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 Date2001 |
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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 Date2001 |
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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 Date2001 |
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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 Date2001 |
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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 Date2001 |
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 |
---|---|---|
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 |
|
Differences in electromechanical coupling between bradykinin and the nonpeptide kinin B2 receptor agonist, FR 190997, in the circular muscle of guinea-pig colon. | 2001 Feb |
|
Accelerated dobutamine stress testing: safety and feasibility in patients with known or suspected coronary artery disease. | 2001 Feb |
|
On the mechanisms of cholinergic control of the sinoatrial node discharge. | 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 |
|
Sublingual hyoscyamine sulfate in combination with ketorolac tromethamine for ureteral colic: a randomized, double-blind, controlled trial. | 2001 Feb |
|
Reversal of rocuronium with edrophonium during propofol versus sevoflurane anesthesia. | 2001 Feb |
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Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells. | 2001 Feb 1 |
|
Acetylcholine-evoked calcium increases in Deiters' cells of the guinea pig cochlea suggest alpha9-like receptors. | 2001 Feb 1 |
|
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors. | 2001 Feb 16 |
|
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder. | 2001 Feb 16 |
|
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery. | 2001 Feb 2 |
|
Facilitation of transmitter release in the urinary bladders of neonatal and adult rats via alpha1-adrenoceptors. | 2001 Feb 23 |
|
Binding of nicotinic ligands to and nicotine-induced calcium signaling in Trypanosoma cruzi. | 2001 Feb 23 |
|
Photochemical N-demethylation of alkaloids. | 2001 Feb 26 |
|
[Availability of antidotes in French emergency medical aid units]. | 2001 Feb 3 |
|
[Experiences with cycloplegic drops in German-speaking centers of pediatric ophthalmology and stabology--results of a 1999 survey]. | 2001 Jan |
|
Preanaesthetic use of atropine in small animals. | 2001 Jan |
|
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 |
|
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 |
|
[Marked bradycardia during anesthetic induction treated with temporary cardiac pacing in a patient with latent sick sinus syndrome]. | 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 |
|
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 |
|
Effects of VIP and NO on the motor activity of vascularly perfused rat proximal colon. | 2001 Jan |
|
Unplanned administration of atropine, succinylcholine and lidocaine. | 2001 Jan |
|
Neuropharmacological actions of some binuclear lanthanide(III) complexes. | 2001 Jan |
|
Role of PAG in the antinociception evoked from the medial or central amygdala in rats. | 2001 Jan 1 |
|
[Atropine. Principles and rules of utilization]. | 2001 Jan 15 |
|
Role of preoptic and anterior hypothalamic cholinergic input on water intake and body temperature. | 2001 Jan 19 |
|
Determination of scopolamine in human serum and microdialysis samples by liquid chromatography-tandem mass spectrometry. | 2001 Jan 5 |
|
Neural-epithelial cell interplay: in vitro evidence that vagal mediators increase PGE2 production by human nasal epithelial cells. | 2001 Jan-Feb |
|
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 |
|
Role of a central muscarinic cholinergic pathway for relaxation of the proximal urethra during the voiding phase in rats. | 2001 Mar |
|
Initiation of distension-induced descending peristaltic reflex in opossum esophagus: role of muscle contractility. | 2001 Mar |
|
Muscarinic stimulation increases basal Ca(2+) and inhibits spontaneous Ca(2+) transients in murine colonic myocytes. | 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 |
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 15 16:28:01 GMT 2023
by
admin
on
Fri Dec 15 16:28:01 GMT 2023
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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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N0000175700
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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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C28840
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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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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR |
BINDING
IC50
|
||
|
TARGET -> INHIBITOR |
IC50
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
ENANTIOMER -> RACEMATE |
|
||
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SALT/SOLVATE -> PARENT |
|
||
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SALT/SOLVATE -> PARENT |
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||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
|
||
|
TARGET -> INHIBITOR |
|
||
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ENANTIOMER -> RACEMATE |
|
||
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SALT/SOLVATE -> PARENT |
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||
|
TARGET -> INHIBITOR |
|
||
|
TARGET -> INHIBITOR |
BINDING
IC50
|
||
|
TARGET -> INHIBITOR |
Atropine is a non-specific antagonist for
muscarinic acetylcholine receptor.
IC50
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
TARGET -> INHIBITOR |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
URINE
|
||
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METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
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