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- Approved, Withdrawn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
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).
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- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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 antagonistblockerHumans - 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
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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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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 SkinMedica Pharmaceuticals, Inc. 2000-08-01 2014-08-01 US 
Vaniqa Cream 13.9 % w/w Topical Cipher Pharmaceuticals Inc. 2005-11-01 Not applicable Canada 
Vaniqa Cream 11.5 % Cutaneous Almirall, S.A. 2020-12-23 Not applicable EU 
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
Categories
- ATC Codes
- P01CX03 — Eflornithine
- P01CX — Other agents against leishmaniasis and trypanosomiasis
- P01C — AGENTS AGAINST LEISHMANIASIS AND TRYPANOSOMIASIS
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Agents Against Leishmaniasis and Trypanosomiasis
- Amino Acids
- Amino Acids, Basic
- Amino Acids, Diamino
- Amino Acids, Peptides, and Proteins
- Anti-Infective Agents
- Antineoplastic Agents
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Decarboxylase Inhibitor
- Decarboxylase Inhibitors
- Dermatologicals
- Enzyme Inhibitors
- Misc. Skin and Mucous Membrane Agents
- Ornithine Decarboxylase Inhibitors
- Trypanocidal Agents
- 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
- 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]
- 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]
- 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]
- Jobanputra KS, Rajpal AV, Nagpur NG: Eflornithine. Indian J Dermatol Venereol Leprol. 2007 Sep-Oct;73(5):365-6. [Article]
- External Links
- FDA label
- Download (243 KB)
- MSDS
- Download (48.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Human African Trypanosomiasis (HAT) 1 4 Completed Treatment Idiopathic Hirsutism 2 4 Not Yet Recruiting Treatment Pseudofolliculitis Barbae 1 3 Completed Prevention Cancer, Cancer Nonmelanoma Skin 1 3 Completed Prevention Precancerous Conditions 1 3 Completed Treatment Bladder Cancer, Cancer 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 % w/w 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
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistBlocker
- 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
- 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 October 22, 2021 23:18