Introduction：Basic information about Eflornithine hydrochloride CAS 68278-23-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Eflornithine hydrochloride Basic information
| Product Name: | Eflornithine hydrochloride |
| Synonyms: | RMI-71782;RMI-71782 HYDROCHLORIDE;2-(difluoromethyl)-dl-ornithinehydrochloridehydrate;alpha-difluoromethylornithinehydrochloridehydrate;dl-ornithine,2-(difluoromethyl)-,monohydrochloride,hydrate;DFMO;DFMO HCL;DFMO HYDROCHLORIDE |
| CAS: | 68278-23-9 |
| MF: | C6H13ClF2N2O2 |
| MW: | 218.63 |
| EINECS: | 269-532-0 |
| Product Categories: | Amino Acids and Derivatives;facial hair remover |
| Mol File: | 68278-23-9.mol |
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Eflornithine hydrochloride Chemical Properties
| Melting point | 181-184°C |
| storage temp. | Store at -20°C |
| solubility | H2O: >10 mg/mL, soluble |
| form | solid |
| color | white |
| Water Solubility | Soluble to 75 mM in water |
| CAS DataBase Reference | 68278-23-9(CAS DataBase Reference) |
Safety Information
Eflornithine hydrochloride Usage And Synthesis
| Uses | Antineoplastic; antiprotozoal. |
| Uses | DL-alpha-Difluoromethylornithine Hydrochloride is an irreversible inhibitor of ornithine decarboxylase. |
| Indications | Vaniqa (eflornithine hydrochloride 13.9%) cream is a unique topical creamthat slows anagen hair growth by irreversibly blocking the enzyme ornithinedecarboxylase. This enzyme produces polyamines in the hair matrix that arepartially responsible for the growth of the anagen hair. The cream was testedonly on the upper lip and chin region. The onset of action is usually within 8weeks of starting the b.i.d. treatment, and the hair growth will return to baselinewithin 8 weeks of discontinuing the drug. Patients need to be reminded that thisproduct does not remove hair but slows its growth in between whatever they usefor hair removal. |
| Brand name | Ornidyl (Sanofi Aventis); Vaniqa (Skinmedica). |
| Synthesis | 15THF was chilled to -80??C and 2.82L of diisopropylamine was added under nitrogen protection, followed by 12L of a 15% butyl lithium hexane solution, added at a rate to maintain the temperature of the reaction solution at -75 to -80??C. Then N,N'-diphenylmethylene ornithine methyl ester (I) dissolved in a solution of 15L THF was added. After addition, the reaction was slowly raised to 35 to 40??C and nitrogen was replaced with a monochlorodifluoromethane bubble. 20 L of saturated sodium chloride solution and 75 L of isopropyl ether were added, the organic layer was separated and the aqueous layer was extracted. The extract and the organic layer were combined, washed with saturated sodium chloride solution and concentrated until an oily substance was left, which was compound (II). The oily material and 30Llmol/L hydrochloric acid were reacted at room temperature for 3h for hydrolysis. At the end of the reaction, it was extracted with chloroform and the extract was discarded. The extracted aqueous layer was diluted with 6L of water, adjusted to Ph 3.3, heated, filtered, washed and recrystallized to obtain eflornithine. |
| in vivo | Eflornithine is the only new molecule registered for the treatment of human African trypanosomiasis over the last 50 years. It is the drug used mainly as a back-up for melarsoprol refractory Trypanosoma brucei gambiense cases[1]. In subjects with excessive, unwanted facial hair, eflornithine 15% cream is superior to placebo in reducing hair growth. After 24 weeks' treatment, 58% of eflornithine and 34% of placebo subjects have at least some improvement in facial hirsutism[2]. The hair growth inhibitory activity of eflornithine is significantly enhanced when the eflornithine cream is applied onto a mouse skin area pretreated with microneedles[3]. Treatment of coarctation hypertensive rats with eflornithine results in a normalization of the contractile intensity to KCI and norepinephrine and relaxations to acetylcholine by 14 days of hypertension[4]. |
| IC 50 | Trypanosoma |
| storage | Desiccate at RT |
Eflornithine hydrochloride Preparation Products And Raw materials
