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?
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 |
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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 |
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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 |
---|---|---|
Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs. | 1976 Aug |
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Neurotransmitter-mediated open-field behavioral action of CGRP. | 1999 |
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The incidence of systemic side-effects following subconjunctival Mydricaine no. 1 injection. | 1999 Dec |
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Progressive treatment of erectile dysfunction with intracorporeal injections of different combinations of vasoactive agents. | 1999 Feb |
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TIVA with propofol and remifentanil. | 1999 May |
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The influence of peripheral site ligands on the reaction of symmetric and chiral organophosphates with wildtype and mutant acetylcholinesterases. | 1999 May 14 |
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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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SCH 23390 affords protection against soman-evoked seizures in the freely moving guinea-pig: a concomitant neurochemical, electrophysiological and behavioural study. | 2001 |
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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 |
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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 |
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Sublingual hyoscyamine sulfate in combination with ketorolac tromethamine for ureteral colic: a randomized, double-blind, controlled trial. | 2001 Feb |
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Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells. | 2001 Feb 1 |
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Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors. | 2001 Feb 16 |
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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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Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery. | 2001 Feb 2 |
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Binding of nicotinic ligands to and nicotine-induced calcium signaling in Trypanosoma cruzi. | 2001 Feb 23 |
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[Availability of antidotes in French emergency medical aid units]. | 2001 Feb 3 |
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[Experiences with cycloplegic drops in German-speaking centers of pediatric ophthalmology and stabology--results of a 1999 survey]. | 2001 Jan |
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Preanaesthetic use of atropine in small animals. | 2001 Jan |
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On the interactions between antimuscarinic atropine and NMDA receptor antagonists in anticholinesterase-treated mice. | 2001 Jan |
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Increase of peak expiratory flow by atropine is dependent on circadian rhythm. | 2001 Jan |
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High concentration sevoflurane induction of anesthesia accelerates onset of vecuronium neuromuscular blockade. | 2001 Jan |
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[Marked bradycardia during anesthetic induction treated with temporary cardiac pacing in a patient with latent sick sinus syndrome]. | 2001 Jan |
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Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation. | 2001 Jan |
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Hypotensive infarction of the spinal cord in a rhesus macaque (Macaca mulatta). | 2001 Jan |
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Neural mechanisms underlying migrating motor complex formation in mouse isolated colon. | 2001 Jan |
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Evidence for cocaine and methylecgonidine stimulation of M(2) muscarinic receptors in cultured human embryonic lung cells. | 2001 Jan |
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Relaxant effect of Pimpinella anisum on isolated guinea pig tracheal chains and its possible mechanism(s). | 2001 Jan |
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Secretion and gene expression of secretory leukocyte protease inhibitor by human airway submucosal glands. | 2001 Jan |
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Non-synaptic transformation of gustatory receptor potential by stimulation of the parasympathetic fiber of the frog glossopharyngeal nerve. | 2001 Jan |
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Vagosympathetic interactions in ischemia-induced myocardial norepinephrine and acetylcholine release. | 2001 Jan |
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Electrical activation of endothelium evokes vasodilation and hyperpolarization along hamster feed arteries. | 2001 Jan |
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Role of PAG in the antinociception evoked from the medial or central amygdala in rats. | 2001 Jan 1 |
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Activation of sympathoadrenomedullary system increases pulmonary nitric oxide production in the rabbit. | 2001 Jan 12 |
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Post-ictal analgesia: involvement of opioid, serotoninergic and cholinergic mechanisms. | 2001 Jan 12 |
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[Atropine. Principles and rules of utilization]. | 2001 Jan 15 |
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Upregulation of immunoreactive angiotensin II release and angiotensinogen mRNA expression by high-frequency preganglionic stimulation at the canine cardiac sympathetic ganglia. | 2001 Jan 19 |
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Activation of the parasympathetic nervous system is necessary for normal meal-induced insulin secretion in rhesus macaques. | 2001 Mar |
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Pharmacological characterization of locomotor sensitization induced by chronic phencyclidine administration. | 2001 Mar |
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Initiation of distension-induced descending peristaltic reflex in opossum esophagus: role of muscle contractility. | 2001 Mar |
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Muscarinic stimulation increases basal Ca(2+) and inhibits spontaneous Ca(2+) transients in murine colonic myocytes. | 2001 Mar |
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Orally administered atropine enhances motor cortex excitability: a transcranial magnetic stimulation study in human subjects. | 2001 Mar 16 |
|
Evidence for a direct action of Tityus serrulatus scorpion venom on the cardiac muscle. | 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.
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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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QA03BA01
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LIVERTOX |
74
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NDF-RT |
N0000175574
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S01FA01
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NDF-RT |
N0000000125
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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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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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78734
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DB00572
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m2136
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1223
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DTXSID4020113
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100000085031
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320
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ACTIVE MOIETY
METABOLITE (PARENT)
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