Eflornithine

Synonyms :
(RS)-2,5-diamino-2-(difluoromethyl)pentanoic acid, DFMO, α-difluoromethylornithine

Status : approved

Category

Antineoplastic Agents

Therapeutic Classification

OTHER DERMATOLOGICAL PREPARATIONS

DERMATOLOGICALS
OTHER DERMATOLOGICAL PREPARATIONS
OTHER DERMATOLOGICAL PREPARATIONS
Enzyme Inhibitors

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. Besides being a non-mechanical and non-cosmetic treatment, eflornithine is the only non-hormonal and non-systemic prescription option available for women who suffer from facial hirsutism. 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.

Used

Eflornithine is indicated in the treatment of facial hirsutism (excessive hair growth).

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.

Dosage

Form Route Strength
Cream topical 13.9 %
Cream topical 139 mg/g

Metabolism

Not metabolized

Half Life

8 hours

Elimination Route

Renal

Chemical Classification

Salt : Eflornithine hydrochloride

Chemical Name

(RS)-2,5-diamino-2-(difluoromethyl)pentanoic acid

Brands

name Dosage form Country
Vaniqa cream US
Vaniqa cream US
Vaniqa cream Canada

Calculated Property

kind Value Source
logP -2 ALOGPS
logS -0.56 ALOGPS
Water Solubility 5.00e+01 g/l ALOGPS
logP -2.9 ChemAxon
IUPAC Name 2,5-diamino-2-(difluoromethyl)pentanoic acid ChemAxon
Traditional IUPAC Name vaniqa ChemAxon
Molecular Weight 182.171 ChemAxon
Monoisotopic Weight 182.08668396 ChemAxon
SMILES NCCCC(N)(C(F)F)C(O)=O ChemAxon
Molecular Formula C6H12F2N2O2 ChemAxon
InChI InChI=1S/C6H12F2N2O2/c7-4(8)6(10,5(11)12)2-1-3-9/h4H,1-3,9-10H2,(H,11,12) ChemAxon
InChIKey VLCYCQAOQCDTCN-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 89.34 ChemAxon
Refractivity 37.73 ChemAxon
Polarizability 15.8 ChemAxon
Rotatable Bond Count 5 ChemAxon
H Bond Acceptor Count 4 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 2.19 ChemAxon
pKa (strongest basic) 10.2 ChemAxon
Physiological Charge 1 ChemAxon
Number of Rings 0 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Ornithine decarboxylase : in Human