U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C6H12F2N2O2.ClH
Molecular Weight 218.629
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EFLORNITHINE HYDROCHLORIDE ANHYDROUS

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21145lbl.pdf

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

Curator's Comment: Eflornithine was discovered in 1980 by Dr Cyrus Bacchi

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VANIQA

Approved Use

Reduction of unwanted facial hair in women.

Launch Date

2000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
484 μM
100 mg/kg 4 times / day steady-state, oral
dose: 100 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFLORNITHINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4430 μM × h
100 mg/kg 4 times / day steady-state, oral
dose: 100 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFLORNITHINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.6 h
100 mg/kg 4 times / day steady-state, oral
dose: 100 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EFLORNITHINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Other AEs: Diarrhea, Dizziness...
Other AEs:
Diarrhea (grade 1, 2 patients)
Dizziness (grade 1-2, 1 patient)
Malaise (grade 1-2, 1 patient)
Mood change (grade 1, 1 patient)
Myalgia (grade 1, 1 patient)
Nausea (grade 1, 3 patients)
Nosebleed (grade 1, 2 patients)
Pruritus (grade 1, 1 patient)
Skin rash (grade 1-2, 1 patient)
Stomatitis (grade 1, 3 patients)
Sources:
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Other AEs: Acne, Pseudofolliculitis barbae...
Other AEs:
Acne (10.8%)
Pseudofolliculitis barbae (4.9%)
Stinging skin (4.1%)
Headache (4%)
Burning skin (3.5%)
Dry skin (3.3%)
Pruritus (3.1%)
Erythema (2.5%)
Tingling skin (2.2%)
Dyspepsia (1.9%)
Skin irritation (1.8%)
Rash (1.5%)
Alopecia (1.3%)
Dizziness (1.3%)
Folliculitis (1%)
Ingrown hair (0.9%)
Edema face (0.7%)
Anorexia (0.7%)
Nausea (0.7%)
Asthenia (0.3%)
Vertigo (0.1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Mood change grade 1, 1 patient
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Myalgia grade 1, 1 patient
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Pruritus grade 1, 1 patient
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Diarrhea grade 1, 2 patients
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Nosebleed grade 1, 2 patients
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Nausea grade 1, 3 patients
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Stomatitis grade 1, 3 patients
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Dizziness grade 1-2, 1 patient
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Malaise grade 1-2, 1 patient
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Skin rash grade 1-2, 1 patient
1 g/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1 g/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1 g/m2, 1 times / day
Sources:
unhealthy, 23-41
n = 6
Health Status: unhealthy
Condition: cervical intraepithelial neoplasia
Age Group: 23-41
Sex: F
Population Size: 6
Sources:
Vertigo 0.1%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Asthenia 0.3%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Anorexia 0.7%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Edema face 0.7%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Nausea 0.7%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Ingrown hair 0.9%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Folliculitis 1%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Alopecia 1.3%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Dizziness 1.3%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Rash 1.5%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Skin irritation 1.8%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Dyspepsia 1.9%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Acne 10.8%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Tingling skin 2.2%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Erythema 2.5%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Pruritus 3.1%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Dry skin 3.3%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Burning skin 3.5%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Headache 4%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Stinging skin 4.1%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
Pseudofolliculitis barbae 4.9%
13.9 % 2 times / day multiple, topical
Recommended
Dose: 13.9 %, 2 times / day
Route: topical
Route: multiple
Dose: 13.9 %, 2 times / day
Sources:
unhealthy, adult
n = 1373
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 1373
Sources:
PubMed

PubMed

TitleDatePubMed
Topical eflornithine.
2001
Hirsutism: diagnosis and management.
2001
Human dermal safety studies with eflornithine HCl 13.9% cream (Vaniqa), a novel treatment for excessive facial hair.
2001
Effect of polyamine depletion on caspase activation: a study with spermine synthase-deficient cells.
2001 Apr 1
Polyamine and thiol metabolism in Trypanosoma granulosum: similarities with Trypanosoma cruzi.
2001 Apr 20
Pneumocystis carinii pneumonia in pregnancy.
2001 Aug
Polyamines, NO and cGMP mediate stimulation of DNA synthesis by tumor necrosis factor and lipopolysaccharide in chick embryo cardiomyocytes.
2001 Feb 1
p53 independent G(1) arrest induced by DL-alpha-difluoromethylornithine.
2001 Jan 26
Thank God for rich women with mustaches.
2001 Jul
Polyamine depletion arrests growth of IEC-6 and Caco-2 cells by different mechanisms.
2001 Jul
A mechanistic study of proliferation induced by Angelica sinensis in a normal gastric epithelial cell line.
2001 Jun 1
Alpha-difluoromethylornithine induction of apoptosis: a mechanism which reverses pre-established cell proliferation and cancer initiation in esophageal carcinogenesis in zinc-deficient rats.
2001 Mar
Role of spermine in amyloid beta-peptide-associated free radical-induced neurotoxicity.
2001 Mar 1
Chemoprevention by difluoromethylornithine: correlation of an in vitro human cell assay with human clinical data for biomarker modulation.
2001 Mar-Apr
Effects of difluoromethylornithine chemoprevention on audiometry thresholds and otoacoustic emissions.
2001 May
Constitutive expression of arginase in microvascular endothelial cells counteracts nitric oxide-mediated vasodilatory function.
2001 May
Polyamine synthesis and interconversion by the Microsporidian Encephalitozoon cuniculi.
2001 May-Jun
Polyamine depletion in human melanoma cells leads to G1 arrest associated with induction of p21WAF1/CIP1/SDI1, changes in the expression of p21-regulated genes, and a senescence-like phenotype.
2001 Nov 1
Spermidine is essential for normal proliferation of trypanosomatid protozoa.
2001 Nov 23
Cytoskeletal organization and cell motility correlates with metastatic potential and state of differentiation in prostate cancer.
2001 Sep
Polyamine depletion stabilizes p53 resulting in inhibition of normal intestinal epithelial cell proliferation.
2001 Sep
Winterbottom's sign and hypertrophic cardiomyopathy.
2002
Chemotherapy of human African trypanosomiasis.
2002
Inhibition of placental ornithine decarboxylase by DL-alpha-difluoro-methyl ornithine causes fetal growth restriction in rat.
2002 Feb 8
African trypanosomiasis in travelers returning to the United Kingdom.
2002 Jan
Activities of arginase I and II are limiting for endothelial cell proliferation.
2002 Jan
[Chemoprevention of colorectal cancer].
2002 Jan 26
Glucocorticoids and polyamine inhibitors synergize to kill human leukemic CEM cells.
2002 Jan-Feb
Polyamine uptake is necessary for a normal biochemical maturation of astrocytes in culture.
2002 Jun 12
Effect of polyamine depletion on cone photoreceptors of the developing rabbit retina.
2002 Sep
Patents

Sample Use Guides

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
Eflornithine (0.01 - 1 mM) treatment suppressed proliferation of 4T1 murine mammary cancer cells in culture.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:47:35 GMT 2023
Edited
by admin
on Sat Dec 16 01:47:35 GMT 2023
Record UNII
UO07O10TCJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EFLORNITHINE HYDROCHLORIDE ANHYDROUS
Common Name English
2,5-DIAMINO-2-(DIFLUOROMETHYL)PENTANOIC ACID, MONOHYDROCHLORIDE
Common Name English
EFLORNITHINE HYDROCHLORIDE [MI]
Common Name English
NSC-337250
Code English
NSC-270295
Code English
2-(DIFLUOROMETHYL)-DL-ORNITHINE MONOHYDROCHLORIDE
Systematic Name English
Code System Code Type Description
SMS_ID
100000089413
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY
FDA UNII
UO07O10TCJ
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY
MERCK INDEX
m4840
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY Merck Index
NSC
337250
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
269-532-0
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY
PUBCHEM
57004
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY
NSC
270295
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID601019072
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY
CAS
68278-23-9
Created by admin on Sat Dec 16 01:47:35 GMT 2023 , Edited by admin on Sat Dec 16 01:47:35 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS