Eflornithine

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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Type Small Molecule Groups Approved, Withdrawn Structure

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Structure for Eflornithine (DB06243)

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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

Pharmacology

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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 WarningsContraindications

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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 EffectsMedicalerrors

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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

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.

Not Available Food Interactions No interactions found.

Products

Products

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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 USUS flag
Vaniqa Cream 11.5 % Cutaneous Almirall, S.A. 2020-12-23 Not applicable EUEU flag
Vaniqa Cream 139 mg/1g Topical Allergan 2013-06-01 Not applicable USUS flag
Vaniqa Cream 11.5 % Cutaneous Almirall, S.A. 2020-12-23 Not applicable EUEU flag
Vaniqa Cream 139 mg/1g Topical SkinMedica Pharmaceuticals, Inc. 2000-08-01 2014-08-01 USUS flag
Vaniqa Cream 13.9 % Topical Cipher Pharmaceuticals Inc. 2005-11-01 Not applicable CanadaCanada flag
Vaniqa Cream 11.5 % Cutaneous Almirall, S.A. 2020-12-23 Not applicable EUEU flag

Categories

ATC Codes P01CX03 — Eflornithine

  • P01CX – Otros agentes contra la leishmaniasis y la tripanosomiasis
  • P01C – AGENTES CONTRA LA LEISHMANIASIS Y LA TRIPANOSOMIASIS
  • P01 – ANTIPROTOZOICOS
  • P – PRODUCTOS ANTIPARASITARIOS, INSECTICIDAS Y REPELENTES

D11AX16 – Eflornitina

  • D11AX – Otros dermatológicos
  • D11A – OTROS PREPARADOS DERMATOLÓGICOS
  • D11 – OTROS PREPARADOS DERMATOLÓGICOS PREPARACIONES
  • D – DERMATOLÓGICOS

    • Categorías de medicamentos Taxonomía químicaProporcionada por Classyfire Descripción Este compuesto pertenece a la clase de compuestos orgánicos conocidos como alfa aminoácidos. Son aminoácidos en los que el grupo amino está unido al átomo de carbono inmediatamente adyacente al grupo carboxilato (carbono alfa). Reino Compuestos orgánicos Superclase Ácidos orgánicos y derivados Clase Ácidos carboxílicos y derivados Subclase Aminoácidos, péptidos y análogos Progenitor directo Aminoácidos alfa Progenitores alternativos Ácidos grasos halogenados / Ácidos grasos ramificados / Aminoácidos / Ácidos monocarboxílicos y derivados / Ácidos carboxílicos / Compuestos organopnictogénicos / Organofluoruros / Óxidos orgánicos / Monoalquilaminas / Derivados de hidrocarburos / Compuestos de carbonilo / Fluoruros de alquilo muestran 2 sustituyentes más Compuesto acíclico alifático / Fluoruro de alquilo / Haluro de alquilo / Alfa-aminoácido / Amina / Aminoácido / Ácido graso ramificado / Grupo carbonilo / Ácido carboxílico / Ácido graso / Ácido graso halogenado / Derivado hidrocarbonado / Ácido monocarboxílico o derivados / Compuesto orgánico nitrogenado / Óxido orgánico / Compuesto orgánico oxigenado / Compuesto organofluorado / Compuesto organohalógeno / Compuesto organoxígeno / Compuesto organopnicógeno / Amina alifática primaria / Amina primaria mostrar 14 más Marco molecular Compuestos acíclicos alifáticos Descriptores externos ácido fluoroamino (CHEBI:41948)

    Identificadores químicos

    UNII ZQN1G5V6SR Número CAS 70052-12-9 Clave InChI VLCYCQAOQCDTCN-UHFFFAOYSA-N InChI

    InChI=1S/C6H12F2N2O2/c7-4(8)6(10,5(11)12)2-1-3-9/h4H,1-3,9-10H2,(H,11,12)

    Nombre IUPAC

    Ácido 2,5-diamino-2-(difluorometil)pentanoico

    SMILES

    NCCCC(N)(C(F)F)C(O)=O

    Referencia de síntesis

    https://www.google.com/patents/US4330559

    Referencias generales

    1. Namazi MR: Hipótesis: la utilidad potencial de la eflornitina tópica contra la leishmaniasis cutánea. Indian J Dermatol Venereol Leprol. 2008 Mar-Apr;74(2):158-9.
    2. 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.
    3. 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.
    4. 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

    Download (243 KB)

    MSDS

    Download (48.1 KB)

    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

    Not Available

    Packagers

    Not Available

    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 USUS flag
    CA2158041 No 2001-04-03 2013-05-27 CanadaCanada flag
    US4330559 No 1982-05-18 1997-07-11 USUS flag

    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

    Kind Protein Organism Humans Pharmacological action

    Yes

    Actions

    Antagonist
    Blocker

    General Function Protein homodimerization activity Specific Function Key enzyme of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine. Gene Name ODC1 Uniprot ID P11926 Uniprot Name Ornithine decarboxylase Molecular Weight 51147.73 Da

    1. 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

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