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 |
|||
| 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 |
|---|---|---|
| [Macroadenoma of the pituitary gland with moderate hyperprolactinaemia]. | 2003-03-28 |
|
| 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. | 2003-03 |
|
| Gender differences in the prevalence, clinical features and response to cabergoline in hyperprolactinemia. | 2003-03 |
|
| Prolactinomas, dopamine agonists and headache: two case reports. | 2003-03 |
|
| Selective control of the estrous cycle of the dog through suppression of estrus and reduction of the length of anestrus. | 2003-03 |
|
| Radioimmunoassay of prolactin for the meerkat (Suricata suricatta), a cooperatively breeding carnivore. | 2003-02-01 |
|
| Treatment with cabergoline is associated with weight loss in patients with hyperprolactinemia. | 2003-02 |
|
| [Efficacy of cabergoline in the treatment of macroprolactinoma]. | 2003-01-18 |
|
| 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 |
|
| Alopecia induced by dopamine agonists. | 2002-12-24 |
|
| Hyperprolactinemia in men: clinical and biochemical features and response to treatment. | 2002-12-20 |
|
| Cabergoline prevents necrotic neuronal death in an in vitro model of oxidative stress. | 2002-12-20 |
|
| Switch to quetiapine in antipsychotic agent-related hyperprolactinemia. | 2002-12 |
|
| Dopamine agonist monotherapy in Parkinson's disease. | 2002-11-30 |
|
| Detecting dose-response using contrasts: asymptotic power and sample size determination for binomial data. | 2002-11-30 |
|
| Hyperprolactinemia: etiology, diagnosis, and management. | 2002-11 |
|
| Cabergoline plasma concentration is increased during concomitant treatment with itraconazole. | 2002-11 |
|
| Characterization of gsp-mediated growth hormone excess in the context of McCune-Albright syndrome. | 2002-11 |
|
| Long term tolerability of high dose ergoline derived dopamine agonist therapy for the treatment of Parkinson's disease. | 2002-11 |
|
| Effect of cabergoline on thyroid function in hyperprolactinaemia. | 2002-11 |
|
| 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. | 2002-11 |
|
| 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. | 2002-11 |
|
| 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. | 2002-11 |
|
| Pregnancy outcome after cabergoline treatment in early weeks of gestation. | 2002-10-29 |
|
| A practical synthesis of cabergoline. | 2002-10-04 |
|
| Circulating nitric oxide changes throughout the menstrual cycle in healthy women and women affected by pathological hyperprolactinemia on dopamine agonist therapy. | 2002-10 |
|
| An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease. | 2002-10 |
|
| Autonomic failure mimicing dopamine agonist induced vertigo in a patient with macroprolactinoma. | 2002-10 |
|
| Use of the dopamine agonist cabergoline in the treatment of movement disorders. | 2002-10 |
|
| 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. | 2002-10 |
|
| Gateways to clinical trials. | 2002-09-13 |
|
| Antioxidant properties of cabergoline: inhibition of brain auto-oxidation and superoxide anion production of microglial cells in rats. | 2002-09-13 |
|
| Combination of two different dopamine agonists in the management of Parkinson's disease. | 2002-09 |
|
| Gateways to Clinical Trials. | 2002-09 |
|
| Microstructure of the non-rapid eye movement sleep electroencephalogram in patients with newly diagnosed Parkinson's disease: effects of dopaminergic treatment. | 2002-09 |
|
| Treatment of Parkinson's disease and restless legs syndrome with cabergoline, a long-acting dopamine agonist. | 2002-08-09 |
|
| Pregnancy termination in the bitch and queen. | 2002-08 |
|
| The dopamine agonist cabergoline provides neuroprotection by activation of the glutathione system and scavenging free radicals. | 2002-07 |
|
| Sleep attacks in patients taking dopamine agonists: review. | 2002-06-22 |
|
| SUNCT syndrome in two patients with prolactinomas and bromocriptine-induced attacks. | 2002-06-11 |
|
| Use of cabergoline to treat primary and secondary anestrus in dogs. | 2002-06-01 |
|
| [Novel pharmacologic therapies in acromegaly]. | 2002-05-12 |
|
| Medical management of prolactin-secreting pituitary adenomas. | 2002 |
|
| [Use of dopamine agonists in the treatment of Parkinson's disease]. | 2002 |
|
| Assessment of cabergoline as a reproductive inhibitor in coyotes (Canis latrans). | 2002 |
|
| DA agonists -- ergot derivatives: cabergoline: management of Parkinson's disease. | 2002 |
|
| DA agonists -- ergot derivatives: bromocriptine: management of Parkinson's disease. | 2002 |
|
| Control of fertility in the red fox (Vulpes vulpes): effect of a single oral dose of cabergoline in early pregnancy. | 2002 |
|
| Successful treatment of a large macroprolactinoma with cabergoline during pregnancy. | 2001-08 |
|
| Minor tumour shrinkage in nonfunctioning pituitary adenomas by long-term treatment with the dopamine agonist cabergoline. | 2001-08 |
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
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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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| 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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| Code System | Code | Type | Description | ||
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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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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
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
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 |
|---|---|---|---|---|---|---|
| Biological Half-life | PHARMACOKINETIC |
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