Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H15NO.ClH |
Molecular Weight | 201.693 |
Optical Activity | ( + ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN[C@@H](C)[C@@H](O)C1=CC=CC=C1
InChI
InChIKey=BALXUFOVQVENIU-KXNXZCPBSA-N
InChI=1S/C10H15NO.ClH/c1-8(11-2)10(12)9-6-4-3-5-7-9;/h3-8,10-12H,1-2H3;1H/t8-,10+;/m0./s1
DescriptionSources: https://www.drugs.com/pseudoephedrine.htmlCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12373557 | http://www.mayoclinic.org/drugs-supplements/ephedra--ma-huang/background/hrb-20059270 | https://www.sudafed.com/adult-products/congestion/sudafed-24-hour#uses-and-directions | https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0011888 | https://www.ncbi.nlm.nih.gov/pubmed/11772135 | https://www.ncbi.nlm.nih.gov/pubmed/10449190 | https://www.ncbi.nlm.nih.gov/pubmed/12954796
Sources: https://www.drugs.com/pseudoephedrine.html
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12373557 | http://www.mayoclinic.org/drugs-supplements/ephedra--ma-huang/background/hrb-20059270 | https://www.sudafed.com/adult-products/congestion/sudafed-24-hour#uses-and-directions | https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0011888 | https://www.ncbi.nlm.nih.gov/pubmed/11772135 | https://www.ncbi.nlm.nih.gov/pubmed/10449190 | https://www.ncbi.nlm.nih.gov/pubmed/12954796
Pseudoephedrine is a sympathomimetic drug. Pseudoephedrine acts as an adrenomimetic and inhibitor of monoamine transporters. Ephedra sinica, a species of ephedra (ma huang), contains ephedrine and pseudoephedrine. Ephedra has been found to stimulate the nervous system, increase airflow into the lungs and constrict blood vessels. In combination with caffeine, ephedra appears to cause weight loss. Pseudoephedrine is a decongestant that shrinks blood vessels in the nasal passages. Pseudoephedrine is used to relieve nasal or sinus congestion caused by the common cold, sinusitis, and hay fever and other respiratory allergies.
Originator
Sources: A. Ladenburg, C. Oelschlägel, Ber. 22, 1823 (1889).
Curator's Comment: (+)-threo-isomer of ephedrine, q.v. Isoln from E. vulgaris: A. Ladenburg, C. Oelschlägel, Ber. 22, 1823 (1889). Synthesis: E. Späth, R. Göhring, Monatsh. Chem. 41, 319 (1920). reference retrieved from http://www.drugfuture.com/chemdata/pseudoephedrine.html
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL238 |
5.6 µM [IC50] | ||
Target ID: CHEMBL222 |
1.18 µM [IC50] | ||
Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796 |
|||
Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10449190 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SUDAFED 24 HOUR Approved Usetemporarily relieves nasal congestion due to the common cold, hay fever or other upper respiratory allergies; reduces swelling of nasal passages; relieves sinus pressure Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
292 ng/mL |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PSEUDOEPHEDRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4346 ng × h/mL |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PSEUDOEPHEDRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.3 h |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PSEUDOEPHEDRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1500 mg single, oral Overdose |
unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: |
Other AEs: Rhabdomyolysis, Creatine kinase increased... Other AEs: Rhabdomyolysis (1 patient) Sources: Creatine kinase increased (1 patient) Blood myoglobin increased (1 patient) |
150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Other AEs: Tension, Dry mouth... Other AEs: Tension (10 patients) Sources: Dry mouth (6 patients) Tachycardia (9 patients) Palpitations (10 patients) Anxiety (13 patients) Insomnia (12 patients) Anorexia (7 patients) Restlessness (10 patients) |
90 mg 1 times / day multiple, oral Overdose Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: |
unhealthy, 3 years n = 1 Health Status: unhealthy Age Group: 3 years Sex: M Population Size: 1 Sources: |
Disc. AE: Urinary retention... AEs leading to discontinuation/dose reduction: Urinary retention (acute, 1 patient) Sources: |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: sinusitis Age Group: 37 years Sex: F Population Size: 1 Sources: |
Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: Abdominal pain (acute, 1 patient) |
720 mg 1 times / day multiple, oral Highest studied dose Dose: 720 mg, 1 times / day Route: oral Route: multiple Dose: 720 mg, 1 times / day Sources: |
unhealthy, 38.8 years n = 38 Health Status: unhealthy Age Group: 38.8 years Sex: M+F Population Size: 38 Sources: |
|
30 mg 3 times / day multiple, oral Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
unhealthy, 44 years n = 1 Health Status: unhealthy Condition: upper airway infection Age Group: 44 years Sex: F Population Size: 1 Sources: |
Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: Abdominal pain (acute, 1 patient) |
120 mg 1 times / day multiple, oral Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic sinusitis | allergic rhinitis Age Group: 46 years Sex: F Population Size: 1 Sources: |
Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: Abdominal pain (acute, 1 patient) |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: chlorpheniramine maleate(2 mg; twice daily, oral) |
unhealthy, 50 years n = 1 Health Status: unhealthy Condition: rhinitis Age Group: 50 years Sex: F Population Size: 1 Sources: |
Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: Abdominal pain (acute, 1 patient) |
720 mg single, oral Overdose |
unhealthy, 87 years n = 1 Health Status: unhealthy Age Group: 87 years Sex: M Population Size: 1 Sources: |
Other AEs: Hypertension... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Blood myoglobin increased | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: |
Creatine kinase increased | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: |
Rhabdomyolysis | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: |
Palpitations | 10 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Restlessness | 10 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Tension | 10 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Insomnia | 12 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Anxiety | 13 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Dry mouth | 6 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Anorexia | 7 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Tachycardia | 9 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Urinary retention | acute, 1 patient Disc. AE |
90 mg 1 times / day multiple, oral Overdose Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: |
unhealthy, 3 years n = 1 Health Status: unhealthy Age Group: 3 years Sex: M Population Size: 1 Sources: |
Ischemic colitis | 1 patient Disc. AE |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: sinusitis Age Group: 37 years Sex: F Population Size: 1 Sources: |
Abdominal pain | acute, 1 patient Disc. AE |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: sinusitis Age Group: 37 years Sex: F Population Size: 1 Sources: |
Ischemic colitis | 1 patient Disc. AE |
30 mg 3 times / day multiple, oral Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
unhealthy, 44 years n = 1 Health Status: unhealthy Condition: upper airway infection Age Group: 44 years Sex: F Population Size: 1 Sources: |
Abdominal pain | acute, 1 patient Disc. AE |
30 mg 3 times / day multiple, oral Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
unhealthy, 44 years n = 1 Health Status: unhealthy Condition: upper airway infection Age Group: 44 years Sex: F Population Size: 1 Sources: |
Ischemic colitis | 1 patient Disc. AE |
120 mg 1 times / day multiple, oral Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic sinusitis | allergic rhinitis Age Group: 46 years Sex: F Population Size: 1 Sources: |
Abdominal pain | acute, 1 patient Disc. AE |
120 mg 1 times / day multiple, oral Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic sinusitis | allergic rhinitis Age Group: 46 years Sex: F Population Size: 1 Sources: |
Ischemic colitis | 1 patient Disc. AE |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: chlorpheniramine maleate(2 mg; twice daily, oral) |
unhealthy, 50 years n = 1 Health Status: unhealthy Condition: rhinitis Age Group: 50 years Sex: F Population Size: 1 Sources: |
Abdominal pain | acute, 1 patient Disc. AE |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: chlorpheniramine maleate(2 mg; twice daily, oral) |
unhealthy, 50 years n = 1 Health Status: unhealthy Condition: rhinitis Age Group: 50 years Sex: F Population Size: 1 Sources: |
Hypertension | 1 patient | 720 mg single, oral Overdose |
unhealthy, 87 years n = 1 Health Status: unhealthy Age Group: 87 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
A Double-blind crossover trial of pseudoephedrine and triprolidine, alone and in combination, for the treatment of allergenic rhinitis. | 1975 Jan |
|
Dextromethorphan- and pseudoephedrine-induced agitated psychosis and ataxia: case report. | 1999 Mar-Apr |
|
Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options? | 2001 |
|
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures. | 2001 Apr |
|
Angle closure risk from proprietary medicines. | 2001 Apr |
|
Mass spectrometric quantitation of chiral drugs by the kinetic method. | 2001 Apr 15 |
|
Study on the chiral recognition of the enantiomers of ephedrine derivatives with neutral and sulfated heptakis(2,3-O-diacetyl)-beta-cyclodextrins using capillary electrophoresis, UV, nuclear magnetic resonance spectroscopy and mass spectrometry. | 2001 Apr 20 |
|
Ischaemic colitis on pseudoephedrine. | 2001 Aug |
|
Hypokalemic metabolic acidosis attributed to cough mixture abuse. | 2001 Aug |
|
A fast and efficient determination of amines and preservatives in cough and cold liquid and suspension formulations using a single isocratic ion-pairing high performance [correction of power] liquid chromatography method. | 2001 Aug |
|
Aziridine ring-opening reactions with chiral enolates. Stereocontrolled synthesis of 5-substituted-3-methyl-pyrrolidin-2-ones. | 2001 Aug 24 |
|
Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat. | 2001 Jan-Feb |
|
Human islet transplantation network for the treatment of Type I diabetes: first data from the Swiss-French GRAGIL consortium (1999-2000). Groupe de Recherche Rhin Rhĵne Alpes Genève pour la transplantation d'Ilots de Langerhans. | 2001 Jul |
|
Cold-syrup induced movement disorder. | 2001 Jun |
|
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations. | 2001 Jun |
|
Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters by Mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines. | 2001 Mar 8 |
|
Comparative oral and topical decongestant effects of phenylpropanolamine and d-pseudoephedrine. | 2001 Mar-Apr |
|
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man. | 2001 May |
|
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr. | 2001 May |
|
Cardiovascular sympathomimetic amine interactions in rats treated with monoamine oxidase inhibitors and the novel oxazolidinone antibiotic linezolid. | 2001 May |
|
Desloratadine reduces nasal congestion in patients with intermittent allergic rhinitis. | 2001 Nov |
|
Acute psychosis due to the interaction of legal compounds--ephedra alkaloids in 'vigueur fit' tablets, caffeine in 'red bull' and alcohol. | 2001 Oct |
|
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry. | 2001 Sep |
|
Toxicity of over-the-counter cough and cold medications. | 2001 Sep |
|
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations. | 2001 Sep |
|
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes. | 2001 Sep 5 |
|
Generalized dermatitis due to pseudoephedrine. | 2002 Aug |
|
Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase. | 2002 Dec 26 |
|
Immediate hypersensitivity due to pseudoephedrine. | 2002 Jan |
|
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use. | 2002 Jun |
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Oral medications. | 2002 Mar |
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[Bacteremia caused by coagulase-negative staphylococci: incidence, frequency of teicoplanin resistance and molecular epidemiology]. | 2002 Nov |
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A moderate dose of pseudoephedrine does not alter muscle contraction strength or anaerobic power. | 2002 Nov |
|
Enhanced enantio- and diastereoselectivity via confinement and cation binding: yang photocyclization of 2-benzoyladamantane derivatives within zeolites. | 2002 Nov 29 |
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[Blood supply of the lips]. | 2002 Oct |
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[Cutaneous complications following liver transplantation: epidemiologic and clinical study in 86 patients]. | 2002 Oct |
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Enzymatic (R)-phenylacetylcarbinol production in benzaldehyde emulsions. | 2002 Oct |
|
[Improving the medical treatment of minors who are victims of sexual assault or physical abuse: a receiving center and partnership between a psychiatric hospital and university hospital]. | 2003 Apr |
|
Controlled porosity osmotic pump-based controlled release systems of pseudoephedrine. I. Cellulose acetate as a semipermeable membrane. | 2003 Apr 14 |
|
Physiological, subjective and performance effects of pseudoephedrine and phenylpropanolamine during endurance running exercise. | 2003 Jan |
|
Efficacy and safety of clemastine-pseudoephedrine-acetaminophen versus pseudoephedrine-acetaminophen in the treatment of seasonal allergic rhinitis in a 1-day, placebo-controlled park study. | 2003 Jan |
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Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs. | 2003 Jul |
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Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction. | 2003 Jul 5 |
|
Safety of selegiline with cold medications. | 2003 Mar |
|
Adrenaline given outside the context of life threatening allergic reactions. | 2003 Mar 15 |
|
Canine model of nasal congestion and allergic rhinitis. | 2003 May |
Sample Use Guides
SUDAFED® 24 HOUR TABLET, EXTENDED RELEASE; ORAL (PSEUDOEPHEDRINE HYDROCHLORIDE) 240MG
adults and children 12 years and older: a tablet with water every 24 hours
children under 12 years: do not use this product in children under 12 years of age
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21631396
Curator's Comment: Pseudoephedrine inhibits interleukin-2 (IL-2) and tumor necrosis factor (TNF) alpha-gene transcription in stimulated Jurkat cells, a human T-cell leukemia cell line.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29709
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CFR |
21 CFR 341.20
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DEA NO. |
8112
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106567
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6V9V2RYJ8N
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100000092030
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SUB04119MIG
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1581005
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C29390
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CHEMBL1590
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DTXSID10889343
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91168
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33634
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206-462-1
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DBSALT000149
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9581
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6V9V2RYJ8N
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m9294
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PRIMARY | Merck Index |
ACTIVE MOIETY
SUBSTANCE RECORD