Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H16O |
Molecular Weight | 152.2334 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=C)[C@H]1CCC(CO)=CC1
InChI
InChIKey=NDTYTMIUWGWIMO-SNVBAGLBSA-N
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m1/s1
Molecular Formula | C10H16O |
Molecular Weight | 152.2334 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Perilla alcohol is a naturally occurring monoterpene related to limonene. It is isolated from the essential oils of lavender, peppermint, spearmint, cherries, celery seeds, and several other plants. It has been used topically as a mosquito repellant and in toiletries and may be touted as a constituent of natural products such as tart cherry juice. Perillyl alcohol has demonstrated antiangiogenesis and anticancer effects in vitro. Purported mechanism of action is suppression of the synthesis of small G proteins, including RAS, thereby arresting tumor cells in the G1 phase of the cell cycle. Early clinical studies did not efficacy in prostate, ovarian or breast cancer, probably due to bad pharmacokinetic properties and toxicity after oral administration. More recent preliminary studies found intranasal delivery in patients with malignant gliomas to be well-tolerated and effective, with one study reporting tumor size regression, and another reporting increased overall survival and no side effects after long-term use.
Approval Year
PubMed
Title | Date | PubMed |
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Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data. | 2000 Jan-Feb |
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Effects of perillyl alcohol in glial C6 cell line in vitro and anti-metastatic activity in chorioallantoic membrane model. | 2002 Dec |
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Antileukemia activity of perillyl alcohol (POH): uncoupling apoptosis from G0/G1 arrest suggests that the primary effect of POH on Bcr/Abl-transformed cells is to induce growth arrest. | 2002 Feb |
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Effects of perillyl alcohol on melanoma in the TPras mouse model. | 2002 Jun |
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Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention. | 2002 Nov-Dec |
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Phase I trial of perillyl alcohol administered four times daily continuously. | 2003 Nov |
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Gateways to clinical trials. | 2003 Sep |
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Perillyl alcohol as a radio-/chemosensitizer in malignant glioma. | 2003 Sep 19 |
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BAK overexpression mediates p53-independent apoptosis inducing effects on human gastric cancer cells. | 2004 Jul 12 |
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Perillyl alcohol is an angiogenesis inhibitor. | 2004 Nov |
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Terpenoids as plant antioxidants. | 2005 |
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Protein and m-RNA expression of farnesyl-transferases, RhoA and RhoB in rat liver hepatocytes: action of perillyl alcohol and vitamin A in vivo. | 2005 |
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The number of functional olfactory receptor genes and the relative size of olfactory brain structures are poor predictors of olfactory discrimination performance with enantiomers. | 2005 Feb |
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Sle1ab mediates the aberrant activation of STAT3 and Ras-ERK signaling pathways in B lymphocytes. | 2005 Feb 1 |
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Cancer preventive role of selected dietary factors. | 2005 Jan-Mar |
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Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells. | 2005 May |
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Effects of perillyl alcohol and heat shock treatment in gene expression of human lung adenocarcinoma cell line A549. | 2006 |
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In vitro induction of apoptosis in U937 cells by perillyl alcohol with sensitization by pentoxifylline: increased BCL-2 and BAX protein expression. | 2006 |
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Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis. | 2006 |
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Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil. | 2006 Aug |
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Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells. | 2006 May 18 |
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Cell cycle arrest by the isoprenoids perillyl alcohol, geraniol, and farnesol is mediated by p21(Cip1) and p27(Kip1) in human pancreatic adenocarcinoma cells. | 2007 Mar |
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Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol. | 2008 |
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Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer. | 2008 |
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A pilot study of perillyl alcohol in pancreatic cancer. | 2008 Jun 15 |
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Prevalence of bortezomib-resistant constitutive NF-kappaB activity in mantle cell lymphoma. | 2008 May 19 |
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Fragrance material review on p-mentha-1,8-dien-7-ol. | 2008 Nov |
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Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas. | 2008 Sep |
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Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol. | 2009 Dec |
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Statin-induced muscle damage and atrogin-1 induction is the result of a geranylgeranylation defect. | 2009 Sep |
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Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin. | 2010 Jan |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:20:34 GMT 2023
by
admin
on
Sat Dec 16 08:20:34 GMT 2023
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Record UNII |
3UL4QIY642
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
453314
Created by
admin on Sat Dec 16 08:20:34 GMT 2023 , Edited by admin on Sat Dec 16 08:20:34 GMT 2023
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369312
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15420
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18457-55-1
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3UL4QIY642
Created by
admin on Sat Dec 16 08:20:34 GMT 2023 , Edited by admin on Sat Dec 16 08:20:34 GMT 2023
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