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
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
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 | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB06243Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21145lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB06243
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18823367 http://www.who.int/trypanosomiasis_african/drugs/en/
Curator's Comment: Eflornithine crossed blood-brain barrier
Originator
Sources: http://www.pharmacy.utoronto.ca/sites/default/files/upload//who_cc/launch/James%20Crombie.pdf
Curator's Comment: Eflornithine was discovered in 1980 by Dr Cyrus Bacchi
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1869 Sources: http://www.drugbank.ca/drugs/DB06243 |
|||
Target ID: CHEMBL612849 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23031595 |
8.3 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VANIQA Approved UseReduction of unwanted facial hair in women. Launch Date2000 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
484 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/15141331 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4430 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/15141331 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/15141331 |
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
Dose | Population | Adverse 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) Sources: 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) |
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%) Sources: 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%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17333337
Eflornithine (0.01 - 1 mM) treatment suppressed proliferation of 4T1 murine mammary cancer cells in culture.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:47:35 GMT 2023
by
admin
on
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Record UNII |
UO07O10TCJ
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Record Status |
Validated (UNII)
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Record Version |
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