Docusate

Identification

Name
Docusate
Accession Number
DB11089
Description

Docusate, or dioctyl sulfosuccinate, is a stool softener indicated for the treatment of constipation1. Docusate acts by increasing the amount of water the stool absorbs in the gut, making the stool softer and easier to pass 6. Docusate can be orally or rectally administered. Docusate is on the World Health Organization's List of Essential Medicines9. However the effectiveness of docusate in treating constipation remains unclear, as several studies report docusate to be no more effective than placebo for increasing the frequency of stool or stool softening 2,5. Recently there has been pressure to stop prescribing docusate as it has been identified as an ineffective medicine3,5,8. Additionally, it does not appear to lessen symptoms associated with constipation such as abdominal cramps. Still docusate is available in over-the-counter products as a common laxative.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 422.577
Monoisotopic: 422.23382426
Chemical Formula
C20H38O7S
Synonyms
  • Dioctyl sulfosuccinate
  • Docusate hydrogen
External IDs
  • E480

Pharmacology

Indication

Indicated for the treatment of constipation associated with dry, hard stools or opioid induced constipation4. Though recently, pressure has been building to end the use of docusate over concerns of efficacy3,5,8.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Docusate sodium is a laxative and an anionic detergent that supposedly promotes incorporation of water and fats into stool through a reduction in surface tension, resulting in softer fecal mass 6,4. Docusate's onset of action is 6-72 hours orally and 2-15 minutes rectally 6,7. The effects of docusate are thought to be exerted locally in the jejunum1.

Mechanism of action

Recent studies suggest that docusate's mechanism of action is due largely to it's surfactant effect in the intestines, which allow fat and water into the feces to soften the stool4.

Docusate’s mechanism of action was investigated in 1985 on healthy patients.1 Docusate was added directly to the jejunum based on calculated concentrations of docusate in the jejunum.1 At this concentration, there was an increase in secretion of water, sodium, chloride, and potassium as well as a decrease in absorption of glucose and bicarbonate1. Based on in vitro data, the authors suggested this effect was due to an increase in intracellular cyclic AMP either directly through docusate or E series prostaglandins.1

Absorption

Docusate is not absorbed systemically6,8. As the actions of docusate are local and it is not absorbed, the pharmacokinetic parameters are not available8.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

If docusate is systemically absorbed, it undergoes biliary excretion 6,8.

Half-life
Not Available
Clearance
Not Available
Adverse Effects
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Toxicity

Docusate is not known to be carcinogenic or cause reproductive toxicity. It was not mutagenic in the Ames assay MSDS. Acute oral LD50 in rat is 1900 mg/kg MSDS.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Docusate.
AclidiniumThe therapeutic efficacy of Docusate can be decreased when used in combination with Aclidinium.
AlfentanilThe therapeutic efficacy of Docusate can be decreased when used in combination with Alfentanil.
AlloinThe risk or severity of adverse effects can be increased when Docusate is combined with Alloin.
AmantadineThe therapeutic efficacy of Docusate can be decreased when used in combination with Amantadine.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Docusate.
AmiodaroneThe therapeutic efficacy of Docusate can be decreased when used in combination with Amiodarone.
AmitriptylineThe therapeutic efficacy of Docusate can be decreased when used in combination with Amitriptyline.
AmlodipineThe therapeutic efficacy of Docusate can be decreased when used in combination with Amlodipine.
AmobarbitalThe therapeutic efficacy of Docusate can be decreased when used in combination with Amobarbital.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Docusate calcium6K7YS503HC128-49-4DWKPZOZZBLWFJX-UHFFFAOYSA-L
Docusate potassiumCIK9F54ZHR7491-09-0CACRHRQTJDKAPJ-UHFFFAOYSA-M
Docusate sodiumF05Q2T2JA0577-11-7APSBXTVYXVQYAB-UHFFFAOYSA-M
Active Moieties
NameKindUNIICASInChI Key
Sodium cationionicLYR4M0NH3717341-25-2FKNQFGJONOIPTF-UHFFFAOYSA-N
Product Images
International/Other Brands
Audinorm / Clear ear / Colace / Correctol / Dialose / Docusol / Docusol 100 / Doxinate / Dulcoease / Rectalad enema / Surfak
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-docusate SodiumCapsuleOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Albert DocusateCapsuleOralAventis Pharma Ltd.1991-12-312001-07-20Canada flag
Alta-docusate SodiumCapsuleOralAltamed Pharma2018-05-25Not applicableCanada flag
Apo-docusate CalciumCapsuleOralApotex Corporation2002-11-25Not applicableCanada flag
Apo-docusate SodiumCapsuleOralApotex Corporation2002-11-04Not applicableCanada flag
Basic Care Stool SoftenerCapsule, liquid filled100 mg/1OralL. Perrigo Company2018-03-27Not applicableUS flag
Basic Care Stool SoftenerCapsule, liquid filled100 mg/1OralAmazon.com Services LLC2020-07-14Not applicableUS flag
Calax Cap 240mgCapsuleOralOdan Laboratories Ltd1989-12-312015-06-16Canada flag
ColaceCapsule50 mg/1OralCardinal Health2011-06-072013-12-31US flag
ColaceCapsule, liquid filled50 mg/1OralAvrio Health L.P.1900-01-07Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2 In 1laxative Stool Softener and Stiulant LaxativeDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)Tablet, coatedOralRite Aid2020-06-01Not applicableUS flag
2 In 1laxative Stool Softener and Stiulant LaxativeDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)Tablet, coatedOralRite Aid2020-06-01Not applicableUS flag
AcidobylDocusate sodium (60 mg) + Dehydrocholic acid (120 mg) + Homatropine methylbromide (0.5 mg) + Sodium taurocholate (120 mg)TabletOralDesbergers LtÉe, Division Of Technilab Inc.1951-12-311999-09-17Canada flag
Calcium Docuphen CapDocusate calcium (60 mg) + Phenolphthalein (65 mg)CapsuleOralPharmascience Inc1988-12-311997-10-10Canada flag
CAREALL Senna-S LaxativeDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)TabletOralNew World Imports, Inc.2016-04-182022-06-01US flag
CitraNatal 90 DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (160 mg/1) + Cupric oxide (2 mg/1) + Folic acid (1 mg/1) + Iron (90 mg/1) + Nicotinamide (20 mg/1) + Potassium triiodide (150 ug/1) + Pyridoxine hydrochloride (20 mg/1) + Riboprine (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal2010-02-01Not applicableUS flag
CitraNatal DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (125 mg/1) + Cupric oxide (2 mg/1) + Folic acid (1 mg/1) + Iron (27 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal2007-11-20Not applicableUS flag
ColaceDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)Tablet, film coatedOralAvrio Health L.P.1957-02-08Not applicableUS flag
ColaceDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)Tablet, film coatedOralAvrio Health L.P.1957-02-08Not applicableUS flag
Colistat PlusDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)Tablet, film coatedOralAmvilab Llc2015-07-16Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BioFerr 90Docusate sodium (55 mg/1) + Ascorbic acid (138 mg/1) + Cyanocobalamin (16.8 ug/1) + Ferrous gluconate dihydrate (13.2 mg/1) + Folic acid (1.4 mg/1) + Iron (88.5 mg/1)Tablet, film coatedOralBiocomp Pharma, Inc.2014-07-01Not applicableUS flag
CitraNatal 90 DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (159 mg/1) + Cupric oxide (2 mg/1) + Ferrous gluconate dihydrate (5 mg/1) + Folic acid (1 mg/1) + Iron (85 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Thiamine mononitrate (4.54 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal Company2014-04-11Not applicableUS flag
CitraNatal 90 DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (160 mg/1) + Cupric oxide (2 mg/1) + Folic acid (1 mg/1) + Iron (90 mg/1) + Nicotinamide (20 mg/1) + Potassium triiodide (150 ug/1) + Pyridoxine hydrochloride (20 mg/1) + Riboprine (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal2010-02-01Not applicableUS flag
CitraNatal AssureDocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (124 mg/1) + Cholecalciferol (400 [iU]/1) + Copper (2 mg/1) + Doconexent (300 mg/1) + Folic acid (1 mg/1) + Icosapent (0.75 mg/1) + Iodine (150 ug/1) + Iron (35 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc (25 mg/1)KitOralMission Pharmacal Company2014-04-30Not applicableUS flag
CitraNatal AssureDocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (125 mg/1) + Cholecalciferol (400 [iU]/1) + Copper (2 mg/1) + Doconexent (300 mg/1) + Folic acid (1 mg/1) + Icosapent (0.75 mg/1) + Iodine (150 ug/1) + Iron (35 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc (25 mg/1)KitOralMission Pharmacal2008-11-19Not applicableUS flag
CitraNatal BloomDocusate sodium (55 mg/1) + Ascorbic acid (138 mg/1) + Cyanocobalamin (16.8 ug/1) + Ferrous gluconate dihydrate (13.2 mg/1) + Folic acid (1.4 mg/1) + Iron (88.5 mg/1)Tablet, film coatedOralMission Pharmacal Company2017-08-01Not applicableUS flag
CitraNatal BloomDocusate sodium (55 mg/1) + Ascorbic acid (138 mg/1) + Cyanocobalamin (16.8 ug/1) + Ferrous gluconate dihydrate (13.2 mg/1) + Folic acid (1.4 mg/1) + Iron (88.5 mg/1)Tablet, film coatedOralMission Pharmacal Company2017-08-012017-07-20US flag
CitraNatal Bloom DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Crypthecodinium cohnii DHA oil (300 mg/300mg) + Cyanocobalamin (12 ug/1) + Ferrous gluconate dihydrate (1.5 mg/1) + Folic acid (1 mg/1) + Iron (88.5 mg/1)KitOralMission Pharmacal Company2018-01-18Not applicableUS flag
CitraNatal DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (124 mg/1) + Cupric oxide (2 mg/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (0.625 mg/1) + Iron (27 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)KitOralMission Pharmacal Company2014-05-22Not applicableUS flag
CitraNatal DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (125 mg/1) + Cupric oxide (2 mg/1) + Folic acid (1 mg/1) + Iron (27 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal2007-11-20Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acid esters
Direct Parent
Fatty acid esters
Alternative Parents
Dicarboxylic acids and derivatives / Sulfonyls / Organosulfonic acids / Alkanesulfonic acids / Carboxylic acid esters / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Alkanesulfonic acid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Fatty acid ester / Hydrocarbon derivative / Organic oxide / Organic oxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
alkanesulfonic acid, succinate ester (CHEBI:534)

Chemical Identifiers

UNII
M7P27195AG
CAS number
10041-19-7
InChI Key
HNSDLXPSAYFUHK-UHFFFAOYSA-N
InChI
InChI=1S/C20H38O7S/c1-5-9-11-16(7-3)14-26-19(21)13-18(28(23,24)25)20(22)27-15-17(8-4)12-10-6-2/h16-18H,5-15H2,1-4H3,(H,23,24,25)
IUPAC Name
1,4-bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonic acid
SMILES
CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(O)(=O)=O

References

General References
  1. Moriarty KJ, Kelly MJ, Beetham R, Clark ML: Studies on the mechanism of action of dioctyl sodium sulphosuccinate in the human jejunum. Gut. 1985 Oct;26(10):1008-13. [PubMed:2414161]
  2. Tarumi Y, Wilson MP, Szafran O, Spooner GR: Randomized, double-blind, placebo-controlled trial of oral docusate in the management of constipation in hospice patients. J Pain Symptom Manage. 2013 Jan;45(1):2-13. doi: 10.1016/j.jpainsymman.2012.02.008. Epub 2012 Aug 11. [PubMed:22889861]
  3. MacMillan TE, Kamali R, Cavalcanti RB: Missed Opportunity to Deprescribe: Docusate for Constipation in Medical Inpatients. Am J Med. 2016 Sep;129(9):1001.e1-7. doi: 10.1016/j.amjmed.2016.04.008. Epub 2016 May 3. [PubMed:27154771]
  4. McRorie JW, Daggy BP, Morel JG, Diersing PS, Miner PB, Robinson M: Psyllium is superior to docusate sodium for treatment of chronic constipation. Aliment Pharmacol Ther. 1998 May;12(5):491-7. [PubMed:9663731]
  5. Hurdon V, Viola R, Schroder C: How useful is docusate in patients at risk for constipation? A systematic review of the evidence in the chronically ill. J Pain Symptom Manage. 2000 Feb;19(2):130-6. [PubMed:10699540]
  6. Docusate sodium/Senna: Drug Information [Link]
  7. Docusate sodium Drug Summary [Link]
  8. Alberta Health Services Drugs and Therapeutics Background- Stool Softeners: WHY Are They Still Used? [Link]
  9. World Health Organization List of Essential Medicines 2017 [Link]
  10. DailyMed: Docusate/Sennosides oral tablet [Link]
Human Metabolome Database
HMDB0032386
KEGG Drug
D00305
KEGG Compound
C07874
PubChem Substance
347911112
ChemSpider
10862
RxNav
82003
ChEBI
534
ChEMBL
CHEMBL1477036
Drugs.com
Drugs.com Drug Page
Wikipedia
Docusate
AHFS Codes
  • 56:12.00 — Cathartics and Laxatives
MSDS
Download (129 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionPostoperative Bowel Movement / Postoperative Passage of Flatus1
4CompletedTreatmentConstipation1
4CompletedTreatmentConstipation / General Surgery / Ileus1
4RecruitingPreventionConstipation1
4TerminatedPreventionAnalgesia / Constipation1
4Unknown StatusPreventionConstipation1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Dyspnea1
3CompletedTreatmentConstipation1
2RecruitingPreventionConstipation1
2TerminatedTreatmentDiabetic Gastroparesis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral5 mg
KitOral
CapsuleOral50 mg/1
Solution / dropsOral
LiquidRectal100 mg/5mL
Solution / dropsAuricular (otic)500 mg/100mL
SyrupOral20 mg/5mL
CapsuleOral240 mg
CapsuleOral240 mg/1
CapsuleOral100 mg/1
CapsuleOral250 mg/1
Capsule, liquid filledOral100 mg/1
Capsule, liquid filledOral50 mg/1
LiquidOral50 mg/5mL
Solution / dropsOral10 mg
SyrupOral20 mg
EnemaRectal283 mg
Capsule, liquid filledOral200 mg
LiquidRectal283 mg/5mL
LiquidRectal
TabletOral
Capsule, liquid filledOral250 mg/1
Capsule, liquid filledOral250 mg/250mg
Capsule, gelatin coatedOral100 mg/601
Solution / dropsAuricular (otic)
Tablet, film coatedOral100 mg/1
Tablet, coatedOral
TabletOral
TabletOral50 MG
Tablet, coatedOral8 mg
CapsuleOral100 MG
CapsuleOral
LiquidOral50 mg/15mL
SyrupOral
Capsule, liquid filledOral
Capsule, gelatin coatedOral
TabletOral100 mg/1
Tablet, film coatedOral
Tablet, coatedOral50 mg
PillOral
LiquidOral10 mg/1mL
SyrupOral60 mg/15mL
Solution / dropsAuricular (otic)0.5 %
Capsule, gelatin coatedOral100 mg/1
Capsule, liquid filledOral200 mg/1
Capsule, liquid filledOral240 mg/1
Capsule, gelatin coatedOral240 mg/1
TabletOral5 mg
CapsuleOral
EnemaRectal283 mg/5mL
EnemaRectal
EnemaRectal13.4 g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)153-157MSDS
water solubilitySolubleMSDS
logP3.95MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.00402 mg/mLALOGPS
logP2.48ALOGPS
logP5.24ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-0.75ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.97 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity107.35 m3·mol-1ChemAxon
Polarizability46.82 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on December 03, 2015 09:51 / Updated on December 02, 2020 00:54

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