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Type Small Molecule Groups Approved, Withdrawn Structure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 – リーシュマニア症およびトリパノソーマ症に対するその他の薬剤
  • P01C – リーシュマニア症およびトリパノソーマ症に対する薬剤
  • P01 – 抗菌薬
  • P – 抗原子菌製品
  • P – 反感染性製品
  • P – 抗原子菌製品
  • P – 抗原子菌製品
  • P – 抗原子菌製品
  • P1 – 抗抗菌薬

    • 。

D11AX16 – Eflornithine

  • D11AX – その他の皮膚科学
  • D11A – その他の皮膚科学的製剤
  • D11 – その他の皮膚科学的製剤
      • D11 – その他の皮膚科学的製剤 li D – DERMATOLOGICALS

    薬剤分類 化学分類 Classyfire提供 Description この化合物は、αアミノ酸として知られる有機化合物のクラスに属しています。 この化合物は、カルボキシル基のすぐ隣の炭素原子（α炭素）にアミノ基が結合しているアミノ酸である。 有機化合物 Super Class Organic Acids and derivatives Class Carboxylic Acids and derivatives Sub Class Amino acids, peptides, および類似体 直接の親 α-アミノ酸 代替の親 ハロゲン化脂肪酸／分岐脂肪酸／アミノ酸／モノカルボン酸および誘導体／カルボン酸／有機ニクトゲン化合物／有機フッ化物／有機酸化物／モノアルキルアミン／炭化水素誘導体／カルボニル化合物／フッ化アルキル基は置換基が2つ多い 脂肪族非環状化合物／フッ化アルキル／ハロゲン化アルキル／β-β-アルキル／α-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／α-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキル／β-アルキルアミノ酸 / アミン / アミノ酸 / 分岐脂肪酸 / カルボニル基 / カルボン酸 / 脂肪酸 / 脂肪アシル / ハロゲン化脂肪酸 / 炭化水素誘導体 / モノカルボン酸またはその誘導体 / 有機窒素化合物 / 有機酸化物 / 有機酸素化合物 / 有機フッ化物 / 有機ハロゲン化合物 / 有機窒素化合物 / 有機酸素化合物 / 有機ニクトゲン化合物 / 第一級脂肪族アミン / 第一級アミン もっと見る 14 分子骨格 脂肪族非環状化合物 外部記述子 フルオロ アミノ酸（CHEBI:41948）

    Chemical Identifiers

    UNII ZQN1G5V6SR CAS番号 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.H) InChI=1S-C6H2F2N2O2/c7-3(8)5(10,5(11)12) 2-1-3-9/h4H,1-3,9-10H2, (H,11.H)12）

    IUPAC名

    2，5-ジアミノ-2-（ジフルオロメチル）ペンタン酸

    SMILES

    NCCCC（N）（C（F）F）C（O）=O

    合成参考資料

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

    一般参考資料

  1. Namazi MR: 仮説：皮膚リーシュマニア症に対するエフルニチン外用薬の潜在的有用性。 インドJ Dermatol Venereol Leprol. 2008年3月-4月;74（2）:158-9。
  2. Priotto G, Pinoges L, Fursa IB, Burke B, Nicolay N, Grillet G, Hewison C, Balasegaram M: First line eflornithine for Trypanosoma brucei gambiense sleeping sickness in Sudan: cohort study.の安全性と有効性。 BMJ. 2008年3月29日;336（7646）:705-8.doi：10.1136/bmj.39485.592674.BE。 Epub 2008年3月5日。
  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

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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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