Eflornithine

Identification

Summary

Eflornithine is a medication used topically to reduce unwanted facial hair growth in women. The postulated mechanism of action is through irreversible inhibition of ornithine decarboxylase (ODC) in the skin.

Brand Names
Vaniqa
Generic Name
Eflornithine
DrugBank Accession Number
DB06243
Background

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Approved, Withdrawn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
Thumb
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).

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
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
Medicalerrors
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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.
Not Available
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Eflornithine hydrochloride4NH22NDW9H96020-91-6FJPAMFNRCFEGSD-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VaniqaCream13.9 % w/wTopicalCipher Pharmaceuticals Inc.2005-11-01Not applicableCanada flag
VaniqaCream139 mg/1gTopicalSkinMedica Pharmaceuticals, Inc.2000-08-012014-08-01US flag
VaniqaCream11.5 %CutaneousAlmirall, S.A.2020-12-23Not applicableEU flag
VaniqaCream11.5 %CutaneousAlmirall, S.A.2020-12-23Not applicableEU flag
VaniqaCream139 mg/1gTopicalPhysicians Total Care, Inc.2004-07-26Not applicableUS flag
VaniqaCream11.5 %CutaneousAlmirall, S.A.2020-12-23Not applicableEU flag
VaniqaCream139 mg/1gTopicalAllergan2013-06-01Not applicableUS flag

Categories

ATC Codes
P01CX03 — EflornithineD11AX16 — Eflornithine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids
Alternative Parents
Halogenated fatty acids / Branched fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organofluorides / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 2 more
Substituents
Aliphatic acyclic compound / Alkyl fluoride / Alkyl halide / Alpha-amino acid / Amine / Amino acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Fatty acid
show 14 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
fluoroamino acid (CHEBI:41948)
Affected organisms
  • Humans and other mammals
  • Yeast, Molds, Trypanosomes
  • Trypanosoma brucei gambiense

Chemical Identifiers

UNII
ZQN1G5V6SR
CAS number
70052-12-9
InChI Key
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)
IUPAC Name
2,5-diamino-2-(difluoromethyl)pentanoic acid
SMILES
NCCCC(N)(C(F)F)C(O)=O

References

Synthesis Reference

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

General References
  1. Namazi MR: Hypothesis: the potential utility of topical eflornithine against cutaneous leishmaniasis. Indian J Dermatol Venereol Leprol. 2008 Mar-Apr;74(2):158-9. [Article]
  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. [Article]
  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. [Article]
  4. Jobanputra KS, Rajpal AV, Nagpur NG: Eflornithine. Indian J Dermatol Venereol Leprol. 2007 Sep-Oct;73(5):365-6. [Article]
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
FDA label
Download (243 KB)
MSDS
Download (48.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHuman African Trypanosomiasis (HAT)1
4CompletedTreatmentIdiopathic Hirsutism2
4Not Yet RecruitingTreatmentPseudofolliculitis Barbae1
3CompletedPreventionNon-Melanoma Skin Cancer (NMSC)1
3CompletedPreventionPrecancerous Conditions1
3CompletedTreatmentCancer, Bladder1
3CompletedTreatmentFamilial Adenomatous Polyposis (FAP)1
3CompletedTreatmentTrypanosoma brucei gambiense infection1
3RecruitingPreventionNeoplasms, Colorectal1
3RecruitingTreatmentAnaplastic Astrocytoma (AA) / Recurrent Anaplastic Astrocytoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamTopical
CreamCutaneous
CreamCutaneous11.5 %
CreamTopical13.9 % w/w
CreamTopical139 mg/1g
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5648394No1997-07-152014-07-15US flag
CA2158041No2001-04-032013-05-27Canada flag
US4330559No1982-05-181997-07-11US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility50.0 mg/mLALOGPS
logP-2ALOGPS
logP-2.9ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)2.19ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.73 m3·mol-1ChemAxon
Polarizability15.8 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0900000000-df91c4b4acdcbe7cee41
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00xr-0900000000-9a7e6cedd31e8d4feff3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-83896c5cd4b28a1aeb5b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-4900000000-3d4818a740257594aecb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00e9-9300000000-3f52c4f986a5917af0ff

Targets

Drugtargets
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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
References
  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. [Article]

Drug created on March 19, 2008 16:19 / Updated on July 22, 2021 22:00