Arachidonic Acid

Identification

Summary

Arachidonic Acid is a natural fatty acid that plays an essential role in physiological homeostases, such as repair and growth of cells.

Generic Name
Arachidonic Acid
DrugBank Accession Number
DB04557
Background

An unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. [PubChem]

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 304.4669
Monoisotopic: 304.240230268
Chemical Formula
C20H32O2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeroxisome proliferator-activated receptor alphaNot AvailableHumans
UBile acid receptor
ligand
Humans
URetinoic acid receptor RXR-alphaNot AvailableHumans
UProstaglandin G/H synthase 1Not AvailableHumans
U14 kDa fatty acid-binding proteinNot AvailableBlood fluke
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Piroxicam Action PathwayDrug action
Rofecoxib Action PathwayDrug action
Diclofenac Action PathwayDrug action
Sulindac Action PathwayDrug action
Nabumetone Action PathwayDrug action
Valdecoxib Action PathwayDrug action
Antipyrine Action PathwayDrug action
Flurbiprofen Action PathwayDrug action
Nepafenac Action PathwayDrug action
Etodolac Action PathwayDrug action
Ketoprofen Action PathwayDrug action
Ibuprofen Action PathwayDrug action
Celecoxib Action PathwayDrug action
Suprofen Action PathwayDrug action
Indomethacin Action PathwayDrug action
Diflunisal Action PathwayDrug action
Leukotriene C4 Synthesis DeficiencyDisease
Antrafenine Action PathwayDrug action
Fenoprofen Action PathwayDrug action
Magnesium Salicylate Action PathwayDrug action
Lornoxicam Action PathwayDrug action
Trisalicylate-Choline Action PathwayDrug action
Tolmetin Action PathwayDrug action
Tiaprofenic Acid Action PathwayDrug action
Tenoxicam Action PathwayDrug action
Salicylic Acid Action PathwayDrug action
Alpha Linolenic Acid and Linoleic Acid MetabolismMetabolic
Arachidonic Acid MetabolismMetabolic
Acetylsalicylic Acid Action PathwayDrug action
Ketorolac Action PathwayDrug action
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
AbataceptThe metabolism of Arachidonic Acid can be increased when combined with Abatacept.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Arachidonic Acid.
AcenocoumarolThe metabolism of Arachidonic Acid can be decreased when combined with Acenocoumarol.
AcetohexamideThe metabolism of Arachidonic Acid can be decreased when combined with Acetohexamide.
Acetyl sulfisoxazoleThe metabolism of Arachidonic Acid can be decreased when combined with Acetyl sulfisoxazole.
Food Interactions
Not Available

Products

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
SIMILAC ALIMENTUM 400 G TOZArachidonic Acid (0.013 g/100ml) + Doconexent (0.007 g/100ml) + Linoleic acid (0.54 g/100ml) + alpha-Linolenic acid (0.058 g/100ml)ABBOTT LABORATUARLARI İTHALAT İHRACAT VE TİC. LTD. ŞTİ.2015-08-18Not applicableTurkey flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Long-chain fatty acids
Alternative Parents
Unsaturated fatty acids / Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Long-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
long-chain fatty acid, omega-6 fatty acid, icosa-5,8,11,14-tetraenoic acid (CHEBI:15843) / Unsaturated fatty acids, Polyunsaturated fatty acids (C00219) / Unsaturated fatty acids (LMFA01030001)
Affected organisms
Not Available

Chemical Identifiers

UNII
27YG812J1I
CAS number
506-32-1
InChI Key
YZXBAPSDXZZRGB-DOFZRALJSA-N
InChI
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
IUPAC Name
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

References

Synthesis Reference

Derek R. Buckle, "Arachidonic acid analogues, processes for their preparation and their use in medicine." U.S. Patent US4699995, issued July, 1973.

US4699995
General References
Not Available
Human Metabolome Database
HMDB0060102
KEGG Compound
C00219
PubChem Compound
444899
PubChem Substance
46506683
ChemSpider
392692
BindingDB
22319
RxNav
1368624
ChEBI
15843
ChEMBL
CHEMBL15594
ZINC
ZINC000004474696
Therapeutic Targets Database
DNC000249
PDBe Ligand
ACD
PDB Entries
1adl / 1cvu / 1diy / 1gnj / 1u67 / 1vyg / 2lbv / 3fg4 / 3hs5 / 3olt
show 19 more

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDevelopment, Child / Premature Births1
Not AvailableCompletedNot AvailableSquamous Cell Carcinoma of the Head and Neck (SCCHN)1
Not AvailableEnrolling by InvitationTreatmentDevelopment, Child / Premature Births1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, liquid filledOral
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)-49.5 °CPhysProp
boiling point (°C)170 °C at 1.50E-01 mm HgPhysProp
logP6.98SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.000151 mg/mLALOGPS
logP6.8ALOGPS
logP6.59Chemaxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.82Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity99.95 m3·mol-1Chemaxon
Polarizability37.2 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9945
Blood Brain Barrier+0.9539
Caco-2 permeable+0.8371
P-glycoprotein substrateNon-substrate0.5962
P-glycoprotein inhibitor INon-inhibitor0.9487
P-glycoprotein inhibitor IINon-inhibitor0.8964
Renal organic cation transporterNon-inhibitor0.9272
CYP450 2C9 substrateNon-substrate0.7643
CYP450 2D6 substrateNon-substrate0.8954
CYP450 3A4 substrateNon-substrate0.6678
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.8972
CYP450 2D6 inhibitorNon-inhibitor0.9545
CYP450 2C19 inhibitorNon-inhibitor0.9467
CYP450 3A4 inhibitorNon-inhibitor0.9295
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9349
Ames testNon AMES toxic0.9674
CarcinogenicityNon-carcinogens0.6568
BiodegradationReady biodegradable0.811
Rat acute toxicity1.3991 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9133
hERG inhibition (predictor II)Non-inhibitor0.9103
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
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-005c-9800000000-87c290971fc8a628fb23
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-7390000000-7004b9cd28a9b3d9c991
GC-MS Spectrum - GC-MSGC-MSsplash10-005c-9800000000-87c290971fc8a628fb23
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-6900000000-6870df266b6c73f2a4a1
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0nmi-0913000000-95846e8d5e8afd29664b
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-005l-0902100000-6fc8730bd28daa779b66
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-005l-0902100000-6fc8730bd28daa779b66
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-005l-0902100000-6fc8730bd28daa779b66
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0udi-0009000000-6bd9d0477c122d3eed94
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0udi-0009000000-510ea33e558fa238a1d2
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0udi-0009000000-73a6b21464acba15463c
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-0udi-0049000000-102d050109d3c78b1a25
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0a4i-0090000000-2fb9003e782ec3d05e20
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0nmi-0913000000-95846e8d5e8afd29664b
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0udi-0009000000-6bd9d0477c122d3eed94
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0udi-0009000000-510ea33e558fa238a1d2
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0udi-0049000000-102d050109d3c78b1a25
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-5592000000-a4cb284192a5379e8498
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-72d7e08f45ac0712b087
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0249000000-addbe76ff7a22a945c93
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01cc-5790000000-6f6c986c160f551716f7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000l-3490000000-749a5c20239a2c162d37
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0536-9600000000-5d62e1d3554798da85ba
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-222.9278022
predicted
DarkChem Lite v0.1.0
[M-H]-223.1946022
predicted
DarkChem Lite v0.1.0
[M-H]-179.2348664
predicted
DarkChem Standard v0.1.0
[M-H]-223.4693022
predicted
DarkChem Lite v0.1.0
[M-H]-223.7542022
predicted
DarkChem Lite v0.1.0
[M-H]-190.8317
predicted
DeepCCS 1.0 (2019)
[M+H]+193.18968
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.28285
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Murakami K, Ide T, Suzuki M, Mochizuki T, Kadowaki T: Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. Biochem Biophys Res Commun. 1999 Jul 14;260(3):609-13. [Article]
  2. Downie MM, Sanders DA, Maier LM, Stock DM, Kealey T: Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. Br J Dermatol. 2004 Oct;151(4):766-75. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxyla...
Gene Name
NR1H4
Uniprot ID
Q96RI1
Uniprot Name
Bile acid receptor
Molecular Weight
55913.915 Da
References
  1. Zhao A, Yu J, Lew JL, Huang L, Wright SD, Cui J: Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets. DNA Cell Biol. 2004 Aug;23(8):519-26. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRA
Uniprot ID
P19793
Uniprot Name
Retinoic acid receptor RXR-alpha
Molecular Weight
50810.835 Da
References
  1. Lengqvist J, Mata De Urquiza A, Bergman AC, Willson TM, Sjovall J, Perlmann T, Griffiths WJ: Polyunsaturated fatty acids including docosahexaenoic and arachidonic acid bind to the retinoid X receptor alpha ligand-binding domain. Mol Cell Proteomics. 2004 Jul;3(7):692-703. Epub 2004 Apr 8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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. [Article]
Kind
Protein
Organism
Blood fluke
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
May play a role in the transport of fatty acids. Binds various fatty acids, such as arachidonic, oleic, palmitic and linolenic acid (in vitro).
Gene Name
Not Available
Uniprot ID
P29498
Uniprot Name
14 kDa fatty acid-binding protein
Molecular Weight
14847.73 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

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. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
General Function
Transporter activity
Specific Function
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds satu...
Gene Name
FABP2
Uniprot ID
P12104
Uniprot Name
Fatty acid-binding protein, intestinal
Molecular Weight
15207.165 Da
References
  1. Rowland A, Knights KM, Mackenzie PI, Miners JO: Characterization of the binding of drugs to human intestinal fatty acid binding protein (IFABP): potential role of IFABP as an alternative to albumin for in vitro-in vivo extrapolation of drug kinetic parameters. Drug Metab Dispos. 2009 Jul;37(7):1395-403. doi: 10.1124/dmd.109.027656. Epub 2009 Apr 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
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. Petitpas I, Grune T, Bhattacharya AA, Curry S: Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids. J Mol Biol. 2001 Dec 14;314(5):955-60. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity).
Gene Name
FABP4
Uniprot ID
P15090
Uniprot Name
Fatty acid-binding protein, adipocyte
Molecular Weight
14718.815 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
Gene Name
SLCO2A1
Uniprot ID
Q92959
Uniprot Name
Solute carrier organic anion transporter family member 2A1
Molecular Weight
70043.33 Da
References
  1. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2021 10:53