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Type Small Molecule Groups Approved, Withdrawn Structure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 – Outros agentes contra a leishmaniose e a tripanossomíase
li>P01C – AGENTES CONTRA A LEISMANIZAÇÃO E A TRIPANOSOMíASISli>P01 – ANTIPROTOZOALSli>P – PRODUTOS ANTIPARÁSTICOS, INSECTICIDAS E REPELENTES
D11AX16 – Eflornitina
- li>D11AX – Outros dermatológicosli>D11A – OUTRAS PREPARAÇÕES DERMATOLÓGICASli>D11 – OUTRAS DERMATOLÓGICAS PREPARAÇÕES
- D – DERMATOLOGICALS
Categorias de Medicamentos Taxonomia QuímicaProcedida pela Classyfire Descrição Este composto pertence à classe dos compostos orgânicos conhecidos como aminoácidos alfa. São aminoácidos nos quais o grupo de aminoácidos está ligado ao átomo de carbono imediatamente adjacente ao grupo dos carboxilatos (carbono alfa). Reino Compostos orgânicos Super Classe Ácidos orgânicos e derivados Classe Ácidos carboxílicos e derivados Sub Classe Aminoácidos, peptídeos, e analógicos Direct Parent Alpha amino acids Alternative Parents Ácidos gordos halogenados / Ácidos gordos ramificados / Aminoácidos / Ácidos monocarboxílicos e derivados / Ácidos carboxílicos / Compostos organopnictogénicos / Organofluoretos / Óxidos orgânicos / Monoalquilaminas / Derivados de hidrocarbonetos / Compostos carbonílicos / Fluoreto de alquilo mostram mais 2 Substituents Aliphatic acyclic compound / Alkyl fluoride / Alkyl halide / Alpha-aminoácido / Amina / Aminoácido / Ácido gordo ramificado / Grupo carbonilo / Ácido carboxílico / Ácido gordo / Acilo gordo / Ácido gordo halogenado / Derivado de hidrocarbonetos / Ácido monocarboxílico ou derivados / Composto nitrogénio orgânico / Óxido orgânico / Composto oxigénio orgânico / Organofluoreto / Composto organo-halogénio / Composto organonitrogénio / Composto organo-oxigénio / Composto organopnictogénico / Amina alifática primária / Amina primária mostra mais 14 compostos acíclicos alifáticos de estrutura molecular Descritores externos ácido fluoroamino (CHEBI:41948)
Identificadores químicos
UNII ZQN1G5V6SR Número CAS 70052-12-9 Chave InChI VLCYCQAOQCDTCN-UHFFFAOYSA-N InChI
Nome IUPAC
SMILES
Referência de Síntese
https://www.google.com/patents/US4330559
Referências Gerais
- Namazi MR: Hipótese: a potencial utilidade da eflornitina tópica contra a leishmaniose cutânea. J Dermatol Venereol Leprol indiano. 2008 Mar-Abr;74(2):158-9.
- Priotto G, Pinoges L, Fursa IB, Burke B, Nicolay N, Grillet G, Hewison C, Balasegaram M: Segurança e eficácia da eflornitina de primeira linha para a doença do sono Trypanosoma brucei gambiense no Sudão: estudo de coorte. 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