Details
Stereochemistry | RACEMIC |
Molecular Formula | C17H23NO3 |
Molecular Weight | 289.3694 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 3 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3
InChI
InChIKey=RKUNBYITZUJHSG-SPUOUPEWSA-N
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16?
Molecular Formula | C17H23NO3 |
Molecular Weight | 289.3694 |
Charge | 0 |
Count |
|
Stereochemistry | EPIMERIC |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68001285 |
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68001285 |
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf
Atropine inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves, and on smooth muscles which respond to endogenous acetylcholine but are not so innervated. As with other antimuscarinic agents, the major action of atropine is a competitive or surmountable antagonism which can be overcome by increasing the concentration of acetylcholine at receptor sites of the effector organ (e.g., by using anticholinesterase agents which inhibit the enzymatic destruction of acetylcholine). The receptors antagonized by atropine are the peripheral structures that are stimulated or inhibited by muscarine (i.e., exocrine glands and smooth and cardiac muscle). Responses to postganglionic cholinergic nerve stimulation also may be inhibited by atropine but this occurs less readily than with responses to injected (exogenous) choline esters. Atropine is relatively selective for muscarinic receptors. Its potency at nicotinic receptors is much lower, and actions at non-muscarinic receptors are generally undetectable clinically. Atropine does not distinguish among the M1, M2, and M3 subgroups of muscarinic receptors.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 |
9.34 null [pKi] | ||
Target ID: CHEMBL211 |
8.95 null [pKi] | ||
Target ID: CHEMBL245 |
9.15 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Atropine sulfate Approved UseAtropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date9.9455042E11 |
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Primary | Atropine sulfate Approved UseAtropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date9.9455042E11 |
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Primary | Atropine sulfate Approved UseAtropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date9.9455042E11 |
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Primary | Atropine sulfate Approved UseAtropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date9.9455042E11 |
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Primary | Atropine sulfate Approved UseAtropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date9.9455042E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
860 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3046815 |
0.4 μg single, ocular dose: 0.4 μg route of administration: Ocular experiment type: SINGLE co-administered: |
ATROPINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
11.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3740650 |
1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
ATROPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.6 ng/mL |
1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
ATROPINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
43245 pg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3046815 |
0.4 μg single, ocular dose: 0.4 μg route of administration: Ocular experiment type: SINGLE co-administered: |
ATROPINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
47.6 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3740650 |
1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
ATROPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3740650 |
1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
ATROPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
82% |
1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
ATROPINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: |
unhealthy, 10 years n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 Sources: |
Disc. AE: Kounis syndrome, Chest discomfort... AEs leading to discontinuation/dose reduction: Kounis syndrome (1 patient) Sources: Chest discomfort (1 patient) Nausea (1 patient) Vomiting (1 patient) |
0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: |
unhealthy, 10.3 years (range: 2.7–16.8 years) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 Sources: |
Other AEs: Photophobia, Reading disorder... Other AEs: Photophobia (70%) Sources: Reading disorder (25.9%) Headache (21.7%) Hot flushes (3.3%) Conjunctivitis (1.7%) Blepharitis (1.7%) |
1 mg single, sublingual Overdose |
unhealthy n = 1 |
Other AEs: Adverse event... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Chest discomfort | 1 patient Disc. AE |
0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: |
unhealthy, 10 years n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 Sources: |
Kounis syndrome | 1 patient Disc. AE |
0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: |
unhealthy, 10 years n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 Sources: |
Nausea | 1 patient Disc. AE |
0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: |
unhealthy, 10 years n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 Sources: |
Vomiting | 1 patient Disc. AE |
0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: |
unhealthy, 10 years n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 Sources: |
Blepharitis | 1.7% | 0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: |
unhealthy, 10.3 years (range: 2.7–16.8 years) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 Sources: |
Conjunctivitis | 1.7% | 0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: |
unhealthy, 10.3 years (range: 2.7–16.8 years) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 Sources: |
Headache | 21.7% | 0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: |
unhealthy, 10.3 years (range: 2.7–16.8 years) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 Sources: |
Reading disorder | 25.9% | 0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: |
unhealthy, 10.3 years (range: 2.7–16.8 years) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 Sources: |
Hot flushes | 3.3% | 0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: |
unhealthy, 10.3 years (range: 2.7–16.8 years) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 Sources: |
Photophobia | 70% | 0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: |
unhealthy, 10.3 years (range: 2.7–16.8 years) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 Sources: |
Adverse event | severe | 1 mg single, sublingual Overdose |
unhealthy n = 1 |
PubMed
Title | Date | PubMed |
---|---|---|
On the anticataleptic action of cyproheptadine. | 1976 Aug |
|
Neurotransmitter-mediated open-field behavioral action of CGRP. | 1999 |
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Effects of topical glucocorticoids on in vitro lactoferrin glandular secretion: comparison between human upper and lower airways. | 2000 Dec |
|
Focal microinjection of carbachol into the periaqueductal gray induces seizures in the forebrain of the rat. | 2000 Dec |
|
Effect of alpha-2 adrenoceptor antagonists on colonic function in rats. | 2000 Jun |
|
Cardiovascular studies on different classes of soft drugs. | 2000 Mar |
|
Near fatal case of atrio-ventricular block induced by amitriptyline at therapeutic dose. | 2000 Sep |
|
Accelerated dobutamine stress testing: safety and feasibility in patients with known or suspected coronary artery disease. | 2001 Feb |
|
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle. | 2001 Feb |
|
Antispasmodic activity of the fruits of Helicteres isora Linn. | 2001 Feb |
|
Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells. | 2001 Feb 1 |
|
Prognostic interaction between viability and residual myocardial ischemia by dobutamine stress echocardiography in patients with acute myocardial infarction and mildly impaired left ventricular function. | 2001 Feb 1 |
|
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery. | 2001 Feb 2 |
|
Photochemical N-demethylation of alkaloids. | 2001 Feb 26 |
|
On the interactions between antimuscarinic atropine and NMDA receptor antagonists in anticholinesterase-treated mice. | 2001 Jan |
|
Mechanisms of acetylcholine-induced vasorelaxation in high K+-stimulated rabbit renal arteries. | 2001 Jan |
|
A clinico-epidemiological study of organophosphorus poisoning at a rural-based teaching hospital in eastern Nepal. | 2001 Jan |
|
Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation. | 2001 Jan |
|
Muscarinic activation of transient inward current and contraction in canine colon circular smooth muscle cells. | 2001 Jan |
|
Hypotensive infarction of the spinal cord in a rhesus macaque (Macaca mulatta). | 2001 Jan |
|
Spectral analysis of circadian rhythms in heart rate variability of dogs. | 2001 Jan |
|
Age-related changes in cholinergic and purinergic neurotransmission in human isolated bladder smooth muscles. | 2001 Jan |
|
Neural mechanisms underlying migrating motor complex formation in mouse isolated colon. | 2001 Jan |
|
Evidence for cocaine and methylecgonidine stimulation of M(2) muscarinic receptors in cultured human embryonic lung cells. | 2001 Jan |
|
Characterization of a novel mechanism accounting for the adverse cholinergic effects of the anticancer drug irinotecan. | 2001 Jan |
|
Reversal of Haemorrhagic Shock in Rats by Tetrahydroaminoacridine. | 2001 Jan |
|
Administration of atropine in the setting of acute myocardial infarction: potentiation of the ischemic process? | 2001 Jan |
|
Secretion and gene expression of secretory leukocyte protease inhibitor by human airway submucosal glands. | 2001 Jan |
|
Non-synaptic transformation of gustatory receptor potential by stimulation of the parasympathetic fiber of the frog glossopharyngeal nerve. | 2001 Jan |
|
Vagosympathetic interactions in ischemia-induced myocardial norepinephrine and acetylcholine release. | 2001 Jan |
|
Electrical activation of endothelium evokes vasodilation and hyperpolarization along hamster feed arteries. | 2001 Jan |
|
Effects of preemptive atropine administration on incidence of medetomidine-induced bradycardia in dogs. | 2001 Jan 1 |
|
Activation of sympathoadrenomedullary system increases pulmonary nitric oxide production in the rabbit. | 2001 Jan 12 |
|
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI. | 2001 Jan 12 |
|
Role of preoptic and anterior hypothalamic cholinergic input on water intake and body temperature. | 2001 Jan 19 |
|
Ghrelin acts in the central nervous system to stimulate gastric acid secretion. | 2001 Jan 26 |
|
Angiotensinergic and noradrenergic mechanisms in the hypothalamic paraventricular nucleus participate in the drinking response induced by activation of the subfornical organ in rats. | 2001 Jan 29 |
|
Determination of scopolamine in human serum and microdialysis samples by liquid chromatography-tandem mass spectrometry. | 2001 Jan 5 |
|
From 'captive' agonism to insurmountable antagonism: demonstrating the power of analytical pharmacology. | 2001 Mar |
|
Pharmacological characterization of locomotor sensitization induced by chronic phencyclidine administration. | 2001 Mar |
|
Low-affinity M(2) receptor binding state mediates mouse atrial bradycardia: comparative effects of carbamylcholine and the M(1) receptor agonists sabcomeline and xanomeline. | 2001 Mar |
|
Respective roles of carbamylcholine and cyclic adenosine monophosphate in their synergistic regulation of cell cycle in thyroid primary cultures. | 2001 Mar |
|
Muscarinic stimulation increases basal Ca(2+) and inhibits spontaneous Ca(2+) transients in murine colonic myocytes. | 2001 Mar |
|
Evidence for a direct action of Tityus serrulatus scorpion venom on the cardiac muscle. | 2001 May |
|
The role of nitric oxide on the relaxations of rabbit corpus cavernosum induced by Androctonus australis and Buthotus judaicus scorpion venoms. | 2001 May |
Sample Use Guides
Atropine as an antisialagogue or for antivagal effects: initial single dose of 0.5 mg to 1 mg; as an antidote for organophosporous or muscarinic mushroom
poisoning: initial single dose of 2 mg to 3 mg, repeated every 20-30 minutes; for bradyasystolic cardiac arrest: 1 mg dose, repeated every 3-5 minutes if asystole persists; in patients with coronary artery disease: total dose should not exceed 0.03 mg/kg to 0.04 mg/kg.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7359946
Atropine in doses -5.44 to -4.74 log mol/L totally inhibited the contraction induced by acetylcholine and carbachol in segmental pulmonary artery specimens taken from the patients undergoing thoracic surgery.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 20:14:30 UTC 2022
by
admin
on
Fri Dec 16 20:14:30 UTC 2022
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Record UNII |
7C0697DR9I
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175370
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NDF-RT |
N0000000125
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WHO-ATC |
A03CB03
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WHO-VATC |
QA03BA01
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LIVERTOX |
74
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NDF-RT |
N0000175574
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WHO-ATC |
S01FA01
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NDF-RT |
N0000000125
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NDF-RT |
N0000000125
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NCI_THESAURUS |
C29704
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WHO-ATC |
A03BA01
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WHO-VATC |
QS01FA01
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CFR |
21 CFR 310.533
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WHO-ESSENTIAL MEDICINES LIST |
4.2
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CFR |
21 CFR 520.2520A
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WHO-VATC |
QA03CB03
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WHO-ESSENTIAL MEDICINES LIST |
21.5
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WHO-ESSENTIAL MEDICINES LIST |
1.3
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WHO-ATC |
S01BB01
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NDF-RT |
N0000175700
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7C0697DR9I
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7C0697DR9I
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D001285
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Atropine
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51-55-8
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ATROPINE
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1044990
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260
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C28840
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SUB00621MIG
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CHEMBL517712
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200-104-8
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DB00572
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M2136
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1223
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DTXSID4020113
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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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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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ENANTIOMER -> RACEMATE |
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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TARGET -> INHIBITOR |
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ENANTIOMER -> RACEMATE |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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Related Record | Type | Details | ||
---|---|---|---|---|
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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 |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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