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
Thumb
Synonyms
  • Acetic acid, glacial
  • Aceticum acidum
  • acide acétique
  • 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
Product Ingredients
IngredientUNIICASInChI Key
Acetyl chlorideQD15RNO45K75-36-5WETWJCDKMRHUPV-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acetic AcidSolution20.65 mg/mLAuricular (otic)Lake Erie Medical Dba Quality Care Produts Llc2010-01-22Not applicableUs
Acetic AcidIrrigant250 mg/100mLIrrigationHospira, Inc.1980-01-01Not applicableUs
Acetic AcidSolution20.65 mg/mLAuricular (otic)A S Medication Solutions2010-01-222017-06-20Us
Acetic AcidIrrigant.25 g/100mLIrrigationB. Braun Medical Inc.1979-08-06Not applicableUs
Acetic AcidSolution20.65 mg/mLAuricular (otic)A S Medication Solutions2010-01-22Not applicableUs
Acetic AcidSolution20.65 mg/mLAuricular (otic)Rebel Distributors2010-01-22Not applicableUs
Acetic AcidSolution20.65 mg/mLAuricular (otic)Dispensing Solutions, Inc.2010-01-22Not applicableUs
Acetic AcidIrrigant250 mg/100mLIrrigationBaxter Laboratories1982-02-19Not applicableUs
Acetic AcidSolution20.65 mg/mLAuricular (otic)Hi Tech Pharmacal Co., Inc.2010-01-22Not applicableUs
VoSoLSolution20.65 mg/mLAuricular (otic)ECR Pharmaceuticals Co., Inc.2010-03-15Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acetic AcidSolution25 mg/mLAuricular (otic)Unit Dose Services1996-07-26Not applicableUs
Acetic AcidSolution.02 mg/mLAuricular (otic)A S Medication Solutions2005-02-242017-05-31Us
Acetic AcidSolution20 mg/mLAuricular (otic)Morton Grove Pharmaceuticals, Inc.1996-07-26Not applicableUs
Acetic AcidSolution25 mg/mLAuricular (otic)A S Medication Solutions1996-07-262017-06-20Us
Acetic AcidSolution.02 mg/mLAuricular (otic)Qualitest2005-02-242017-05-31Us
Acetic AcidSolution25 mg/mLAuricular (otic)Nu Care Pharmaceuticals,inc.1996-07-262017-09-29Us
BorofairSolution / drops2 mg/mLAuricular (otic)Major1994-02-25Not applicableUs
International/Other Brands
Acetasol / Orlex / Volsol
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Acetasol HCAcetic acid (2.41 g/100mL) + Hydrocortisone (1.1 g/100mL)SolutionAuricular (otic)Actavis Mid Atlantic LLC,2002-09-10Not applicableUs
Acid Concentrate D12028Acetic acid (8.85 g) + Calcium Chloride (7.16 g) + Magnesium chloride (0.88 g) + Potassium Chloride (2.75 g) + Sodium Chloride (172 g)LiquidHemodialysisAlthin Biopharm Inc.1986-12-311997-08-13Canada
Acid Concentrate D12054Acetic acid (8.85 g) + Calcium Chloride (6.13 g) + Magnesium chloride (2.63 g) + Potassium Chloride (5.49 g) + Sodium Chloride (172.2 g)LiquidHemodialysisAlthin Biopharm Inc.1986-12-311997-08-13Canada
Acid Concentrate D12092Acetic acid (5.41 g) + Calcium Chloride (7.49 g) + Magnesium chloride (3.21 g) + Potassium Chloride (5.02 g) + Sodium Chloride (263 g)SolutionHemodialysisAlthin Biopharm Inc.1985-12-311998-08-27Canada
Acid Concentrate D12093Acetic acid (5.41 g) + Calcium Chloride (7.49 g) + Magnesium chloride (3.21 g) + Potassium Chloride (10.1 g) + Sodium Chloride (263 g)LiquidHemodialysisBaxter Laboratories1985-12-312002-08-01Canada
Acid Concentrate D12095Acetic acid (5.41 g) + Calcium Chloride (7.49 g) + Magnesium chloride (1.61 g) + Potassium Chloride (3.35 g) + Sodium Chloride (263 g)LiquidHemodialysisBaxter Laboratories1986-12-312002-08-01Canada
Acid Concentrate D12119Acetic acid (8.85 g) + Calcium Chloride (6.13 g) + Magnesium chloride (0.88 g) + Potassium Chloride (2.75 g) + Sodium Chloride (172 g)LiquidHemodialysisAlthin Biopharm Inc.1988-12-312001-02-02Canada
Acid Concentrate D12132Acetic acid (8.85 g) + Calcium Chloride (5.11 g) + Magnesium chloride (2.63 g) + Potassium Chloride (5.49 g) + Sodium Chloride (172.2 g)LiquidHemodialysisAlthin Biopharm Inc.1988-12-311998-08-27Canada
Acid Concentrate D12150Acetic acid (5.41 g) + Calcium Chloride (4.99 g) + Magnesium chloride (2.14 g) + Potassium Chloride (5.02 g) + Sodium Chloride (263 g)LiquidHemodialysisAlthin Biopharm Inc.1989-12-311999-09-23Canada
Acid Concentrate D12247Acetic acid (10.8 g) + Calcium Chloride (3.25 g) + Magnesium chloride (2.14 g) + Potassium Chloride (5.02 g) + Sodium Chloride (263 g)LiquidHemodialysisAlthin Biopharm Inc.1995-12-311999-09-23Canada
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.

Structured Indications
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
PathwayCategory
Pyruvate MetabolismMetabolic
Canavan DiseaseDisease
Pyruvate kinase deficiencyDisease
Leigh SyndromeDisease
Sialuria or French Type SialuriaDisease
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseDisease
Sialuria or French Type SialuriaDisease
Heroin Action PathwayDrug action
Primary hyperoxaluria II, PH2Disease
Heroin Metabolism PathwayDrug metabolism
Amino Sugar MetabolismMetabolic
Aspartate MetabolismMetabolic
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)Disease
Tay-Sachs DiseaseDisease
HypoacetylaspartiaDisease
Pyruvate Dehydrogenase Complex DeficiencyDisease
Salla Disease/Infantile Sialic Acid Storage DiseaseDisease
Disulfiram Action PathwayDrug action
Ethanol DegradationMetabolic
Fatty Acid BiosynthesisMetabolic
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
  1. eMedicine [Link]
External Links
Human Metabolome Database
HMDB00042
KEGG Drug
D00010
KEGG Compound
C00033
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 acidG01AD02 — Acetic acid
AHFS Codes
  • 40:04.00 — Acidifying Agents
  • 40:34.00* — Hemodialysis Solution
  • 52:04.92 — Miscellaneous Anti-infectives
PDB Entries
1a3i / 1a7p / 1aa5 / 1at5 / 1bdw / 1be0 / 1bez / 1bkv / 1c0n / 1cag
show 775 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingDiagnosticGastric Intestinal Metaplasia1
Not AvailableActive Not RecruitingPreventionCervical Cancers1
Not AvailableEnrolling by InvitationBasic ScienceBrain Function / Cerebral Blood Flow / Gut Microbiome / Metabolism1
Not AvailableRecruitingDiagnosticCervical Cancers1
Not AvailableRecruitingDiagnosticEsophagus, Barrett1
Not AvailableUnknown StatusDiagnosticColon Nos Polypectomy Tubular Adenoma / Colorectal Cancers / Serrated Adenomas1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
IrrigantIrrigation.25 g/100mL
IrrigantIrrigation250 mg/100mL
SolutionAuricular (otic).02 mg/mL
SolutionAuricular (otic)20 mg/mL
SolutionAuricular (otic)25 mg/mL
LiquidHemodialysis
Solution / dropsAuricular (otic)2 mg/mL
JellyVaginal
SolutionHemodialysis
GelTopical
SolutionAuricular (otic)20.65 mg/mL
SolutionAuricular (otic)
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)16.6 °CPhysProp
boiling point (°C)117.9 °CPhysProp
water solubility1E+006 mg/L (at 25 °C)MERCK INDEX (1996)
logP-0.17HANSCH,C ET AL. (1995)
logS1.22ADME Research, USCD
pKa4.76 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility323.0 mg/mLALOGPS
logP-0.12ALOGPS
logP-0.22ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)4.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity12.64 m3·mol-1ChemAxon
Polarizability5.34 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9502
Blood Brain Barrier+0.9742
Caco-2 permeable+0.5968
P-glycoprotein substrateNon-substrate0.8714
P-glycoprotein inhibitor INon-inhibitor0.99
P-glycoprotein inhibitor IINon-inhibitor0.992
Renal organic cation transporterNon-inhibitor0.9466
CYP450 2C9 substrateNon-substrate0.7913
CYP450 2D6 substrateNon-substrate0.9384
CYP450 3A4 substrateNon-substrate0.7921
CYP450 1A2 substrateNon-inhibitor0.8774
CYP450 2C9 inhibitorNon-inhibitor0.9482
CYP450 2D6 inhibitorNon-inhibitor0.9667
CYP450 2C19 inhibitorNon-inhibitor0.9786
CYP450 3A4 inhibitorNon-inhibitor0.9854
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9818
Ames testNon AMES toxic0.9635
CarcinogenicityCarcinogens 0.6222
BiodegradationReady biodegradable0.9758
Rat acute toxicity1.6315 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9666
hERG inhibition (predictor II)Non-inhibitor0.9889
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0007-9000000000-a9a21f72ec25efbc1650
Mass Spectrum (Electron Ionization)MSsplash10-01oy-9000000000-181ada67a3e5798d4419
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-03di-9000000000-044b361cb9f5775c43fe
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-01ox-9000000000-6437eb5f6a38c054dc37
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-0505dfa8ee07a18a3ef3
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0007-9000000000-a0d65dd4e056c1482aaa
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0a4i-9000000000-a845ea0157abb3d7783b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0a4i-9000000000-42ec023f024176a1c692
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a4i-9000000000-2bbab52cd9d076b89b2c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4i-9000000000-fb6d2f6298dd5bc37c2e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4i-9000000000-bc47c47ade16451259c7
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
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-a845ea0157abb3d7783b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-42ec023f024176a1c692
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-2bbab52cd9d076b89b2c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-fb6d2f6298dd5bc37c2e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-bc47c47ade16451259c7
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot 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

Kind
Protein
Organism
Human
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
  1. 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]
  2. 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]
Kind
Protein
Organism
Human
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
  1. 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 October 21, 2017 09:34