Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H6N4O3S2 |
Molecular Weight | 222.245 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)NC1=NN=C(S1)S(N)(=O)=O
InChI
InChIKey=BZKPWHYZMXOIDC-UHFFFAOYSA-N
InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9)
Molecular Formula | C4H6N4O3S2 |
Molecular Weight | 222.245 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Acetazolamide, usually sold under the trade name Diamox in some countries. DIAMOX is used for adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure. DIAMOX is also indicated for the prevention or amelioration of symptoms associated with acute mountain sickness despite gradual ascent. DIAMOX is an enzyme inhibitor that acts specifically on carbonic anhydrase, the enzyme that catalyzes the reversible reaction involving the hydration of carbon dioxide and the dehydration of carbonic acid. In the eye, this inhibitory action of acetazolamide decreases the secretion of aqueous humor and results in a drop in intraocular pressure, a reaction considered desirable in cases of glaucoma and even in certain non-glaucomatous conditions. Evidence seems to indicate that DIAMOX has utility as an adjuvant in treatment of certain dysfunctions of the central nervous system (e.g., epilepsy). The diuretic effect of DIAMOX is due to its action in the kidney on the reversible reaction involving hydration of carbon dioxide and dehydration of carbonic acid. The result is renal loss of HCO3 ion, which carries out sodium, water, and potassium. It is on the World Health Organization's List of Essential Medicines, a list of the most important medications needed in a basic health system.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11430635 |
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Target ID: CHEMBL3729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=18336310 |
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Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=18336310 |
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Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11430635 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | DIAMOX Approved UseFor adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure. DIAMOX is also indicated for the prevention or amelioration of symptoms associated with acute mountain sickness despite gradual ascent. Launch Date-5.18572802E11 |
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Preventing | DIAMOX Approved UseFor adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure. DIAMOX is also indicated for the prevention or amelioration of symptoms associated with acute mountain sickness despite gradual ascent. Launch Date-5.18572802E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
776 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACETAZOLAMIDE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1313 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACETAZOLAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
52130 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACETAZOLAMIDE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6735 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACETAZOLAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACETAZOLAMIDE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
13.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACETAZOLAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% |
unknown, oral |
ACETAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy, 21–80 years n = 52 Health Status: unhealthy Condition: elevated intraocular pressure Age Group: 21–80 years Sex: M+F Population Size: 52 Sources: |
Disc. AE: Leukopenia... AEs leading to discontinuation/dose reduction: Leukopenia Sources: |
500 mg 4 times / day multiple, oral Studied dose Dose: 500 mg, 4 times / day Route: oral Route: multiple Dose: 500 mg, 4 times / day Sources: |
unhealthy, 70 years n = 1 Health Status: unhealthy Condition: Diabetes | Chronic Renal Failure Age Group: 70 years Sex: F Population Size: 1 Sources: |
Other AEs: Metabolic acidosis, Coma... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Leukopenia | Disc. AE | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy, 21–80 years n = 52 Health Status: unhealthy Condition: elevated intraocular pressure Age Group: 21–80 years Sex: M+F Population Size: 52 Sources: |
Coma | 500 mg 4 times / day multiple, oral Studied dose Dose: 500 mg, 4 times / day Route: oral Route: multiple Dose: 500 mg, 4 times / day Sources: |
unhealthy, 70 years n = 1 Health Status: unhealthy Condition: Diabetes | Chronic Renal Failure Age Group: 70 years Sex: F Population Size: 1 Sources: |
|
Metabolic acidosis | grade 3 | 500 mg 4 times / day multiple, oral Studied dose Dose: 500 mg, 4 times / day Route: oral Route: multiple Dose: 500 mg, 4 times / day Sources: |
unhealthy, 70 years n = 1 Health Status: unhealthy Condition: Diabetes | Chronic Renal Failure Age Group: 70 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 |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >5000 uM] | ||||
weak [IC50 425 uM] | ||||
weak [IC50 816 uM] | ||||
yes [IC50 75 uM] | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
weak |
PubMed
Title | Date | PubMed |
---|---|---|
Renal failure associated with acetazolamide therapy for glaucoma. | 1975 Apr |
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[Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid]. | 1999 Feb |
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Calcium phosphate stones during long-term acetazolamide treatment for epilepsy. | 1999 Jul |
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Pseudotumor cerebri induced by all-trans-retinoic acid in a child treated for acute promyelocytic leukemia. | 2000 Apr |
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Acetazolamide and enalapril combination offers complete protection from nitric oxide-deficient stroke in stroke-prone spontaneously hypertensive rats. | 2000 Jun |
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Management strategies for refractory localization-related seizures. | 2001 |
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Diuretic therapy for newborn infants with posthemorrhagic ventricular dilatation. | 2001 |
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Vasoconstrictive drugs increase carbonic anhydrase I in vascular smooth muscle while vasodilating drugs reduce the activity of this isozyme by a direct mechanism of action. | 2001 |
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Treatment options for sleep apnoea. | 2001 |
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[A case of potassium-sensitive periodic paralysis with cardiac dysrhythmia controlled with imipramine and acetazolamide]. | 2001 Apr |
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Acetazolamide treatment for infantile central sleep apnea. | 2001 Aug |
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Physiological and molecular biological characterization of intracellular carbonic anhydrase from the marine diatom Phaeodactylum tricornutum. | 2001 Aug |
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Minocycline and Pseudotumor cerebri: The well-known but well-kept secret. | 2001 Aug |
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Cerebrovascular reserve in patients with carotid occlusive disease assessed by stable xenon-enhanced ct cerebral blood flow and transcranial Doppler. | 2001 Aug |
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Carbonic anhydrase isozyme distribution and characterization in metabolic fiber types of the dorsal levator muscle of the blue crab, Callinectes sapidus. | 2001 Aug 1 |
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Effect of familial hypertension on glomerular hemodynamics and tubulo-glomerular feedback after uninephrectomy. | 2001 Feb |
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Indapamide, a thiazide-like diuretic, decreases bone resorption in vitro. | 2001 Feb |
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Asymmetric subcellular mRNA distribution correlates with carbonic anhydrase activity in Acetabularia acetabulum. | 2001 Feb |
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Measurement of cerebral hemodynamics with perfusion-weighted MR imaging: comparison with pre- and post-acetazolamide 133Xe-SPECT in occlusive carotid disease. | 2001 Feb |
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Long-term follow-up of asymptomatic patients with major artery occlusion: rate of symptomatic change and evaluation of cerebral hemodynamics. | 2001 Feb |
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The spray drying of acetazolamide as method to modify crystal properties and to improve compression behaviour. | 2001 Feb 1 |
|
Influence of nitrovasodilators and cyclooxygenase inhibitors on cerebral vasoreactivity in conscious rabbits. | 2001 Feb 2 |
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Quantitative volumetry in patients with carotid disease--effects of acetazolamide. | 2001 Jan |
|
In vivo evidence for K(Ca) channel opening properties of acetazolamide in the human vasculature. | 2001 Jan |
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Use of acetazolamide to decrease cerebrospinal fluid production in chronically ventilated patients with ventriculopleural shunts. | 2001 Jan |
|
Preferential acetazolamide-induced vasodilation based on vessel size and organ: confirmation of peripheral vasodilation with use of colored microspheres. | 2001 Jul |
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Cerebral vasoreactivity and internal carotid artery flow help to identify patients at risk for hyperperfusion after carotid endarterectomy. | 2001 Jul |
|
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system. | 2001 Jul |
|
Extracellular carbonic anhydrase in the dogfish, Squalus acanthias: a role in CO2 excretion. | 2001 Jul-Aug |
|
[Mountaineering and altitude sickness]. | 2001 Jun |
|
Correlation of optic nerve head tomography with visual field sensitivity in papilledema. | 2001 Jun |
|
Sporadic late onset paroxysmal cerebellar ataxia in four unrelated patients: a new disease? | 2001 Mar |
|
Compromised hemodynamics associated with multipedicular lesions of cerebral arteries. | 2001 Mar |
|
Acute mountain sickness score and hypoxemia. | 2001 May |
|
Transient renal tubular acidosis in a neonate following transplacental acetazolamide. | 2001 May |
|
Revisiting the question, "is the acetazolamide test valid for quantitative assessment of maximal cerebral autoregulatory vasodilation?". | 2001 May |
|
Quantitative cerebral blood flow imaging in a patient with the Heidenhain variant of Creutzfeldt-Jakob disease. | 2001 Sep |
|
Timolol may inhibit aqueous humor secretion by cAMP-independent action on ciliary epithelial cells. | 2001 Sep |
Patents
Sample Use Guides
Glaucoma:
The recommended dosage is 1 capsule (500 mg) two times a day. Usually 1 capsule is administered in the morning and 1 capsule in the evening. It may be necessary to adjust the dose, but it has usually been found that dosage in excess of 2 capsules (1 g) does not produce an increased effect
Acute Mountain Sickness:
Dosage is 500 mg to 1000 mg daily, in divided doses using tablets or extended-release capsules as appropriate. In circumstances of rapid ascent, such as in rescue or military operations, the higher dose level of 1000 mg is recommended
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25937211
In both, piriform and entorhinal cortices (PC and EC, respectively), acetazolamide (10 uM): (i) reduced the duration and the interval of ccurrence of ictal discharges along with the associated ripples and fast ripples; (ii) decreased the interval of occurrence of interictal discharges and the rates of associated fast ripples; and (iii)diminished the duration and amplitude of pharmacologically isolated GABAergic events while increasing their interval of occurrence.
Substance Class |
Chemical
Created
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Record UNII |
O3FX965V0I
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QS01EC01
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NCI_THESAURUS |
C448
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NDF-RT |
N0000175517
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CFR |
21 CFR 522.44
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NCI_THESAURUS |
C29577
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WHO-ATC |
S01EC01
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NDF-RT |
N0000000235
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WHO-ESSENTIAL MEDICINES LIST |
21.4
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CFR |
21 CFR 520.28
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LIVERTOX |
NBK548664
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145177
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50634
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Acetazolamide
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481
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M1322
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CHEMBL20
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O3FX965V0I
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31163
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SUB05219MIG
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D000086
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ACETAZOLAMIDE
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59-66-5
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27690
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O3FX965V0I
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3002
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1986
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ACETAZOLAMIDE
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PRIMARY | Description: A white, or almost white, crystalline powder; odourless. Solubility: Very slightly soluble in water; slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Carbonic anhydrase inhibitor. Storage: Acetazolamide should be kept in a well-closed container. Definition: Acetazolamide contains not less than 99.0% and not more than 101.0% of C4H6N4O3S2, calculated with reference to the dried substance. | ||
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DTXSID7022544
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200-440-5
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C28809
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DB00819
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1005004
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167
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TARGET -> INHIBITOR |
Ki
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TARGET -> INHIBITOR |
Ki
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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BINDING
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
Ki
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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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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