FARNESOL

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17333335
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21893226 | https://www.ncbi.nlm.nih.gov/pubmed/20014777 | https://www.ncbi.nlm.nih.gov/pubmed/21862726 | https://www.ncbi.nlm.nih.gov/pubmed/21030469

Farnesol, (2E,6E)- is an isoprenoid found in many aromatic plants and is also produced in humans, where it acts on numerous nuclear receptors and has received considerable attention due to its apparent anticancer properties. Farnesol is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam, and tolu. It is used in perfumery to emphasize the odors of sweet floral perfumes. Its method of action for enhancing perfume scent is as a co-solvent that regulates the volatility of the odorants. It is especially used in lilac perfumes. Farnesol is a natural pesticide for mites and is a pheromone for several other insects. In a 1994 report released by five top cigarette companies, farnesol was listed as one of 599 additives to cigarettes. Farnesol has been suggested to function as a chemopreventative and anti-tumor agent. Farnesol is subject to restrictions on its use in perfumery as some people may become sensitized to it, however, the evidence that farnesol can cause an allergic reaction in humans is disputed.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Neuraminidase 21 Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20014777	Inhibitor 8297	81.4 µM [IC50]
UDP-glucuronosyltransferase 1-1 15 Target ID: CHEMBL1287617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21030469	Inhibitor 8297	47.0 µM [IC50]
Bile acid receptor FXR 31 Target ID: CHEMBL2047 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21893226	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17333335	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antifungal properties of essential oils and their main components upon Cryptococcus neoformans.	1994 Dec	7739729
Identification of a nuclear receptor that is activated by farnesol metabolites.	1995 Jun 2	7774010
Lovastatin induces apoptosis by inhibiting mitotic and post-mitotic events in cultured mesangial cells.	1997 Oct 30	9398081
Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study.	1998 Feb	9491760
Xol INXS: role of the liver X and the farnesol X receptors.	2001 Apr	11264982
Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism.	2002 Mar 25	11958988
Farnesol is glucuronidated in human liver, kidney and intestine in vitro, and is a novel substrate for UGT2B7 and UGT1A1.	2004 Dec 15	15320866
Lysine beta311 of protein geranylgeranyltransferase type I partially replaces magnesium.	2004 Jul 16	15131129
Omega-hydroxylation of farnesol by mammalian cytochromes p450.	2004 Jun 1	15158752
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.	2004 Oct	15491415
Cytochrome P450 expression and activities in human tongue cells and their modulation by green tea extract.	2005 Jan 15	15629189
Biologically active fluorescent farnesol analogs.	2005 Jun	15975508
Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro.	2007 Oct	17924309
Farnesol, a mevalonate pathway intermediate, stimulates MCF-7 breast cancer cell growth through farnesoid-X-receptor-mediated estrogen receptor activation.	2008 Jan	17333335
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.	2011 Feb 3	21291553

Patents

Sample Use Guides

In Vivo Use Guide

mice were maintained for 5 wk on adiet containing 0.25%, 0.5% farnesol

Route of Administration: Oral

In Vitro Use Guide

The ER-positive MCF-7 breast cancer cell line and MDAMB-231 breast carcinoma cells (ATCC HTB-26) lacking ER expression were used for activity evaluation. Cells were cultured at 37C in a humidified 95% air and 5% CO2 atmosphere. One day after seeding, the culture medium was replaced by fresh SFM containing farnesol (10-200mkM, MP Biomedicals, Aurora, OH), 17b-estradiol (Sigma, St Louis, MO), 4-hydroxytamoxifen (Sigma, St Louis, MO), the raloxifen analog LY 117,018 (a gift from Eli Lilly & Co., Indianapolis, IN), fulvestrant (ICI 182,780, Tocris, Bristol, UK), ibandronate (a gift from Hoffmann-LaRoche, Basel, Switzerland), mevastatin (Sigma, St Louis, MO), or vehicle. Cells were treated for 1–3 days, with drugs alone or in combinations. The FXR activator farnesol, a mevalonate pathway intermediate, exerts a mitogenic effect on MCF-7 cells.

Substance Class	Mixture Created by `admin` on `Sat Dec 16 20:01:21 UTC 2023` Edited by `admin` on `Sat Dec 16 20:01:21 UTC 2023`
Record UNII	EB41QIU6JL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FARNESOL

Official Name

English

NSC-60597

Code

English

FARNESYL ALCOHOL

Common Name

English

FCI-119A

Code

English

FARNESOL [MI]

Common Name

English

FEMA NO. 2478

Code

English

NIKKOSOME

Common Name

English

FARNESOL [FCC]

Common Name

English

FARNESOL [FHFI]

Common Name

English

FARNESOL [HSDB]

Common Name

English

FARNESOL [INCI]

Common Name

English

3,7,11-TRIMETHYL-2,6,10-DODECATRIEN-1-OL

Common Name

English

2,6,10-DODECATRIEN-1-OL, 3,7,11-TRIMETHYL-

Common Name

English

TRIMETHYL DODECATRIENOL

Common Name

English

Classification Tree Code System Code

EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION

SCCS/1459/11