Squalene

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name

Squalene

DrugBank Accession Number

DB11460

Background

Squalene is originally obtained from shark liver oil. It is a natural 30-carbon isoprenoid compound and intermediate metabolite in the synthesis of cholesterol. It is not susceptible to lipid peroxidation and provides skin protection. It is ubiquitously distributed in human tissues where it is transported in serum generally in association with very low density lipoproteins. Squalene is investigated as an adjunctive cancer therapy.

Type

Small Molecule

Groups

Approved, Vet approved

Structure

Similar Structures

Weight: Average: 410.73
Monoisotopic: 410.39125161
Chemical Formula: C₃₀H₅₀

Synonyms

(all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene
(E,E,E,E)-Squalene
Spinacene
Squalene
Supraene

Pharmacology

Indication

Not Available

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Associated Conditions

Mild Joint Pain

Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions: This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions: Not Available

Products

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Arepanrix H5n1	Squalene (10.69 mg / 0.5 mL) + DL-alpha-Tocopherol (11.86 mg / 0.5 mL) + Influenza A virus A/Vietnam/1194/2004 (H5N1) antigen (formaldehyde inactivated) (3.75 mcg / 0.5 mL) + Polysorbate 80 (4.86 mg / 0.5 mL)	Emulsion	Intramuscular	ID Biomedical Corporation of Quebec	Not applicable	Not applicable
Fluad Tetra	Squalene (9.75 mg) + Citric acid (0.04 mg) + Influenza A virus A/Cambodia/e0826360/2020 IVR-224 (H3N2) antigen (formaldehyde inactivated) (15 μg) + Influenza A virus A/Victoria/2570/2019 IVR-215 (H1N1) antigen (formaldehyde inactivated) (15 μg) + Influenza B virus B/Phuket/3073/2013 antigen (formaldehyde inactivated) (15 μg) + Influenza virus type B (Victoria) (15 μg) + Polysorbate 80 (1.175 mg) + Sodium citrate (0.66 mg) + Sorbitol (1.175 mg)	Injection, suspension	Intramuscular	Seqirus Netherlands B.V.	2022-06-06	Not applicable
Fluad Tetra	Squalene (9.75 mg) + Citric acid (0.04 mg) + Influenza A virus A/Cambodia/e0826360/2020 IVR-224 (H3N2) antigen (formaldehyde inactivated) (15 μg) + Influenza A virus A/Victoria/2570/2019 IVR-215 (H1N1) antigen (formaldehyde inactivated) (15 μg) + Influenza B virus B/Phuket/3073/2013 antigen (formaldehyde inactivated) (15 μg) + Influenza virus type B (Victoria) (15 μg) + Polysorbate 80 (1.175 mg) + Sodium citrate (0.66 mg) + Sorbitol (1.175 mg)	Injection, suspension	Intramuscular	Seqirus Netherlands B.V.	2022-06-06	Not applicable
Fluad Tetra	Squalene (9.75 mg) + Citric acid (0.04 mg) + Influenza A virus A/Cambodia/e0826360/2020 IVR-224 (H3N2) antigen (formaldehyde inactivated) (15 μg) + Influenza A virus A/Victoria/2570/2019 IVR-215 (H1N1) antigen (formaldehyde inactivated) (15 μg) + Influenza B virus B/Phuket/3073/2013 antigen (formaldehyde inactivated) (15 μg) + Influenza virus type B (Victoria) (15 μg) + Polysorbate 80 (1.175 mg) + Sodium citrate (0.66 mg) + Sorbitol (1.175 mg)	Injection, suspension	Intramuscular	Seqirus Netherlands B.V.	2022-06-06	Not applicable
Fluad Tetra	Squalene (9.75 mg) + Citric acid (0.04 mg) + Influenza A virus A/Cambodia/e0826360/2020 IVR-224 (H3N2) antigen (formaldehyde inactivated) (15 μg) + Influenza A virus A/Victoria/2570/2019 IVR-215 (H1N1) antigen (formaldehyde inactivated) (15 μg) + Influenza B virus B/Phuket/3073/2013 antigen (formaldehyde inactivated) (15 μg) + Influenza virus type B (Victoria) (15 μg) + Polysorbate 80 (1.175 mg) + Sodium citrate (0.66 mg) + Sorbitol (1.175 mg)	Injection, suspension	Intramuscular	Seqirus Netherlands B.V.	2022-06-06	Not applicable

Chemical Identifiers

UNII: 7QWM220FJH
CAS number: 111-02-4
InChI Key: YYGNTYWPHWGJRM-AAJYLUCBSA-N
InChI: InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+
IUPAC Name: (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
SMILES: CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C

References

General References

Popjak G, Agnew WS: Squalene synthetase. Mol Cell Biochem. 1979 Oct 15;27(2):97-116. [Article]
VILLALBA GOMEZ GM: [Squalene index]. Rev Sanid Asist Soc. 1956 May-Aug;21(3-4):155-69. [Article]
Sato R, Hirano Y, Shimizu M: [Squalene synthase]. Nihon Rinsho. 2001 Feb;59 Suppl 2:161-6. [Article]
Agnew WS: Squalene synthetase. Methods Enzymol. 1985;110:359-73. [Article]
Smith TJ: Squalene: potential chemopreventive agent. Expert Opin Investig Drugs. 2000 Aug;9(8):1841-8. [Article]
FLESCH P: Hair loss from squalene. Proc Soc Exp Biol Med. 1951 Apr;76(4):801-3. [Article]
LANGDON RG, BLOCH K: The biosynthesis of squalene. J Biol Chem. 1953 Jan;200(1):129-34. [Article]
Molbak K: [Squalene unlikely sinner]. Ugeskr Laeger. 2013 May 13;175(20):1444. [Article]
Authors unspecified: SQUALENE, an essential nutrient? Nutr Rev. 1955 Nov;13(11):348-9. [Article]
Samman N, Ignasiak T, Chen CJ, Strausz OP, Montgomery DS: Squalene in petroleum asphaltenes. Science. 1981 Sep 18;213(4514):1381-3. [Article]
Kanter JL, Narayana S, Ho PP, Catz I, Warren KG, Sobel RA, Steinman L, Robinson WH: Lipid microarrays identify key mediators of autoimmune brain inflammation. Nat Med. 2006 Jan;12(1):138-43. Epub 2005 Dec 11. [Article]
de Jong A, Cheng TY, Huang S, Gras S, Birkinshaw RW, Kasmar AG, Van Rhijn I, Pena-Cruz V, Ruan DT, Altman JD, Rossjohn J, Moody DB: CD1a-autoreactive T cells recognize natural skin oils that function as headless antigens. Nat Immunol. 2014 Feb;15(2):177-85. doi: 10.1038/ni.2790. Epub 2013 Dec 22. [Article]
Kelly GS: Squalene and its potential clinical uses. Altern Med Rev. 1999 Feb;4(1):29-36. [Article]

External Links

KEGG Compound: C00751
PubChem Compound: 638072
PubChem Substance: 347827980
ChemSpider: 553635
RxNav: 10014
ChEBI: 15440
ChEMBL: CHEMBL458402
ZINC: ZINC000006845904
PDBe Ligand: SQL
Wikipedia: Squalene

PDB Entries

3wqj / 4fbz / 4md1 / 4md2 / 4omk / 7wwd / 7z0e

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Emulsion	Intramuscular
Injection, suspension	Intramuscular
Capsule, liquid filled	Oral
Capsule	Oral

Prices

Not Available

Patents

Not Available

Properties

State

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.000502 mg/mL	ALOGPS
logP	8.64	ALOGPS
logP	10.42	Chemaxon
logS	-5.9	ALOGPS
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	0	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	0 Å²	Chemaxon
Rotatable Bond Count	15	Chemaxon
Refractivity	144.62 m³·mol^-1	Chemaxon
Polarizability	56.17 Å³	Chemaxon
Number of Rings	0	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-MS	GC-MS	splash10-001i-9600000000-280b7ccaed0215f0937c
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-015i-9500000000-63fc959bf17e2f6e0381
Mass Spectrum (Electron Ionization)	MS	splash10-0159-9610000000-aaf0145da95343082ae1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
13C NMR Spectrum	1D NMR	Not Applicable

Drug created at February 25, 2016 18:56 / Updated at June 07, 2022 22:57

Squalene

Identification

Structure for Squalene (DB11460)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra