Identification

Name
Meclofenamic acid
Accession Number
DB00939  (APRD01090)
Type
Small Molecule
Groups
Approved, Vet approved
Description

A non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis. [PubChem]

Structure
Thumb
Synonyms
  • Acide meclofenamique
  • Acido meclofenamico
  • Acidum meclofenamicum
  • Meclofenamate
  • Meclofenamic acid
  • N-(2,6-Dichloro-3-methylphenyl)anthranilic acid
  • N-(2,6-Dichloro-m-tolyl)anthranilic acid
  • N-(3-Methyl-2,6-dichlorophenyl)anthranilic acid
External IDs
CI 583 / CI-583 / Cl 583 / INF 4668 / INF-4668
Product Ingredients
IngredientUNIICASInChI Key
Meclofenamate sodium94NJ818U2W67254-91-5QHJLLDJTVQAFAN-UHFFFAOYSA-M
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Meclofenamate SodiumCapsule50 mg/1OralPhysicians Total Care, Inc.1986-09-032002-06-30Us
Meclofenamate SodiumCapsule100 mg/1OralMylan Pharmaceuticals Inc.1986-09-03Not applicableUs
Meclofenamate SodiumCapsule50 mg/1OralMylan Pharmaceuticals Inc.1986-09-03Not applicableUs
International/Other Brands
Ethos (Yung Shin) / Eucome (U-Liang) / Meclomen (Pfizer)
Categories
UNII
48I5LU4ZWD
CAS number
644-62-2
Weight
Average: 296.149
Monoisotopic: 295.016684015
Chemical Formula
C14H11Cl2NO2
InChI Key
SBDNJUWAMKYJOX-UHFFFAOYSA-N
InChI
InChI=1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19)
IUPAC Name
2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid
SMILES
CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1

Pharmacology

Indication

For the relief of mild to moderate pain, for the treatment of primary dysmenorrhea and for the treatment of idiopathic heavy menstrual blood loss. Also for relief of the signs and symptoms of acute and chronic rheumatoid arthritis and osteoarthritis.

Associated Conditions
Pharmacodynamics

Meclofenamic acid is a nonsteroidal agent which has demonstrated anti-inflammatory, analgesic, and antipyretic activity in laboratory animals.

Mechanism of action

The mode of action, like that of other nonsteroidal anti-inflammatory agents, is not known. Therapeutic action does not result from pituitary-adrenal stimulation. In animal studies, meclofenamic acid was found to inhibit prostaglandin synthesis and to compete for binding at the prostaglandin receptor site. In vitro meclofenamic acid was found to be an inhibitor of human leukocyte 5-lipoxygenase activity. These properties may be responsible for the anti-inflammatory action of meclofenamic acid. There is no evidence that meclofenamic acid alters the course of the underlying disease.

TargetActionsOrganism
AProstaglandin G/H synthase 1
inhibitor
Human
AProstaglandin G/H synthase 2
inhibitor
Human
AArachidonate 5-lipoxygenase
inhibitor
Human
UPotassium voltage-gated channel subfamily KQT member 2
other
Human
UPotassium voltage-gated channel subfamily KQT member 3
other
Human
Absorption

Rapidly absorbed in man following single and multiple oral doses with peak plasma concentrations occurring in 0.5 to 2 hours. The concomitant administration of antacids (aluminum and magnesium hydroxides) does not interfere with absorption of meclofenamic acid. Unlike most NSAIDs, which when administered with food have a decrease in rate but not in extent of absorption, meclofenamic acid is decreased in both. It has been reported that following the administration of meclofenamic acid capsules one-half hour after a meal, the average extent of bioavailability decreased by 26%, the average peak concentration (Cmax) decreased fourfold and the time to Cmax was delayed by 3 hours.

Volume of distribution
  • 9.1 to 43.2 L
Protein binding

Greater than 99% bound to plasma proteins over a wide drug concentration range.

Metabolism

Hepatic. Meclofenamic acid is extensively metabolized to an active metabolite (Metabolite I; 3-hydroxymethyl metabolite of meclofenamic acid) and at least six other less well characterized minor metabolites. Only Metabolite I has been shown in vitro to inhibit cyclooxygenase activity with approximately one fifth the activity of meclofenamic acid.

Route of elimination

Other metabolites, whose excretion rates are unknown, account for the remaining 35% to 62% of the dose excreted in the urine. The remainder of the administered dose (approximately 30%) is eliminated in the feces (apparently through biliary excretion). Trace amounts of meclofenamate sodium are excreted in human breast milk.

Half life

In a study in 10 healthy subjects following a single oral dose the apparent elimination half-life ranged from 0.8 to 5.3 hours. Metabolite I (3-hydroxymethyl metabolite of meclofenamic acid) has a mean half-life of approximately 15 hours.

Clearance
  • Oral cl=206 mL/min
Toxicity

After a massive overdose, CNS stimulation may be manifested by irrational behavior, marked agitation and generalized seizures. Following this phase, renal toxicity (falling urine output, rising creatinine, abnormal urinary cellular elements) may be noted with possible oliguria or anuria and azotemia. A 24 year-old male was anuric for approximately one week after ingesting an overdose of 6 to 7 grams of meclofenamate sodium. Spontaneous diuresis and recovery subsequently occurred.

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

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Meclofenamic acid is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Meclofenamic acid is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Meclofenamic acid is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Meclofenamic acid is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when Meclofenamic acid is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Meclofenamic acid is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of hypertension can be increased when Meclofenamic acid is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when Meclofenamic acid is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Meclofenamic acid is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when Meclofenamic acid is combined with 4-Methoxyamphetamine.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,313,848.

General References
Not Available
External Links
Human Metabolome Database
HMDB0015074
KEGG Drug
D02341
KEGG Compound
C07117
PubChem Compound
4037
PubChem Substance
46507887
ChemSpider
3897
BindingDB
22971
ChEBI
6710
ChEMBL
CHEMBL509
Therapeutic Targets Database
DNC000919
PharmGKB
PA450341
HET
JMS
RxList
RxList Drug Page
Wikipedia
Meclofenamic_acid
ATC Codes
M01AG04 — Meclofenamic acidM02AA18 — Meclofenamic acid
PDB Entries
3r6i / 4n6p / 4qkn / 5ikq
MSDS
Download (74.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Enrolling by InvitationTreatmentBipolar Disorder (BD) / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders1
Not AvailableActive Not RecruitingTreatmentProgressive Brain Metastases / Recurrent Brain Metastases1

Pharmacoeconomics

Manufacturers
  • Quantum pharmics ltd
  • American therapeutics inc
  • Barr laboratories inc
  • Mylan pharmaceuticals inc
  • Par pharmaceutical inc
  • Sandoz inc
  • Usl pharma inc
  • Vitarine pharmaceuticals inc
  • Watson laboratories inc
  • Parke davis div warner lambert co
Packagers
  • Dispensing Solutions
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Sandhills Packaging Inc.
Dosage forms
FormRouteStrength
CapsuleOral100 mg/1
CapsuleOral50 mg/1
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)248-250U.S. Patent 3,313,848.
water solubility30 mg/LMERCK INDEX (1996)
logP5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00366 mg/mLALOGPS
logP5.11ALOGPS
logP6.09ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)3.79ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity76.45 m3·mol-1ChemAxon
Polarizability28.44 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9393
Blood Brain Barrier+0.8668
Caco-2 permeable+0.8398
P-glycoprotein substrateNon-substrate0.806
P-glycoprotein inhibitor INon-inhibitor0.8943
P-glycoprotein inhibitor IINon-inhibitor0.9474
Renal organic cation transporterNon-inhibitor0.9094
CYP450 2C9 substrateNon-substrate0.6402
CYP450 2D6 substrateNon-substrate0.9164
CYP450 3A4 substrateNon-substrate0.6566
CYP450 1A2 substrateInhibitor0.9236
CYP450 2C9 inhibitorInhibitor0.9106
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.8271
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.558
Ames testNon AMES toxic0.8633
CarcinogenicityNon-carcinogens0.5329
BiodegradationNot ready biodegradable0.9709
Rat acute toxicity3.0345 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9502
hERG inhibition (predictor II)Non-inhibitor0.872
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
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-QFT , negativeLC-MS/MSsplash10-0006-0090000000-dc6d0aaa7ee199899830
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-052f-0090000000-4f2a28033e59bab0257a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0190000000-b6abcaff657bfa67b599
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03fr-0690000000-eccbe792d08156c89c39
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0920000000-fdcf8eff9ac77cf86d5b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-77140947d50a131a9be6
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-5d2a4942eea2a2d2f252
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0090000000-85032b374ac40bac481a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004l-0090000000-a2cbafbde1150bf5812e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0090000000-47d80abc4f95a2c5ef4c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0090000000-cfa40a800c6a52f6a264
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0290000000-2e34cb2892f6263b39fa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0563-0980000000-54fb4017b6a67acb639b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0910000000-26fefd3e49fc0ba3e36e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fb9-1900000000-448908b1e79c92a656d7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fb9-2900000000-71b13766bf05541800b4

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Aminobenzoic acids
Alternative Parents
Benzoic acids / Aminotoluenes / Aniline and substituted anilines / Dichlorobenzenes / Benzoyl derivatives / Aryl chlorides / Vinylogous amides / Amino acids / Secondary amines / Monocarboxylic acids and derivatives
show 6 more
Substituents
Aminobenzoic acid / Benzoic acid / Benzoyl / 1,3-dichlorobenzene / Aniline or substituted anilines / Aminotoluene / Toluene / Chlorobenzene / Halobenzene / Aryl chloride
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organochlorine compound, secondary amino compound, aminobenzoic acid (CHEBI:6710)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Perez-Vizcaino F, Lopez-Lopez JG, Santiago R, Cogolludo A, Zaragoza-Arnaez F, Moreno L, Alonso MJ, Salaices M, Tamargo J: Postnatal maturation in nitric oxide-induced pulmonary artery relaxation involving cyclooxygenase-1 activity. Am J Physiol Lung Cell Mol Physiol. 2002 Oct;283(4):L839-48. [PubMed:12225961]
  2. Shiels IA, Whitehouse MW: Lyprinol: anti-inflammatory and uterine-relaxant activities in rats, with special reference to a model for dysmenorrhoea. Allerg Immunol (Paris). 2000 Sep;32(7):279-83. [PubMed:11094641]
  3. Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222]
  4. Kalgutkar AS, Crews BC, Rowlinson SW, Marnett AB, Kozak KR, Remmel RP, Marnett LJ: Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. Proc Natl Acad Sci U S A. 2000 Jan 18;97(2):925-30. [PubMed:10639181]
  5. Meade EA, Smith WL, DeWitt DL: Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1993 Mar 25;268(9):6610-4. [PubMed:8454631]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Kalgutkar AS, Crews BC, Rowlinson SW, Marnett AB, Kozak KR, Remmel RP, Marnett LJ: Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. Proc Natl Acad Sci U S A. 2000 Jan 18;97(2):925-30. [PubMed:10639181]
  2. Traupe T, Lang M, Goettsch W, Munter K, Morawietz H, Vetter W, Barton M: Obesity increases prostanoid-mediated vasoconstriction and vascular thromboxane receptor gene expression. J Hypertens. 2002 Nov;20(11):2239-45. [PubMed:12409963]
  3. Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222]
  4. Narsinghani T, Chaturvedi SC: QSAR analysis of meclofenamic acid analogues as selective COX-2 inhibitors. Bioorg Med Chem Lett. 2006 Jan 15;16(2):461-8. Epub 2005 Nov 14. [PubMed:16290292]
  5. Smith WL, Meade EA, DeWitt DL: Interactions of PGH synthase isozymes-1 and -2 with NSAIDs. Ann N Y Acad Sci. 1994 Nov 15;744:50-7. [PubMed:7825862]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Iron ion binding
Specific Function
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name
ALOX5
Uniprot ID
P09917
Uniprot Name
Arachidonate 5-lipoxygenase
Molecular Weight
77982.595 Da
References
  1. Yu XY, Hubbard W, Spannhake EW: Inhibition of canine tracheal smooth muscle by mediators from cultured bronchial epithelial cells. Am J Physiol. 1992 Feb;262(2 Pt 1):L229-34. [PubMed:1539679]
  2. Boctor AM, Eickholt M, Pugsley TA: Meclofenamate sodium is an inhibitor of both the 5-lipoxygenase and cyclooxygenase pathways of the arachidonic acid cascade in vitro. Prostaglandins Leukot Med. 1986 Aug;23(2-3):229-38. [PubMed:3020588]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Other
General Function
Voltage-gated potassium channel activity
Specific Function
Probably important in the regulation of neuronal excitability. Associates with KCNQ3 to form a potassium channel with essentially identical properties to the channel underlying the native M-current...
Gene Name
KCNQ2
Uniprot ID
O43526
Uniprot Name
Potassium voltage-gated channel subfamily KQT member 2
Molecular Weight
95846.575 Da
References
  1. Peretz A, Degani N, Nachman R, Uziyel Y, Gibor G, Shabat D, Attali B: Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties. Mol Pharmacol. 2005 Apr;67(4):1053-66. Epub 2004 Dec 14. [PubMed:15598972]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Other
General Function
Voltage-gated potassium channel activity
Specific Function
Probably important in the regulation of neuronal excitability. Associates with KCNQ2 or KCNQ5 to form a potassium channel with essentially identical properties to the channel underlying the native ...
Gene Name
KCNQ3
Uniprot ID
O43525
Uniprot Name
Potassium voltage-gated channel subfamily KQT member 3
Molecular Weight
96741.515 Da
References
  1. Peretz A, Degani N, Nachman R, Uziyel Y, Gibor G, Shabat D, Attali B: Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties. Mol Pharmacol. 2005 Apr;67(4):1053-66. Epub 2004 Dec 14. [PubMed:15598972]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Thyroid hormone transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-gluc...
Gene Name
SLCO1C1
Uniprot ID
Q9NYB5
Uniprot Name
Solute carrier organic anion transporter family member 1C1
Molecular Weight
78695.625 Da
References
  1. Westholm DE, Stenehjem DD, Rumbley JN, Drewes LR, Anderson GW: Competitive inhibition of organic anion transporting polypeptide 1c1-mediated thyroxine transport by the fenamate class of nonsteroidal antiinflammatory drugs. Endocrinology. 2009 Feb;150(2):1025-32. doi: 10.1210/en.2008-0188. Epub 2008 Oct 9. [PubMed:18845642]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 16, 2018 06:44