Tannic acid

Identification

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Name
Tannic acid
Accession Number
DB09372
Type
Small Molecule
Groups
Approved
Description

Tannic acid is a polyphenolic compound. It is a type of the commercially available tannins. It acts as a weak acid. Tannic acid is found in the nutgalls formed by insects on twigs of certain oak trees (Quercus infectoria and other Quercus species). It is removed and used as medicine. In the old days it was used as antidote against different poisons. Nowadays, tannic acid is applied topically for the treatment of cold sores, diaper rash, fever blisters and poison ivy. Tannic acid is also taken by mouth and applied directly for bleeding, chronic diarrhea, dysentery, bloody urine, painful joints, persistent coughs, and cancer.

Structure
Thumb
Synonyms
  • ácido tánico
  • Gallotannic acid
  • Gallotannin
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Zilactin Medicated Gel 7%Gel7 %TopicalZila, Inc.1991-12-311996-09-09Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
4JointzTannic acid (5 g/100g) + Allantoin (0.025 g/100g) + Eucalyptus oil (4 g/100g)CreamTopicalArp(usa) Pty Ltd2017-01-312018-04-05Us
Blood Stop LiqTannic acid (62.2 mg) + Potassium alum (62.2 mg)LiquidTopicalLaboratoire Romilo1979-12-311999-08-18Canada
Extrait De FraisesTannic acid (1.3 g) + Strawberry (2.5 ml)LiquidOralProduits Marc O (1987) Inc., Division Of Technilab Inc.1980-04-022000-08-24Canada
Germa TanTannic acid (.4 %) + Triclosan (.01 %)AerosolTopicalMueller Sports Medicine, Inc.1970-12-312002-07-15Canada
NitrotanTannic acid (0.015 g/1g) + Benzyl alcohol (0.061 g/1g) + Isopropyl alcohol (0.62 g/1g) + Picric acid (0.002 g/1g)Aerosol, sprayTopicalCramer Products, Inc1992-07-15Not applicableUs
Opium Camphre Tanin TabTannic acid (120 mg) + Camphor (60 mg) + Opium (15 mg)TabletOralRougier Pharma Division Of Ratiopharm Inc1951-12-311999-09-27Canada
Outgro LiquidTannic acid (23.5 %) + Chlorobutanol (4.7 %)LiquidTopicalWhitehall Robins Inc.1993-12-311997-08-07Canada
Tanac LiquidTannic acid (6 %) + Benzalkonium chloride (0.12 %) + Benzocaine (10 %)LiquidTopicalInsight Pharmaceuticals2004-04-052015-06-24Canada
Tanac LiquidTannic acid (6 %) + Benzalkonium chloride (0.125 %) + Benzocaine (8 %)LiquidTopicalDel Pharmaceuticals Inc.1983-12-312004-04-05Canada
Categories
UNII
28F9E0DJY6
CAS number
1401-55-4
Weight
Average: 1701.206
Monoisotopic: 1700.172974194
Chemical Formula
C76H52O46
InChI Key
LRBQNJMCXXYXIU-YIILYMKVSA-N
InChI
InChI=1S/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64+,65-,76?/m1/s1
IUPAC Name
(2R,3R,4S,5R)-4,5,6-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-2-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-3-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate
SMILES
OC1=CC(=CC(O)=C1O)C(=O)OC1=C(O)C(O)=CC(=C1)C(=O)OC[C@H]1OC(OC(=O)C2=CC(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C(O)C(O)=C2)[C@@H](OC(=O)C2=CC(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C(O)C(O)=C2)[C@@H]1OC(=O)C1=CC(OC(=O)C2=CC(O)=C(O)C(O)=C2)=C(O)C(O)=C1

Pharmacology

Indication

Tannic acid is indicated for cold sores, fever blisters, diaper rash, minor burn or sunburn and prickly heat. Vaginally, tannic acid is used as a douche for leukorrhea. It has been also indicated for sore throat, inflamed tonsils, spongy or receding gums, and acute dermatitis.

Pharmacodynamics
Not Available
Mechanism of action

Pharmaceutical grade tannic acid is generally considered to be pentadigalloylglucose. It has an astringent effect. When used internally, it dehydrates tissues when cause reduction in secretions. Externally, it works through formation of protective layer of harder and constricted cells. Tannic acid is thought to exert antiviral and antibacterial effects.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

After ingestion it has poor bioavailability, due to large size, high affinity to bound to plasma proteins and low lipid solubility. Its main actions are due to local effects.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Orally administered Tannic acid is hydrolysable tannin which releases gallic acid and other compounds upon decomposition.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

LD50 is 2.26 g/Kg in rats.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. article [Link]
  2. Book [Link]
  3. database [Link]
External Links
PubChem Substance
347910448
ChemSpider
17288010
ChEBI
75211
Wikipedia
Tannic_acid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAbdominal Pain (AP) / Gastro-esophageal Reflux Disease (GERD) / Indigestion / Intestinal Malabsorption1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamTopical
LiquidOral
AerosolTopical
Aerosol, sprayTopical
TabletOral
LiquidTopical
GelTopical7 %
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.407 mg/mLALOGPS
logP4.73ALOGPS
logP13.51ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.61ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count36ChemAxon
Hydrogen Donor Count25ChemAxon
Polar Surface Area777.98 Å2ChemAxon
Rotatable Bond Count31ChemAxon
Refractivity393.57 m3·mol-1ChemAxon
Polarizability152.88 Å3ChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Drug created on November 30, 2015 12:10 / Updated on June 04, 2019 07:12