Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H22FN3O2 |
Molecular Weight | 379.4274 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
FC1=CC=C(C=C1)C(=O)CCCN2CCC(=CC2)N3C(=O)NC4=CC=CC=C34
InChI
InChIKey=RMEDXOLNCUSCGS-UHFFFAOYSA-N
InChI=1S/C22H22FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-11H,3,6,12-15H2,(H,24,28)
Molecular Formula | C22H22FN3O2 |
Molecular Weight | 379.4274 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00450Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/droperidol.html
Sources: http://www.drugbank.ca/drugs/DB00450
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/droperidol.html
Droperidol produces marked tranquilization and sedation. It allays apprehension and provides a state of mental detachment and indifference while maintaining a state of reflex alertness. Droperidol produces an antiemetic effect as evidenced by the antagonism of apomorphine in dogs. It lowers the incidence of nausea and vomiting during surgical procedures and provides antiemetic protection in the postoperative period. Droperidol potentiates other CNS depressants. It produces mild alpha-adrenergic blockade, peripheral vascular dilatation and reduction of the pressor effect of epinephrine. It can produce hypotension and decreased peripheral vascular resistance and may decrease pulmonary arterial pressure (particularly if it is abnormally high). It may reduce the incidence of epinephrine-induced arrhythmias, but it does not prevent other cardiac arrhythmias. The exact mechanism of action is unknown, however, droperidol causes a CNS depression at subcortical levels of the brain, midbrain, and brainstem reticular formation. It may antagonize the actions of glutamic acid within the extrapyramidal system. It may also inhibit cathecolamine receptors and the reuptake of neurotransmiters and has strong central antidopaminergic action and weak central anticholinergic action. It can also produce ganglionic blockade and reduced affective response. The main actions seem to stem from its potent Dopamine (2) receptor antagonism with minor antagonistic effects on alpha-1 adrenergic receptors as well. Droperidol is used to produce tranquilization and to reduce the incidence of nausea and vomiting in surgical and diagnostic procedures.
CNS Activity
Sources: http://www.drugbank.ca/drugs/DB00450
Curator's Comment: Droperidol causes a CNS depression at subcortical levels of the brain, midbrain, and brainstem reticular formation.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: http://www.drugbank.ca/drugs/DB00450 |
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Target ID: CHEMBL229 Sources: http://www.drugbank.ca/drugs/DB00450 |
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Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12190308 |
32.2 nM [IC50] | ||
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2879412 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | INAPSINE Approved UseDroperidol injection is indicated to reduce the incidence of nausea and vomiting associated with surgical and diagnostic procedures. Launch Date1.3824E10 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.5 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30574300/ |
0.02 mg/kg single, nasal dose: 0.02 mg/kg route of administration: Nasal experiment type: SINGLE co-administered: |
DROPERIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
26.6 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30574300/ |
0.02 mg/kg single, intravenous dose: 0.02 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DROPERIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.7 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30574300/ |
0.02 mg/kg single, nasal dose: 0.02 mg/kg route of administration: Nasal experiment type: SINGLE co-administered: |
DROPERIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
40 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30574300/ |
0.02 mg/kg single, intravenous dose: 0.02 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DROPERIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30574300/ |
0.02 mg/kg single, nasal dose: 0.02 mg/kg route of administration: Nasal experiment type: SINGLE co-administered: |
DROPERIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30574300/ |
0.02 mg/kg single, intravenous dose: 0.02 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DROPERIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.4 mg/kg multiple, oral Dose: 0.4 mg/kg Route: oral Route: multiple Dose: 0.4 mg/kg Sources: |
unhealthy, 2-9 years Health Status: unhealthy Age Group: 2-9 years Sources: |
Disc. AE: QT interval prolonged... AEs leading to discontinuation/dose reduction: QT interval prolonged Sources: |
8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Other AEs: Asthenia, Chills... Other AEs: Asthenia (24.6%) Sources: Chills (3.3%) Anorexia (3.3%) Akathisia (16.4%) Anxiety (27.9%) Confusion (3.3%) Dizziness (9.8%) Dry mouth (9.8%) Nervousness (4.9%) Paresthesia (3.3%) Somnolence (24.6%) Tremor (1.6%) Pharyngitis (4.9%) Rhinitis (4.9%) Sweaty (8.2%) |
2.5 mg multiple, intravenous (starting) Dose: 2.5 mg Route: intravenous Route: multiple Dose: 2.5 mg Sources: |
unhealthy |
Disc. AE: Torsades de pointes... AEs leading to discontinuation/dose reduction: Torsades de pointes Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
QT interval prolonged | Disc. AE | 0.4 mg/kg multiple, oral Dose: 0.4 mg/kg Route: oral Route: multiple Dose: 0.4 mg/kg Sources: |
unhealthy, 2-9 years Health Status: unhealthy Age Group: 2-9 years Sources: |
Tremor | 1.6% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Akathisia | 16.4% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Asthenia | 24.6% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Somnolence | 24.6% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Anxiety | 27.9% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Anorexia | 3.3% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Chills | 3.3% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Confusion | 3.3% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Paresthesia | 3.3% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Nervousness | 4.9% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Pharyngitis | 4.9% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Rhinitis | 4.9% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Sweaty | 8.2% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Dizziness | 9.8% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Dry mouth | 9.8% | 8.25 mg single, intramuscular Highest studied dose Dose: 8.25 mg Route: intramuscular Route: single Dose: 8.25 mg Sources: |
unhealthy, 42 ± 10.0 years n = 61 Health Status: unhealthy Condition: acute migraine headache Age Group: 42 ± 10.0 years Sex: M+F Population Size: 61 Sources: |
Torsades de pointes | Disc. AE | 2.5 mg multiple, intravenous (starting) Dose: 2.5 mg Route: intravenous Route: multiple Dose: 2.5 mg Sources: |
unhealthy |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 19.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
major |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
The effects of ketamine and of Innovar anesthesia on digitalis tolerance in dogs. | 1975 Jan-Feb |
|
[Postoperative nausea and vomiting--still a problem?]. | 2001 |
|
Droperidol for acute psychosis. | 2001 |
|
A small dose of droperidol decreases postoperative nausea and vomiting in adults but cannot improve an already excellent patient satisfaction. | 2001 Apr |
|
Patient-controlled epidural analgesia versus continuous epidural analgesia after total knee arthroplasty. | 2001 Apr |
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Preparation, premedication, and surveillance. | 2001 Feb |
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[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo]. | 2001 Feb |
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Droperidol: an effective adjuvant for difficult cases of conscious sedation? | 2001 Jul |
|
Combination of droperidol and ondansetron reduces PONV after pediatric strabismus surgery more than single drug therapy. | 2001 Jul |
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Pharmacological control of opioid-induced pruritus: a quantitative systematic review of randomized trials. | 2001 Jun |
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Plasma glucocorticoid concentrations after fentanyl-droperidol, ketamine-xylazine and ketamine-diazepam anaesthesia in New Zealand white rabbits. | 2001 Jun 23 |
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Optimising management of delirium. Withdrawal of Droleptan (droperidol). | 2001 Jun 30 |
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Pediatric renal transplantation: anesthesia and perioperative complications. | 2001 Mar |
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Dexamethasone for preventing nausea and vomiting associated with epidural morphine: a dose-ranging study. | 2001 Mar |
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In vitro neuromuscular effects of droperidol in rats. | 2001 May |
|
[Therapy of angina pectoris: morphine or thalamonal?]. | 2001 May 11 |
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IM droperidol as premedication attenuates intraoperative hypothermia. | 2001 Oct |
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Whose drug is it anyway? | 2001 Oct 13 |
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[Therapy of angina pectoris pain: morphine or thalamonal?]. | 2001 Oct 26 |
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Prehospital sedation with intramuscular droperidol: a one-year pilot. | 2001 Oct-Dec |
|
[Continuous epidural administration of droperidol for the prevention of postoperative nausea]. | 2001 Sep |
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Antipsychotic-related QTc prolongation, torsade de pointes and sudden death. | 2002 |
|
Droperidol inhibits GABA(A) and neuronal nicotinic receptor activation. | 2002 Apr |
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Droperidol: cardiovascular toxicity and deaths. | 2002 Apr 2 |
|
P6 acupoint injections are as effective as droperidol in controlling early postoperative nausea and vomiting in children. | 2002 Aug |
|
[Prophylaxis of Postoperative Nausea and Vomiting FollowingGynaecological Laparoscopy]. | 2002 Jan |
|
Premedication, preparation, and surveillance. | 2002 Jan |
|
The FDA droperidol warning: is it justified? | 2002 Jul |
|
Droperidol--behind the black box warning. | 2002 Jun |
|
Superior prolonged antiemetic prophylaxis with a four-drug multimodal regimen - comparison with propofol or placebo. | 2002 Mar |
|
Psychotropic drugs and the ECG: focus on the QTc interval. | 2002 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/droperidol.html
Curator's Comment: Intravenous or Intramuscular
Dosage: The dosage should be individualized. Factors to be considered in determining dose are age, body weight, physical status, underlying pathological condition, use of other drugs, the type of anesthesia to be used, and the surgical procedure involved. Vital signs and ECG should be monitored closely.
Maximum Dosage: The maximum recommended initial dose is 2.5 mg IM or slow IV. Additional 1.25 mg doses of droperidol may be administered to achieve the desired effect. The additional doses should be administered with caution and only if the potential benefit outweighs the potential risk.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16492829
Droperidol (10(-7) M) caused vasodilator effect (approximately 20% of vasorelaxation compared with maximal vasorelaxation induced by papaverine [3 x 10(-4) M] in rat vascular smooth muscle cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:00:07 UTC 2023
by
admin
on
Thu Jul 06 22:00:07 UTC 2023
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Record UNII |
O9U0F09D5X
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-ATC |
N05AD08
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CFR |
21 CFR 522.800
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LIVERTOX |
332
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NCI_THESAURUS |
C323
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NDF-RT |
N0000175800
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NDF-RT |
N0000175799
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WHO-VATC |
QN05AD08
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WHO-ATC |
N01AX01
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D004329
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966
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4717
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DB00450
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548-73-2
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208-957-8
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C458
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1229001
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Droperidol
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Droperidol
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SUB06410MIG
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3320
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3648
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M4769
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O9U0F09D5X
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169874
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7172
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CHEMBL1108
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1609
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DTXSID6022973
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100000081007
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3168
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BINDER->LIGAND |
BINDING
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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