclische Verbindungen Externe Deskriptoren Fluoraminosäure (CHEBI:41948)
Chemical Identifiers
UNII ZQN1G5V6SR CAS Nummer 70052-12-9 InChI Key VLCYCQAOQCDTCN-UHFFFAOYSA-N InChI
IUPAC-Name
SMILES
Synthesereferenz
https://www.google.com/patents/US4330559
Allgemeine Referenzen
- Namazi MR: Hypothese: Der potentielle Nutzen von topischem Eflornithin gegen kutane Leishmaniose. Indian J Dermatol Venereol Leprol. 2008 Mar-Apr;74(2):158-9.
- Priotto G, Pinoges L, Fursa IB, Burke B, Nicolay N, Grillet G, Hewison C, Balasegaram M: Safety and effectiveness of first line eflornithine for Trypanosoma brucei gambiense sleeping sickness in Sudan: cohort study. BMJ. 2008 Mar 29;336(7646):705-8. doi: 10.1136/bmj.39485.592674.BE. Epub 2008 Mar 5.
- Hoffmann R: A 4-month, open-label study evaluating the efficacy of eflornithine 11.5% cream in the treatment of unwanted facial hair in women using TrichoScan. Eur J Dermatol. 2008 Jan-Feb;18(1):65-70. Epub 2007 Dec 18.
- Jobanputra KS, Rajpal AV, Nagpur NG: Eflornithine. Indian J Dermatol Venereol Leprol. 2007 Sep-Oct;73(5):365-6.
External Links KEGG Drug D07883 KEGG Compound C07997 PubChem Compound 3009 PubChem Substance 310264864 ChemSpider 2902 BindingDB 50028197 RxNav 569 ChEBI 41948 ChEMBL CHEMBL830 Drugs.com Drugs.com Drug Page Wikipedia Eflornithine AHFS Codes
- 84:92.00 — Misc. Skin and Mucous Membrane Agents
FDA label
MSDS
Clinical Trials
Clinical Trials
| Phase | Status | Purpose | Conditions | Count |
|---|---|---|---|---|
| 4 | Completed | Treatment | Hirsutism | 2 |
| 4 | Completed | Treatment | Human African Trypanosomiasis (HAT) | 1 |
| 4 | Not Yet Recruiting | Treatment | Pseudofolliculitis Barbae | 1 |
| 3 | Completed | Prevention | Non-Melanomatous Skin Cancer | 1 |
| 3 | Completed | Prevention | Precancerous Conditions | 1 |
| 3 | Completed | Treatment | Cancer, Bladder | 1 |
| 3 | Completed | Treatment | Familial Adenomatous Polyposis (FAP) | 1 |
| 3 | Completed | Treatment | Trypanosoma brucei gambiense infection | 1 |
| 3 | Recruiting | Prevention | Neoplasms, Colorectal | 1 |
| 3 | Recruiting | Treatment | Anaplastic Astrocytoma (AA) / Recurrent Anaplastic Astrocytoma | 1 |
Pharmacoeconomics
Manufacturers
Packagers
Dosage Forms
| Form | Route | Strength |
|---|---|---|
| Cream | Topical | |
| Cream | Cutaneous | |
| Cream | Cutaneous | 11.5 % |
| Cream | Topical | 13.9 % |
| Cream | Topical | 139 mg/1g |
Prices Not Available Patents
| Patent Number | Pediatric Extension | Approved | Expires (estimated) | Region |
|---|---|---|---|---|
| US5648394 | No | 1997-07-15 | 2014-07-15 | US |
| CA2158041 | No | 2001-04-03 | 2013-05-27 | Canada |
| US4330559 | No | 1982-05-18 | 1997-07-11 | US |
Properties
State Solid Experimental Properties Not Available Predicted Properties
| Property | Value | Source |
|---|---|---|
| Water Solubility | 50.0 mg/mL | ALOGPS |
| logP | -2 | ALOGPS |
| logP | -2.9 | ChemAxon |
| logS | -0.56 | ALOGPS |
| pKa (Strongest Acidic) | 2.19 | ChemAxon |
| pKa (Strongest Basic) | 10.2 | ChemAxon |
| Physiological Charge | 1 | ChemAxon |
| Hydrogen Acceptor Count | 4 | ChemAxon |
| Hydrogen Donor Count | 3 | ChemAxon |
| Polar Surface Area | 89.34 Å2 | ChemAxon |
| Rotatable Bond Count | 5 | ChemAxon |
| Refractivity | 37.73 m3·mol-1 | ChemAxon |
| Polarizability | 15.8 Å3 | ChemAxon |
| Number of Rings | 0 | ChemAxon |
| Bioavailability | 1 | ChemAxon |
| Rule of Five | Yes | ChemAxon |
| Ghose Filter | No | ChemAxon |
| Veber’s Rule | No | ChemAxon |
| MDDR-like Rule | No | ChemAxon |
Predicted ADMET Features Not Available
Spectra
Mass Spec (NIST) Not Available Spectra
| Spectrum | Spectrum Type | Splash Key |
|---|---|---|
| Predicted GC-MS Spectrum – GC-MS | Predicted GC-MS | Not Available |
| Predicted MS/MS Spectrum – 10V, Positive (Annotated) | Predicted LC-MS/MS | Not Available |
| Predicted MS/MS Spectrum – 20V, Positive (Annotated) | Predicted LC-MS/MS | Not Available |
| Predicted MS/MS Spectrum – 40V, Positive (Annotated) | Predicted LC-MS/MS | Not Available |
| Predicted MS/MS Spectrum – 10V, Negative (Annotated) | Predicted LC-MS/MS | Not Available |
| Predicted MS/MS Spectrum – 20V, Negative (Annotated) | Predicted LC-MS/MS | Not Available |
| Predicted MS/MS Spectrum – 40V, Negative (Annotated) | Predicted LC-MS/MS | Not Available |
| LC-MS/MS Spectrum – LC-ESI-QQ , positive | LC-MS/MS | splash10-001i-0900000000-df91c4b4acdcbe7cee41 |
| LC-MS/MS Spectrum – LC-ESI-QQ , positive | LC-MS/MS | splash10-00xr-0900000000-9a7e6cedd31e8d4feff3 |
| LC-MS/MS Spectrum – LC-ESI-QQ , positive | LC-MS/MS | splash10-00di-0900000000-83896c5cd4b28a1aeb5b |
| LC-MS/MS Spectrum – LC-ESI-QQ , positive | LC-MS/MS | splash10-00di-4900000000-3d4818a740257594aecb |
| LC-MS/MS Spectrum – LC-ESI-QQ , positive | LC-MS/MS | splash10-00e9-9300000000-3f52c4f986a5917af0ff |
Targets
Actions
- Poulin R, Lu L, Ackermann B, Bey P, Pegg AE: Mechanism of the irreversible inactivation of mouse ornithine decarboxylase by alpha-difluoromethylornithine. Characterization of sequences at the inhibitor and coenzyme binding sites. J Biol Chem. 1992 Jan 5;267(1):150-8.
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Drug created on March 19, 2008 16:19 / Updated on March 23, 2021 14:29