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Identification
NameAdenosine monophosphate
Accession NumberDB00131  (EXPT00512, NUTR00011)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

Adenylic acid. Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
5'-Adenosine monophosphateNot AvailableNot Available
5'-Adenylic acidNot AvailableNot Available
5'-AMPNot AvailableNot Available
5'-O-PhosphonoadenosineNot AvailableNot Available
Adenosine 5'-(dihydrogen phosphate)Not AvailableNot Available
Adenosine 5'-monophosphateNot AvailableNot Available
Adenosine 5'-phosphateNot AvailableNot Available
ADENOSINE monophosphateNot AvailableNot Available
Adenosine phosphateNot AvailableINN
Adenosine-5'-MonophosphateNot AvailableNot Available
Adenosine-5'-monophosphoric acidNot AvailableNot Available
Adenosine-5'pNot AvailableNot Available
Adenosini phosphasNot AvailableNot Available
AdenylateNot AvailableNot Available
Adenylic acidNot AvailableNot Available
Ado5'pNot AvailableNot Available
AMPNot AvailableNot Available
Fosfato de adenosinaNot AvailableNot Available
PAdoNot AvailableNot Available
PhosadenNot AvailableNot Available
PhosphadenNot AvailableNot Available
Phosphate d'adenosineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
My-B-DenNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number61-19-8
WeightAverage: 347.2212
Monoisotopic: 347.063084339
Chemical FormulaC10H14N5O7P
InChI KeyUDMBCSSLTHHNCD-KQYNXXCUSA-N
InChI
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor nutritional supplementation, also for treating dietary shortage or imbalance
PharmacodynamicsAdenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP is used as a dietary supplement to boost immune activity, and is also used as a substitute sweetener to aid in the maintenance of a low-calorie diet.
Mechanism of actionNucleotides such as Adenosine-5'-Monophosphate affect a number of immune functions, including the reversal of malnutrition and starvation-induced immunosuppression, the enhancement of T-cell maturation and function, the enhancement of natural killer cell activity, the improvement of delayed cutaneous hypersensitivity, helping resistance to such infectious agents as Staphylococcus aureus and Candida albicans, and finally the modulation of T-cell responses toward type 1 CD4 helper lymphocytes or Th1 cells. Studies have shown that mice fed a nucleotide-free diet have both impaired humoral and cellular immune responses. The addition of dietary nucleotides normalizes both types of responses. RNA, a delivery form of nucleotides, and ribonucleotides were used in these studies. The mechanism of the immune-enhancing activity of nucleic acids/nucleotides is not clear.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6115
Blood Brain Barrier+0.9402
Caco-2 permeable-0.7398
P-glycoprotein substrateNon-substrate0.6874
P-glycoprotein inhibitor INon-inhibitor0.9111
P-glycoprotein inhibitor IINon-inhibitor0.9852
Renal organic cation transporterNon-inhibitor0.947
CYP450 2C9 substrateNon-substrate0.848
CYP450 2D6 substrateNon-substrate0.8331
CYP450 3A4 substrateNon-substrate0.5462
CYP450 1A2 substrateNon-inhibitor0.9078
CYP450 2C9 substrateNon-inhibitor0.9419
CYP450 2D6 substrateNon-inhibitor0.921
CYP450 2C19 substrateNon-inhibitor0.9293
CYP450 3A4 substrateNon-inhibitor0.9296
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9633
Ames testNon AMES toxic0.8718
CarcinogenicityNon-carcinogens0.9239
BiodegradationNot ready biodegradable0.9793
Rat acute toxicity2.0220 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.976
hERG inhibition (predictor II)Non-inhibitor0.8625
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Adenosine-5 monophosphate19.74USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point195 dec °CPhysProp
water solubility1E+004 mg/L (at 20 °C)BEILSTEIN
logP-3.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.31 mg/mLALOGPS
logP-3.1ALOGPS
logP-4.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area186.07 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.07 m3·mol-1ChemAxon
Polarizability30 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Shigehiro Kataoka, Ayako Nasu, Nobuyuki Yamaji, Motohiko Kato, “Process for preparation of N.sup.6 -substituted 3’,5’-cyclic adenosine monophosphate and salt thereof.” U.S. Patent US4751293, issued July, 1984.

US4751293
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 5'-AMP-activated protein kinase subunit beta-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: activator

Components

Name UniProt ID Details
5'-AMP-activated protein kinase subunit beta-1 Q9Y478 Details

References:

  1. Richter EA, Kiens B, Wojtaszewski JF: [5’-adenosine monophosphate-activated protein kinase and lifestyle-mediated diseases] Ugeskr Laeger. 2006 Feb 27;168(9):896-900. Pubmed
  2. Neurath KM, Keough MP, Mikkelsen T, Claffey KP: AMP-dependent protein kinase alpha 2 isoform promotes hypoxia-induced VEGF expression in human glioblastoma. Glia. 2006 May;53(7):733-43. Pubmed
  3. McGee SL, Hargreaves M: Exercise and skeletal muscle glucose transporter 4 expression: molecular mechanisms. Clin Exp Pharmacol Physiol. 2006 Apr;33(4):395-9. Pubmed
  4. Whitehead JP, Richards AA, Hickman IJ, Macdonald GA, Prins JB: Adiponectin—a key adipokine in the metabolic syndrome. Diabetes Obes Metab. 2006 May;8(3):264-80. Pubmed
  5. Ruderman NB, Saha AK: Metabolic syndrome: adenosine monophosphate-activated protein kinase and malonyl coenzyme A. Obesity (Silver Spring). 2006 Feb;14 Suppl 1:25S-33S. Pubmed

2. Acetyl-coenzyme A synthetase 2-like, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
Acetyl-coenzyme A synthetase 2-like, mitochondrial Q9NUB1 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. Acetyl-coenzyme A synthetase, cytoplasmic

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
Acetyl-coenzyme A synthetase, cytoplasmic Q9NR19 Details

References:

  1. Ingram-Smith C, Smith KS: AMP-forming acetyl-CoA synthetases in Archaea show unexpected diversity in substrate utilization. Archaea. 2007 May;2(2):95-107. Pubmed
  2. Linne U, Schafer A, Stubbs MT, Marahiel MA: Aminoacyl-coenzyme A synthesis catalyzed by adenylation domains. FEBS Lett. 2007 Mar 6;581(5):905-10. Epub 2007 Feb 7. Pubmed
  3. Ingram-Smith C, Woods BI, Smith KS: Characterization of the acyl substrate binding pocket of acetyl-CoA synthetase. Biochemistry. 2006 Sep 26;45(38):11482-90. Pubmed
  4. Reger AS, Carney JM, Gulick AM: Biochemical and crystallographic analysis of substrate binding and conformational changes in acetyl-CoA synthetase. Biochemistry. 2007 Jun 5;46(22):6536-46. Epub 2007 May 12. Pubmed

4. 5'-AMP-activated protein kinase catalytic subunit alpha-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: activator

Components

Name UniProt ID Details
5'-AMP-activated protein kinase catalytic subunit alpha-1 Q13131 Details

References:

  1. Mayes MA, Laforest MF, Guillemette C, Gilchrist RB, Richard FJ: Adenosine 5’-monophosphate kinase-activated protein kinase (PRKA) activators delay meiotic resumption in porcine oocytes. Biol Reprod. 2007 Apr;76(4):589-97. Epub 2006 Dec 13. Pubmed

5. 5'-AMP-activated protein kinase subunit beta-2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: activator

Components

Name UniProt ID Details
5'-AMP-activated protein kinase subunit beta-2 O43741 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

6. Adenylate cyclase type 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
Adenylate cyclase type 1 Q08828 Details

References:

  1. Yang ZF, Sun Y, Li CZ, Wang HW, Wang XJ, Zheng YQ, Liu K, Liu YM: Reduced sinoatrial cAMP content plays a role in postnatal heart rate slowing in the rabbit. Clin Exp Pharmacol Physiol. 2006 Aug;33(8):757-62. Pubmed
  2. Nicol X, Bennis M, Ishikawa Y, Chan GC, Reperant J, Storm DR, Gaspar P: Role of the calcium modulated cyclases in the development of the retinal projections. Eur J Neurosci. 2006 Dec;24(12):3401-14. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

7. Long-chain-fatty-acid--CoA ligase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
Long-chain-fatty-acid--CoA ligase 1 P33121 Details

References:

  1. Ingram-Smith C, Woods BI, Smith KS: Characterization of the acyl substrate binding pocket of acetyl-CoA synthetase. Biochemistry. 2006 Sep 26;45(38):11482-90. Pubmed
  2. Ingram-Smith C, Smith KS: AMP-forming acetyl-CoA synthetases in Archaea show unexpected diversity in substrate utilization. Archaea. 2007 May;2(2):95-107. Pubmed

8. Cyclic AMP-responsive element-binding protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: activator

Components

Name UniProt ID Details
Cyclic AMP-responsive element-binding protein 1 P16220 Details

References:

  1. Ulfhammer E, Larsson P, Karlsson L, Hrafnkelsdottir T, Bokarewa M, Tarkowski A, Jern S: TNF-alpha mediated suppression of tissue type plasminogen activator expression in vascular endothelial cells is NF-kappaB- and p38 MAPK-dependent. J Thromb Haemost. 2006 Aug;4(8):1781-9. Pubmed
  2. Saha B, Singh SK, Sarkar C, Bera R, Ratha J, Tobin DJ, Bhadra R: Activation of the Mitf promoter by lipid-stimulated activation of p38-stress signalling to CREB. Pigment Cell Res. 2006 Dec;19(6):595-605. Pubmed
  3. Kozinn J, Mao L, Arora A, Yang L, Fibuch EE, Wang JQ: Inhibition of glutamatergic activation of extracellular signal-regulated protein kinases in hippocampal neurons by the intravenous anesthetic propofol. Anesthesiology. 2006 Dec;105(6):1182-91. Pubmed
  4. Perlis RH, Purcell S, Fagerness J, Cusin C, Yamaki L, Fava M, Smoller JW: Clinical and genetic dissection of anger expression and CREB1 polymorphisms in major depressive disorder. Biol Psychiatry. 2007 Sep 1;62(5):536-40. Epub 2007 Feb 14. Pubmed
  5. Brenhouse HC, Howe ML, Stellar JR: Differential activation of cAMP response element binding protein in discrete nucleus accumbens subregions during early and late cocaine sensitization. Behav Neurosci. 2007 Feb;121(1):212-7. Pubmed

9. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: unknown

Actions: component of

Components

Name UniProt ID 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. Kostylina G, Simon D, Fey MF, Yousefi S, Simon HU: Neutrophil apoptosis mediated by nicotinic acid receptors (GPR109A). Cell Death Differ. 2007 Oct 12;. Pubmed

10. Serine/threonine-protein kinase pim-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
Serine/threonine-protein kinase pim-1 P11309 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

11. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4B Q07343 Details

References:

  1. Siuciak JA, Chapin DS, McCarthy SA, Martin AN: Antipsychotic profile of rolipram: efficacy in rats and reduced sensitivity in mice deficient in the phosphodiesterase-4B (PDE4B) enzyme. Psychopharmacology (Berl). 2007 Jun;192(3):415-24. Epub 2007 Mar 2. Pubmed
  2. Porteous DJ, Thomson P, Brandon NJ, Millar JK: The genetics and biology of DISC1—an emerging role in psychosis and cognition. Biol Psychiatry. 2006 Jul 15;60(2):123-31. Pubmed
  3. Terrin A, Di Benedetto G, Pertegato V, Cheung YF, Baillie G, Lynch MJ, Elvassore N, Prinz A, Herberg FW, Houslay MD, Zaccolo M: PGE stimulation of HEK293 cells generates multiple contiguous domains with different [cAMP]: role of compartmentalized phosphodiesterases. J Cell Biol. 2006 Nov 6;175(3):441-51. Pubmed

12. Glycogen phosphorylase, liver form

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: activator

Components

Name UniProt ID Details
Glycogen phosphorylase, liver form P06737 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

13. Histidine triad nucleotide-binding protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
Histidine triad nucleotide-binding protein 1 P49773 Details

References:

  1. Chou TF, Tikh IB, Horta BA, Ghosh B, De Alencastro RB, Wagner CR: Engineered monomeric human histidine triad nucleotide-binding protein 1 hydrolyzes fluorogenic acyl-adenylate and lysyl-tRNA synthetase-generated lysyl-adenylate. J Biol Chem. 2007 May 18;282(20):15137-47. Epub 2007 Mar 2. Pubmed
  2. Chou TF, Wagner CR: Lysyl-tRNA synthetase-generated lysyl-adenylate is a substrate for histidine triad nucleotide binding proteins. J Biol Chem. 2007 Feb 16;282(7):4719-27. Epub 2006 Dec 8. Pubmed
  3. Chou TF, Baraniak J, Kaczmarek R, Zhou X, Cheng J, Ghosh B, Wagner CR: Phosphoramidate pronucleotides: a comparison of the phosphoramidase substrate specificity of human and Escherichia coli histidine triad nucleotide binding proteins. Mol Pharm. 2007 Mar-Apr;4(2):208-17. Epub 2007 Jan 12. Pubmed

14. cAMP-specific 3',5'-cyclic phosphodiesterase 4D

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4D Q08499 Details

References:

  1. Terrin A, Di Benedetto G, Pertegato V, Cheung YF, Baillie G, Lynch MJ, Elvassore N, Prinz A, Herberg FW, Houslay MD, Zaccolo M: PGE stimulation of HEK293 cells generates multiple contiguous domains with different [cAMP]: role of compartmentalized phosphodiesterases. J Cell Biol. 2006 Nov 6;175(3):441-51. Pubmed

15. Fructose-1,6-bisphosphatase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist inhibitory allosteric modulator

Components

Name UniProt ID Details
Fructose-1,6-bisphosphatase 1 P09467 Details

References:

  1. Xue Y, Huang S, Liang JY, Zhang Y, Lipscomb WN: Crystal structure of fructose-1,6-bisphosphatase complexed with fructose 2,6-bisphosphate, AMP, and Zn2+ at 2.0-A resolution: aspects of synergism between inhibitors. Proc Natl Acad Sci U S A. 1994 Dec 20;91(26):12482-6. Pubmed
  2. Hebeisen P, Kuhn B, Kohler P, Gubler M, Huber W, Kitas E, Schott B, Benz J, Joseph C, Ruf A: Allosteric FBPase inhibitors gain 10(5) times in potency when simultaneously binding two neighboring AMP sites. Bioorg Med Chem Lett. 2008 Aug 15;18(16):4708-12. Epub 2008 Jul 5. Pubmed

16. Adenosine kinase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: product of

Components

Name UniProt ID Details
Adenosine kinase P55263 Details

References:

  1. Park J, Gupta RS: Adenosine kinase and ribokinase—the RK family of proteins. Cell Mol Life Sci. 2008 Sep;65(18):2875-96. Pubmed
  2. Leoncini R, Vannoni D, Santoro A, Giglioni S, Carli R, Marinello E: Adenosine kinase from rat liver: new biochemical properties. Nucleosides Nucleotides Nucleic Acids. 2006;25(9-11):1107-12. Pubmed

Enzymes

1. AMP deaminase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
AMP deaminase 1 P23109 Details

References:

  1. Hanisch F, Hellsten Y, Zierz S: Ecto- and cytosolic 5’-nucleotidases in normal and AMP deaminase-deficient human skeletal muscle. Biol Chem. 2006 Jan;387(1):53-8. Pubmed
  2. Palecz D, Jaszczuk E, Gabryelak T: In vitro study of AMP-deaminase from fish (Cyprinus carpio) treated with hydrolyzable tannins. Acta Biol Hung. 2006 Mar;57(1):49-56. Pubmed

2. Adenine phosphoribosyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Adenine phosphoribosyltransferase P07741 Details

References:

  1. Barrett C, Alley J, Pulido JC, Spurling H, Li P, Parsons T, Mallender WD, Bembenek ME: Configuration of a scintillation proximity assay for the activity assessment of recombinant human adenine phosphoribosyltransferase. Assay Drug Dev Technol. 2006 Dec;4(6):661-9. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08