Details
Stereochemistry | EPIMERIC |
Molecular Formula | C17H23NO3 |
Molecular Weight | 289.3701 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@@]2([H])CC[C@]1([H])C[C@@]([H])(C2)OC(=O)C([H])(CO)c3ccccc3
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 | 289.3701 |
Charge | 0 |
Count |
|
Stereochemistry | EPIMERIC |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 3 |
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 |
---|---|---|
Selective blocking effects of tropisetron and atropine on recombinant glycine receptors. | 1999 Aug |
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Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate. | 1999 Nov |
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Focal microinjection of carbachol into the periaqueductal gray induces seizures in the forebrain of the rat. | 2000 Dec |
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Acute cardiac rupture during dobutamine-atropine echocardiography stress test. | 2000 Feb |
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Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus. | 2001 |
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Endothelin receptors in human and guinea-pig gallbladder muscle. | 2001 Apr 20 |
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Localisation and neural control of the release of calcitonin gene-related peptide (CGRP) from the isolated perfused porcine ileum. | 2001 Apr 20 |
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Accelerated dobutamine stress testing: safety and feasibility in patients with known or suspected coronary artery disease. | 2001 Feb |
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On the mechanisms of cholinergic control of the sinoatrial node discharge. | 2001 Feb |
|
Sublingual hyoscyamine sulfate in combination with ketorolac tromethamine for ureteral colic: a randomized, double-blind, controlled trial. | 2001 Feb |
|
Cardiac sympathetic overactivity and decreased baroreflex sensitivity in L-NAME hypertensive rats. | 2001 Feb |
|
Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells. | 2001 Feb 1 |
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Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder. | 2001 Feb 16 |
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Stimulation of M3 muscarinic receptors induces phosphorylation of the Cdc42 effector activated Cdc42Hs-associated kinase-1 via a Fyn tyrosine kinase signaling pathway. | 2001 Feb 23 |
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Increase of peak expiratory flow by atropine is dependent on circadian rhythm. | 2001 Jan |
|
High concentration sevoflurane induction of anesthesia accelerates onset of vecuronium neuromuscular blockade. | 2001 Jan |
|
Tachykinins contribute to nerve-mediated contractions in the human esophagus. | 2001 Jan |
|
Influence of patient posture on oxygen saturation during fibre-optic bronchoscopy. | 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 |
|
Effects of VIP and NO on the motor activity of vascularly perfused rat proximal colon. | 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 |
|
Comparison of myocardial blood flow during dobutamine-atropine infusion with that after dipyridamole administration in normal men. | 2001 Jan |
|
Reversal of Haemorrhagic Shock in Rats by Tetrahydroaminoacridine. | 2001 Jan |
|
Non-synaptic transformation of gustatory receptor potential by stimulation of the parasympathetic fiber of the frog glossopharyngeal nerve. | 2001 Jan |
|
Xerostomia, xerophthalmia, and plasmacytic infiltrates of the salivary glands (Sjögren's-like syndrome) in a cat. | 2001 Jan 1 |
|
Effects of preemptive atropine administration on incidence of medetomidine-induced bradycardia in dogs. | 2001 Jan 1 |
|
Post-ictal analgesia: involvement of opioid, serotoninergic and cholinergic mechanisms. | 2001 Jan 12 |
|
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI. | 2001 Jan 12 |
|
Determination of scopolamine in human serum and microdialysis samples by liquid chromatography-tandem mass spectrometry. | 2001 Jan 5 |
|
Activation of the parasympathetic nervous system is necessary for normal meal-induced insulin secretion in rhesus macaques. | 2001 Mar |
|
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 |
|
Orally administered atropine enhances motor cortex excitability: a transcranial magnetic stimulation study in human subjects. | 2001 Mar 16 |
|
5-Hydroxytryptamine and atropine inhibit nicotinic receptors in submucosal neurons. | 2001 Mar 2 |
|
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 Jun 25 21:11:21 UTC 2021
by
admin
on
Fri Jun 25 21:11:21 UTC 2021
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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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Classification Tree | Code System | Code | ||
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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
Created by
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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
Created by
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WHO-VATC |
QA03CB03
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WHO-ESSENTIAL MEDICINES LIST |
21.5
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admin on Fri Jun 25 21:11:21 UTC 2021 , Edited by admin on Fri Jun 25 21:11:21 UTC 2021
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WHO-ESSENTIAL MEDICINES LIST |
1.3
Created by
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WHO-ATC |
S01BB01
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NDF-RT |
N0000175700
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1044990
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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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260
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PRIMARY | |||
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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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2199
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M2136
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PRIMARY | Merck Index | ||
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1223
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PRIMARY | RxNorm | ||
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51-55-8
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320
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PRIMARY |
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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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE | |||
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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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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
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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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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