Acetic acid

Identification

Summary

Acetic acid is an antimicrobial agent used to treat susceptible infections of the external auditory canal.

Brand Names
Fem Ph, Naturalyte, Relagard, Selectbag One
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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute otitis externa••••••••••••
Used in combination to treatExternal ear infection nosCombination Product in combination with: Hydrocortisone (DB00741)••••••••••••
Used in combination to treatExternal ear infection nosCombination Product in combination with: Acetic acid (DB03166), Aluminum acetate (DB14518), Aluminium (DB01370)••••••••••••
Prophylaxis ofInfections••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

Pathways
PathwayCategory
Aspartate MetabolismMetabolic
Canavan DiseaseDisease
HypoacetylaspartiaDisease
Amino Sugar MetabolismMetabolic
Ethanol DegradationMetabolic
G(M2)-Gangliosidosis: Variant B, Tay-Sachs DiseaseDisease
Pyruvate Kinase DeficiencyDisease
Heroin Metabolism PathwayDrug metabolism
Pyruvate MetabolismMetabolic
Leigh SyndromeDisease
Pyruvate Dehydrogenase Complex DeficiencyDisease
Sialuria or French Type SialuriaDisease
Sialuria or French Type SialuriaDisease
Salla Disease/Infantile Sialic Acid Storage DiseaseDisease
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)Disease
Tay-Sachs DiseaseDisease
Heroin Action PathwayDrug action
Disulfiram Action PathwayDrug action
Fatty Acid BiosynthesisMetabolic
Primary Hyperoxaluria II, PH2Disease
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.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Acetic acid is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Acetic acid.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Benzocaine.
Food Interactions
No interactions found.

Products

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International/Other Brands
Acetasol / Orlex / Volsol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Acetic AcidSolution20.65 mg/1mLAuricular (otic)A S Medication Solutions2010-01-22Not applicableUS flag
Acetic AcidIrrigant250 mg/100mLIrrigationHospira, Inc.1980-01-012022-05-01US flag
Acetic AcidIrrigant250 mg/100mLIrrigationBaxter Healthcare Corporation1982-02-19Not applicableUS flag
Acetic AcidIrrigant250 mg/100mLIrrigationIcu Medical Inc.2019-11-25Not applicableUS flag
Acetic AcidSolution20.65 mg/1mLAuricular (otic)Rebel Distributors2010-01-22Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Acetic AcidSolution0.02 mg/1mLAuricular (otic)Qualitest2005-02-242017-05-31US flag
Acetic AcidSolution20.65 mg/1mLAuricular (otic)Nucare Pharmaceuticals,inc.2020-06-05Not applicableUS flag
Acetic AcidSolution20.65 mg/1mLAuricular (otic)Trupharma, Llc2020-06-05Not applicableUS flag
Acetic AcidSolution / drops2 mg/1mLAuricular (otic)Bauch & Lomb Incorporated1994-02-252017-09-01US flag
Acetic AcidSolution0.02 mg/1mLAuricular (otic)A-S Medication Solutions2005-02-242017-05-31US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
New CleanFlexLiquid1.5 g/100mLTopicalD.O Bio2021-12-24Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Acetasol HCAcetic acid (2.41 g/100mL) + Hydrocortisone (1.1 g/100mL)SolutionAuricular (otic)Physicians Total Care, Inc.1994-12-152012-06-30US flag
Acetasol HCAcetic acid (2.41 g/100mL) + Hydrocortisone (1.1 g/100mL)SolutionAuricular (otic)Actavis Pharma, Inc.2002-09-102017-05-31US flag
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)LiquidHemodialysisGenpharm Ulc1997-05-212004-07-30Canada flag
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)LiquidHemodialysisGenpharm Ulc1987-12-312001-08-03Canada flag
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)LiquidHemodialysisGenpharm Ulc1988-12-312004-07-30Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Fem pHAcetic acid (0.009 g/1g) + Oxyquinoline sulfate (0.00025 g/1g)JellyVaginalPharmics, Inc.1999-07-15Not applicableUS flag
New CleanFlexAcetic acid (1.5 g/100mL)LiquidTopicalD.O Bio2021-12-24Not applicableUS flag
Otic EdgeAcetic acid (100 ug/1mL) + Antipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)River's Edge Pharmaceuticals, LLC2008-09-012012-09-30US flag
RelegardAcetic acid (0.9 mg/1mL) + Oxyquinoline (0.025 mg/1mL)GelTopicalBlansett Pharmacal Co2017-03-20Not applicableUS flag
Treagan OticAcetic acid (0.1 mg/1mL) + Antipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionTopicalTrigen Laboratories, Inc.2009-09-012010-11-30US flag

Categories

ATC Codes
S02AA10 — Acetic acidG01AD02 — Acetic acid
Drug Categories
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
  1. eMedicine [Link]
Human Metabolome Database
HMDB0000042
KEGG Drug
D00010
KEGG Compound
C00033
PubChem Compound
176
PubChem Substance
46506148
ChemSpider
171
BindingDB
50074329
RxNav
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 928 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3TerminatedDiagnosticBarrett's Esophagus1
2, 3WithdrawnTreatmentCIN1 / Trichloroacetic Acid1
1RecruitingTreatmentAnatomic Stage IV Breast Cancer AJCC v8 / HER2-Positive Breast Carcinoma / Metastatic Breast Carcinoma / Refractory Breast Carcinoma1
1Unknown StatusDiagnosticGastric Intestinal Metaplasia1
0CompletedDiagnosticCervical Cancer1

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
FormRouteStrength
IrrigantIrrigation0.25 g/100mL
IrrigantIrrigation250 mg/100mL
SolutionAuricular (otic)0.02 mg/1mL
SolutionAuricular (otic)0.02 mL/1mL
SolutionAuricular (otic)20 mg/1mL
SolutionAuricular (otic)20.65 mg/1mL
Solution / dropsAuricular (otic)2 mg/1mL
SolutionIntravenous
Injection, solutionIntravenous
InjectionIntravenous0.52 g/l
SolutionTopical; Vaginal0.077 g
SolutionTopical250 mg
JellyVaginal
SolutionIrrigation; Parenteral
SolutionHemodialysis
SolutionHemodialysis7.77 g/l
SolutionHemodialysis8.46 g/l
SolutionHemodialysis8.8 g/l
SolutionHemodialysis8.85 g/l
LiquidHemodialysis
SolutionHemodialysis6.77 g/l
GelCutaneous; Infiltration
InjectionIntravenous0.37 g/l
LiquidTopical1.5 g/100mL
SolutionAuricular (otic)
SolutionCutaneous
GelTopical
SolutionTopical
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-MSsplash10-03dl-9000000000-b96ad978047d68715939
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-cbb8e3580bb4dd92a3e5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-e43947f7b54b268fba7e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-18065da3ebdf0e5441b3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-7b02e00786b8485297a9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-c91e61311a9a5c8fcdbd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-005ecd90225a48a31330
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-cbb8e3580bb4dd92a3e5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-e43947f7b54b268fba7e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-18065da3ebdf0e5441b3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-7b02e00786b8485297a9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-005ecd90225a48a31330
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-c91e61311a9a5c8fcdbd
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
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-95.163922
predicted
DarkChem Lite v0.1.0
[M-H]-95.172722
predicted
DarkChem Lite v0.1.0
[M-H]-122.62053
predicted
DeepCCS 1.0 (2019)
[M-H]-95.163922
predicted
DarkChem Lite v0.1.0
[M-H]-95.172722
predicted
DarkChem Lite v0.1.0
[M-H]-122.62053
predicted
DeepCCS 1.0 (2019)
[M+H]+124.71846
predicted
DeepCCS 1.0 (2019)
[M+H]+124.71846
predicted
DeepCCS 1.0 (2019)
[M+Na]+133.18752
predicted
DeepCCS 1.0 (2019)
[M+Na]+133.18752
predicted
DeepCCS 1.0 (2019)

Transporters

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
  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. [Article]
  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. [Article]
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
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51