Isopropyl myristate

Identification

Name
Isopropyl myristate
Accession Number
DB13966
Type
Small Molecule
Groups
Approved, Experimental
Description

Isopropyl myristate is a polar emollient and is used in cosmetic and topical medicinal preparations where good absorption into the skin is desired. Isopropyl myristate is being studied as a skin enhancer.

At the moment the primary usage for which ispropyl myristate is formally indicated is as the active ingredient in a non-prescription pediculicide rinse [3, 7, 8].

Structure
Thumb
Synonyms
  • 1-Methylethyl tetradecanoate
  • Isopropyl tetradecanoate
External IDs
BRN 1781127 / FEMA NO. 3556
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ResultzSolution50 %TopicalMedical Futures Inc2006-09-01Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SecolIsopropyl myristate (10 %) + Lanolin (4 %) + Mineral oil (80 %)LiquidTopicalOdan Laboratories Ltd1975-12-312012-12-31Canada
International/Other Brands
Estergel
Categories
UNII
0RE8K4LNJS
CAS number
110-27-0
Weight
Average: 270.4507
Monoisotopic: 270.255880332
Chemical Formula
C17H34O2
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

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].

Associated Conditions
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 [6]. 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 [7, 8, 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 [7, 8, 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 [7, 8, 3, 4]. Moreover, isopropyl myristate is capable of eliciting its pediculicide action in a contact time of only 10 minutes per each necessary administration [7, 8, 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 [9]. 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 [11, 5].

Protein binding

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available [11, 5].

Metabolism

Any isopropyl myristate that is absorbed is likely to be hydrolyzed to its component compounds of isopropylalcohol and myristic acid [10].

Route of elimination

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available [11, 5].

Half life

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available [11, 5].

Clearance

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available [11, 5].

Toxicity

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available [11, 5].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:19423676]
  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. [PubMed:18563737]
  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. [PubMed:17942025]
  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. [PubMed:22943314]
  5. Kathy Moscou, Karen Snipe (2014). Pharmacology for Pharmacy Technicians. Elsevier Health Sciences. [ISBN:9780323292658]
  6. Cosmetic Ingredient Review: Amended Safety Assessment of Alkyl Esters as Used in Cosmetics [Link]
  7. Canadian Paediatric Society: Head Lice Infestations - A clinical update [Link]
  8. Resultz: Why Resultz is the Best Choice For Your Patients [Link]
  9. ECHA Registration Dossier: Isopropyl Myristate [Link]
  10. NIH Toxnet: Isopropyl Myristate [Link]
  11. Journal of the American College of Toxicology: Final Report on the Safety Assessment of Myristyl Myristate and Isopropyl Myristate [Link]
External Links
Human Metabolome Database
HMDB0040392
ChemSpider
7751
ChEBI
90027
ChEMBL
CHEMBL207602
Wikipedia
Isopropyl_myristate
AHFS Codes
  • 84:04.12 — Scabicides and Pediculicides
FDA label
Download (1.33 MB)
MSDS
Download (47 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionTopical50 %
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

Taxonomy

Classification
Not classified

Drug created on January 17, 2018 12:19 / Updated on November 18, 2018 04:57