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Details

Stereochemistry RACEMIC
Molecular Formula C6H12F2N2O2
Molecular Weight 182.1685
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EFLORNITHINE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula C6H12F2N2O2
Molecular Weight 182.1685
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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. 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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
8.3 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VANIQA

Cmax

ValueDoseCo-administeredAnalytePopulation
484 μM
100 mg/kg 4 times / day steady-state, oral
EFLORNITHINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4430 μM × h
100 mg/kg 4 times / day steady-state, oral
EFLORNITHINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10.6 h
100 mg/kg 4 times / day steady-state, oral
EFLORNITHINE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Hirsutism Apply a thin layer of eflornithine topical cream to affected areas of the face and adjacent involved areas under the chin and rub in thoroughly. Do not wash treated area for at least 4 hours. Use twice a day, allowing at least 8 hours between applications or as directed by a physician. Continue to use hair removal techniques as needed in conjunction with eflornithine. Apply eflornithine at least 5 minutes after hair removal.
Route of Administration: Topical
In Vitro Use Guide
Eflornithine (0.01 - 1 mM) treatment suppressed proliferation of 4T1 murine mammary cancer cells in culture.
Substance Class Chemical
Record UNII
ZQN1G5V6SR
Record Status Validated (UNII)
Record Version