Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H21NO4 |
Molecular Weight | 303.3529 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12O[C@]1([H])[C@H]3C[C@H](C[C@@H]2N3C)OC(=O)[C@H](CO)C4=CC=CC=C4
InChI
InChIKey=STECJAGHUSJQJN-FWXGHANASA-N
InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1
Molecular Formula | C17H21NO4 |
Molecular Weight | 303.3529 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
The alkaloid L-(-)-scopolamine [L-(-)-hyoscine], a belladonna alkaloid, competitively inhibits muscarinic receptors for acetylcholine and acts as a nonselective muscarinic antagonist, producing both peripheral antimuscarinic properties and central sedative, antiemetic, and amnestic effects. Scopolamine acts: i) as a competitive inhibitor at postganglionic muscarinic receptor sites of the parasympathetic nervous system, and ii) on smooth muscles that respond to acetylcholine but lack cholinergic innervation. It has been suggested that scopolamine acts in the central nervous system (CNS) by blocking cholinergic transmission from the vestibular nuclei to higher centers in the CNS and from the reticular formation to the vomiting center. Scopolamine can inhibit the secretion of saliva and sweat, decrease gastrointestinal secretions and motility, cause drowsiness, dilate the pupils, increase heart rate, and depress motor function. Scopolamine is used for premedication in anesthesia and for the prevention of nausea and vomiting (post operative and associated with motion sickness).
Originator
Sources: A. Ladenburg, Ann. 206, 274 (1881); E. Schmidt, Arch. Pharm. 230, 207 (1892).
Curator's Comment: Scopolamine is an anticholinergic, tropane alkaloid isolated from Datura metel L., Scopola carniolica Jacq. and other Solanaceae. Constituent of impure duboisine from Duboisia myoporoides R. Br., pure duboisine is l-hyoscyamine, q.v. reference retrieved from http://www.drugfuture.com/chemdata/scopolamine.html
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27108935 |
2.09 µM [IC50] | ||
Target ID: CHEMBL2094109 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | TRANSDERM SCOP Approved UseTransderm Scōp is an anticholinergic agent indicated in adults for the prevention of nausea and vomiting associated with:
Motion Sickness and Post Operative Nausea and Vomiting (PONV) Launch Date3.15446395E11 |
|||
Preventing | TRANSDERM SCOP Approved UseTransderm Scōp is an anticholinergic agent indicated in adults for the prevention of nausea and vomiting associated with:
Motion Sickness and Post Operative Nausea and Vomiting (PONV) Launch Date3.15446395E11 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5 ng/mL |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.1 ng × h/mL |
1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
369 ng × min/mL |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.5 h |
1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
68.7 min |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
70% |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SCOPOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: |
healthy, 21 - 47 years n = 12 Health Status: healthy Age Group: 21 - 47 years Sex: M+F Population Size: 12 Sources: |
Other AEs: Dizziness, Lightheadedness... Other AEs: Dizziness (3 patients) Sources: Lightheadedness (3 patients) Nasal burning (1 patient) |
0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: |
healthy, 21.4 years n = 35 Health Status: healthy Age Group: 21.4 years Sex: M Population Size: 35 Sources: |
Other AEs: Blurred vision, Dizziness... |
6 ug/kg single, intravenous Dose: 6 ug/kg Route: intravenous Route: single Dose: 6 ug/kg Sources: |
healthy, 22.8 years n = 9 Health Status: healthy Age Group: 22.8 years Sex: M Population Size: 9 Sources: |
|
1.2 mg single, oral Highest studied dose |
healthy, 24 years (range: 19-38 years) n = 12 Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Population Size: 12 Sources: |
Other AEs: Dizziness, Dry mouth... Other AEs: Dizziness (4 patients) Sources: Dry mouth (3 patients) Blurred vision (4 patients) |
10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 83 years n = 1 Health Status: unhealthy Age Group: 83 years Sex: F Population Size: 1 Sources: |
Other AEs: Consciousness abnormal, Hyperthermia... Other AEs: Consciousness abnormal (1 patient) Sources: Hyperthermia (1 patient) |
0.5 mg single, intravenous Dose: 0.5 mg Route: intravenous Route: single Dose: 0.5 mg Sources: |
healthy, adult n = 6 Health Status: healthy Age Group: adult Sex: M Population Size: 6 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nasal burning | 1 patient | 0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: |
healthy, 21 - 47 years n = 12 Health Status: healthy Age Group: 21 - 47 years Sex: M+F Population Size: 12 Sources: |
Dizziness | 3 patients | 0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: |
healthy, 21 - 47 years n = 12 Health Status: healthy Age Group: 21 - 47 years Sex: M+F Population Size: 12 Sources: |
Lightheadedness | 3 patients | 0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: |
healthy, 21 - 47 years n = 12 Health Status: healthy Age Group: 21 - 47 years Sex: M+F Population Size: 12 Sources: |
Blurred vision | 0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: |
healthy, 21.4 years n = 35 Health Status: healthy Age Group: 21.4 years Sex: M Population Size: 35 Sources: |
|
Dizziness | 0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: |
healthy, 21.4 years n = 35 Health Status: healthy Age Group: 21.4 years Sex: M Population Size: 35 Sources: |
|
Dry mouth | 3 patients | 1.2 mg single, oral Highest studied dose |
healthy, 24 years (range: 19-38 years) n = 12 Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Population Size: 12 Sources: |
Blurred vision | 4 patients | 1.2 mg single, oral Highest studied dose |
healthy, 24 years (range: 19-38 years) n = 12 Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Population Size: 12 Sources: |
Dizziness | 4 patients | 1.2 mg single, oral Highest studied dose |
healthy, 24 years (range: 19-38 years) n = 12 Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Population Size: 12 Sources: |
Consciousness abnormal | 1 patient | 10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 83 years n = 1 Health Status: unhealthy Age Group: 83 years Sex: F Population Size: 1 Sources: |
Hyperthermia | 1 patient | 10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 83 years n = 1 Health Status: unhealthy Age Group: 83 years Sex: F Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 21.0 |
yes [IC50 119.2 uM] | |||
Page: 21.0 |
yes [IC50 217.9 uM] | |||
Page: 21.0 |
yes [IC50 540.8 uM] | |||
Page: 21.0 |
yes [IC50 6.7 uM] | |||
Page: 21.0 |
yes [IC50 699.9 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | yes (co-administration study) Comment: The AUC0–24h values of scopolamine were higher during the grapefruit juice period. They reached approximately 142% of the values associated with the control group (water period; P . 0.005) Sources: https://pubmed.ncbi.nlm.nih.gov/16175141/ |
PubMed
Title | Date | PubMed |
---|---|---|
A novel nitrate ester reverses the cognitive impairment caused by scopolamine in the Morris water maze. | 2000 Nov 27 |
|
Probing peripheral and central cholinergic system responses. | 2000 Sep |
|
Scopolamine does not restore normal conditioned avoidance performance in raclopride-treated rats. | 2001 |
|
Nucleus accumbens muscarinic receptors in the control of behavioral depression: antidepressant-like effects of local M1 antagonist in the Porsolt swim test. | 2001 |
|
Interactions between cholinergic and GABAergic neurotransmitters in and around the locus coeruleus for the induction and maintenance of rapid eye movement sleep in rats. | 2001 |
|
Intrastriatal GABA(A) receptor blockade does not alter dopamine D(1)/D(2) receptor interactions in the intact rat striatum. | 2001 |
|
Effects of MDL 73005 on water-maze performances and locomotor activity in scopolamine-treated rats. | 2001 Apr |
|
Interactions between allosteric modulators and 4-DAMP and other antagonists at muscarinic receptors: potential significance of the distance between the N and carboxyl C atoms in the molecules of antagonists. | 2001 Apr |
|
Infralimbic muscarinic M1 receptors modulate anxiety-like behaviour and spontaneous working memory in mice. | 2001 Apr |
|
Tiotropium bromide. | 2001 Apr |
|
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism. | 2001 Apr 27 |
|
Antimuscarinic treatment for lung diseases from research to clinical practice. | 2001 Apr 27 |
|
M5 muscarinic receptors are needed for slow activation of dopamine neurons and for rewarding brain stimulation. | 2001 Apr 27 |
|
Ultrasonic vocalizations as an index of social memory in female mice. | 2001 Aug |
|
Cholinergic synaptic potentials in the supragranular layers of auditory cortex. | 2001 Aug |
|
Reversal caused by n-butylidenephthalide from the deficits of inhibitory avoidance performance in rats. | 2001 Feb |
|
Evaluation of novel PET ligands (+)N-[11C]methyl-3-piperidyl benzilate ([11C](+)3-MPB) and its stereoisomer [11C](-)3-MPB for muscarinic cholinergic receptors in the conscious monkey brain: a PET study in comparison with. | 2001 Feb |
|
Dehydroevodiamine attenuates beta-amyloid peptide-induced amnesia in mice. | 2001 Feb 16 |
|
Inhaled anticholinergic therapy: applied pharmacology and interesting developments. | 2001 Jan |
|
The ameliorating effect of the water layer of Fructus Schisandrae on cycloheximide-induced amnesia in rats: interaction with drugs acting at neurotransmitter receptors. | 2001 Jan |
|
Designing of an orally active complement C3a agonist peptide with anti-analgesic and anti-amnesic activity. | 2001 Jan |
|
Developmental exposure to methylmercury alters behavioral sensitivity to D-amphetamine and pentobarbital in adult rats. | 2001 Jan-Feb |
|
Effects of Hypericum perforatum (St. John's wort) on passive avoidance in the rat: evaluation of potential neurochemical mechanisms underlying its antidepressant activity. | 2001 Jul |
|
Differential effects of trihexyphenidyl on place preference conditioning and locomotor stimulant activity of cocaine and methamphetamine. | 2001 Jul |
|
Occurrence of cadaverine in hairy roots of Brugmansia candida. | 2001 Jul |
|
Anti-ischemic and cognition-enhancing properties of NNC-711, a gamma-aminobutyric acid reuptake inhibitor. | 2001 Jul 13 |
|
Effects of vasopressin on histamine H(1) receptor antagonist-induced spatial memory deficits in rats. | 2001 Jul 6 |
|
Interaction between the cholinergic system and CRH in the modulation of spatial discrimination learning in mice. | 2001 Jul 6 |
|
Hairy roots of Brugmansia candida that grow without agitation: biotechnological implications. | 2001 Jul-Aug |
|
Drug-induced variations in the probability of occurrence of multiple corrective saccades. | 2001 Jun |
|
The alpha 2 adrenoceptor antagonists RX 821002 and yohimbine delay-dependently impair choice accuracy in a delayed non-matching-to-position task in rats. | 2001 Jun |
|
Y-27632, an inhibitor of Rho-kinase, antagonizes noradrenergic contractions in the rabbit and human penile corpus cavernosum. | 2001 Jun |
|
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats. | 2001 Mar |
|
Evidence for involvement of central 5-HT(4) receptors in cholinergic function associated with cognitive processes: behavioral, electrophysiological, and neurochemical studies. | 2001 Mar |
|
Comparative effects of scopolamine and quinpirole on the striatal fos expression induced by stimulation of D(1) dopamine receptors in the rat. | 2001 Mar 2 |
|
Scopolamine reduces the P35m and P60m deflections of the human somatosensory evoked magnetic fields. | 2001 Mar 5 |
|
The role of the cholinergic system of the sensorimotor cortex of the rat brain in controlling different types of movement. | 2001 Mar-Apr |
|
Memory impairment induced by cholinergic antagonists injected into the mushroom bodies of the honeybee. | 2001 May |
|
Subchronic administration of various pretreatments of nerve agent poisoning. II. Compared efficacy against soman toxicity. | 2001 May |
|
Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity. | 2001 May |
|
The role of nitric oxide on the relaxations of rabbit corpus cavernosum induced by Androctonus australis and Buthotus judaicus scorpion venoms. | 2001 May |
|
Excitatory nicotinic and desensitizing muscarinic (M2) effects on C-nociceptors in isolated rat skin. | 2001 May 1 |
|
The role of muscarinic cholinoceptors in the retrieval of an operant food-related conditioned reflex in cats. | 2001 May-Jun |
|
Release of non-neuronal acetylcholine from the human placenta: difference to neuronal acetylcholine. | 2001 Sep |
|
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats. | 2001 Sep |
|
Substance P and its transglutaminase-synthesized spermine derivative elicit yawning behavior via nitric oxide in rats. | 2001 Sep |
|
Pharmacological modulation of behavioral and neuronal correlates of repetition priming. | 2001 Sep 1 |
Sample Use Guides
Transderm Scōp (scopolamine) transdermal system patch. Each Transderm Scōp patch is formulated to deliver in-vivo approximately 1 mg of scopolamine over 3 days.
Initiation of Therapy
Motion Sickness
To prevent the nausea and vomiting associated with motion sickness, one Transderm Scōp patch (formulated to deliver approximately 1 mg of scopolamine over 3 days) should be applied to the hairless area behind one ear at least 4 hours before the antiemetic effect is required.
Post Operative Nausea and Vomiting
To prevent post operative nausea and vomiting, one Transderm Scōp patch should be applied the evening before scheduled surgery, except for caesarian section.
For caesarian section surgery, to minimize exposure of the newborn baby to the drug, apply the patch one hour
prior to caesarian section.
Continuation of Therapy
Should the patch become displaced, it should be discarded, and a fresh one placed on the hairless area behind the other ear.
Motion Sickness
If therapy is required for longer than 3 days, the first patch should be removed and a fresh one placed on the hairless area behind the other ear.
Post Operative Nausea and Vomiting
For perioperative use, the patch should be kept in place for 24 hours following surgery at which time it should be removed and discarded.
Route of Administration:
Transdermal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27163641
Rosmarinic acid treatment increases the expression of BDNF and GluR-2 proteins and prevents cell death of scopolamine-exposed (300 μM) organotypic hippocampal slice cultures.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:58:25 UTC 2023
by
admin
on
Wed Jul 05 23:58:25 UTC 2023
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Record UNII |
DL48G20X8X
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
A04AD51
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WHO-ATC |
A04AD01
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WHO-ATC |
N05CM05
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CFR |
21 CFR 310.533
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WHO-VATC |
QA04AD51
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NDF-RT |
N0000175574
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NDF-RT |
N0000175370
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WHO-ATC |
S01FA02
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WHO-ATC |
S01BB01
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LIVERTOX |
875
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WHO-VATC |
QS01FA02
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WHO-VATC |
QN05CM05
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NCI_THESAURUS |
C29704
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WHO-VATC |
QA04AD01
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NCI_THESAURUS |
C29706
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DL48G20X8X
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Scopolamine
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DL48G20X8X
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SUB14152MIG
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SCOPOLAMINE
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CHEMBL1187846
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DB00747
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C47712
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200-090-3
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M9813
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PRIMARY | Merck Index | ||
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9601
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PRIMARY | RxNorm | ||
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51-34-3
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4074
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100000092042
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE | |||
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METABOLITE -> PARENT |
URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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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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