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Economics

Properties

Spectra

Taxonomy

Acetic acid

Transporters (2)

Identification

Name

Acetic acid

Accession Number

DB03166 (EXPT00423, DB04184)

Type

Small Molecule

Groups

Approved

Description

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.

Structure

Similar Structures

Synonyms

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

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Acetic Acid	Solution	0.02 mL/1mL	Auricular (otic)	Vintage Pharmaceuticals, LLC	2007-01-25	2007-01-25
Acetic Acid	Solution	20.65 mg/1mL	Auricular (otic)	Rebel Distributors	2010-01-22	Not applicable
Acetic Acid	Solution	20.65 mg/1mL	Auricular (otic)	Lake Erie Medical DBA Quality Care Products LLC	2010-01-22	Not applicable
Acetic Acid	Solution	20.65 mg/1mL	Auricular (otic)	Preferreed Pharmaceuticals Inc.	2018-08-06	Not applicable
Acetic Acid	Solution	20.65 mg/1mL	Auricular (otic)	A-S Medication Solutions	2010-01-22	Not applicable
Acetic Acid	Irrigant	250 mg/100mL	Irrigation	Hospira, Inc.	1980-01-01	Not applicable
Acetic Acid	Irrigant	0.25 g/100mL	Irrigation	B. Braun Medical Inc.	1979-08-06	Not applicable
Acetic Acid	Solution	20.65 mg/1mL	Auricular (otic)	Hi Tech Pharmacal Co., Inc.	2010-01-22	Not applicable
Acetic Acid	Solution	20.65 mg/1mL	Auricular (otic)	Dispensing Solutions, Inc.	2010-01-22	Not applicable
Acetic Acid	Solution	20.65 mg/1mL	Auricular (otic)	Nucare Pharmaceuticals,inc.	2010-01-22	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Acetic Acid	Solution	20 mg/1mL	Auricular (otic)	A-S Medication Solutions	1996-07-26	Not applicable
Acetic Acid	Solution	0.02 mg/1mL	Auricular (otic)	A-S Medication Solutions	2005-02-24	2017-05-31
Acetic Acid	Solution	20 mg/1mL	Auricular (otic)	Morton Grove Pharmaceuticals, Inc.	1996-07-26	Not applicable
Acetic Acid	Solution	20 mg/1mL	Auricular (otic)	Unit Dose Services	1996-07-26	Not applicable
Acetic Acid	Solution	20 mg/1mL	Auricular (otic)	Rising Pharmaceuticals, Inc.	2018-03-14	Not applicable
Acetic Acid	Solution	25 mg/1mL	Auricular (otic)	Nucare Pharmaceuticals,inc.	1996-07-26	Not applicable
Acetic Acid	Solution / drops	2 mg/1mL	Auricular (otic)	Bauch & Lomb Incorporated	1994-02-25	2017-09-01
Acetic Acid	Solution	0.02 mg/1mL	Auricular (otic)	Qualitest	2005-02-24	2017-05-31
Borofair	Solution / drops	2 mg/1mL	Auricular (otic)	Major	1994-02-25	2018-07-06

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Acetasol HC	Acetic acid (2.41 g/100mL) + Hydrocortisone (1.1 g/100mL)	Solution	Auricular (otic)	Actavis Pharma Company	2002-09-10	Not applicable
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
Acid Concentrate (r04146)	Acetic acid (8.846 g) + Calcium Chloride (9.477 g) + Dextrose, unspecified form (60.8 g) + Magnesium chloride (3.744 g) + Sodium chloride (184 g)	Liquid	Hemodialysis	Genpharm Ulc	1997-05-21	2004-07-30
Acid Concentrate (r04938)	Acetic acid (8.846 g) + Calcium Chloride (9.476 g) + Dextrose, unspecified form (60.77 g) + Magnesium chloride (3.744 g) + Potassium chloride (5.491 g) + Sodium chloride (172.2 g)	Liquid	Hemodialysis	Genpharm Ulc	1987-12-31	2001-08-03
Acid Concentrate (r04968)	Acetic acid (8.846 g) + Calcium Chloride (3.384 g) + Magnesium chloride (3.744 g) + Potassium chloride (5.491 g) + Sodium chloride (180.8 g)	Liquid	Hemodialysis	Genpharm Ulc	1988-12-31	2004-07-30
Acid Concentrate (r04969)	Acetic acid (8.846 g) + Calcium Chloride (3.384 g) + Magnesium chloride (3.744 g) + Potassium chloride (2.746 g) + Sodium chloride (180.8 g)	Liquid	Hemodialysis	Genpharm Ulc	1988-12-31	2004-07-30
Acid Concentrate (r04974)	Acetic acid (8.846 g) + Calcium Chloride (6.769 g) + Magnesium chloride (3.744 g) + Potassium chloride (8.237 g) + Sodium chloride (172.2 g)	Liquid	Hemodialysis	Genpharm Ulc	1988-12-31	2004-07-30
Acid Concentrate (r04975)	Acetic acid (8.846 g) + Calcium Chloride (6.769 g) + Magnesium chloride (3.744 g) + Potassium chloride (2.746 g) + Sodium chloride (172.2 g)	Liquid	Hemodialysis	Genpharm Ulc	1988-12-31	2004-07-30
Acid Concentrate (r04976)	Acetic acid (8.846 g) + Calcium Chloride (6.769 g) + Magnesium chloride (3.744 g) + Potassium chloride (5.491 g) + Sodium chloride (172.2 g)	Liquid	Hemodialysis	Genpharm Ulc	1988-12-31	2004-07-30
Acid Concentrate (r04981)	Acetic acid (8.846 g) + Calcium Chloride (8.122 g) + Dextrose, unspecified form (40.51 g) + Magnesium chloride (3.744 g) + Potassium chloride (2.746 g) + Sodium chloride (180.8 g)	Liquid	Hemodialysis	Genpharm Ulc	1989-12-31	2004-07-30

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Fem pH	Acetic acid (0.009 g/1g) + Oxyquinoline sulfate (0.00025 g/1g)	Jelly	Vaginal	Pharmics, Inc.	1999-07-15	Not applicable
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
Relegard	Acetic acid (0.9 mg/1mL) + Oxyquinoline (0.025 mg/1mL)	Gel	Topical	Blansett Pharmacal Co	2017-03-20	Not applicable
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

International/Other Brands

Acetasol / Orlex / Volsol

Categories

UNII

Q40Q9N063P

CAS number

64-19-7

Weight

Average: 60.052
Monoisotopic: 60.021129372

Chemical Formula

C₂H₄O₂

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

Pharmacology

Indication

Used to treat infections in the ear canal.

Associated Conditions

Associated Therapies

Bladder irrigation therapy

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

Toxicity

Not Available

Affected organisms

Bacteria

Pathways

Pathway	Category
Pyruvate Metabolism	Metabolic
Pyruvate Kinase Deficiency	Disease
Cysteine Biosynthesis	Metabolic
Secondary Metabolites: Cysteine Biosynthesis from Serine	Metabolic
Lipopolysaccharide Biosynthesis II	Metabolic
Pyruvate to Cytochrome bd Terminal Oxidase Electron Transfer	Metabolic
Acetate Metabolism	Metabolic
Aspartate Metabolism	Metabolic
Fatty Acid Biosynthesis	Metabolic
Aspartate Metabolism	Metabolic
Pyruvate Dehydrogenase Complex Deficiency	Disease
Heroin Action Pathway	Drug action
Primary Hyperoxaluria II, PH2	Disease
Amino Sugar and Nucleotide Sugar Metabolism II	Metabolic
Sulfur Metabolism (Propanesulfonate)	Metabolic
Citrate Lyase Activation	Metabolic
Methionine Metabolism and Salvage	Metabolic
Fatty Acid Biosynthesis	Metabolic
Selenocompound Metabolism	Metabolic
Arginine Metabolism	Metabolic
Amino Sugar Metabolism	Metabolic
Sialuria or French Type Sialuria	Disease
Disulfiram Action Pathway	Drug action
Ethanol Degradation	Metabolic
Fatty Acid Biosynthesis	Metabolic
Lipopolysaccharide Biosynthesis	Metabolic
Sulfur Metabolism	Metabolic
Sulfur Metabolism (Ethanesulfonate)	Metabolic
Sulfur Metabolism (Isethionate)	Metabolic
Cysteine Metabolism	Metabolic

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions: Not Available
Food Interactions: Not Available

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
ChEBI: 15366
ChEMBL: CHEMBL539
PharmGKB: PA448021
IUPHAR: 1058
Guide to Pharmacology: GtP Drug Page
HET: ACY
Drugs.com: Drugs.com Drug Page
Wikipedia: Acetic_acid

ATC Codes

S02AA10 — Acetic acid

G01AD02 — Acetic acid

PDB Entries

1a3i / 1a7p / 1aa5 / 1at5 / 1bdw / 1be0 / 1bez / 1bkv / 1c0n / 1cag …

show 814 more

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Active Not Recruiting	Diagnostic	Cervical Cancers	1
1	Recruiting	Diagnostic	Gastric Intestinal Metaplasia	1
Not Available	Active Not Recruiting	Prevention	Cervical Cancers	1
Not Available	Enrolling by Invitation	Basic Science	Brain Function / Cerebral Blood Flow / Gut Microbiome / Metabolism	1
Not Available	Recruiting	Diagnostic	Esophagus, Barrett	1
Not Available	Unknown Status	Diagnostic	Colon Nos Polypectomy Tubular Adenoma / Colorectal Cancers / Serrated Adenomas	1

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	Auricular (otic)	25 mg/1mL
Liquid	Hemodialysis
Solution / drops	Auricular (otic)	2 mg/1mL
Jelly	Vaginal
Solution	Hemodialysis
Gel	Topical
Solution	Auricular (otic)
Solution	Topical

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

ADMET data is predicted using admetSAR, 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	splash10-0007-9000000000-a9a21f72ec25efbc1650
Mass Spectrum (Electron Ionization)	MS	splash10-01oy-9000000000-181ada67a3e5798d4419
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	LC-MS/MS	splash10-03di-9000000000-044b361cb9f5775c43fe
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	LC-MS/MS	splash10-01ox-9000000000-6437eb5f6a38c054dc37
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	LC-MS/MS	splash10-0006-9000000000-0505dfa8ee07a18a3ef3
MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	LC-MS/MS	splash10-0007-9000000000-a0d65dd4e056c1482aaa
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	LC-MS/MS	splash10-0a4i-9000000000-a845ea0157abb3d7783b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	LC-MS/MS	splash10-0a4i-9000000000-42ec023f024176a1c692
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	LC-MS/MS	splash10-0a4i-9000000000-2bbab52cd9d076b89b2c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	LC-MS/MS	splash10-0a4i-9000000000-fb6d2f6298dd5bc37c2e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	LC-MS/MS	splash10-0a4i-9000000000-bc47c47ade16451259c7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-0a4i-9000000000-a845ea0157abb3d7783b
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-0a4i-9000000000-42ec023f024176a1c692
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-0a4i-9000000000-2bbab52cd9d076b89b2c
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-0a4i-9000000000-fb6d2f6298dd5bc37c2e
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-0a4i-9000000000-bc47c47ade16451259c7
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 NMR Spectrum	1D NMR	Not Applicable
[1H,1H] 2D NMR Spectrum	2D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Taxonomy

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: Monocarboxylic acid or derivatives / Carboxylic acid / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group / Aliphatic acyclic 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)

Transporters

Details1. Solute carrier organic anion transporter family member 2B1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name: SLCO2B1
Uniprot ID: O94956
Uniprot Name: Solute carrier organic anion transporter family member 2B1
Molecular Weight: 76709.98 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. [PubMed:12724351]
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. [PubMed:14610227]

Details2. Monocarboxylate transporter 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Symporter activity
Specific Function: Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
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. [PubMed:10579682]

Drug created on June 13, 2005 07:24 / Updated on November 03, 2018 15:33

Acetic acid

Identification

Structure for Acetic acid (DB03166)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Transporters

References

References