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Identification
- Summary
Acetic acid is an antimicrobial agent used to treat susceptible infections of the external auditory canal.
- Brand Names
- Fem Ph, Naturalyte, Relagard
- Generic Name
- Acetic acid
- DrugBank Accession Number
- DB03166
- Background
Acetic acid is a product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed) Acetic acid otic (for the ear) is an antibiotic that treats infections caused by bacteria or fungus.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Acetic acid (DB03166)
- Weight
- Average: 60.052
Monoisotopic: 60.021129372 - Chemical Formula
- C2H4O2
- Synonyms
- Acetic acid
- Acetic acid, glacial
- Aceticum acidum
- acide acétique
- ácido acético
- Essigsäure
- Ethanoat
- Ethanoate
- Ethanoic acid
- Ethoic acid
- Ethylic acid
- Glacial acetic acid
- HOAc
- Methanecarboxylic acid
- Vinegar
- External IDs
- E-260
- FEMA NO. 2006
- INS NO.260
- INS-260
- NSC-111201
- NSC-112209
- NSC-115870
- NSC-127175
- NSC-132953
- NSC-406306
Pharmacology
- Indication
Used to treat infections in the ear canal.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute otitis externa •••••••••••• Used in combination to treat External ear infection nos Combination Product in combination with: Hydrocortisone (DB00741) •••••••••••• Used in combination to treat External ear infection nos Combination Product in combination with: Acetic acid (DB03166), Aluminum acetate (DB14518), Aluminium (DB01370) •••••••••••• Prophylaxis of Infections •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Aspartate Metabolism Metabolic Canavan Disease Disease Hypoacetylaspartia Disease Amino Sugar Metabolism Metabolic Ethanol Degradation Metabolic G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease Disease Pyruvate Kinase Deficiency Disease Heroin Metabolism Pathway Drug metabolism Pyruvate Metabolism Metabolic Leigh Syndrome Disease Pyruvate Dehydrogenase Complex Deficiency Disease Sialuria or French Type Sialuria Disease Sialuria or French Type Sialuria Disease Salla Disease/Infantile Sialic Acid Storage Disease Disease Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) Disease Tay-Sachs Disease Disease Heroin Action Pathway Drug action Disulfiram Action Pathway Drug action Fatty Acid Biosynthesis Metabolic Primary Hyperoxaluria II, PH2 Disease - 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Acetic acid is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Acetic acid. Benzocaine The risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Benzocaine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Acetasol / Orlex / Volsol
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acetic Acid Solution 20.65 mg/1mL Auricular (otic) A-S Medication Solutions 2010-01-22 Not applicable US 
Acetic Acid Solution 20.65 mg/1mL Auricular (otic) Rebel Distributors 2010-01-22 Not applicable US Acetic Acid Solution 20.65 mg/1mL Auricular (otic) Preferred Pharmaceuticals Inc. 2018-08-06 Not applicable US Acetic Acid Irrigant 250 mg/100mL Irrigation Baxter Healthcare Corporation 1982-02-19 Not applicable US Acetic Acid Solution 0.02 mL/1mL Auricular (otic) Vintage Pharmaceuticals, LLC 2007-01-25 2007-01-25 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acetic Acid Solution / drops 2 mg/1mL Auricular (otic) Bauch & Lomb Incorporated 1994-02-25 2017-09-01 US Acetic Acid Solution 20.65 mg/1mL Auricular (otic) A-S Medication Solutions 2020-06-05 Not applicable US Acetic Acid Solution 0.02 mg/1mL Auricular (otic) A-S Medication Solutions 2005-02-24 2017-05-31 US Acetic Acid Solution 20 mg/1mL Auricular (otic) Nucare Pharmaceuticals,inc. 1996-07-26 Not applicable US Acetic Acid Solution 20.65 mg/1mL Auricular (otic) Trupharma, Llc 2020-06-05 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image New CleanFlex Liquid 1.5 g/100mL Topical D.O Bio 2021-12-24 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acetasol HC Acetic acid (2.41 g/100mL) + Hydrocortisone (1.1 g/100mL) Solution Auricular (otic) Physicians Total Care, Inc. 1994-12-15 2012-06-30 US Acetasol HC Acetic acid (2.41 g/100mL) + Hydrocortisone (1.1 g/100mL) Solution Auricular (otic) Actavis Pharma, Inc. 2002-09-10 2017-05-31 US Acid Concentrate (r04146) Acetic acid (8.846 g / L) + Calcium chloride (9.477 g / L) + Dextrose, unspecified form (60.8 g / L) + Magnesium chloride (3.744 g / L) + Sodium chloride (184 g / L) Liquid Hemodialysis Genpharm Ulc 1997-05-21 2004-07-30 Canada 
Acid Concentrate (r04938) Acetic acid (8.846 g / L) + Calcium chloride (9.476 g / L) + Dextrose, unspecified form (60.77 g / L) + Magnesium chloride (3.744 g / L) + Potassium chloride (5.491 g / L) + Sodium chloride (172.2 g / L) Liquid Hemodialysis Genpharm Ulc 1987-12-31 2001-08-03 Canada Acid Concentrate (r04968) Acetic acid (8.846 g / L) + Calcium chloride (3.384 g / L) + Magnesium chloride (3.744 g / L) + Potassium chloride (5.491 g / L) + Sodium chloride (180.8 g / L) Liquid Hemodialysis Genpharm Ulc 1988-12-31 2004-07-30 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Fem pH Acetic acid (0.009 g/1g) + Oxyquinoline sulfate (0.00025 g/1g) Jelly Vaginal Pharmics, Inc. 1999-07-15 Not applicable US New CleanFlex Acetic acid (1.5 g/100mL) Liquid Topical D.O Bio 2021-12-24 Not applicable US Otic Edge Acetic acid (100 ug/1mL) + Antipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL) Solution Auricular (otic) River's Edge Pharmaceuticals, LLC 2008-09-01 2012-09-30 US Relegard Acetic acid (0.9 mg/1mL) + Oxyquinoline (0.025 mg/1mL) Gel Topical Blansett Pharmacal Co 2017-03-20 Not applicable US Treagan Otic Acetic acid (0.1 mg/1mL) + Antipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL) Solution Topical Trigen Laboratories, Inc. 2009-09-01 2010-11-30 US
Categories
- ATC Codes
- S02AA10 — Acetic acidG01AD02 — Acetic acid
- Drug Categories
- Acetates
- Acids, Acyclic
- Anti-Bacterial Agents
- Anti-Infective Agents
- Compounds used in a research, industrial, or household setting
- Fatty Acids
- Fatty Acids, Volatile
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Indicators and Reagents
- Laboratory Chemicals
- Lipids
- OATP2B1/SLCO2B1 substrates
- Organic Acids
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Otologicals
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- 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
- monocarboxylic acid (CHEBI:15366) / Straight chain fatty acids, Saturated fatty acids (C00033) / Straight chain fatty acids (LMFA01010002)
- Affected organisms
- Bacteria
Chemical Identifiers
- UNII
- Q40Q9N063P
- CAS number
- 64-19-7
- InChI Key
- QTBSBXVTEAMEQO-UHFFFAOYSA-N
- InChI
- InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
- IUPAC Name
- acetic acid
- SMILES
- CC(O)=O
References
- Synthesis Reference
Earl M. Chamberlin, Warren K. Russ, Jr., George G. Hazen, "Process for preparing [1-oxo-2-cyclopentyl (or 2-isopropyl)-2-methyl-6,7-dichloro-5-indanyloxy] acetic acid." U.S. Patent US3950408, issued April, 1928.
US3950408- General References
- eMedicine [Link]
- External Links
- Human Metabolome Database
- HMDB0000042
- KEGG Drug
- D00010
- KEGG Compound
- C00033
- PubChem Compound
- 176
- PubChem Substance
- 46506148
- ChemSpider
- 171
- BindingDB
- 50074329
- 168
- ChEBI
- 15366
- ChEMBL
- CHEMBL539
- ZINC
- ZINC000005224164
- PharmGKB
- PA448021
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- ACY
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Acetic_acid
- PDB Entries
- 1a3i / 1a7p / 1aa5 / 1at5 / 1bdw / 1be0 / 1bez / 1bkv / 1c0n / 1cag … show 945 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Basic Science Brain Function / Cerebral Blood Flows 1 somestatus stop reason just information to hide Not Available Completed Diagnostic Barrett's Esophagus 1 somestatus stop reason just information to hide Not Available Completed Prevention Cervical Cancer 1 somestatus stop reason just information to hide Not Available Completed Prevention Irreversible Pulpitis (Toothache) / Periapical Abscess / Periodontitis, Apical / Root canal infection 1 somestatus stop reason just information to hide Not Available Completed Prevention Irreversible Pulpitis (Toothache) / Periodontitis, Apical / Root canal infection 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- B. Braun Melsungen AG
- Bausch & Lomb Inc.
- Baxter International Inc.
- Dispensing Solutions
- Hi Tech Pharmacal Co. Inc.
- Hospira Inc.
- Major Pharmaceuticals
- Qualitest
- Taro Pharmaceuticals USA
- Vintage Pharmaceuticals Inc.
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Irrigant Irrigation 0.25 g/100mL Irrigant Irrigation 250 mg/100mL Solution Auricular (otic) 0.02 mL/1mL Solution Auricular (otic) 0.02 mg/1mL Solution Auricular (otic) 20 mg/1mL Solution Auricular (otic) 20.65 mg/1mL Solution / drops Auricular (otic) 2 mg/1mL Liquid Hemodialysis Solution Intravenous Injection, solution Intravenous Injection Intravenous 0.52 g/l Solution Topical; Vaginal 0.077 g Solution Topical 250 mg Jelly Vaginal Solution Irrigation; Parenteral Solution Hemodialysis Solution Hemodialysis 7.77 g/l Solution Hemodialysis 8.46 g/l Solution Hemodialysis 8.8 g/l Solution Hemodialysis 8.85 g/l Solution Hemodialysis 6.77 g/l Gel Cutaneous; Infiltration Injection Intravenous 0.37 g/l Liquid Topical 1.5 g/100mL Solution Auricular (otic) Solution Cutaneous Gel Topical Solution Solution Topical Liquid Auricular (otic) - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 16.6 °C PhysProp boiling point (°C) 117.9 °C PhysProp water solubility 1E+006 mg/L (at 25 °C) MERCK INDEX (1996) logP -0.17 HANSCH,C ET AL. (1995) logS 1.22 ADME Research, USCD pKa 4.76 (at 25 °C) SERJEANT,EP & DEMPSEY,B (1979) - Predicted Properties
Property Value Source Water Solubility 323.0 mg/mL ALOGPS logP -0.12 ALOGPS logP -0.22 Chemaxon logS 0.73 ALOGPS pKa (Strongest Acidic) 4.54 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 0 Chemaxon Refractivity 12.64 m3·mol-1 Chemaxon Polarizability 5.34 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 + 0.9502 Blood Brain Barrier + 0.9742 Caco-2 permeable + 0.5968 P-glycoprotein substrate Non-substrate 0.8714 P-glycoprotein inhibitor I Non-inhibitor 0.99 P-glycoprotein inhibitor II Non-inhibitor 0.992 Renal organic cation transporter Non-inhibitor 0.9466 CYP450 2C9 substrate Non-substrate 0.7913 CYP450 2D6 substrate Non-substrate 0.9384 CYP450 3A4 substrate Non-substrate 0.7921 CYP450 1A2 substrate Non-inhibitor 0.8774 CYP450 2C9 inhibitor Non-inhibitor 0.9482 CYP450 2D6 inhibitor Non-inhibitor 0.9667 CYP450 2C19 inhibitor Non-inhibitor 0.9786 CYP450 3A4 inhibitor Non-inhibitor 0.9854 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9818 Ames test Non AMES toxic 0.9635 Carcinogenicity Carcinogens 0.6222 Biodegradation Ready biodegradable 0.9758 Rat acute toxicity 1.6315 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9666 hERG inhibition (predictor II) Non-inhibitor 0.9889
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 95.163922 predictedDarkChem Lite v0.1.0 [M-H]- 95.172722 predictedDarkChem Lite v0.1.0 [M-H]- 122.62053 predictedDeepCCS 1.0 (2019) [M-H]- 95.163922 predictedDarkChem Lite v0.1.0 [M-H]- 95.172722 predictedDarkChem Lite v0.1.0 [M-H]- 122.62053 predictedDeepCCS 1.0 (2019) [M+H]+ 124.71846 predictedDeepCCS 1.0 (2019) [M+H]+ 124.71846 predictedDeepCCS 1.0 (2019) [M+Na]+ 133.18752 predictedDeepCCS 1.0 (2019) [M+Na]+ 133.18752 predictedDeepCCS 1.0 (2019)
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Mediates the Na(+)-independent transport of steroid sulfate conjugates and other specific organic anions (PubMed:10873595, PubMed:11159893, PubMed:11932330, PubMed:12724351, PubMed:14610227, PubMed:16908597, PubMed:18501590, PubMed:20507927, PubMed:22201122, PubMed:23531488, PubMed:25132355, PubMed:26383540, PubMed:27576593, PubMed:28408210, PubMed:29871943, PubMed:34628357). Responsible for the transport of estrone 3-sulfate (E1S) through the basal membrane of syncytiotrophoblast, highlighting a potential role in the placental absorption of fetal-derived sulfated steroids including the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S) (PubMed:11932330, PubMed:12409283). Also facilitates the uptake of sulfated steroids at the basal/sinusoidal membrane of hepatocytes, therefore accounting for the major part of organic anions clearance of liver (PubMed:11159893). Mediates the intestinal uptake of sulfated steroids (PubMed:12724351, PubMed:28408210). Mediates the uptake of the neurosteroids DHEA-S and pregnenolone sulfate (PregS) into the endothelial cells of the blood-brain barrier as the first step to enter the brain (PubMed:16908597, PubMed:25132355). Also plays a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May act as a heme transporter that promotes cellular iron availability via heme oxygenase/HMOX2 and independently of TFRC (PubMed:35714613). Also transports heme by-product coproporphyrin III (CPIII), and may be involved in their hepatic disposition (PubMed:26383540). Mediates the uptake of other substrates such as prostaglandins D2 (PGD2), E1 (PGE1) and E2 (PGE2), taurocholate, L-thyroxine, leukotriene C4 and thromboxane B2 (PubMed:10873595, PubMed:14610227, PubMed:19129463, PubMed:29871943, Ref.25). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:14610227, PubMed:19129463, PubMed:22201122). The exact transport mechanism has not been yet deciphered but most likely involves an anion exchange, coupling the cellular uptake of organic substrate with the efflux of an anionic compound (PubMed:19129463, PubMed:20507927, PubMed:26277985). Hydrogencarbonate/HCO3(-) acts as a probable counteranion that exchanges for organic anions (PubMed:19129463). Cytoplasmic glutamate may also act as counteranion in the placenta (PubMed:26277985). An inwardly directed proton gradient has also been proposed as the driving force of E1S uptake with a (H(+):E1S) stoichiometry of (1:1) (PubMed:20507927)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76697.93 Da
References
- Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane. J Pharmacol Exp Ther. 2003 Aug;306(2):703-8. Epub 2003 Apr 30. [Article]
- Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human. J Pharmacol Exp Ther. 2004 Feb;308(2):438-45. Epub 2003 Nov 10. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Bidirectional proton-coupled monocarboxylate transporter (PubMed:12946269, PubMed:32946811, PubMed:33333023). Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, acetate and the ketone bodies acetoacetate and beta-hydroxybutyrate, and thus contributes to the maintenance of intracellular pH (PubMed:12946269, PubMed:33333023). The transport direction is determined by the proton motive force and the concentration gradient of the substrate monocarboxylate. MCT1 is a major lactate exporter (By similarity). Plays a role in cellular responses to a high-fat diet by modulating the cellular levels of lactate and pyruvate that contribute to the regulation of central metabolic pathways and insulin secretion, with concomitant effects on plasma insulin levels and blood glucose homeostasis (By similarity). Facilitates the protonated monocarboxylate form of succinate export, that its transient protonation upon muscle cell acidification in exercising muscle and ischemic heart (PubMed:32946811). Functions via alternate outward- and inward-open conformation states. Protonation and deprotonation of 309-Asp is essential for the conformational transition (PubMed:33333023)
- Specific Function
- carboxylic acid transmembrane transporter activity
- Gene Name
- SLC16A1
- Uniprot ID
- P53985
- Uniprot Name
- Monocarboxylate transporter 1
- Molecular Weight
- 53943.685 Da
References
- Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51