Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H8N4O2 |
Molecular Weight | 180.164 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C=NC2=C1C(=O)NC(=O)N2C
InChI
InChIKey=YAPQBXQYLJRXSA-UHFFFAOYSA-N
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
Molecular Formula | C7H8N4O2 |
Molecular Weight | 180.164 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Theobromine is the primary alkaloid present in the cocoa and chocolate. Theobromine is found in the shells and beans of the cacao plant and it is extracted from the husks of the bean and used for the synthesis of caffeine. Theobromine is an adenosine A1 and A2a receptor antagonist. Thesodate is used as a vasodilator, a diuretic, and heart stimulant. And similar to caffeine, it may be useful in management of fatigue and orthostatic hypotension. The symptomatic adverse reactions produced by theobromine are more or less tolerable and if they become severe, they can be treated symptomatically, these include anxiety, restlessness, tremors, sleeplessness, nausea and vomiting, loss of appetite. Theobromine is currently not in use as a medicinal drug.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P30543 Gene ID: 25369.0 Gene Symbol: Adora2a Target Organism: Rattus norvegicus (Rat) |
250.0 µM [IC50] | ||
Target ID: CHEMBL318 |
120.0 µM [Ki] | ||
Target ID: P05177 Gene ID: 1544.0 Gene Symbol: CYP1A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10215755 |
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Target ID: P05181 Gene ID: 1571.0 Gene Symbol: CYP2E1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10215755 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Thesodate Approved UseTheobromine was used as a diuretic and in the treatment of angina pectoris and hypertension. |
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Palliative | Unknown Approved UseUnknown |
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Primary | Thesodate Approved UseTheobromine used as a diuretic and in the treatment of angina pectoris and hypertension |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.38 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27662634 |
4 mg/kg bw single, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
92 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27662634 |
4 mg/kg bw single, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
13351 mg × min/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6729831 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27662634 |
4 mg/kg bw single, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.23 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6729831 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
88% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6729831 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
Title | Date | PubMed |
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Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1. | 1992 Apr |
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Effects of caffeine and its reactive metabolites theophylline and theobromine on the differentiating testis. | 2001 |
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Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
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Improved high-performance liquid chromatography method to determine theobromine and caffeine in cocoa and cocoa products. | 2001 Aug |
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Synergism between A(2A)-adenosine receptor activation and vasoactive intestinal peptide to facilitate [3H]-acetylcholine release from the rat motor nerve terminals. | 2001 Aug 24 |
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Minoxidil-induced hair growth is mediated by adenosine in cultured dermal papilla cells: possible involvement of sulfonylurea receptor 2B as a target of minoxidil. | 2001 Dec |
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Effect of methylxanthine derivatives on doxorubicin transport and antitumor activity. | 2001 Dec |
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Evidence for the presence of A(1) adenosine receptors in the aorta of spontaneously hypertensive rats. | 2001 Dec |
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Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors. | 2001 Dec |
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Simultaneous determination of artificial sweeteners, preservatives, caffeine, theobromine and theophylline in food and pharmaceutical preparations by ion chromatography. | 2001 Dec 7 |
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Protection by aspirin of indomethacin-induced small intestinal damage in rats: mediation by salicylic acid. | 2001 Jan-Dec |
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A novel analgesic compound OT-7100 attenuates nociceptive responses in animal models of inflammatory and neuropathic hyperalgesia: a possible involvement of adenosinergic anti-nociception. | 2001 Nov |
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In vivo effects of adenosine A(2) receptor agonist and antagonist on neuronal and astrocytic intermediary metabolism studied with ex vivo (13)C MR spectroscopy. | 2001 Nov |
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Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. | 2001 Nov-Dec |
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Role of adenosine in renal protection induced by a brief episode of ischemic preconditioning in rats. | 2001 Oct |
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Methotrexate suppresses NF-kappaB activation through inhibition of IkappaBalpha phosphorylation and degradation. | 2001 Sep 1 |
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Determination of theophylline by HPLC and GC-IDMS, the effect of chemically similar xanthine derivatives on the specificity of the method and the possibility of paracetamol as interfering substance. | 2002 |
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Simultaneous determination of caffeine, theobromine, and theophylline by high-performance liquid chromatography. | 2002 Jan |
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Activation of adenosine A2a receptor pathway reduces leukocyte infiltration but enhances edema formation in rat caerulein pancreatitis. | 2002 Jan |
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Inhibition of vaccinia virus replication by adenosine in BSC-40 cells: involvement of A(2) receptor-mediated PKA activation. | 2002 Jul |
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Cacao usage by the earliest Maya civilization. | 2002 Jul 18 |
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Enhanced analysis of purine and pyrimidine bases by the use of double-strand polyaniline coatings in micellar electrokinetic capillary chromatography. | 2002 Jun |
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Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use. | 2002 Jun |
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Synergistic up-regulation of vascular endothelial growth factor expression in murine macrophages by adenosine A(2A) receptor agonists and endotoxin. | 2002 Jun |
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The involvement of nitric oxide on the adenosine A(2) receptor-induced cardiovascular inhibitory responses in the posterior hypothalamus of rats. | 2002 Jun 21 |
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Selective solid-phase extraction sorbent for caffeine made by molecular imprinting. | 2002 Mar 1 |
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Cocaine withdrawal severity and urine toxicology results from treatment entry predict outcome in medication trials for cocaine dependence. | 2002 Mar-Apr |
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Adenosine inhibits calcium channel currents via A1 receptors on salamander retinal ganglion cells in a mini-slice preparation. | 2002 May |
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Spinal noradrenergic activation mediates allodynia reduction from an allosteric adenosine modulator in a rat model of neuropathic pain. | 2002 May |
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Theacrine (1,3,7,9-tetramethyluric acid) synthesis in leaves of a Chinese tea, kucha (Camellia assamica var. kucha). | 2002 May |
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Glucan stimulates human dermal fibroblast collagen biosynthesis through a nuclear factor-1 dependent mechanism. | 2002 May-Jun |
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Chocolate feeding of pregnant mice influences length of limbs of their progeny. | 2003 |
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RNA binding efficacy of theophylline, theobromine and caffeine. | 2003 Apr |
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De-intercalation of ethidium bromide and acridine orange by xanthine derivatives and their modulatory effect on anticancer agents: a study of DNA-directed toxicity enlightened by time correlated single photon counting. | 2003 Apr |
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Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine. | 2003 Apr 15 |
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Polydeoxyribonucleotide (PDRN) promotes human osteoblast proliferation: a new proposal for bone tissue repair. | 2003 Aug 29 |
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Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. | 2003 Feb |
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Researching on new species of "Mate": Ilex brevicuspis: phytochemical and pharmacology study. | 2003 Jan |
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Regional differences in the adenosine A(2) receptor-mediated modulation of contractions in rat vas deferens. | 2003 Jan 24 |
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Intraspinal adenosine induces spinal cord norepinephrine release in spinal nerve-ligated rats but not in normal or sham controls. | 2003 Jun |
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Producing decaffeinated coffee plants. | 2003 Jun 19 |
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Endogenous adenosine prevents post-tetanic release facilitation mediated by alpha3beta2 nicotinic autoreceptors. | 2003 Mar 19 |
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Study on the paper substrate room temperature phosphorescence of theobromine, caffeine and theophylline and analytical application. | 2003 May |
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Adenosine A1 receptor activation reduces myocardial reperfusion effects on intrinsic cardiac nervous system. | 2003 May |
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Inhibition of caffeine biosynthesis in tea (Camellia sinensis) and coffee (Coffea arabica) plants by ribavirin. | 2003 Nov 20 |
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Adenosinergic protection of dopaminergic and GABAergic neurons against mitochondrial inhibition through receptors located in the substantia nigra and striatum, respectively. | 2003 Nov 26 |
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Study on inclusion complex of cyclodextrin with methyl xanthine derivatives by fluorimetry. | 2003 Oct |
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Purine alkaloids in Paullinia. | 2003 Oct |
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Adenosine kinase inhibitors. 3. Synthesis, SAR, and antiinflammatory activity of a series of l-lyxofuranosyl nucleosides. | 2003 Oct 23 |
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Antioxidant and prooxidant properties of caffeine, theobromine and xanthine. | 2003 Sep |
Patents
Sample Use Guides
1 tablet (500 mg of theobromide sodium acetate) 3–4 times daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27913821
Alkaline phosphatase activity, a marker of early to mid-stage osteogenesis, was elevated in cultures of Human Mesenchymal Stem Cells that received 25 uM theobromine and reached a maximal level of stimulation at 50–100 uM theobromine.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 17:28:47 UTC 2022
by
admin
on
Fri Dec 16 17:28:47 UTC 2022
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Record UNII |
OBD445WZ5P
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
R03DA57
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WHO-VATC |
QC03BD01
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WHO-ATC |
R03DA07
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WHO-VATC |
QR03DA57
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WHO-VATC |
QR03DA07
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DSLD |
2375 (Number of products:275)
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NCI_THESAURUS |
C319
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WHO-ATC |
C03BD01
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SUB15511MIG
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83-67-0
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C87684
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10437
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340
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2618
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28946
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OBD445WZ5P
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CHEMBL1114
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5429
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OBD445WZ5P
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THEOBROMINE
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201-494-2
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D013805
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5039
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7332
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M10703
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DTXSID9026132
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DB01412
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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EXCRETED UNCHANGED->SUBSTANCE |
MAJOR
URINE
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Secondary metabolite detected in developing cacao seeds.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
AMOUNT EXCRETED
MAJOR
PLASMA; URINE
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PARENT -> METABOLITE ACTIVE |
MINOR
PLASMA
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
PERCENT OF AMOUNT EXCRETED
MAJOR
PLASMA; URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |