Identification

Summary

Isopropyl myristate is a polar skin moisturizer that is used to enhance skin penetration of drugs.

Generic Name
Isopropyl myristate
DrugBank Accession Number
DB13966
Background

Isopropyl myristate is a moisturizer with polar characteristics used in cosmetics and topical medical preparations to ameliorate the skin absorption. Isopropyl myristate has been largely studied and impulsed as a skin penetration enhancer.5

At the moment the primary usage for which isopropyl myristate is formally indicated is as the active ingredient in a non-prescription pediculicide rinse 3,8,9.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Weight
Average: 270.4507
Monoisotopic: 270.255880332
Chemical Formula
C17H34O2
Synonyms
  • 1-Methylethyl tetradecanoate
  • Isopropyl myristate
  • Isopropyl tetradecanoate
External IDs
  • BRN 1781127
  • FEMA NO. 3556

Pharmacology

Indication

The primary medical indication for which isopropyl myristate is formally used as an active ingredient in a patient care product is as a non-prescription pediculicide rinse 1.

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Associated Conditions
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Pharmacodynamics

Isopropyl myristate is an emollient vehicle that is effective at enhancing the penetration of other medical agents that may be incorporated into the vehicle as active agents 7. In one study, a 50:50 isopropanol-isopropyl myristate binary enhancer synergistically increased the transport of estradiol across a two-layer human epidermis in vitro 2.

Mechanism of action

As a pediculicide, isopropyl myristate is capable of physically coating the exoskeleton bodies of lice 8,9,3,4. This physical coating subsequently immobilizes the lice and works to dissolve the wax covering on the insect exoskeleton and blocks the insects' airways, leading to death by dehydration 8,9,3,4. Although this physical action of isopropyl myristate results in little lice resistance (given the lack of immunologic or chemical activity in this mechanism of action), the substance is also not ovicidal, which means any eggs that may have been laid by lice would not be affected 8,9,3,4. Moreover, isopropyl myristate is capable of eliciting its pediculicide action in a contact time of only 10 minutes per each necessary administration 8,9,3,4.

Absorption

Dermal absorption of isopropyl myristate is predicated to be 0.00020 mg/cm2/event, which is considered a very low absorption rate 10. In a study, topically applied isopropyl myristate was largely retained in the stratum corneum 2. It was not detected in the receptor fluid of flow-through diffusion cells in in-vitro skin permeation experiments using human epidermis (stratum corneum and viable epidermis) and dermis of varying thickness 2.

Volume of distribution

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available 12,6.

Protein binding

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available 12,6.

Metabolism

Any isopropyl myristate that is absorbed is likely to be hydrolyzed to its component compounds of isopropylalcohol and myristic acid 11.

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Route of elimination

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available 12,6.

Half-life

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available 12,6.

Clearance

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available 12,6.

Adverse Effects
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Toxicity

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available 12,6.

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
No interactions found.

Products

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International/Other Brands
Estergel
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ResultzSolution50 % w/wTopicalAralez Pharmaceuticals Canada Inc2006-09-01Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
SecolIsopropyl myristate (10 %) + Lanolin (4 %) + Mineral oil (80 %)LiquidTopicalOdan Laboratories Ltd1975-12-312012-12-31Canada flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
0RE8K4LNJS
CAS number
110-27-0
InChI Key
AXISYYRBXTVTFY-UHFFFAOYSA-N
InChI
InChI=1S/C17H34O2/c1-4-5-6-7-8-9-10-11-12-13-14-15-17(18)19-16(2)3/h16H,4-15H2,1-3H3
IUPAC Name
propan-2-yl tetradecanoate
SMILES
CCCCCCCCCCCCCC(=O)OC(C)C

References

General References
  1. Authors unspecified: Update on treatments for head lice. Drug Ther Bull. 2009 May;47(5):50-2. doi: 10.1136/dtb.2009.04.0014. [Article]
  2. Liu P, Cettina M, Wong J: Effects of isopropanol-isopropyl myristate binary enhancers on in vitro transport of estradiol in human epidermis: a mechanistic evaluation. J Pharm Sci. 2009 Feb;98(2):565-72. doi: 10.1002/jps.21459. [Article]
  3. Kaul N, Palma KG, Silagy SS, Goodman JJ, Toole J: North American efficacy and safety of a novel pediculicide rinse, isopropyl myristate 50% (Resultz). J Cutan Med Surg. 2007 Sep-Oct;11(5):161-7. doi: 10.2310/7750.2007.00045. [Article]
  4. Barnett E, Palma KG, Clayton B, Ballard T: Effectiveness of isopropyl myristate/cyclomethicone D5 solution of removing cuticular hydrocarbons from human head lice (Pediculus humanus capitis). BMC Dermatol. 2012 Sep 3;12:15. doi: 10.1186/1471-5945-12-15. [Article]
  5. Eichner A, Stahlberg S, Sonnenberger S, Lange S, Dobner B, Ostermann A, Schrader TE, Hauss T, Schroeter A, Huster D, Neubert RH: Influence of the penetration enhancer isopropyl myristate on stratum corneum lipid model membranes revealed by neutron diffraction and (2)H NMR experiments. Biochim Biophys Acta Biomembr. 2017 May;1859(5):745-755. doi: 10.1016/j.bbamem.2017.01.029. Epub 2017 Jan 26. [Article]
  6. Kathy Moscou, Karen Snipe (2014). Pharmacology for Pharmacy Technicians. Elsevier Health Sciences. [ISBN:9780323292658]
  7. Cosmetic Ingredient Review: Amended Safety Assessment of Alkyl Esters as Used in Cosmetics [Link]
  8. Canadian Paediatric Society: Head Lice Infestations - A clinical update [Link]
  9. Resultz: Why Resultz is the Best Choice For Your Patients [Link]
  10. ECHA Registration Dossier: Isopropyl Myristate [Link]
  11. NIH Toxnet: Isopropyl Myristate [Link]
  12. Journal of the American College of Toxicology: Final Report on the Safety Assessment of Myristyl Myristate and Isopropyl Myristate [Link]
Human Metabolome Database
HMDB0040392
ChemSpider
7751
RxNav
27985
ChEBI
90027
ChEMBL
CHEMBL207602
ZINC
ZINC000008214588
Wikipedia
Isopropyl_myristate
FDA label
Download (1.33 MB)
MSDS
Download (47 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LotionTopical50 g
SolutionTopical50 % w/w
LiquidTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00011 mg/mLALOGPS
logP7.02ALOGPS
logP6.29Chemaxon
logS-6.4ALOGPS
pKa (Strongest Basic)-7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area26.3 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity81.82 m3·mol-1Chemaxon
Polarizability36.05 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0pb9-9320000000-555fda071da050d8d712
GC-MS Spectrum - EI-BGC-MSsplash10-01ox-9210000000-fe05458ea214ddbf37c9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at January 17, 2018 19:19 / Updated at November 29, 2022 21:14