Identification

Name
Gliclazide
Accession Number
DB01120
Description

Gliclazide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It has been classified differently according to its drug properties in which based on its chemical structure, gliclazide is considered a first-generation sulfonylurea due to the structural presence of a sulfonamide group able to release a proton and the presence of one aromatic group.1 On the other hand, based on the pharmacological efficacy, gliclazide is considered a second-generation sulfonylurea which presents a higher potency and a shorter half-life.2,3 Gliclazide belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Gliclazide has been shown to decrease fasting plasma glucose, postprandial blood glucose and glycosolated hemoglobin (HbA1c) levels (reflective of the last 8-10 weeks of glucose control). Gliclazide is extensively metabolized by the liver; its metabolites are excreted in both urine (60-70%) and feces (10-20%).

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 323.41
Monoisotopic: 323.130362722
Chemical Formula
C15H21N3O3S
Synonyms
  • 1-(3-azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)urea
  • 1-(hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)urea
  • Gliclazida
  • Gliclazide
  • Gliclazidum
External IDs
  • J3.151H
  • S-1702
  • S-852
  • SE 1702
  • SE-1702

Pharmacology

Indication

For the treatment of NIDDM in conjunction with diet and exercise.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Based on the pharmacological properties, gliclazide is a second generation sulphonylurea which acts as a hypoglycemic agent. It stimulates β cells of the islet of Langerhans in the pancreas to release insulin. It also enhances peripheral insulin sensitivity. Overall, it potentiates insulin release and improves insulin dynamics.

Mechanism of action

Gliclazide binds to the β cell sulfonyl urea receptor (SUR1). This binding subsequently blocks the ATP sensitive potassium channels. The binding results in closure of the channels and leads to a resulting decrease in potassium efflux leads to depolarization of the β cells. This opens voltage-dependent calcium channels in the β cell resulting in calmodulin activation, which in turn leads to exocytosis of insulin containing secretorty granules.

TargetActionsOrganism
AATP-binding cassette sub-family C member 8
binder
Humans
UVascular endothelial growth factor A
other/unknown
Humans
Absorption

Rapidly and well absorbed but may have wide inter- and intra-individual variability. Peak plasma concentrations occur within 4-6 hours of oral administration.

Volume of distribution
Not Available
Protein binding

94%, highly bound to plasma proteins

Metabolism

Extensively metabolized in the liver. Less than 1% of the orally administered dose appears unchanged in the urine. Metabolites include oxidized and hydroxylated derivates, as well as glucuronic acid conjugates.

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Route of elimination

Metabolites and conjugates are eliminated primarily by the kidneys (60-70%) and also in the feces (10-20%).

Half-life

10.4 hours. Duration of action is 10-24 hours.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

LD50=3000 mg/kg (orally in mice). Gliclazide and its metabolites may accumulate in those with severe hepatic and/or renal dysfunction. Symptoms of hypoglycemia include: dizziness, lack of energy, drowsiness, headache and sweating.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Gliclazide Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYP2C19*2(A;A) / (A;G)681G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with reduction in gliclazide metabolism.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with reduction in gliclazide metabolism.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer.Details

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
AbaloparatideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Abaloparatide.
AbataceptThe metabolism of Gliclazide can be increased when combined with Abatacept.
AbirateroneThe metabolism of Gliclazide can be decreased when combined with Abiraterone.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Gliclazide.
AcebutololThe therapeutic efficacy of Gliclazide can be increased when used in combination with Acebutolol.
AceclofenacThe protein binding of Gliclazide can be decreased when combined with Aceclofenac.
AcemetacinThe protein binding of Gliclazide can be decreased when combined with Acemetacin.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Gliclazide.
AcetazolamideThe therapeutic efficacy of Gliclazide can be increased when used in combination with Acetazolamide.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Gliclazide.
Additional Data Available
  • Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
  • Avoid alcohol.
  • Take with or without food. Consistent food intake reduces the risk of hypoglycemia.

Products

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International/Other Brands
Glimicron / Nordialex
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DiamicronTabletOralServier1990-12-31Not applicableCanada flag
Diamicron MrTablet, extended releaseOralServier2010-12-09Not applicableCanada flag
Diamicron MrTablet, extended releaseOralServier2001-04-04Not applicableCanada flag
GlicTabletOralPrempharm Inc2003-10-022005-08-05Canada flag
GliclazideTabletOralSanis Health Inc2010-02-25Not applicableCanada flag
Gliclazide -tab 80mgTabletOralProval Pharma Division Of Servier Canada Inc1997-08-132012-02-13Canada flag
Gliclazide-80TabletOralPro Doc Limitee2003-12-10Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    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
    Available for Purchase

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

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-gliclazide MrTablet, extended releaseOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-gliclazide MrTablet, extended releaseOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-gliclazideTabletOralApotex Corporation2002-07-02Not applicableCanada flag
Apo-gliclazide MrTablet, extended releaseOralApotex Corporation2008-06-04Not applicableCanada flag
Apo-gliclazide MrTablet, extended releaseOralApotex Corporation2015-04-14Not applicableCanada flag
Ava-gliclazideTabletOralAvanstra Inc2011-08-112014-08-21Canada flag
Jamp Gliclazide-MRTablet, extended releaseOralJamp Pharma Corporation2015-03-31Not applicableCanada flag
Jamp Gliclazide-MRTablet, extended releaseOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Mint-gliclazide MrTablet, extended releaseOralMint Pharmaceuticals Inc2016-11-14Not applicableCanada flag
Mint-gliclazide MrTablet, extended releaseOralMint Pharmaceuticals Inc2014-06-02Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    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
    Available for Purchase

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Categories

ATC Codes
A10BB09 — Gliclazide
Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
G4PX8C4HKV
CAS number
21187-98-4
InChI Key
BOVGTQGAOIONJV-BETUJISGSA-N
InChI
InChI=1S/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)/t12-,13+
IUPAC Name
3-[(3aR,6aS)-octahydrocyclopenta[c]pyrrol-2-yl]-1-(4-methylbenzenesulfonyl)urea
SMILES
[H][[email protected]@]12CCC[[email protected]]1([H])CN(C2)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1

References

Synthesis Reference

U.S. Patent 3,501,495

General References
  1. Ballagi-Pordany G, Koszeghy A, Koltai MZ, Aranyi Z, Pogatsa G: Divergent cardiac effects of the first and second generation hypoglycemic sulfonylurea compounds. Diabetes Res Clin Pract. 1990 Jan;8(2):109-14. [PubMed:2106423]
  2. Scholar E. (2007). XPharm: The comprehensive Pharmacology Reference. Elsevier.
  3. Ghosh S. and Collier A. (2012). Churchill's pocketbook of diabetes (2nd ed.). Elsevier.
Human Metabolome Database
HMDB0015252
KEGG Drug
D01599
PubChem Compound
3475
PubChem Substance
46505475
ChemSpider
580820
BindingDB
50103512
RxNav
4816
ChEBI
31654
ChEMBL
CHEMBL427216
ZINC
ZINC000012461841
Therapeutic Targets Database
DAP000522
PharmGKB
PA10892
PDBe Ligand
GCZ
Wikipedia
Gliclazide
AHFS Codes
  • 68:20.20 — Sulfonylureas
PDB Entries
4zfc
MSDS
Download (57.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceType 2 Diabetes Mellitus1
4CompletedPreventionNephropathy, Diabetic / Type 2 Diabetes Mellitus1
4CompletedTreatmentDiabetes2
4CompletedTreatmentDiabetes / Type 2 Diabetes Mellitus2
4CompletedTreatmentMenopause / Osteopenia / Osteoporosis / Type 2 Diabetes Mellitus1
4CompletedTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD) / Type2 Diabetes1
4CompletedTreatmentType 2 Diabetes Mellitus9
4RecruitingTreatmentType 2 Diabetes Mellitus1
4RecruitingTreatmentType2 Diabetes1
4TerminatedTreatmentType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral80 MG
Tablet, extended releaseOral
Tablet, extended releaseOral60 mg
TabletOral0.08 G
Tablet, delayed releaseOral60 MG
TabletOral30 MG
TabletOral60 MG
Tablet, delayed releaseOral90 mg
Tablet, delayed releaseOral30 MG
TabletOral90 MG
Tablet, extended releaseOral30 mg
TabletOral
Prices
Unit descriptionCostUnit
Diamicron 80 mg Tablet0.42USD tablet
Apo-Gliclazide 80 mg Tablet0.23USD tablet
Gliclazide 80 mg Tablet0.23USD tablet
Mylan-Gliclazide 80 mg Tablet0.23USD tablet
Novo-Gliclazide 80 mg Tablet0.23USD tablet
Pms-Gliclazide 80 mg Tablet0.23USD tablet
Diamicron Mr 30 mg Sustained-Release Tablet0.16USD tablet
Apo-Gliclazide Mr 30 mg Sustained-Release Tablet0.15USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2273420No2002-07-092019-05-27Canada flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)180-182U.S. Patent 3,501,495
logP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 mg/mLALOGPS
logP1.52ALOGPS
logP1.73ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
pKa (Strongest Basic)1.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.51 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity83.88 m3·mol-1ChemAxon
Polarizability33.72 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.8445
Caco-2 permeable-0.6543
P-glycoprotein substrateSubstrate0.6982
P-glycoprotein inhibitor INon-inhibitor0.8619
P-glycoprotein inhibitor IINon-inhibitor0.931
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateSubstrate0.6226
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6925
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9218
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8751
Ames testNon AMES toxic0.8047
CarcinogenicityNon-carcinogens0.7944
BiodegradationNot ready biodegradable0.7997
Rat acute toxicity2.0016 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5992
hERG inhibition (predictor II)Non-inhibitor0.8064
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Binder
General Function
Sulfonylurea receptor activity
Specific Function
Subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release.
Gene Name
ABCC8
Uniprot ID
Q09428
Uniprot Name
ATP-binding cassette sub-family C member 8
Molecular Weight
176990.36 Da
References
  1. Gribble FM, Ashcroft FM: Sulfonylurea sensitivity of adenosine triphosphate-sensitive potassium channels from beta cells and extrapancreatic tissues. Metabolism. 2000 Oct;49(10 Suppl 2):3-6. [PubMed:11078468]
  2. Harrower A: Gliclazide modified release: from once-daily administration to 24-hour blood glucose control. Metabolism. 2000 Oct;49(10 Suppl 2):7-11. [PubMed:11078469]
  3. Lawrence CL, Proks P, Rodrigo GC, Jones P, Hayabuchi Y, Standen NB, Ashcroft FM: Gliclazide produces high-affinity block of KATP channels in mouse isolated pancreatic beta cells but not rat heart or arterial smooth muscle cells. Diabetologia. 2001 Aug;44(8):1019-25. [PubMed:11484080]
  4. Reimann F, Ashcroft FM, Gribble FM: Structural basis for the interference between nicorandil and sulfonylurea action. Diabetes. 2001 Oct;50(10):2253-9. [PubMed:11574406]
  5. Proks P, Reimann F, Green N, Gribble F, Ashcroft F: Sulfonylurea stimulation of insulin secretion. Diabetes. 2002 Dec;51 Suppl 3:S368-76. [PubMed:12475777]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Vascular endothelial growth factor receptor binding
Specific Function
Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of...
Gene Name
VEGFA
Uniprot ID
P15692
Uniprot Name
Vascular endothelial growth factor A
Molecular Weight
27042.205 Da
References
  1. Mamputu JC, Renier G: Advanced glycation end products increase, through a protein kinase C-dependent pathway, vascular endothelial growth factor expression in retinal endothelial cells. Inhibitory effect of gliclazide. J Diabetes Complications. 2002 Jul-Aug;16(4):284-93. [PubMed:12126787]
  2. Mamputu JC, Renier G: Signalling pathways involved in retinal endothelial cell proliferation induced by advanced glycation end products: inhibitory effect of gliclazide. Diabetes Obes Metab. 2004 Mar;6(2):95-103. [PubMed:14746574]
  3. Li L, Renier G: Activation of nicotinamide adenine dinucleotide phosphate (reduced form) oxidase by advanced glycation end products links oxidative stress to altered retinal vascular endothelial growth factor expression. Metabolism. 2006 Nov;55(11):1516-23. [PubMed:17046555]
  4. Kimura T, Takagi H, Suzuma K, Kita M, Watanabe D, Yoshimura N: Comparisons between the beneficial effects of different sulphonylurea treatments on ischemia-induced retinal neovascularization. Free Radic Biol Med. 2007 Aug 1;43(3):454-61. Epub 2007 May 3. [PubMed:17602961]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Yao Y, Han WW, Zhou YH, Li ZS, Li Q, Chen XY, Zhong DF: The metabolism of CYP2C9 and CYP2C19 for gliclazide by homology modeling and docking study. Eur J Med Chem. 2009 Feb;44(2):854-61. doi: 10.1016/j.ejmech.2008.04.015. Epub 2008 May 2. [PubMed:18541345]
  3. Elliot DJ, Suharjono, Lewis BC, Gillam EM, Birkett DJ, Gross AS, Miners JO: Identification of the human cytochromes P450 catalysing the rate-limiting pathways of gliclazide elimination. Br J Clin Pharmacol. 2007 Oct;64(4):450-7. Epub 2007 May 22. [PubMed:17517049]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Zhang Y, Si D, Chen X, Lin N, Guo Y, Zhou H, Zhong D: Influence of CYP2C9 and CYP2C19 genetic polymorphisms on pharmacokinetics of gliclazide MR in Chinese subjects. Br J Clin Pharmacol. 2007 Jul;64(1):67-74. Epub 2007 Feb 12. [PubMed:17298483]
  2. Yao Y, Han WW, Zhou YH, Li ZS, Li Q, Chen XY, Zhong DF: The metabolism of CYP2C9 and CYP2C19 for gliclazide by homology modeling and docking study. Eur J Med Chem. 2009 Feb;44(2):854-61. doi: 10.1016/j.ejmech.2008.04.015. Epub 2008 May 2. [PubMed:18541345]
  3. Elliot DJ, Suharjono, Lewis BC, Gillam EM, Birkett DJ, Gross AS, Miners JO: Identification of the human cytochromes P450 catalysing the rate-limiting pathways of gliclazide elimination. Br J Clin Pharmacol. 2007 Oct;64(4):450-7. Epub 2007 May 22. [PubMed:17517049]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Igaki A, Kobayashi K, Kimura M, Sakoguchi T, Matsuoka A: Influence of blood proteins on biomedical analysis. XII. Effects of glycation on gliclazide (oral hypoglycemic drug)-binding with serum albumin in diabetics. Chem Pharm Bull (Tokyo). 1992 Jan;40(1):255-7. [PubMed:1576681]
  2. Kobayashi K, Kimura M, Sakoguchi T, Hase A, Matsuoka A: Influence of blood proteins on biomedical analysis. V. Effect of ethyl alcohol on gliclazide-binding with bovine serum albumin. Chem Pharm Bull (Tokyo). 1982 Mar;30(3):1077-80. [PubMed:7094168]

Drug created on June 13, 2005 07:24 / Updated on November 23, 2020 09:08

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