General
Preferred name
propanoic acid
Synonyms
Propionate ()
CALCIUM PROPIONATE ()
PROPIONIC ACID ()
Ethanecarboxylic acid ()
FEMA NO. 2924 ()
E-280 ()
Luprosil ()
INS-280 ()
INS NO.280 ()
Antischim b ()
E280 ()
Metacetonic acid ()
Propionic Acid-d5 ()
P&D ID
PD007256
CAS
72-03-7
68937-68-8
784139-72-6
79-09-4
60153-92-6
Tags
available
drug candidate
drug
Drug Status
investigational
approved
vet_approved
Drug indication
Discovery agent
Pharmaceutic Aid (acidifying agent)
Antimicrobial
Max Phase
Phase 2
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE Most absorbed propionic acid is passed to the liver, which removes nearly all of it from the portal blood [L2725].; ; Three days after a single oral administration of labeled sodium propionate, 77% of the radioactivity was found in expired air, and 7% in urine and feces [L2725].
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 body [A32977, L2722]. 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 affected [L2722].; ; In the human body, however, propionic acid is generally metabolized with little ill effect and ultimately becomes a chemical intermediate in the citric acid cycle [L2722].
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 blood [L2725]. Propionic acid represents 20-25% of absorbed volatile fatty acids [L2725].; ; Propionic acid is rapidly absorbed through the gastrointestinal tract [L2725].
METABOLISM Propionic acid is first converted to propionyl coenzyme A (propionyl-CoA), however, it directly enter either beta oxidation or the citric acid cycles [L2722]. As propionic acid has three carbons, propionyl-CoA [L2722]. In the majority of vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is then isomerised to L-methylmalonyl-CoA [L2722]. 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 cycle [L2722].
MOA The metabolic fate of propionates varies in different microorganisms [L2722]. Some have enzyme systems that can convert succinate to propionyl-coenzyme A and through various further steps to propionate, CO2, or propionyl phoshpate [L2722]. Still others can convert propionic acid to B-alanine or directly to CO2 [L2722]. 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 syntheses [L2722].; ; 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 cells [L2724]. Additionally, there are also studies that suggest 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-derivative [A32977].
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 consumption [L2715, L2716].; ; 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 cervix [T193]. In such products, the sodium propionate was primarily used to elicit a preservative, bacteriostatic [L2710, F50] effect 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, respectively [L2710, A32973].; ; Nevertheless, a great variety of propionic acid derivatives exist as separate pharmaceuticals, each with their own unique therapeutic categories, pharmacodynamics, and pharmacokinetics.
Compound Sets
11
Cayman Chemical Bioactives
39159
ChEMBL Drugs
CHEMBL14021
Concise Guide to Pharmacology 2017/18
1062
Concise Guide to Pharmacology 2019/20
1062
Concise Guide to Pharmacology 2021/22
1062
Concise Guide to Pharmacology 2023/24
1062
DrugBank
DB03766
DrugBank Approved Drugs
DB03766
DrugMAP
DM9TN2W
DM0O8N6
Guide to Pharmacology
1062
ReFrame library
External IDs
62
Properties
(calculated by RDKit )
Molecular Weight
74.04
Hydrogen Bond Acceptors
1
Hydrogen Bond Donors
1
Rotatable Bonds
1
Ring Count
0
Aromatic Ring Count
0
cLogP
0.48
TPSA
37.3
Fraction CSP3
0.67
Chiral centers
0.0
Largest ring
0.0
QED
0.49
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
MOA
Endogenous Metabolite
Pathway
Metabolic Enzyme/Protease
Source data