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Identification
NameEthanol
Accession NumberDB00898  (APRD00738)
Typesmall molecule
Groupsapproved
Description

A clear, colorless liquid rapidly absorbed from the gastrointestinal tract and distributed throughout the body. It has bactericidal activity and is used often as a topical disinfectant. It is widely used as a solvent and preservative in pharmaceutical preparations as well as serving as the primary ingredient in alcoholic beverages. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
AlcoholNot AvailableNot Available
Alcohol etílicoSpanishNot Available
Alcool éthyliqueFrenchNot Available
AlkoholNot AvailableNot Available
Ethyl AlcoholNot AvailableNot Available
HydroxyethaneNot AvailableNot Available
MethylcarbinolNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Dehydrated ethanolNot Available
Brand mixturesNot Available
Categories
CAS number64-17-5
WeightAverage: 46.0684
Monoisotopic: 46.041864814
Chemical FormulaC2H6O
InChI KeyLFQSCWFLJHTTHZ-UHFFFAOYSA-N
InChI
InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
IUPAC Name
ethanol
SMILES
CCO
Mass Specshow(2.96 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsPrimary Alcohols
Substituentsalcohol
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
Pharmacology
IndicationFor therapeutic neurolysis of nerves or ganglia for the relief of intractable chronic pain in such conditions as inoperable cancer and trigeminal neuralgia (tic douloureux), in patients for whom neurosurgical procedures are contraindicated.
PharmacodynamicsAlcohol produces injury to cells by dehydration and precipitation of the cytoplasm or protoplasm. This accounts for its bacteriocidal and antifungal action. When alcohol is injected in close proximity to nerve tissues, it produces neuritis and nerve degeneration (neurolysis). Ninety to 98% of ethanol that enters the body is completely oxidized. Ethanol is also used as a cosolvent to dissolve many insoluble drugs and to serve as a mild sedative in some medicinal formulations. Ethanol also binds to GABA, glycine, NMDA receptors and modulates their effects. Ethanol is also metabolised by the hepatic enzyme alcohol dehydrogenase.
Mechanism of actionEthanol affects the brain’s neurons in several ways. It alters their membranes as well as their ion channels, enzymes, and receptors. Alcohol also binds directly to the receptors for acetylcholine, serotonin, GABA, and the NMDA receptors for glutamate. The sedative effects of ethanol are mediated through binding to GABA receptors and glycine receptors (alpha 1 and alpha 2 subunits). It also inhibits NMDA receptor functioning. In its role as an anti-infective, ethanol acts as an osmolyte or dehydrating agent that disrupts the osmotic balance across cell membranes.
AbsorptionRapidly absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. Metabolized by cytochrome P450 enzyme CYP2E1.

SubstrateEnzymesProduct
Ethanol
acetaldehydeDetails
Ethanol
Not Available
Ethyl glucuronideDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, rat LD50: 5628 mg/kg. Symptoms and effects of overdose include nausea, vomiting, CNS depression, acute respiratory failure or death and with chronic use, severe health problems, such as liver and brain damage.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Disulfiram Action PathwayDrug actionSMP00429
Ethanol DegradationMetabolicSMP00449
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9948
Blood Brain Barrier + 0.9539
Caco-2 permeable + 0.726
P-glycoprotein substrate Non-substrate 0.8197
P-glycoprotein inhibitor I Non-inhibitor 0.9678
P-glycoprotein inhibitor II Non-inhibitor 0.9542
Renal organic cation transporter Non-inhibitor 0.9157
CYP450 2C9 substrate Non-substrate 0.7857
CYP450 2D6 substrate Non-substrate 0.9266
CYP450 3A4 substrate Non-substrate 0.8073
CYP450 1A2 substrate Non-inhibitor 0.726
CYP450 2C9 substrate Non-inhibitor 0.9346
CYP450 2D6 substrate Non-inhibitor 0.9702
CYP450 2C19 substrate Non-inhibitor 0.9296
CYP450 3A4 substrate Non-inhibitor 0.9772
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9163
Ames test Non AMES toxic 0.9132
Carcinogenicity Carcinogens 0.7654
Biodegradation Ready biodegradable 0.9074
Rat acute toxicity 1.3676 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9319
hERG inhibition (predictor II) Non-inhibitor 0.9586
Pharmacoeconomics
Manufacturers
  • Miles laboratories inc
Packagers
Dosage forms
FormRouteStrength
AerosolTopical
GelTopical
LiquidIntramuscular
LiquidIntravenous
LiquidOral
LiquidTopical
LotionTopical
SolutionTopical
Solution / dropsOral
SprayTopical
Prices
Unit descriptionCostUnit
Ethanol 98% ampul7.8USDml
Alcohol, dehydrated 98% amp4.68USDml
Alcohol, denatured0.02USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point-114.1 °CPhysProp
boiling point78.2 °CPhysProp
water solubility1E+006 mg/L (at 25 °C)RIDDICK,JA ET AL. (1986)
logP-0.31HANSCH,C ET AL. (1995)
pKa15.9 (at 25 °C)RIDDICK,JA ET AL. (1986)
Predicted Properties
PropertyValueSource
water solubility5.79e+02 g/lALOGPS
logP-0.4ALOGPS
logP-0.16ChemAxon
logS1.1ALOGPS
pKa (strongest acidic)16.47ChemAxon
pKa (strongest basic)-2.2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count0ChemAxon
refractivity13.01ChemAxon
polarizability5.3ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
References
Synthesis Reference

William S. Hedrick, “Process for ethanol production from cellulosic materials.” U.S. Patent US4650689, issued June, 1917.

US4650689
General Reference
  1. Snyder R, Kalf GF: A perspective on benzene leukemogenesis. Crit Rev Toxicol. 1994;24(3):177-209. Pubmed
  2. Chastain G: Alcohol, neurotransmitter systems, and behavior. J Gen Psychol. 2006 Oct;133(4):329-35. Pubmed
  3. McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev. 1999 Jan;12(1):147-79. Pubmed
  4. Barceloux DG, Bond GR, Krenzelok EP, Cooper H, Vale JA: American Academy of Clinical Toxicology practice guidelines on the treatment of methanol poisoning. J Toxicol Clin Toxicol. 2002;40(4):415-46. Pubmed
  5. Hingson R, Winter M: Epidemiology and consequences of drinking and driving. Alcohol Res Health. 2003;27(1):63-78. Pubmed
External Links
ResourceLink
KEGG DrugD00068
KEGG CompoundC00469
PubChem Compound702
PubChem Substance46506969
ChemSpider682
ChEBI16236
ChEMBLCHEMBL545
Therapeutic Targets DatabaseDAP000681
PharmGKBPA448073
IUPHAR2299
Guide to Pharmacology2299
HET168
Drug Product Database724947
RxListhttp://www.rxlist.com/cgi/generic/dhydalco.htm
Drugs.comhttp://www.drugs.com/alcohol.html
WikipediaEthanol
ATC CodesD01AE06D08AX08V03AB16V03AZ01
AHFS Codes
  • 84:04.92
  • 92:00.00
  • 92:02.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.1 KB)
Interactions
Drug Interactions
Drug
AbacavirAbacavir is partly metabolized through the alcohol dehydrogenase enzyme system. Alcohol increases the area under the curve (about 41%) of Abacavir. Interaction does not appear to be clinically significant.
gabapentin enacarbilAvoid combination due to ethanol induced increased absorption of gabapentin enacarbil and increased CNS depression.
MipomersenThe combination of these drugs will likely enhance mipomersen related hepatotoxicity. Therefore patients using both these drugs, should limit their alcohol to a daily maximum of 1 drink (or equivalent).
PerampanelAvoid combination due to the enhanced central nervous system depression, and likely worse behavioral and psychiatric adverse reactions.
TizanidineEthanol increases the adverse effects of Tizanidine. The CNS depressant effects of these agents are additive.
TriprolidineTriprolidine may enhance the CNS depressant effects of Ethanol.
Food InteractionsNot Available

Targets

1. Gamma-aminobutyric acid receptor subunit alpha-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-1 P14867 Details

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. Pubmed
  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. Pubmed
  3. Santhakumar V, Wallner M, Otis TS: Ethanol acts directly on extrasynaptic subtypes of GABAA receptors to increase tonic inhibition. Alcohol. 2007 May;41(3):211-21. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  5. Earl DE, Tietz EI: Inhibition of recombinant L-type voltage-gated calcium channels by positive allosteric modulators of {gamma}-aminobutyric acid type A receptors. J Pharmacol Exp Ther. 2011 Jan 24. Pubmed

2. Glutamate receptor ionotropic, NMDA 3A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 3A Q8TCU5 Details

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. Pubmed
  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. Pubmed
  3. Wang J, Lanfranco MF, Gibb SL, Ron D: Ethanol-mediated long-lasting adaptations of the NR2B-containing NMDA receptors in the dorsomedial striatum. Channels (Austin). 2011 Jul 1;5(4). Pubmed
  4. Ron D, Wang J: The NMDA Receptor and Alcohol Addiction Pubmed
  5. Williams K: Extracellular Modulation of NMDA Receptors Pubmed
  6. Xu M, Thetford Smothers C, Woodward JJ: Effects of ethanol on phosphorylation site mutants of recombinant N-methyl-d-aspartate receptors. Alcohol. 2010 Dec 14. Pubmed

3. Glycine receptor subunit alpha-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glycine receptor subunit alpha-1 P23415 Details

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. Pubmed
  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. Pubmed
  3. Fuentealba J, Munoz B, Yevenes G, Moraga-Cid G, Perez C, Guzman L, Rigo JM, Aguayo LG: Potentiation and inhibition of glycine receptors by tutin. Neuropharmacology. 2011 Feb-Mar;60(2-3):453-9. Epub 2010 Oct 31. Pubmed
  4. Baenziger JE, Corringer PJ: 3D structure and allosteric modulation of the transmembrane domain of pentameric ligand-gated ion channels. Neuropharmacology. 2011 Jan;60(1):116-25. Epub 2010 Aug 14. Pubmed
  5. Ye Q, Koltchine VV, Mihic SJ, Mascia MP, Wick MJ, Finn SE, Harrison NL, Harris RA: Enhancement of glycine receptor function by ethanol is inversely correlated with molecular volume at position alpha267. J Biol Chem. 1998 Feb 6;273(6):3314-9. Pubmed

4. Glycine receptor subunit alpha-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glycine receptor subunit alpha-2 P23416 Details

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. Pubmed
  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. Pubmed
  3. Ye Q, Koltchine VV, Mihic SJ, Mascia MP, Wick MJ, Finn SE, Harrison NL, Harris RA: Enhancement of glycine receptor function by ethanol is inversely correlated with molecular volume at position alpha267. J Biol Chem. 1998 Feb 6;273(6):3314-9. Pubmed
  4. Baenziger JE, Corringer PJ: 3D structure and allosteric modulation of the transmembrane domain of pentameric ligand-gated ion channels. Neuropharmacology. 2011 Jan;60(1):116-25. Epub 2010 Aug 14. Pubmed

5. Alcohol dehydrogenase 1A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alcohol dehydrogenase 1A P07327 Details

References:

  1. Hernandez-Tobias A, Julian-Sanchez A, Pina E, Riveros-Rosas H: Natural alcohol exposure: Is ethanol the main substrate for alcohol dehydrogenases in animals? Chem Biol Interact. 2011 Feb 14. Pubmed
  2. Matsumoto M, Cyganek I, Sanghani PC, Cho WK, Liangpunsakul S, Crabb DW: Ethanol metabolism by HeLa cells transduced with human alcohol dehydrogenase isoenzymes: control of the pathway by acetaldehyde concentration. Alcohol Clin Exp Res. 2011 Jan;35(1):28-38. Pubmed
  3. Nishimura FT, Kimura Y, Abe S, Fukunaga T, Saijoh K: Effects of polymorphisms in untranslated regions of the class I alcohol dehydrogenase (ADH) genes on alcohol metabolism in Japanese subjects and transcriptional activity in HepG2 cells. Nihon Arukoru Yakubutsu Igakkai Zasshi. 2009 Jun;44(3):139-55. Pubmed
  4. Jelski W, Kozlowski M, Laudanski J, Niklinski J, Szmitkowski M: The activity of class I, II, III, and IV alcohol dehydrogenase (ADH) isoenzymes and aldehyde dehydrogenase (ALDH) in esophageal cancer. Dig Dis Sci. 2009 Apr;54(4):725-30. Epub 2008 Aug 9. Pubmed

6. Alcohol dehydrogenase 1B

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alcohol dehydrogenase 1B P00325 Details

References:

  1. Hernandez-Tobias A, Julian-Sanchez A, Pina E, Riveros-Rosas H: Natural alcohol exposure: Is ethanol the main substrate for alcohol dehydrogenases in animals? Chem Biol Interact. 2011 Feb 14. Pubmed
  2. Matsumoto M, Cyganek I, Sanghani PC, Cho WK, Liangpunsakul S, Crabb DW: Ethanol metabolism by HeLa cells transduced with human alcohol dehydrogenase isoenzymes: control of the pathway by acetaldehyde concentration. Alcohol Clin Exp Res. 2011 Jan;35(1):28-38. Pubmed
  3. Nishimura FT, Kimura Y, Abe S, Fukunaga T, Saijoh K: Effects of polymorphisms in untranslated regions of the class I alcohol dehydrogenase (ADH) genes on alcohol metabolism in Japanese subjects and transcriptional activity in HepG2 cells. Nihon Arukoru Yakubutsu Igakkai Zasshi. 2009 Jun;44(3):139-55. Pubmed
  4. Jelski W, Kozlowski M, Laudanski J, Niklinski J, Szmitkowski M: The activity of class I, II, III, and IV alcohol dehydrogenase (ADH) isoenzymes and aldehyde dehydrogenase (ALDH) in esophageal cancer. Dig Dis Sci. 2009 Apr;54(4):725-30. Epub 2008 Aug 9. Pubmed

7. Alcohol dehydrogenase 1C

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alcohol dehydrogenase 1C P00326 Details

References:

  1. Hernandez-Tobias A, Julian-Sanchez A, Pina E, Riveros-Rosas H: Natural alcohol exposure: Is ethanol the main substrate for alcohol dehydrogenases in animals? Chem Biol Interact. 2011 Feb 14. Pubmed
  2. Matsumoto M, Cyganek I, Sanghani PC, Cho WK, Liangpunsakul S, Crabb DW: Ethanol metabolism by HeLa cells transduced with human alcohol dehydrogenase isoenzymes: control of the pathway by acetaldehyde concentration. Alcohol Clin Exp Res. 2011 Jan;35(1):28-38. Pubmed
  3. Nishimura FT, Kimura Y, Abe S, Fukunaga T, Saijoh K: Effects of polymorphisms in untranslated regions of the class I alcohol dehydrogenase (ADH) genes on alcohol metabolism in Japanese subjects and transcriptional activity in HepG2 cells. Nihon Arukoru Yakubutsu Igakkai Zasshi. 2009 Jun;44(3):139-55. Pubmed
  4. Jelski W, Kozlowski M, Laudanski J, Niklinski J, Szmitkowski M: The activity of class I, II, III, and IV alcohol dehydrogenase (ADH) isoenzymes and aldehyde dehydrogenase (ALDH) in esophageal cancer. Dig Dis Sci. 2009 Apr;54(4):725-30. Epub 2008 Aug 9. Pubmed

Enzymes

1. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  3. Lewis DF, Modi S, Dickins M: Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. Pubmed

2. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 4A11

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 4A11 Q02928 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12