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Identification
NameDiazoxide
Accession NumberDB01119  (APRD00914)
TypeSmall Molecule
GroupsApproved
Description

A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group. [PubChem]

Structure
Thumb
Synonyms
Diazossido
Diazoxide
Diazoxido
Diazoxidum
Eudemine
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hyperstat Inj 15mg/mlliquid15 mgintravenousSchering Plough Canada Inc1973-12-312003-07-14Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Proglycemsuspension50 mg/mLoralTeva Branded Pharmaceutical Products R&D, Inc.1990-09-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Proglycemcapsule100 mgoralMerck Canada Inc1985-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Proglycem Susp 50mg/mlsuspension50 mgoralSchering Plough Canada Inc1984-12-312006-03-23Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
EudemineMercury
HyperstatSchering
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number364-98-7
WeightAverage: 230.671
Monoisotopic: 229.991675875
Chemical FormulaC8H7ClN2O2S
InChI KeyInChIKey=GDLBFKVLRPITMI-UHFFFAOYSA-N
InChI
InChI=1S/C8H7ClN2O2S/c1-5-10-7-3-2-6(9)4-8(7)14(12,13)11-5/h2-4H,1H3,(H,10,11)
IUPAC Name
7-chloro-3-methyl-4H-1λ⁶,2,4-benzothiadiazine-1,1-dione
SMILES
CC1=NS(=O)(=O)C2=C(N1)C=CC(Cl)=C2
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzothiadiazines. These are organic compounds containing a benzene fused to a thiadiazine ring (a six-member ring with two nitrogen atoms and a sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiadiazines
Sub ClassBenzothiadiazines
Direct ParentBenzothiadiazines
Alternative Parents
Substituents
  • Benzothiadiazine
  • Chlorobenzene
  • Imidolactam
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Sulfonic acid derivative
  • Azacycle
  • Amidine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed parentally to treat hypertensive emergencies. Also used to treat hypoglycemia secondary to insulinoma.
PharmacodynamicsDiazoxide is a potassium channel activator, which causes local relaxation in smooth muscle by increasing membrane permeability to potassium ions. This switches off voltage-gated calcium ion channels which inhibits the generation of an action potential.
Mechanism of actionAs a diuretic, diazoxide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like diazoxide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of diazoxide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle. As a antihypoglycemic, diazoxide inhibits insulin release from the pancreas, probably by opening potassium channels in the beta cell membrane.
AbsorptionReadily absorbed following oral administration.
Volume of distributionNot Available
Protein bindingVery high (more than 90%) to serum proteins.
Metabolism

Hepatic.

Route of eliminationProglycem is extensively bound (more than 90%) to serum proteins, and is excreted in the kidneys.
Half life28 ±8.3 hours in normal adults.
ClearanceNot Available
ToxicityOral LD50 in rat and mouse: 980 mg/kg and 444 mg/kg, respectively.
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+1.0
Blood Brain Barrier+0.5923
Caco-2 permeable-0.5765
P-glycoprotein substrateNon-substrate0.6817
P-glycoprotein inhibitor INon-inhibitor0.6924
P-glycoprotein inhibitor IINon-inhibitor0.6927
Renal organic cation transporterNon-inhibitor0.8107
CYP450 2C9 substrateNon-substrate0.5606
CYP450 2D6 substrateNon-substrate0.8064
CYP450 3A4 substrateNon-substrate0.5774
CYP450 1A2 substrateInhibitor0.9108
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7977
Ames testNon AMES toxic0.7888
CarcinogenicityNon-carcinogens0.8304
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3408 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9233
hERG inhibition (predictor II)Non-inhibitor0.9271
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Liquidintravenous15 mg
Capsuleoral100 mg
Suspensionoral50 mg/mL
Suspensionoral50 mg
Prices
Unit descriptionCostUnit
Proglycem 50 mg/ml Suspension 30ml Bottle197.05USD bottle
Diazoxide powder85.07USD g
Proglycem 100 mg Capsule1.65USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point330Topliss, J.G., Sperber, N. and Rubin, A.A.; U.S. Patent 2,986,573; May 30, 1961; assigned to Schering Corporation. Topliss, J.G., Sperber, N. and Rubin, A.A.; U.S. Patent 3,345,365; October 3, 1967; assigned to Schering Corporation.
water solubility2850 mg/LNot Available
logP1.20HANSCH,C ET AL. (1995)
pKa8.74SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.552 mg/mLALOGPS
logP1.09ALOGPS
logP1ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)10.48ChemAxon
pKa (Strongest Basic)1.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.84 m3·mol-1ChemAxon
Polarizability20.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Topliss, J.G., Sperber, N. and Rubin, A.A.; U.S. Patent 2,986,573; May 30, 1961; assigned
to Schering Corporation.
Topliss, J.G., Sperber, N. and Rubin, A.A.; U.S. Patent 3,345,365; October 3, 1967; assigned
to Schering Corporation.

General ReferencesNot Available
External Links
ATC CodesC02DA01V03AH01
AHFS Codes
  • 24:08.20
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73 KB)
Interactions
Drug Interactions
Drug
AcebutololDiazoxide may increase the hypotensive activities of Acebutolol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Diazoxide.
AliskirenDiazoxide may increase the hypotensive activities of Aliskiren.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Diazoxide.
AmilorideDiazoxide may increase the hypotensive activities of Amiloride.
AmlodipineDiazoxide may increase the hypotensive activities of Amlodipine.
AtenololDiazoxide may increase the hypotensive activities of Atenolol.
Azilsartan medoxomilDiazoxide may increase the hypotensive activities of Azilsartan medoxomil.
BenazeprilDiazoxide may increase the hypotensive activities of Benazepril.
BetaxololDiazoxide may increase the hypotensive activities of Betaxolol.
BisoprololDiazoxide may increase the hypotensive activities of Bisoprolol.
BumetanideDiazoxide may increase the hypotensive activities of Bumetanide.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Diazoxide.
CandesartanDiazoxide may increase the hypotensive activities of Candesartan.
CaptoprilDiazoxide may increase the hypotensive activities of Captopril.
CarvedilolDiazoxide may increase the hypotensive activities of Carvedilol.
ChlorothiazideThe risk or severity of adverse effects can be increased when Chlorothiazide is combined with Diazoxide.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Diazoxide.
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Diazoxide.
CilazaprilDiazoxide may increase the hypotensive activities of Cilazapril.
ClevidipineDiazoxide may increase the hypotensive activities of Clevidipine.
ClonidineDiazoxide may increase the hypotensive activities of Clonidine.
DiltiazemDiazoxide may increase the hypotensive activities of Diltiazem.
DoxazosinDiazoxide may increase the hypotensive activities of Doxazosin.
EnalaprilDiazoxide may increase the hypotensive activities of Enalapril.
EnalaprilatDiazoxide may increase the hypotensive activities of Enalaprilat.
EplerenoneDiazoxide may increase the hypotensive activities of Eplerenone.
EprosartanDiazoxide may increase the hypotensive activities of Eprosartan.
EsmololDiazoxide may increase the hypotensive activities of Esmolol.
Ethacrynic acidDiazoxide may increase the hypotensive activities of Ethacrynic acid.
FelodipineDiazoxide may increase the hypotensive activities of Felodipine.
FosinoprilDiazoxide may increase the hypotensive activities of Fosinopril.
FosphenytoinThe serum concentration of Fosphenytoin can be decreased when it is combined with Diazoxide.
FurosemideDiazoxide may increase the hypotensive activities of Furosemide.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Diazoxide.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Diazoxide.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Diazoxide.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Diazoxide.
GuanfacineDiazoxide may increase the hypotensive activities of Guanfacine.
HydralazineDiazoxide may increase the hypotensive activities of Hydralazine.
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Diazoxide.
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Diazoxide.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Diazoxide.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Diazoxide.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Diazoxide.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Diazoxide.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Diazoxide.
Insulin RegularThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Diazoxide.
Insulin, isophaneThe therapeutic efficacy of Insulin, isophane can be decreased when used in combination with Diazoxide.
IrbesartanDiazoxide may increase the hypotensive activities of Irbesartan.
IsradipineDiazoxide may increase the hypotensive activities of Isradipine.
LabetalolDiazoxide may increase the hypotensive activities of Labetalol.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Diazoxide.
LisinoprilDiazoxide may increase the hypotensive activities of Lisinopril.
LosartanDiazoxide may increase the hypotensive activities of Losartan.
MannitolDiazoxide may increase the hypotensive activities of Mannitol.
MecamylamineDiazoxide may increase the hypotensive activities of Mecamylamine.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Diazoxide.
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Diazoxide.
MethyldopaDiazoxide may increase the hypotensive activities of Methyldopa.
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Diazoxide.
MetoprololDiazoxide may increase the hypotensive activities of Metoprolol.
MinoxidilDiazoxide may increase the hypotensive activities of Minoxidil.
MoexiprilDiazoxide may increase the hypotensive activities of Moexipril.
MoxonidineDiazoxide may increase the hypotensive activities of Moxonidine.
NadololDiazoxide may increase the hypotensive activities of Nadolol.
NebivololDiazoxide may increase the hypotensive activities of Nebivolol.
NicardipineDiazoxide may increase the hypotensive activities of Nicardipine.
NifedipineDiazoxide may increase the hypotensive activities of Nifedipine.
NimodipineDiazoxide may increase the hypotensive activities of Nimodipine.
NisoldipineDiazoxide may increase the hypotensive activities of Nisoldipine.
NitroprussideDiazoxide may increase the hypotensive activities of Nitroprusside.
OlmesartanDiazoxide may increase the hypotensive activities of Olmesartan.
PenbutololDiazoxide may increase the hypotensive activities of Penbutolol.
PerindoprilDiazoxide may increase the hypotensive activities of Perindopril.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Diazoxide.
PhenoxybenzamineDiazoxide may increase the hypotensive activities of Phenoxybenzamine.
PhentolamineDiazoxide may increase the hypotensive activities of Phentolamine.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Diazoxide.
PindololDiazoxide may increase the hypotensive activities of Pindolol.
PrazosinDiazoxide may increase the hypotensive activities of Prazosin.
PropranololDiazoxide may increase the hypotensive activities of Propranolol.
QuinaprilDiazoxide may increase the hypotensive activities of Quinapril.
RamiprilDiazoxide may increase the hypotensive activities of Ramipril.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Diazoxide.
ReserpineDiazoxide may increase the hypotensive activities of Reserpine.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Diazoxide.
SotalolDiazoxide may increase the hypotensive activities of Sotalol.
SpironolactoneDiazoxide may increase the hypotensive activities of Spironolactone.
TelmisartanDiazoxide may increase the hypotensive activities of Telmisartan.
TerazosinDiazoxide may increase the hypotensive activities of Terazosin.
ThiopentalThiopental may increase the hypotensive activities of Diazoxide.
TimololDiazoxide may increase the hypotensive activities of Timolol.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Diazoxide.
TorasemideDiazoxide may increase the hypotensive activities of Torasemide.
TrandolaprilDiazoxide may increase the hypotensive activities of Trandolapril.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Diazoxide.
TriamtereneDiazoxide may increase the hypotensive activities of Triamterene.
TrichlormethiazideThe risk or severity of adverse effects can be increased when Trichlormethiazide is combined with Diazoxide.
ValsartanDiazoxide may increase the hypotensive activities of Valsartan.
VerapamilDiazoxide may increase the hypotensive activities of Verapamil.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Diazoxide.
Food InteractionsNot Available

Targets

1. ATP-sensitive inward rectifier potassium channel 11

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
ATP-sensitive inward rectifier potassium channel 11 Q14654 Details

References:

  1. D’hahan N, Moreau C, Prost AL, Jacquet H, Alekseev AE, Terzic A, Vivaudou M: Pharmacological plasticity of cardiac ATP-sensitive potassium channels toward diazoxide revealed by ADP. Proc Natl Acad Sci U S A. 1999 Oct 12;96(21):12162-7. Pubmed
  2. Sakura H, Trapp S, Liss B, Ashcroft FM: Altered functional properties of KATP channel conferred by a novel splice variant of SUR1. J Physiol. 1999 Dec 1;521 Pt 2:337-50. Pubmed
  3. Shindo T, Katayama Y, Horio Y, Kurachi Y: MCC-134, a novel vascular relaxing agent, is an inverse agonist for the pancreatic-type ATP-sensitive K(+) channel. J Pharmacol Exp Ther. 2000 Jan;292(1):131-5. Pubmed
  4. de Lonlay P, Fournet JC, Touati G, Groos MS, Martin D, Sevin C, Delagne V, Mayaud C, Chigot V, Sempoux C, Brusset MC, Laborde K, Bellane-Chantelot C, Vassault A, Rahier J, Junien C, Brunelle F, Nihoul-Fekete C, Saudubray JM, Robert JJ: Heterogeneity of persistent hyperinsulinaemic hypoglycaemia. A series of 175 cases. Eur J Pediatr. 2002 Jan;161(1):37-48. Pubmed
  5. Russ U, Lange U, Loffler-Walz C, Hambrock A, Quast U: Binding and effect of K ATP channel openers in the absence of Mg2+. Br J Pharmacol. 2003 May;139(2):368-80. Pubmed

2. Carbonic anhydrase 1

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 1 P00915 Details

References:

  1. Domoki F, Bari F, Nagy K, Busija DW, Siklos L: Diazoxide prevents mitochondrial swelling and Ca2+ accumulation in CA1 pyramidal cells after cerebral ischemia in newborn pigs. Brain Res. 2004 Sep 3;1019(1-2):97-104. Pubmed
  2. Erdemli G, Krnjevic K: Diazoxide suppresses slowly-inactivating outward and inward currents in CA1 hippocampal neurones. Neuroreport. 1993 Dec 13;5(3):249-51. Pubmed
  3. Erdemli G, Krnjevic K: Actions of diazoxide on CA1 neurons in hippocampal slices from rats. Can J Physiol Pharmacol. 1995 May;73(5):608-18. Pubmed
  4. Scuvee-Moreau J, Seutin V, Vrijens B, Pirotte B, De Tullio P, Massotte L, Albert A, Delarge J, Dresse A: Effect of potassium channel openers on the firing rate of hippocampal pyramidal cells and A10 dopaminergic neurons in vitro. Arch Physiol Biochem. 1997 Sep;105(5):421-8. Pubmed
  5. Crepel V, Rovira C, Ben-Ari Y: The K+ channel opener diazoxide enhances glutamatergic currents and reduces GABAergic currents in hippocampal neurons. J Neurophysiol. 1993 Feb;69(2):494-503. Pubmed

3. Carbonic anhydrase 2

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 2 P00918 Details

References:

  1. Munoz A, Nakazaki M, Goodman JC, Barrios R, Onetti CG, Bryan J, Aguilar-Bryan L: Ischemic preconditioning in the hippocampus of a knockout mouse lacking SUR1-based K(ATP) channels. Stroke. 2003 Jan;34(1):164-70. Pubmed
  2. Sekine N, Ullrich S, Regazzi R, Pralong WF, Wollheim CB: Postreceptor signalling of growth hormone and prolactin and their effects in the differentiated insulin-secreting cell line, INS-1. Endocrinology. 1996 May;137(5):1841-50. Pubmed

4. Sodium/potassium-transporting ATPase subunit alpha-1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: other

Components

Name UniProt ID Details
Sodium/potassium-transporting ATPase subunit alpha-1 P05023 Details

References:

  1. Lawrence CL, Rainbow RD, Davies NW, Standen NB: Effect of metabolic inhibition on glimepiride block of native and cloned cardiac sarcolemmal K(ATP) channels. Br J Pharmacol. 2002 Jul;136(5):746-52. Pubmed
  2. Guo W, Chen N, Chen Y, Xia Q, Shen Y: Activation of Mitochondrial ATP-Sensitive Potassium Channel Contributes to Protective Effect in Prolonged Myocardial Preservation. Conf Proc IEEE Eng Med Biol Soc. 2005;4:4027-30. Pubmed
  3. Comelli M, Metelli G, Mavelli I: Downmodulation of mitochondrial F0F1 ATP synthase by diazoxide in cardiac myoblasts: a dual effect of the drug. Am J Physiol Heart Circ Physiol. 2007 Feb;292(2):H820-9. Pubmed

5. Calcium-activated potassium channel subunit alpha-1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: other

Components

Name UniProt ID Details
Calcium-activated potassium channel subunit alpha-1 Q12791 Details

References:

  1. Klockner U, Trieschmann U, Isenberg G: Pharmacological modulation of calcium and potassium channels in isolated vascular smooth muscle cells. Arzneimittelforschung. 1989 Jan;39(1A):120-6. Pubmed
  2. O’Malley D, Shanley LJ, Harvey J: Insulin inhibits rat hippocampal neurones via activation of ATP-sensitive K+ and large conductance Ca2+-activated K+ channels. Neuropharmacology. 2003 Jun;44(7):855-63. Pubmed
  3. Zhang L, Li X, Zhou R, Xing G: Possible role of potassium channel, big K in etiology of schizophrenia. Med Hypotheses. 2006;67(1):41-3. Epub 2006 Jan 30. Pubmed

6. Solute carrier family 12 member 3

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: unknown

Components

Name UniProt ID Details
Solute carrier family 12 member 3 P55017 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

Enzymes

1. Glutamine synthetase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Glutamine synthetase P15104 Details

References:

  1. Velloso LA, Bjork E, Ballagi AE, Funa K, Andersson A, Kampe O, Karlsson FA, Eizirik DL: Regulation of GAD expression in islets of Langerhans occurs both at the mRNA and protein level. Mol Cell Endocrinol. 1994 Jun;102(1-2):31-7. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 11, 2014 14:53