Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H37N5O2 |
Molecular Weight | 451.6043 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCNC(=O)N(CCCN(C)C)C(=O)[C@@H]1C[C@H]2[C@@H](CC3=CNC4=C3C2=CC=C4)N(CC=C)C1
InChI
InChIKey=KORNTPPJEAJQIU-KJXAQDMKSA-N
InChI=1S/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1
Molecular Formula | C26H37N5O2 |
Molecular Weight | 451.6043 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/dosage/cabergoline.html
http://www.wikidoc.org/index.php/Cabergoline
http://www.rxlist.com/dostinex-drug.htm
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/dosage/cabergoline.html
http://www.wikidoc.org/index.php/Cabergoline
http://www.rxlist.com/dostinex-drug.htm
Cabergoline is a long-acting dopamine receptor agonist with a high affinity for D2 receptors. Results of in vitro studies demonstrate that cabergoline exerts a direct inhibitory effect on the secretion of prolactin by rat pituitary lactotrophs. It is FDA approved for the treatment of hyperprolactinemic disorders, either idiopathic or due to pituitary adenomas. Common adverse reactions include constipation, nausea, dizziness, headache and fatigue. Cabergoline should not be administered concurrently with D-antagonists, such as phenothiazines, butyrophenones, thioxanthenes, or metoclopramide.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18691132 |
1.5 nM [Ki] | ||
Target ID: CHEMBL2095169 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18691132 |
0.5 nM [Ki] | ||
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18691132 |
1.2 nM [Ki] | ||
Target ID: CHEMBL217 |
0.69 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CABERGOLINE Approved UseCabergoline tablets are indicated for the treatment of hyperprolactinemic disorders, either idiopathic or due to pituitary adenomas. Launch Date2005 |
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Primary | CABERGOLINE Approved UseCabergoline tablets are indicated for the treatment of hyperprolactinemic disorders, either idiopathic or due to pituitary adenomas. Launch Date2005 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.3 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CABERGOLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
40.3 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
CABERGOLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
67 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CABERGOLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1295 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CABERGOLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1884 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
CABERGOLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2546 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CABERGOLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
68.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7884663 |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
CABERGOLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60% |
unknown, unknown |
CABERGOLINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, 41.0–73.5 Health Status: unhealthy Age Group: 41.0–73.5 Sex: M+F Sources: |
|
2 mg 1 times / day multiple, oral Overdose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Cardiac valvulopathy... Other AEs: Cardiac valvulopathy Sources: |
0.5 mg 2 times / week multiple, oral Recommended Dose: 0.5 mg, 2 times / week Route: oral Route: multiple Dose: 0.5 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Headache, Nausea... AEs leading to discontinuation/dose reduction: Headache (1.4%) Sources: Nausea (0.9%) Vomiting (0.9%) |
1 mg 2 times / week multiple, oral Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Pleural effusion, Pulmonary fibrosis... Other AEs: Cardiac valvulopathy, Pericardial fibrosis... AEs leading to discontinuation/dose reduction: Pleural effusion Other AEs:Pulmonary fibrosis Cardiac valvulopathy Sources: Pericardial fibrosis Retroperitoneal fibrosis |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cardiac valvulopathy | 2 mg 1 times / day multiple, oral Overdose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Nausea | 0.9% Disc. AE |
0.5 mg 2 times / week multiple, oral Recommended Dose: 0.5 mg, 2 times / week Route: oral Route: multiple Dose: 0.5 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Vomiting | 0.9% Disc. AE |
0.5 mg 2 times / week multiple, oral Recommended Dose: 0.5 mg, 2 times / week Route: oral Route: multiple Dose: 0.5 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Headache | 1.4% Disc. AE |
0.5 mg 2 times / week multiple, oral Recommended Dose: 0.5 mg, 2 times / week Route: oral Route: multiple Dose: 0.5 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Cardiac valvulopathy | 1 mg 2 times / week multiple, oral Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Pericardial fibrosis | 1 mg 2 times / week multiple, oral Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Retroperitoneal fibrosis | 1 mg 2 times / week multiple, oral Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Pleural effusion | Disc. AE | 1 mg 2 times / week multiple, oral Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Pulmonary fibrosis | Disc. AE | 1 mg 2 times / week multiple, oral Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/31183987/ Page: - |
likely |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes | yes (co-administration study) Comment: n healthy male volunteers, the mean of Cmax and AUC of cabergoline increased around 2.7 times by coadministration of clarithromycin. Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
Bait-delivered cabergoline for the reproductive control of the red fox (Vulpes vulpes): estimating mammalian non-target risk in south-eastern Australia. | 2001 |
|
Prolactinomas in children and adolescents--consequences in adult life. | 2001 |
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Clinical data on restless legs syndrome: a dose-finding study with cabergoline. | 2001 |
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Successful treatment of a large macroprolactinoma with cabergoline during pregnancy. | 2001 Aug |
|
A review of canine pseudocyesis. | 2001 Dec |
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Effectiveness of cabergoline for termination of pregnancy in silver fox (Vulpes vulpes fulva). | 2001 Oct |
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Treatment of risperidone-induced hyperprolactinemia with a dopamine agonist in children. | 2001 Winter |
|
Medical management of prolactin-secreting pituitary adenomas. | 2002 |
|
[Use of dopamine agonists in the treatment of Parkinson's disease]. | 2002 |
|
DA agonists -- ergot derivatives: cabergoline: management of Parkinson's disease. | 2002 |
|
DA agonists -- ergot derivatives: bromocriptine: management of Parkinson's disease. | 2002 |
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Control of fertility in the red fox (Vulpes vulpes): effect of a single oral dose of cabergoline in early pregnancy. | 2002 |
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Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. | 2002 |
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A case of macroprolactinoma with subclinical growth hormone production. | 2002 Feb |
|
Giant prolactinomas presenting as skull base tumors. | 2002 Feb |
|
Restless legs syndrome: treatment with dopaminergic agents. | 2002 Feb 26 |
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Alteration of glutamate receptors in the striatum of dyskinetic 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated monkeys following dopamine agonist treatment. | 2002 Jan |
|
Effects of short- and long-acting dopamine agonists on sensitized dopaminergic neurotransmission in rats with unilateral 6-OHDA lesions. | 2002 Jan 18 |
|
The dopamine agonist cabergoline provides neuroprotection by activation of the glutathione system and scavenging free radicals. | 2002 Jul |
|
Gateways to clinical trials. | 2002 Jul-Aug |
|
Treatment of Parkinson's disease and restless legs syndrome with cabergoline, a long-acting dopamine agonist. | 2002 Jul-Aug |
|
Dopamine receptor agonists for treating prolactinomas. | 2002 Jun |
|
Use of cabergoline to treat primary and secondary anestrus in dogs. | 2002 Jun 1 |
|
SUNCT syndrome in two patients with prolactinomas and bromocriptine-induced attacks. | 2002 Jun 11 |
|
Sleep attacks in patients taking dopamine agonists: review. | 2002 Jun 22 |
|
Cabergoline can increase penile erections and libido. | 2002 Mar 12 |
|
[Novel pharmacologic therapies in acromegaly]. | 2002 May 12 |
|
Effect of cabergoline on thyroid function in hyperprolactinaemia. | 2002 Nov |
|
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. III. Agonist and antagonist properties at serotonin, 5-HT(1) and 5-HT(2), receptor subtypes. | 2002 Nov |
|
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. II. Agonist and antagonist properties at subtypes of dopamine D(2)-like receptor and alpha(1)/alpha(2)-adrenoceptor. | 2002 Nov |
|
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes. | 2002 Nov |
|
Dopamine agonist monotherapy in Parkinson's disease. | 2002 Nov 30 |
|
Pregnancy outcome after cabergoline treatment in early weeks of gestation. | 2002 Nov-Dec |
|
Circulating nitric oxide changes throughout the menstrual cycle in healthy women and women affected by pathological hyperprolactinemia on dopamine agonist therapy. | 2002 Oct |
|
An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease. | 2002 Oct |
|
Autonomic failure mimicing dopamine agonist induced vertigo in a patient with macroprolactinoma. | 2002 Oct |
|
Use of the dopamine agonist cabergoline in the treatment of movement disorders. | 2002 Oct |
|
The novel use of very high doses of cabergoline and a combination of testosterone and an aromatase inhibitor in the treatment of a giant prolactinoma. | 2002 Oct |
|
Combination of two different dopamine agonists in the management of Parkinson's disease. | 2002 Sep |
|
Antioxidant properties of cabergoline: inhibition of brain auto-oxidation and superoxide anion production of microglial cells in rats. | 2002 Sep 13 |
|
Accurate mass measurement at enhanced mass-resolution on a triple quadrupole mass-spectrometer for the identification of a reaction impurity and collisionally-induced fragment ions of cabergoline. | 2003 |
|
Treatment with cabergoline is associated with weight loss in patients with hyperprolactinemia. | 2003 Feb |
|
Radioimmunoassay of prolactin for the meerkat (Suricata suricatta), a cooperatively breeding carnivore. | 2003 Feb 1 |
|
Hyperprolactinemia in men: clinical and biochemical features and response to treatment. | 2003 Feb-Mar |
|
[Efficacy of cabergoline in the treatment of macroprolactinoma]. | 2003 Jan 18 |
|
Involvement of PI3'-K, mitogen-activated protein kinase and protein kinase B in the up-regulation of the expression of nNOSalpha and nNOSbeta splicing variants induced by PRL-receptor activation in GH3 cells. | 2003 Mar |
|
Gender differences in the prevalence, clinical features and response to cabergoline in hyperprolactinemia. | 2003 Mar |
|
Prolactinomas, dopamine agonists and headache: two case reports. | 2003 Mar |
|
Selective control of the estrous cycle of the dog through suppression of estrus and reduction of the length of anestrus. | 2003 Mar |
|
[Macroadenoma of the pituitary gland with moderate hyperprolactinaemia]. | 2003 Mar 28 |
Sample Use Guides
The recommended dosage for initiation of therapy is 0.25 mg twice a week. Dosage may be increased by 0.25 mg twice weekly up to a dosage of 1 mg twice a week according to the patient’s serum prolactin level. Dosage increases should not occur more rapidly than every 4 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12464354
Tert-butylhydroperoxide caused a 42+/-4% neuronal death, which was prevented by cabergoline (2 h before) in a concentration-dependent manner (EC(50): 1.24 microM).
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 07:45:54 GMT 2025
by
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on
Wed Apr 02 07:45:54 GMT 2025
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Record UNII |
LL60K9J05T
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66884
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NCI_THESAURUS |
C38149
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WHO-VATC |
QG02CB03
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WHO-ATC |
N04BC06
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NDF-RT |
N0000007618
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LIVERTOX |
135
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WHO-VATC |
QN04BC06
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NDF-RT |
N0000175827
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WHO-ATC |
G02CB03
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NDF-RT |
N0000007618
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EMA VETERINARY ASSESSMENT REPORTS |
VELACTIS [SUSPENDED]
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CHEMBL1201087
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460
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C047047
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CABERGOLINE
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81409-90-7
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37
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C47428
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5860
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100000092143
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II-10
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DTXSID6022719
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47579
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3286
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1084306
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54746
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Cabergoline
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SUB06041MIG
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DB00248
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LL60K9J05T
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LL60K9J05T
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m2876
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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TARGET -> AGONIST | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
7% in urine
MINOR
URINE
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METABOLITE -> PARENT |
41% in urine
MAJOR
URINE
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Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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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