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
[H][C@@]12CC3=CNC4=C3C(=CC=C4)[C@@]1([H])C[C@H](CN2CC=C)C(=O)N(CCCN(C)C)C(=O)NCC
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 |
---|---|---|---|---|
12952 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 Co-administed with:: L-dopa, po(370.6 mg) Sources: Page: p.18, p.19, p.22 |
unhealthy, 41.0–73.5 n = 34 Health Status: unhealthy Condition: Parkinson’s disease Age Group: 41.0–73.5 Sex: M+F Population Size: 34 Sources: Page: p.18, p.19, p.22 |
|
2 mg 1 times / day multiple, oral (min) Overdose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Parkinson’s disease Sources: Page: p.4 |
Other AEs: Cardiac valvulopathy... Other AEs: Cardiac valvulopathy Sources: Page: p.4 |
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: Page: p.9 |
unhealthy n = 221 Health Status: unhealthy Condition: Hyperprolactinemic disorders Population Size: 221 Sources: Page: p.9 |
Disc. AE: Headache, Nausea... AEs leading to discontinuation/dose reduction: Headache (1.4%) Sources: Page: p.9Nausea (0.9%) Vomiting (0.9%) |
1 mg 2 times / week multiple, oral (max) Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Hyperprolactinemic disorders Sources: Page: p.4 |
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: Page: p.4Pericardial fibrosis Retroperitoneal fibrosis |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cardiac valvulopathy | 2 mg 1 times / day multiple, oral (min) Overdose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Parkinson’s disease Sources: Page: p.4 |
|
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: Page: p.9 |
unhealthy n = 221 Health Status: unhealthy Condition: Hyperprolactinemic disorders Population Size: 221 Sources: Page: p.9 |
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: Page: p.9 |
unhealthy n = 221 Health Status: unhealthy Condition: Hyperprolactinemic disorders Population Size: 221 Sources: Page: p.9 |
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: Page: p.9 |
unhealthy n = 221 Health Status: unhealthy Condition: Hyperprolactinemic disorders Population Size: 221 Sources: Page: p.9 |
Cardiac valvulopathy | 1 mg 2 times / week multiple, oral (max) Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Hyperprolactinemic disorders Sources: Page: p.4 |
|
Pericardial fibrosis | 1 mg 2 times / week multiple, oral (max) Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Hyperprolactinemic disorders Sources: Page: p.4 |
|
Retroperitoneal fibrosis | 1 mg 2 times / week multiple, oral (max) Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Hyperprolactinemic disorders Sources: Page: p.4 |
|
Pleural effusion | Disc. AE | 1 mg 2 times / week multiple, oral (max) Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Hyperprolactinemic disorders Sources: Page: p.4 |
Pulmonary fibrosis | Disc. AE | 1 mg 2 times / week multiple, oral (max) Recommended Dose: 1 mg, 2 times / week Route: oral Route: multiple Dose: 1 mg, 2 times / week Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Hyperprolactinemic disorders Sources: Page: p.4 |
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 |
---|---|---|
Clinical data on restless legs syndrome: a dose-finding study with cabergoline. | 2001 |
|
Actigraph analysis of diurnal motor fluctuations during dopamine agonist therapy. | 2001 |
|
Cabergoline for levodopa-induced complications in Parkinson's disease. | 2001 |
|
Successful treatment of a large macroprolactinoma with cabergoline during pregnancy. | 2001 Aug |
|
Upregulation of lymphocyte apoptosis as a strategy for preventing and treating autoimmune disorders: a role for whole-food vegan diets, fish oil and dopamine agonists. | 2001 Aug |
|
Control of unremitting rheumatoid arthritis by the prolactin antagonist cabergoline. | 2001 Feb |
|
ACTH silent adenoma shrinking under cabergoline. | 2001 Jan |
|
Tumour shrinkage and chiasmal herniation after successful cabergoline treatment for a macroprolactinoma. | 2001 Jan |
|
Control of red fox (Vulpes vulpes) fertility with cabergoline: dose response and timing of intervention. | 2001 Jul |
|
Clusterlike headache as first manifestation of a prolactinoma. | 2001 Jul-Aug |
|
[Pharmacological effects of cabergoline against parkinsonism]. | 2001 Jun |
|
Study of the change of prolactin and progesterone during dopaminergic agonist treatments in pseudopregnant bitches. | 2001 May 31 |
|
Resistance to cabergoline as compared with bromocriptine in hyperprolactinemia: prevalence, clinical definition, and therapeutic strategy. | 2001 Nov |
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Cabergoline influences ovarian stimulation in hyperprolactinaemic patients with polycystic ovary syndrome. | 2001 Nov |
|
Effectiveness of cabergoline for termination of pregnancy in silver fox (Vulpes vulpes fulva). | 2001 Oct |
|
Determination of cabergoline by electrospray ionization tandem mass spectrometry: picogram detection via column focusing sample introduction. | 2001 Oct 15 |
|
[A case of elderly onset Parkinson's disease complicated by dropped head syndrome]. | 2001 Sep |
|
Comparison of the effects of cabergoline and bromocriptine on prolactin levels in hyperprolactinemic patients. | 2001 Sep |
|
Cabergoline, a hopeful medicine for prolactinomas and non-tumoral hyperprolactinemia. | 2001 Sep |
|
Disorders of prolactin secretion. | 2001 Sep |
|
Treatment of risperidone-induced hyperprolactinemia with a dopamine agonist in children. | 2001 Winter |
|
DA agonists -- ergot derivatives: bromocriptine: management of Parkinson's disease. | 2002 |
|
Macroprolactinoma associated with Cushing's disease, successfully treated with cabergoline. | 2002 Feb |
|
Giant prolactinomas presenting as skull base tumors. | 2002 Feb |
|
Restless legs syndrome: treatment with dopaminergic agents. | 2002 Feb 26 |
|
Long-term studies of dopamine agonists. | 2002 Feb 26 |
|
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 |
|
Dopamine receptor agonists for treating prolactinomas. | 2002 Jun |
|
Cabergoline can increase penile erections and libido. | 2002 Mar 12 |
|
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 |
|
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 |
|
A practical synthesis of cabergoline. | 2002 Oct 4 |
|
Gateways to Clinical Trials. | 2002 Sep |
|
Microstructure of the non-rapid eye movement sleep electroencephalogram in patients with newly diagnosed Parkinson's disease: effects of dopaminergic treatment. | 2002 Sep |
|
Gender differences in the prevalence, clinical features and response to cabergoline in hyperprolactinemia. | 2003 Mar |
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
Sat Dec 16 16:22:08 GMT 2023
by
admin
on
Sat Dec 16 16:22:08 GMT 2023
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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 |
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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