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Identification
NameMisoprostol
Accession NumberDB00929  (APRD00037)
TypeSmall Molecule
GroupsApproved
Description

A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties. [PubChem]

Structure
Thumb
Synonyms
Cytotec
Misoprostolum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cytotectablet100 ug/1oralG.D. Searle LLC Division of Pfizer Inc1986-12-27Not applicableUs
Cytotectablet100 ug/1oralPhysicians Total Care, Inc.1996-07-02Not applicableUs
Cytotectablet200 ug/1oralA S Medication Solutions Llc1986-12-27Not applicableUs
Cytotectablet200 ug/1oralApotheca, Inc2010-01-01Not applicableUs
Cytotectablet100 ug/1oralPd Rx Pharmaceuticals, Inc.1986-12-27Not applicableUs
Cytotectablet100 ug/1oralCardinal Health1988-12-27Not applicableUs
Cytotectablet200 ug/1oralG.D. Searle LLC Division of Pfizer Inc1986-12-27Not applicableUs
Cytotectablet200 ug/1oralCardinal Health1988-12-27Not applicableUs
Cytotec 100 Mcgtablet100 mcgoralPfizer Canada Inc1989-12-312004-07-26Canada
Cytotec 200 Mcgtablet200 mcgoralPfizer Canada Inc1986-12-312005-08-05Canada
Misoprostoltablet200 ug/1oralGreenstone LLC2009-12-27Not applicableUs
Misoprostoltablet100 ug/1oralGreenstone LLC2009-12-27Not applicableUs
Misoprostoltablet200 ug/1oralClinical Solutions Wholesale2009-12-27Not applicableUs
Misoprostoltablet100 ug/1oralH.J. Harkins Company, Inc.2009-12-27Not applicableUs
Misoprostoltablet100 ug/1oralPd Rx Pharmaceuticals, Inc.2009-12-27Not applicableUs
Misoprostoltablet200 mcgoralAa Pharma Inc2001-06-18Not applicableCanada
Misoprostoltablet200 ug/1oralApotheca, Inc.1997-09-17Not applicableUs
Misoprostoltablet100 mcgoralAa Pharma Inc2001-06-18Not applicableCanada
Misoprostoltablet200 ug/1oralDispensing Solutions, Inc.2009-12-27Not applicableUs
Misoprostol-200tablet200 mcgoralPro Doc Limitee2004-04-012009-07-23Canada
Novo-misoprostol Tabletstablet100 mcgoralNovopharm Limited2001-11-15Not applicableCanada
Novo-misoprostol Tabletstablet200 mcgoralNovopharm Limited2001-11-15Not applicableCanada
PMS-misoprostol (0.1mg)tablet0.1 mgoralPharmascience Inc2001-09-20Not applicableCanada
PMS-misoprostol (0.2mg)tablet0.2 mgoralPharmascience Inc2001-09-20Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Misoprostoltablet100 ug/1oralAmerican Health Packaging2013-07-16Not applicableUs
Misoprostoltablet100 ug/1oralApotheca, Inc.2010-02-25Not applicableUs
Misoprostoltablet200 ug/1oralAvera Mc Kennan Hospital2015-04-06Not applicableUs
Misoprostoltablet100 ug/1oralGAVIS Pharmaceuticals, LLC2012-07-25Not applicableUs
Misoprostoltablet200 ug/1oralReady Meds2012-07-25Not applicableUs
Misoprostoltablet200 ug/1oralPd Rx Pharmaceuticals, Inc.2012-07-25Not applicableUs
Misoprostoltablet200 ug/1oralPharmacist Pharmaceutical, LLC2013-04-12Not applicableUs
Misoprostoltablet200 ug/1oralNovel Laboratories, Inc.2012-07-25Not applicableUs
Misoprostoltablet200 ug/1oralbryant ranch prepack2002-07-10Not applicableUs
Misoprostoltablet100 ug/1oralNovel Laboratories, Inc.2012-07-25Not applicableUs
Misoprostoltablet200 ug/1oralCardinal Health2013-07-16Not applicableUs
Misoprostoltablet100 ug/1oralAidarex Pharmaceuticals LLC2012-07-25Not applicableUs
Misoprostoltablet200 ug/1oralGen Bio Pro Inc2013-01-02Not applicableUs
Misoprostoltablet200 ug/1oralAmerican Health Packaging2013-07-16Not applicableUs
Misoprostoltablet200 ug/1oralAidarex Pharmaceuticals LLC2012-07-25Not applicableUs
Misoprostoltablet200 ug/1oralGAVIS Pharmaceuticals, LLC2012-07-25Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Act Diclo-misoActavis Pharma Company
ArthrotecG.D. Searle LLC Division of Pfizer Inc
Arthrotec 50Pfizer Canada Inc
Arthrotec 75Pfizer Canada Inc
Diclofenac MisoprostolAbri Pharmaceuticals Inc
Diclofenac Sodium and MisoprostolActavis Pharma, Inc.
Diclofenac Sodium and Misoprostol Delayed-releaseEagle Pharmaceuticals, Inc.
Gd-diclofenac/misoprostol 50Genmed A Division Of Pfizer Canada Inc
Gd-diclofenac/misoprostol 75Genmed A Division Of Pfizer Canada Inc
MifegymisoLinepharma International Limited
PMS-diclofenac-misoprostolPharmascience Inc
Sandoz Diclofenac MisoprostolSandoz Canada Incorporated
SaltsNot Available
Categories
UNII0E43V0BB57
CAS number59122-46-2
WeightAverage: 382.5341
Monoisotopic: 382.271924326
Chemical FormulaC22H38O5
InChI KeyInChIKey=OJLOPKGSLYJEMD-URPKTTJQSA-N
InChI
InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1
IUPAC Name
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate
SMILES
CCCCC(C)(O)C\C=C\[[email protected]]1[[email protected]](O)CC(=O)[C@@H]1CCCCCCC(=O)OC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Fatty acid methyl ester
  • Fatty acid ester
  • Cyclopentanol
  • Methyl ester
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationIndicated for the treatment of ulceration (duodenal, gastric and NSAID induced) and prophylaxis for NSAID induced ulceration. Misoprostol is also indicated for other uses that are not approved in Canada, including the medical termination of an intrauterine pregnancy used alone or in combination with methotrexate,as well as the induction of labour in a selected population of pregnant women with unfavourable cervices. This indication is avoided in women with prior uterine surgery or cesarean surgery due to an increased risk of possible uterine rupture. Misoprostol is also used for the prevention or treatment of serious postpartum hemorrhage.
PharmacodynamicsMisoprostol is a prostaglandin E1 (PGE1) analogue used for the treatment and prevention of stomach ulcers. When administered, misoprostol stimulates increased secretion of the protective mucus that lines the gastrointestinal tract and increases mucosal blood flow, thereby increasing mucosal integrity. It is sometimes co-prescribed with non-steroidal anti-inflammatory drugs (NSAIDs) to prevent the occurrence of gastric ulceration, a common adverse effect of the NSAIDs.
Mechanism of actionMisoprostol seems to inhibit gastric acid secretion by a direct action on the parietal cells through binding to the prostaglandin receptor. The activity of this receptor is mediated by G proteins which normally activate adenylate cyclase. The indirect inhibition of adenylate cyclase by Misoprostol may be dependent on guanosine-5’-triphosphate (GTP). The significant cytoprotective actions of misoprostol are related to several mechanisms. These include: 1. Increased secretion of bicarbonate, 2. Considerable decrease in the volume and pepsin content of the gastric secretions, 3. It prevents harmful agents from disrupting the tight junctions between the epithelial cells which stops the subsequent back diffusion of H+ ions into the gastric mucosa, 4. Increased thickness of mucus layer, 5. Enhanced mucosal blood flow as a result of direct vasodilatation, 6. Stabilization of tissue lysozymes/vascular endothelium, 7. Improvement of mucosal regeneration capacity, and 8. Replacement of prostaglandins that have been depleted as a result of various insults to the area. Misoprostol has also been shown to increase the amplitude and frequency of uterine contractions during pregnancy via selective binding to the EP-2/EP-3 prostanoid receptors.
Related Articles
AbsorptionMisoprostol is extensively absorbed.
Volume of distributionNot Available
Protein binding85%
Metabolism

Rapidly de-esterified to misoprostol acid. The de-esterified metabolite undergoes further metabolism by beta and omega oxidation; oxidation is followed by reduction of the ketone to yield prostaglandin F analogs.

Route of eliminationAfter a single oral dose of misoprostol to nursing mothers, misoprostol acid was excreted in breast milk.
Half life20-40 minutes
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+0.9157
Blood Brain Barrier+0.938
Caco-2 permeable-0.5339
P-glycoprotein substrateSubstrate0.6607
P-glycoprotein inhibitor INon-inhibitor0.7261
P-glycoprotein inhibitor IIInhibitor0.6504
Renal organic cation transporterNon-inhibitor0.9146
CYP450 2C9 substrateNon-substrate0.857
CYP450 2D6 substrateNon-substrate0.9024
CYP450 3A4 substrateSubstrate0.6281
CYP450 1A2 substrateNon-inhibitor0.8358
CYP450 2C9 inhibitorNon-inhibitor0.8175
CYP450 2D6 inhibitorNon-inhibitor0.9459
CYP450 2C19 inhibitorNon-inhibitor0.8199
CYP450 3A4 inhibitorNon-inhibitor0.795
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9591
Ames testNon AMES toxic0.8289
CarcinogenicityNon-carcinogens0.8941
BiodegradationNot ready biodegradable0.8797
Rat acute toxicity3.7051 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.964
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Gd searle llc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Packagers
Dosage forms
FormRouteStrength
Tablet, film coatedoral
Tabletoral
Tabletoral100 ug/1
Tabletoral200 ug/1
Tablet (enteric-coated)oral
Tablet, delayed releaseoral
Kit; tabletbuccal; oral
Tabletoral100 mcg
Tabletoral200 mcg
Tabletoral0.1 mg
Tabletoral0.2 mg
Prices
Unit descriptionCostUnit
Misoprostol hpmc powder152.0USD g
Cytotec 60 200 mcg tablet Bottle121.93USD bottle
Cytotec 60 100 mcg tablet Bottle81.36USD bottle
Arthrotec 75 tablet ec4.07USD tablet
Arthrotec ec 50 mg-200 mcg tablet2.99USD tablet
Arthrotec ec 75 mg-200 mcg tablet2.99USD tablet
Arthrotec ec 75 tablet2.96USD tablet
Arthrotec 75 75-200 mg-mcg tablet2.82USD tablet
Arthrotec 50 50-200 mg-mcg tablet2.7USD tablet
Cytotec 200 mcg tablet1.95USD tablet
Cytotec 100 mcg tablet1.34USD tablet
Misoprostol 200 mcg tablet1.22USD tablet
Misoprostol 100 mcg tablet0.84USD tablet
Apo-Misoprostol 200 mcg Tablet0.45USD tablet
Apo-Misoprostol 100 mcg Tablet0.27USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5601843 No1994-02-112014-02-11Us
US5698225 No1993-05-032010-05-03Us
Properties
StateLiquid
Experimental Properties
PropertyValueSource
water solubility>1.6 mg/mL at 25.0 °CNot Available
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0164 mg/mLALOGPS
logP3.88ALOGPS
logP3.86ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity107.88 m3·mol-1ChemAxon
Polarizability45.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Salah Ahmed, Raj Mahajan, “Vaginal tablets comprising misoprostol and methods of making and using the same.” U.S. Patent US20070071814, issued March 29, 2007.

US20070071814
General References
  1. Costa SH, Vessey MP: Misoprostol and illegal abortion in Rio de Janeiro, Brazil. Lancet. 1993 May 15;341(8855):1258-61. [PubMed:8098402 ]
  2. Coelho HL, Teixeira AC, Cruz Mde F, Gonzaga SL, Arrais PS, Luchini L, La Vecchia C, Tognoni G: Misoprostol: the experience of women in Fortaleza, Brazil. Contraception. 1994 Feb;49(2):101-10. [PubMed:8143449 ]
  3. Barbosa RM, Arilha M: The Brazilian experience with Cytotec. Stud Fam Plann. 1993 Jul-Aug;24(4):236-40. [PubMed:8212093 ]
  4. Rocha J: Brazil investigates drug's possible link with birth defects. BMJ. 1994 Sep 24;309(6957):757-8. [PubMed:7950553 ]
  5. Gonzalez CH, Vargas FR, Perez AB, Kim CA, Brunoni D, Marques-Dias MJ, Leone CR, Correa Neto J, Llerena Junior JC, de Almeida JC: Limb deficiency with or without Mobius sequence in seven Brazilian children associated with misoprostol use in the first trimester of pregnancy. Am J Med Genet. 1993 Aug 1;47(1):59-64. [PubMed:8368254 ]
External Links
ATC CodesA02BB01G02AD06M01AE56
AHFS Codes
  • 56:28.28
PDB EntriesNot Available
FDA labelDownload (246 KB)
MSDSDownload (147 KB)
Interactions
Drug Interactions
Drug
Aluminum hydroxideThe risk or severity of adverse effects can be increased when Aluminum hydroxide is combined with Misoprostol.
Calcium carbonateThe risk or severity of adverse effects can be increased when Calcium carbonate is combined with Misoprostol.
CarbetocinThe risk or severity of adverse effects can be increased when Misoprostol is combined with Carbetocin.
Magnesium hydroxideThe risk or severity of adverse effects can be increased when Magnesium hydroxide is combined with Misoprostol.
Magnesium oxideThe risk or severity of adverse effects can be increased when Magnesium oxide is combined with Misoprostol.
OxytocinThe risk or severity of adverse effects can be increased when Misoprostol is combined with Oxytocin.
Food Interactions
  • Take with food to decrease the incidence of diarrhea.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Rna polymerase ii transcription factor activity, ligand-activated sequence-specific dna binding
Specific Function:
Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition of sodium and water reabsorption in kidney tubulus and contraction in uterine smooth muscle. The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G-I protei...
Gene Name:
PTGER3
Uniprot ID:
P43115
Molecular Weight:
43309.335 Da
References
  1. Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053 ]
  2. Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336 ]
  3. Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143 ]
  4. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928 ]
  5. Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Prostaglandin e receptor activity
Specific Function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
Gene Name:
PTGER2
Uniprot ID:
P43116
Molecular Weight:
39759.945 Da
References
  1. Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053 ]
  2. Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336 ]
  3. Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143 ]
  4. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928 ]
  5. Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Prostaglandin e receptor activity
Specific Function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. Has a relaxing effect on smooth muscle. May play an important role in regulating renal hemodynamics, intestinal epithelial transport, adrenal aldosterone secretion, and uterine function.
Gene Name:
PTGER4
Uniprot ID:
P35408
Molecular Weight:
53118.845 Da
References
  1. Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053 ]
  2. Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336 ]
  3. Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143 ]
  4. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928 ]
  5. Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631 ]
  6. Crider JY, Xu SX, Sharif NA: Pharmacology of functional endogenous IP prostanoid receptors in NCB-20 cells: comparison with binding data from human platelets. Prostaglandins Leukot Essent Fatty Acids. 2001 Nov-Dec;65(5-6):253-8. [PubMed:11993717 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23