Identification

Summary

Propanoic acidis an antimicrobial food additive.

Generic Name
Propanoic acid
DrugBank Accession Number
DB03766
Background

丙酸钠是丙的钠盐acid that exists as colorless, transparent crystals or a granular crystalline powder. It is considered generally recognized as safe (GRAS) food ingredient by FDA, where it acts as an antimicrobial agent for food preservation and flavoring agent. Its use as a food additive is also approved in Europe. Sodium propionate is is prepared by neutralizing propionic acid with sodium hydroxide. Sodium propionate was previously approved in Canada as an active ingredient in Amino-Cerv (used to treat inflammation or injury of the cervix).

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 74.0785
Monoisotopic: 74.036779436
Chemical Formula
C3H6O2
Synonyms
  • Propionic acid
External IDs
  • E-280
  • FEMA NO. 2924
  • INS NO.280
  • INS-280

Pharmacology

Indication

Propanoic acid and various direct sodium or calcium salt formulations of the acid are currently most commonly approved and indicated by organizations like the FDA and EMA for use as an antibacterial food additive preservative in animal feed and food for human consumption5,6

Similarly, although the use of propanoic acid or any of its direct sodium or calcium salt formulations as excipient ingredients in pharmaceuticals is not necessarily a major role for the compound today, sodium propionate was used in some vaginal cream preparations indicated for cervicitis, cervical tears, and/or postcauterization, postcryosurgery, and postconization of the cervix3.In such products, the sodium propionate was primarily used to elicit a preservative, bacteriostatic4,11effect while other active ingredients combined in the formulation like urea, benzalkonium chloride, inositol, and methionine and cystine amino acids facilitated debridement, enhanced medication spread, epithelialization promotion, and wound healing, respectively4,1

Nevertheless, a great variety of propionic acid derivatives exist as separate pharmaceuticals, each with their own unique therapeutic categories, pharmacodynamics, and pharmacokinetics.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
Improve clinical decision support with information oncontraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

As a naturally occurring carboxylic acid, propionic acid typically undergoes metabolism via conversion to propionyl coenzyme A (propionyl-CoA), which is part of the usual metabolic pathway that carboxylic acids participate within in the human body2,7.Most of propionic acid's antibacterial and preservative activities subsequently stem from this metabolic pathway as the metabolic fate of propionates varies in different microorganisms, resulting in antimicrobial mechanisms of action that may revolve around differing propionate metabolites causing competition, inhibition, and/or interference effects along other metabolic pathways in the various microorganisms affected7

In the human body, however, propionic acid is generally metabolized with little ill effect and ultimately becomes a chemical intermediate in the citric acid cycle7

Mechanism of action

The metabolic fate of propionates varies in different microorganisms7.Some have enzyme systems that can convert succinate to propionyl-coenzyme A and through various further steps to propionate, CO2, or propionyl phoshpate7.Still others can convert propionic acid to B-alanine or directly to CO27.Whatever the case, the inhibiting effect for microbials is likely related to competition with acetate in the acetokinase system, to the blockage of pyruvate conversion to acetyl-coenzyme A and to interference with B-alanine in pantothenic acid syntheses7

Moreover, other studies suggest the antimicrobial activity of propionic acid revolves around its ability to reduce the pH of its immediate environment to levels of acidity that are harmful to pathogenic microbes as well as its ability to dissociate such that its lipid soluble undissociated form is capable of entering microbial cells8.此外,也有研究的措施t that propionic acid's antifungal activity may be the result of propionyl-CoA inhibiting glucose metabolism in certain species of fungus via the accumulation of the CoA-derivative2

Target Actions Organism
UAlanine racemase Not Available Geobacillus stearothermophilus
UGephyrin Not Available Humans
U2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase Not Available Pseudomonas fluorescens
Absorption

Some propionic acid is oxidized to lactic acid during absorption, but most passes to the liver, which removes nearly all of it from the portal blood9.Propionic acid represents 20-25% of absorbed volatile fatty acids9

Propionic acid is rapidly absorbed through the gastrointestinal tract9

Volume of distribution

三天后的单一口服labeled sodium propionate, 77% of the radioactivity was found in expired air, and 7% in urine and feces9.The radioactivity found in skin, liver, intestine, and adipose tissue was 3.9, 1.1, 0.9, and 0.7%, respectively9

Readily accessible data regarding the volume of distribution of propionic acid is not available.

Protein binding

Readily accessible data regarding the protein binding of propionic acid is not available.

Metabolism

Propionic acid is first converted to propionyl coenzyme A (propionyl-CoA), however, it directly enter either beta oxidation or the citric acid cycles7.As propionic acid has three carbons, propionyl-CoA7.In the majority of vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is then isomerised to L-methylmalonyl-CoA7.A vitamin B12-dependent enzyme catalyzes rearrangement of L-methylmalonyl-CoA to succinyl-CoA, which can then be used as a substrate in the citric acid cycle7

Hover over products below to view reaction partners

Route of elimination

Most absorbed propionic acid is passed to the liver, which removes nearly all of it from the portal blood9

三天后的单一口服labeled sodium propionate, 77% of the radioactivity was found in expired air, and 7% in urine and feces9

Half-life

The half-life of iv sodium propionate administered in the sheep animal model is about 6.9 +/- 0.4 minutes9

Clearance

Readily accessible data regarding the clearance of propionic acid is not available.

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including:blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

As a compound that is typically found naturally in the body, little to no adverse cumulative health effects have been associated with exposure to propionic acid10.Medical reports of acute exposures of workers to propionic acid show mild to moderate skin burns, mild eye redness, and one case of a mild cough and asthmatic response10

Pathways
Pathway Category
Propanoate Metabolism Metabolic
Malonic Aciduria Disease
Methylmalonic Aciduria Due to Cobalamin-Related Disorders Disease
Vitamin K Metabolism Metabolic
Malonyl-CoA Decarboxylase Deficiency Disease
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
Ingredient UNII CAS InChI Key
Sodium propionate DK6Y9P42IN 6700-17-0 HOAUAOBUGFYWMK-UHFFFAOYSA-M
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Amino-cerv Sodium propionate(0.50 %)+Cystine(0.354 %)+Inositol(0.83 %)+Racemethionine(0.83 %)+Urea(8.34 %) Cream Vaginal Milex, A Coopersurgical Co. 1952-12-31 2007-07-26 Canada flag

Categories

ATC Codes
S01AX10 — Sodium propionate
Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Carboxylic acids
Direct Parent
Carboxylic acids
Alternative Parents
Monocarboxylic acids and derivatives/Organic oxides/Hydrocarbon derivatives/Carbonyl compounds
Substituents
Aliphatic acyclic compound/Carbonyl group/Carboxylic acid/Hydrocarbon derivative/Monocarboxylic acid or derivatives/Organic oxide/Organic oxygen compound/Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
saturated fatty acid, short-chain fatty acid (CHEBI:30768)/Straight chain fatty acids, Saturated fatty acids (C00163)/Straight chain fatty acids (LMFA01010003)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
JHU490RVYR
CAS number
79-09-4
InChI Key
XBDQKXXYIPTUBI-UHFFFAOYSA-N
InChI
InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
IUPAC Name
propanoic acid
SMILES
CCC(O)=O

References

Synthesis Reference

James R. Hazen, "Process for production of 3-(hydroxyphenylphosphinyl)-propanoic acid." U.S. Patent US4769182, issued March, 1978.

US4769182
General References
  1. Ilic L, Gowrishankar TR, Vaughan TE, Herndon TO, Weaver JC: Spatially constrained skin electroporation with sodium thiosulfate and urea creates transdermal microconduits. J Control Release. 1999 Aug 27;61(1-2):185-202. [Article]
  2. 布洛克M,上W: t的作用机制he antifungal agent propionate. Eur J Biochem. 2004 Aug;271(15):3227-41. doi: 10.1111/j.1432-1033.2004.04255.x. [Article]
  3. Leonard G. Gomella, Steven A. Haist, Steven Haist (2003). Clinician's Pocket Drug Reference 2004 (3rd ed.). McGraw-Hill/Appleton & Lange. [ISBN:978-0071429450]
  4. RXmed.com: AMINO-CERV Monograph [Link]
  5. FDA Listing of Propionic Acid [Link]
  6. EFSA Journal: Safety of the extension of use of sodium propionate (E 281) as a food additive [Link]
  7. INCHEM Propionic Acid and its Calcium, Potassium, and Sodium Salts (WHO Food Additive Series 5) [Link]
  8. PROPIONIC ACID IS AN ALTERNATIVE TO ANTIBIOTICS IN POULTRY DIET [Link]
  9. PubChem Propionic Acid Profile [Link]
  10. NIH Toxnet: Propionic Acid Profile [Link]
  11. Compendium of Pharmaceutical Excipients for Vaginal Formulations [File]
Human Metabolome Database
HMDB0000237
KEGG Drug
D02310
KEGG Compound
C00163
PubChem Compound
1032
PubChem Substance
46508742
ChemSpider
1005
BindingDB
50082199
RxNav
34658
ChEBI
30768
ChEMBL
CHEMBL14021
ZINC
ZINC000006050663
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
PPI
Wikipedia
Propionic_acid
PDB Entries
1a8s/1adl/1lic/1lie/1seg/1tu9/1uk6/1uux/1uuy/2hub
show 42 more
MSDS
Download (62.7 KB)

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
1, 2 Not Yet Recruiting Treatment Radiation Toxicity/Therapeutic Agent Toxicity 1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Form Route Strength
Cream Vaginal
Mouthwash Buccal 0.25 %
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) -20.7 °C PhysProp
boiling point (°C) 141.1 °C PhysProp
water solubility 1E+006 mg/L (at 25 °C) US EPA (1981)
logP 0.33 HANSCH,C ET AL. (1995)
pKa 4.88 SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
Property Value Source
Water Solubility 352.0 mg/mL ALOGPS
logP 0.31 ALOGPS
logP 0.48 ChemAxon
logS 0.68 ALOGPS
pKa (Strongest Acidic) 4.75 ChemAxon
Physiological Charge -1 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 Å2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 17.27 m3·mol-1 ChemAxon
Polarizability 7.24 Å3 ChemAxon
Number of Rings 0 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five Yes ChemAxon
Ghose Filter No ChemAxon
Veber's Rule Yes ChemAxon
MDDR-like Rule No ChemAxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9893
Blood Brain Barrier + 0.941
Caco-2 permeable + 0.6324
P-glycoprotein substrate Non-substrate 0.7959
P-glycoprotein inhibitor I Non-inhibitor 0.9671
P-glycoprotein inhibitor II Non-inhibitor 0.9909
Renal organic cation transporter Non-inhibitor 0.9624
CYP450 2C9 substrate Non-substrate 0.788
CYP450 2D6 substrate Non-substrate 0.9394
CYP450 3A4 substrate Non-substrate 0.8006
CYP450 1A2 substrate Non-inhibitor 0.8922
CYP450 2C9 inhibitor Non-inhibitor 0.9639
CYP450 2D6 inhibitor Non-inhibitor 0.9667
CYP450 2C19 inhibitor Non-inhibitor 0.9794
CYP450 3A4 inhibitor Non-inhibitor 0.9763
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9876
Ames test Non AMES toxic 0.9401
Carcinogenicity Carcinogens 0.6548
Biodegradation Ready biodegradable 0.9079
Rat acute toxicity 1.4864 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9681
hERG inhibition (predictor II) Non-inhibitor 0.9778
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
GC-MS Spectrum - EI-B GC-MS splash10-004i-9000000000-51f674be972a6c17185b
GC-MS Spectrum - EI-B GC-MS splash10-004i-9000000000-691dcd080b30c9898350
Mass Spectrum (Electron Ionization) MS splash10-00b9-9000000000-0bb3297c4159bed2316e
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) LC-MS/MS splash10-004i-9000000000-1af60fc458a7f351a9b0
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) LC-MS/MS splash10-004i-9000000000-aa6e765fc867ac8be641
MS/MS Spectrum - Quattro_QQQ 40V, Positive LC-MS/MS splash10-0006-9000000000-27e0b790e192d1304449
MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive LC-MS/MS splash10-004i-9000000000-51f674be972a6c17185b
MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive LC-MS/MS splash10-004i-9000000000-90d9e0181596093a2f85
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative LC-MS/MS splash10-00di-9000000000-bdd7baa3d1bda886fb77
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative LC-MS/MS splash10-00di-9000000000-e73379c8765802cf3228
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative LC-MS/MS splash10-00di-9000000000-d6832c04c8b2ca0fdfa3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative LC-MS/MS splash10-00di-9000000000-d0c93844dbfaed791bb0
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-47364fadf00a5a2b7e93
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-9000000000-76fad523c005a6510264
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-9000000000-a1c0234da57ff32c6e12
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-47364fadf00a5a2b7e93
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-9000000000-76fad523c005a6510264
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-9000000000-a1c0234da57ff32c6e12
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-9000000000-db59da781a70634d2526
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05fr-9000000000-bea4ff21e6ab6c664412
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-782832f8f5ab85f2ef4f
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-9000000000-db59da781a70634d2526
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05fr-9000000000-bea4ff21e6ab6c664412
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-782832f8f5ab85f2ef4f
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-00di-9000000000-bdd7baa3d1bda886fb77
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-00di-9000000000-e73379c8765802cf3228
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-00di-9000000000-d6832c04c8b2ca0fdfa3
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-00di-9000000000-d0c93844dbfaed791bb0
13C NMR Spectrum 1D NMR Not Applicable
1H NMR Spectrum 1D NMR Not Applicable
1H NMR Spectrum 1D NMR Not Applicable
13C NMR Spectrum 1D NMR Not Applicable
1H NMR Spectrum 1D NMR Not Applicable
13C NMR Spectrum 1D NMR Not Applicable
[1H,1H] 2D NMR Spectrum 2D NMR Not Applicable
[1H,13C] 2D NMR Spectrum 2D NMR Not Applicable

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets tounlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the interconversion of L-alanine and D-alanine. Also weakly active on serine.
Gene Name
alr
Uniprot ID
P10724
Uniprot Name
Alanine racemase
分子量
43592.715 Da
References
  1. Morollo AA,宠物sko GA, Ringe D: Structure of a Michaelis complex analogue: propionate binds in the substrate carboxylate site of alanine racemase. Biochemistry. 1999 Mar 16;38(11):3293-301. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Molybdopterin molybdotransferase activity
Specific Function
Microtubule-associated protein involved in membrane protein-cytoskeleton interactions. It is thought to anchor the inhibitory glycine receptor (GLYR) to subsynaptic microtubules (By similarity). Ca...
Gene Name
GPHN
Uniprot ID
Q9NQX3
Uniprot Name
Gephyrin
分子量
79747.635 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
Unknown
General Function
Hydrolase activity
Specific Function
Not Available
Gene Name
cumD
Uniprot ID
P96965
Uniprot Name
2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase
分子量
31489.385 Da

Enzymes

Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcription regulatory region sequence-specific dna binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...

Components:
References
  1. Ganapathy V, Thangaraju M, Gopal E, Martin PM, Itagaki S, Miyauchi S, Prasad PD: Sodium-coupled monocarboxylate transporters in normal tissues and in cancer. AAPS J. 2008;10(1):193-9. doi: 10.1208/s12248-008-9022-y. Epub 2008 Apr 2. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity).
Gene Name
FABP4
Uniprot ID
P15090
Uniprot Name
Fatty acid-binding protein, adipocyte
分子量
14718.815 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. [Article]
  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. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at April 30, 2021 13:05