Propylene glycol

Identification

Name
Propylene glycol
Accession Number
DB01839  (EXPT02572, DB11078)
Type
Small Molecule
Groups
Approved, Investigational
Description

A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.

Structure
Thumb
Synonyms
  • 1,2-dihydroxypropane
  • 1,2-Propanediol
  • 1,2-Propylenglykol
  • 2-hydroxypropanol
  • isopropylene glycol
  • methyl glycol
  • methylethyl glycol
  • methylethylene glycol
  • monopropylene glycol
  • PPD
  • Propane-1,2-diol
  • propane-1,2-diol
  • α-propyleneglycol
External IDs
E-1520 / INS NO.1520 / INS-1520 / NSC-69860
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Equate Support Moisture Lubricant EyeSolution / drops6 mg/mLOphthalmicWalmart Stores2015-02-04Not applicableUs
Opti-freeEmulsion.06 mg/mLOphthalmicAlcon, Inc.2015-06-18Not applicableUs
Systane BalanceEmulsion.06 mg/mLOphthalmicAlcon, Inc.2010-07-27Not applicableUs
Systane COMPLETESolution / drops.06 mg/mLOphthalmicAlcon, Inc.2018-01-18Not applicableUs
Walgreen Sterile LubricantSolution / drops.06 mg/mLOphthalmicWalgreen2015-07-27Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Advanced Eye Relief Dry Eye RejuvenationPropylene glycol (10 mg/mL) + Glycerin (3 mg/mL)Solution / dropsOphthalmicBauch & Lomb Incorporated2010-09-01Not applicableUs
Aloe Vera GelPropylene glycol (4 g/100g) + Glycerin (10 g/100g)GelTopicalNINGBO JIANGBEI OCEAN STAR TRADING CO.,LTD2015-02-20Not applicableUs
Aloe Vera SprayerPropylene glycol (2 g/100g) + Aloe Polysaccharide (2 g/100g) + Glycerin (4 g/100g) + Tocopherol (.5 g/100g)LiquidTopicalNINGBO JIANGBEI OCEAN STAR TRADING CO.,LTD2015-02-20Not applicableUs
Artifical TearsPropylene glycol (10 mg/mL) + Glycerin (3 mg/mL)Solution / dropsOphthalmicWalmart Stores2010-09-01Not applicableUs
Artifical TearsPropylene glycol (1 g/100mL) + Glycerin (.3 g/100mL)Solution / dropsOphthalmicRite Aid2010-09-01Not applicableUs
Artificial Tears Lubricant Eye DropsPropylene glycol (10 mg/mL) + Glycerin (3 mg/mL)Solution / dropsOphthalmicCVS Health2010-09-01Not applicableUs
CareOne LubricantPropylene glycol (3 mg/mL) + Polyethylene glycol 400 (4 mg/mL)Solution / dropsOphthalmicFoodhold U.S.A.2017-05-18Not applicableUs
CareOne LubricantPropylene glycol (.3 g/100mL) + Polyethylene glycol 400 (.4 g/100mL)Solution / dropsOphthalmicAmerican Sales Company2013-07-09Not applicableUs
CareOne Ultra LubricantPropylene glycol (3 mg/mL) + Polyethylene glycol 400 (4 mg/mL)Solution / dropsOphthalmicFoodhold U.S.A.2017-05-18Not applicableUs
CVS Long Lasting Lubricant EyePropylene glycol (.3 mg/mg) + Polyethylene glycol 400 (.4 mg/mg)Solution / dropsOphthalmicCVS Health2013-09-17Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MSM (MoSaengMo)Propylene glycol (23.85 mL/150mL)LiquidTopicalHandock Cosmetics Inc2011-08-30Not applicableUs
MSM (MoSaengMo)Propylene glycol (23.85 mL/150mL)LiquidTopicalHandock Cosmetics Inc2011-11-11Not applicableUs
MSM (MoSaengMo)Propylene glycol (23.85 mL/150mL)LiquidTopicalHandock Cosmetics Inc2011-11-11Not applicableUs
Secret Key Tattoo Cover Cushion Spf50 Plus (21 Light Beige)Propylene glycol (5 g/100g) + Cyclomethicone 5 (8 g/100g) + Octinoxate (7 g/100g) + Phenyl trimethicone (3.5 g/100g) + Titanium dioxide (12 g/100g)LiquidTopicalZenpia2016-09-27Not applicableUs
Secret Key Tattoo Cover Cushion Spf50 Plus (23 Natural Beige)Propylene glycol (5 g/100g) + Cyclomethicone 5 (8 g/100g) + Octinoxate (7 g/100g) + Phenyl trimethicone (3.5 g/100g) + Titanium dioxide (12 g/100g)LiquidTopicalZenpia2016-09-27Not applicableUs
Vitabrid SCALP CAREPropylene glycol (10 g/500mL)ShampooTopicalHyundai Ibt Co., Ltd.2016-11-012018-03-15Us
Categories
UNII
6DC9Q167V3
CAS number
57-55-6
Weight
Average: 76.0944
Monoisotopic: 76.0524295
Chemical Formula
C3H8O2
InChI Key
DNIAPMSPPWPWGF-UHFFFAOYSA-N
InChI
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3
IUPAC Name
propane-1,2-diol
SMILES
CC(O)CO

Pharmacology

Indication
Not Available
Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCoagulation factor XIII A chainNot AvailableHuman
UHaloalkane dehalogenaseNot AvailablePseudomonas paucimobilis
UClavaminate synthase 1Not AvailableStreptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
ULactaldehyde reductaseNot AvailableEscherichia coli (strain K12)
UB12-independent glycerol dehydrataseNot AvailableClostridium butyricum
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Leigh SyndromeDisease
Primary hyperoxaluria II, PH2Disease
Pyruvate Dehydrogenase Complex DeficiencyDisease
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)Disease
Pyruvate MetabolismMetabolic
Pyruvate kinase deficiencyDisease
Pyruvate MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Rudolf Huettinger, Ulrich Holtschmidt, "Polyoxyalkylene ethers of glycerin or 1,2-propanediol, esterified with fatty acid and/or isostearic acid, their synthesis and use as thickening or solubilizing agents." U.S. Patent US4614622, issued June, 1968.

US4614622
General References
Not Available
External Links
Human Metabolome Database
HMDB0001881
KEGG Drug
D00078
KEGG Compound
C00583
PubChem Compound
1030
PubChem Substance
46505685
ChemSpider
13835224
ChEBI
16997
ChEMBL
CHEMBL286398
Wikipedia
Propylene_glycol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2Enrolling by InvitationTreatmentDeficiency, Vitamin D / Orthopedic Disorders / Polytrauma1
2CompletedDiagnosticTuberculosis2
2CompletedTreatmentEye Dryness1
2CompletedTreatmentMacular Edema (ME) / Retinopathy, Diabetic1
2WithdrawnTreatmentLacrimation increased1
3CompletedPreventionRadiation Dermatitis1
3CompletedTreatmentEye Dryness1
3CompletedTreatmentBacterial blepharitis / Xerophthalmia1
4CompletedNot AvailableEye Dryness2
4CompletedNot AvailableMyopia1
4CompletedBasic ScienceEye Dryness1
4CompletedTreatmentDry Eye Syndromes3
4CompletedTreatmentDry Eye Syndromes / Eye Dryness1
4CompletedTreatmentEye Dryness2
4RecruitingTreatmentDry Eye Syndrome (DES)1
4Unknown StatusTreatmentEye Dryness1
Not AvailableCompletedBasic ScienceDry Eye Syndrome (DES)1
Not AvailableCompletedBasic ScienceNormal Contact Lens Wear1
Not AvailableCompletedPreventionCataracts1
Not AvailableCompletedTreatmentDry Eye Syndrome (DES)4
Not AvailableCompletedTreatmentEye Dryness1
Not AvailableCompletedTreatmentIntraocular Pressure1
Not AvailableCompletedTreatmentKeratoconjunctivitis Sicca1
Not AvailableCompletedTreatmentMeibomian Gland Dysfunction (MGD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
GelTopical
Solution / dropsOphthalmic6 mg/mL
LiquidOphthalmic
SolutionOphthalmic
Solution, gel forming / dropsOphthalmic
GelNasal
Aerosol, meteredNasal
LiquidTopical23.85 mL/150mL
Spray, meteredNasal
LiquidNasal
SprayNasal
LiquidTopical
GelOphthalmic
EmulsionOphthalmic.06 mg/mL
Kit
Solution / dropsOphthalmic
ShampooTopical10 g/500mL
Solution / dropsOphthalmic.06 mg/mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)-60 °CPhysProp
boiling point (°C)187.6 °CPhysProp
water solubility1E+006 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.92HANSCH,C ET AL. (1995)
pKa14.9SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility952.0 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.79ChemAxon
logS1.1ALOGPS
pKa (Strongest Acidic)14.47ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.97 m3·mol-1ChemAxon
Polarizability8.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9832
Blood Brain Barrier+0.7184
Caco-2 permeable-0.6594
P-glycoprotein substrateNon-substrate0.7162
P-glycoprotein inhibitor INon-inhibitor0.9157
P-glycoprotein inhibitor IINon-inhibitor0.944
Renal organic cation transporterNon-inhibitor0.9401
CYP450 2C9 substrateNon-substrate0.832
CYP450 2D6 substrateNon-substrate0.8739
CYP450 3A4 substrateNon-substrate0.7434
CYP450 1A2 substrateNon-inhibitor0.7858
CYP450 2C9 inhibitorNon-inhibitor0.9388
CYP450 2D6 inhibitorNon-inhibitor0.9526
CYP450 2C19 inhibitorNon-inhibitor0.8969
CYP450 3A4 inhibitorNon-inhibitor0.9599
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.958
Ames testNon AMES toxic0.9132
CarcinogenicityCarcinogens 0.5
BiodegradationReady biodegradable0.9505
Rat acute toxicity0.6112 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9568
hERG inhibition (predictor II)Non-inhibitor0.9008
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014j-0900000000-d90655d5a614c4ddf998
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-014i-1900000000-ab4a1ff05d1275711170
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0002-9000000000-a18bede40461dace657b
GC-MS Spectrum - EI-BGC-MSsplash10-0002-9000000000-6d2345a66e2cf8d2d379
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014j-0900000000-d90655d5a614c4ddf998
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1900000000-ab4a1ff05d1275711170
Mass Spectrum (Electron Ionization)MSsplash10-0002-9000000000-cbc512db1a4c5510015e
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0a7i-9000000000-6c96c59f8ba2e0e5353e
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-005d-9000000000-ae07e4049d24341335ec
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00aj-9000000000-f455f8f0f79f9970711a
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-0002-9000000000-c5bf57086deb14e12495
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0002-9000000000-6d2345a66e2cf8d2d379
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
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
1,2-diols
Alternative Parents
Secondary alcohols / Primary alcohols / Hydrocarbon derivatives
Substituents
Secondary alcohol / 1,2-diol / Hydrocarbon derivative / Primary alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
propane-1,2-diols, glycol (CHEBI:16997) / DL-12-Propanediol (PROPANE-1-2-DIOL)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Factor XIII is activated by thrombin and calcium ion to a transglutaminase that catalyzes the formation of gamma-glutamyl-epsilon-lysine cross-links between fibrin chains, thus stabilizing the fibr...
Gene Name
F13A1
Uniprot ID
P00488
Uniprot Name
Coagulation factor XIII A chain
Molecular Weight
83266.805 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Pseudomonas paucimobilis
Pharmacological action
Unknown
General Function
Haloalkane dehalogenase activity
Specific Function
Catalyzes hydrolytic cleavage of carbon-halogen bonds in halogenated aliphatic compounds, leading to the formation of the corresponding primary alcohols, halide ions and protons. Has a broad substr...
Gene Name
linB
Uniprot ID
P51698
Uniprot Name
Haloalkane dehalogenase
Molecular Weight
33107.275 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Streptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Not Available
Gene Name
cs1
Uniprot ID
Q05581
Uniprot Name
Clavaminate synthase 1
Molecular Weight
35369.325 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Lactaldehyde reductase activity
Specific Function
Not Available
Gene Name
fucO
Uniprot ID
P0A9S1
Uniprot Name
Lactaldehyde reductase
Molecular Weight
40513.025 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Clostridium butyricum
Pharmacological action
Unknown
General Function
Catalytic activity
Specific Function
Not Available
Gene Name
dhaB1
Uniprot ID
Q8GEZ8
Uniprot Name
B12-independent glycerol dehydratase
Molecular Weight
88046.08 Da

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 06:54