Details
Stereochemistry | RACEMIC |
Molecular Formula | 2C17H23NO3.H2O.H2O4S |
Molecular Weight | 694.833 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 6 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OS(O)(=O)=O.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3.CN4[C@H]5CC[C@@H]4C[C@@H](C5)OC(=O)C(CO)C6=CC=CC=C6
InChI
InChIKey=JPKKQJKQTPNWTR-CHYDPLAESA-N
InChI=1S/2C17H23NO3.H2O4S.H2O/c2*1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12;1-5(2,3)4;/h2*2-6,13-16,19H,7-11H2,1H3;(H2,1,2,3,4);1H2/t2*13-,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 |
---|---|---|
Neurotransmitter-mediated open-field behavioral action of CGRP. | 1999 |
|
Selective blocking effects of tropisetron and atropine on recombinant glycine receptors. | 1999 Aug |
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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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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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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 |
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Cardiac sympathetic overactivity and decreased baroreflex sensitivity in L-NAME hypertensive rats. | 2001 Feb |
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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 |
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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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Photochemical N-demethylation of alkaloids. | 2001 Feb 26 |
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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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Tachykinins contribute to nerve-mediated contractions in the human esophagus. | 2001 Jan |
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Muscarinic activation of transient inward current and contraction in canine colon circular smooth muscle cells. | 2001 Jan |
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Spectral analysis of circadian rhythms in heart rate variability of dogs. | 2001 Jan |
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Unplanned administration of atropine, succinylcholine and lidocaine. | 2001 Jan |
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Neuropharmacological actions of some binuclear lanthanide(III) complexes. | 2001 Jan |
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Age-related changes in cholinergic and purinergic neurotransmission in human isolated bladder smooth muscles. | 2001 Jan |
|
Assessment of autonomic cardiovascular indices in non-stationary data in rats. | 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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Activation of sympathoadrenomedullary system increases pulmonary nitric oxide production in the rabbit. | 2001 Jan 12 |
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[Atropine. Principles and rules of utilization]. | 2001 Jan 15 |
|
Ghrelin acts in the central nervous system to stimulate gastric acid secretion. | 2001 Jan 26 |
|
Evidence of alpha-adrenoceptor-mediated chronotropic action in children. | 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 |
|
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29704
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CFR |
21 CFR 310.533
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DBSALT000281
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03J5ZE7KA5
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100000143430
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1045009
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DTXSID3040724
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C2744
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5908-99-6
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SUB00625MIG
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03J5ZE7KA5
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SUB120273
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ATROPINE SULFATE
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PRIMARY | Description: Colourless crystal or a white, crystalline powder; odourless. Solubility: Soluble in less than 1 part of water; freely soluble in ethanol (~750 g/l) TS; practically insoluble in ether R and benzene R. Category: Cholinergic blocking agent (parasympatholytic). Storage: Atropine sulfate should be kept in a tightly closed container, protected from light. Additional information: Atropine sulfate is very poisonous; it effloresces in dry air; it is slowly affected by light. Definition: Atropine sulfate contains not less than 98.5% and not more than 101.0% of (C17H23NO3)2,H2SO4, calculated with reference to the dried substance. | ||
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CHEMBL517712
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755889
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SUB126811
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m2136
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153971
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PRIMARY | RxNorm |
ACTIVE MOIETY
SUBSTANCE RECORD