Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H11I3NO4.Na |
Molecular Weight | 672.9553 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C([O-])=O
InChI
InChIKey=SBXXSUDPJJJJLC-YDALLXLXSA-M
InChI=1S/C15H12I3NO4.Na/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22;/h1-4,6,12,20H,5,19H2,(H,21,22);/q;+1/p-1/t12-;/m0./s1
Molecular Formula | C15H11I3NO4 |
Molecular Weight | 649.9656 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/6617571http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/10379s47lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68014284
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6617571http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/10379s47lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68014284
Liothyronine (CYTOMEL®) is a T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than its prohormone thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3. The mechanisms by which thyroid hormones exert their physiologic action are not well understood. These hormones enhance oxygen consumption by most tissues of the body, increase the basal metabolic rate and the metabolism of carbohydrates, lipids, and proteins. Thus, they exert a profound influence on every organ system in the body and are of particular importance in the development of the central nervous system. Thyroid hormone drugs are indicated: as the replacement or supplemental therapy in patients with hypothyroidism of any etiology; as pituitary thyroid-stimulating hormone (TSH) suppressants, in the treatment or prevention of various types of euthyroid goiters; as diagnostic agents in suppression tests to differentiate suspected mild hyperthyroidism or thyroid gland autonomy.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1860 |
0.1 nM [Kd] | ||
Target ID: CHEMBL1947 |
0.1 nM [Kd] | ||
Target ID: CHEMBL1860 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12109914 |
0.1 nM [Kd] | ||
Target ID: CHEMBL1947 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12109914 |
0.1 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CYTOMEL Approved UseThyroid hormone drugs are indicated:
1. As replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyroidism during the recovery phase of subacute thyroiditis. This category includes cretinism, myxedema and ordinary hypothyroidism in patients of any age (pediatric patients, adults, the elderly), or state (including pregnancy); primary hypothyroidism resulting from functional deficiency, primary atrophy, partial or total absence of thyroid gland, or the effects of surgery, radiation, or drugs, with or without the presence of goiter; and secondary (pituitary) or tertiary (hypothalamic) hypothyroidism.
2. As pituitary thyroid-stimulating hormone (TSH) suppressants, in the treatment or prevention of various types of euthyroid goiters, including thyroid nodules, subacute or chronic lymphocytic thyroiditis (Hashimoto’s) and multinodular goiter.
3. As diagnostic agents in suppression tests to differentiate suspected mild hyperthyroidism or thyroid gland autonomy. Launch Date1956 |
|||
Primary | CYTOMEL Approved UseThyroid hormone drugs are indicated:
1. As replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyroidism during the recovery phase of subacute thyroiditis. This category includes cretinism, myxedema and ordinary hypothyroidism in patients of any age (pediatric patients, adults, the elderly), or state (including pregnancy); primary hypothyroidism resulting from functional deficiency, primary atrophy, partial or total absence of thyroid gland, or the effects of surgery, radiation, or drugs, with or without the presence of goiter; and secondary (pituitary) or tertiary (hypothalamic) hypothyroidism.
2. As pituitary thyroid-stimulating hormone (TSH) suppressants, in the treatment or prevention of various types of euthyroid goiters, including thyroid nodules, subacute or chronic lymphocytic thyroiditis (Hashimoto’s) and multinodular goiter.
3. As diagnostic agents in suppression tests to differentiate suspected mild hyperthyroidism or thyroid gland autonomy. Launch Date1956 |
|||
Diagnostic | CYTOMEL Approved UseThyroid hormone drugs are indicated:
1. As replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyroidism during the recovery phase of subacute thyroiditis. This category includes cretinism, myxedema and ordinary hypothyroidism in patients of any age (pediatric patients, adults, the elderly), or state (including pregnancy); primary hypothyroidism resulting from functional deficiency, primary atrophy, partial or total absence of thyroid gland, or the effects of surgery, radiation, or drugs, with or without the presence of goiter; and secondary (pituitary) or tertiary (hypothalamic) hypothyroidism.
2. As pituitary thyroid-stimulating hormone (TSH) suppressants, in the treatment or prevention of various types of euthyroid goiters, including thyroid nodules, subacute or chronic lymphocytic thyroiditis (Hashimoto’s) and multinodular goiter.
3. As diagnostic agents in suppression tests to differentiate suspected mild hyperthyroidism or thyroid gland autonomy. Launch Date1956 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
346 ng/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
342 ng/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
404 ng/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4370 ng × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4740 ng × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4926 ng × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
12929 ng × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
13938 ng × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22.04 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24977379 |
50 μg 1 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
LIOTHYRONINE SODIUM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
10794.4 ug 2 times / day multiple, oral Overdose Dose: 10794.4 ug, 2 times / day Route: oral Route: multiple Dose: 10794.4 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Fatigue Age Group: 20 Sex: M Population Size: 1 Sources: Page: p.2 |
Disc. AE: Anxiety, Palpitations... AEs leading to discontinuation/dose reduction: Anxiety (severe) Sources: Page: p.2Palpitations Agitation Shortness of breath Irritability Tachycardia Tremor |
15000 ug 2 times / day multiple, oral Overdose Dose: 15000 ug, 2 times / day Route: oral Route: multiple Dose: 15000 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Hypothyroidism Age Group: 30 Sex: F Population Size: 1 Sources: Page: p.2 |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea Sources: Page: p.2Vomiting Abdominal pain Headache (severe) Confusion Disorientation Diplopia |
50 ug 2 times / day multiple, oral Highest studied dose Dose: 50 ug, 2 times / day Route: oral Route: multiple Dose: 50 ug, 2 times / day Sources: Page: p.3 |
unhealthy, 39 ± 6.2 n = 2 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 39 ± 6.2 Sex: M+F Population Size: 2 Sources: Page: p.3 |
DLT: Anxiety, Tachycardia... Dose limiting toxicities: Anxiety (50%) Sources: Page: p.3Tachycardia (50%) Loose stools (100%) |
37.5 ug 2 times / day multiple, oral MTD Dose: 37.5 ug, 2 times / day Route: oral Route: multiple Dose: 37.5 ug, 2 times / day Sources: Page: p.3 |
unhealthy, 39 ± 6.2 n = 4 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 39 ± 6.2 Sex: M+F Population Size: 4 Sources: Page: p.3 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Agitation | Disc. AE | 10794.4 ug 2 times / day multiple, oral Overdose Dose: 10794.4 ug, 2 times / day Route: oral Route: multiple Dose: 10794.4 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Fatigue Age Group: 20 Sex: M Population Size: 1 Sources: Page: p.2 |
Irritability | Disc. AE | 10794.4 ug 2 times / day multiple, oral Overdose Dose: 10794.4 ug, 2 times / day Route: oral Route: multiple Dose: 10794.4 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Fatigue Age Group: 20 Sex: M Population Size: 1 Sources: Page: p.2 |
Palpitations | Disc. AE | 10794.4 ug 2 times / day multiple, oral Overdose Dose: 10794.4 ug, 2 times / day Route: oral Route: multiple Dose: 10794.4 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Fatigue Age Group: 20 Sex: M Population Size: 1 Sources: Page: p.2 |
Shortness of breath | Disc. AE | 10794.4 ug 2 times / day multiple, oral Overdose Dose: 10794.4 ug, 2 times / day Route: oral Route: multiple Dose: 10794.4 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Fatigue Age Group: 20 Sex: M Population Size: 1 Sources: Page: p.2 |
Tachycardia | Disc. AE | 10794.4 ug 2 times / day multiple, oral Overdose Dose: 10794.4 ug, 2 times / day Route: oral Route: multiple Dose: 10794.4 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Fatigue Age Group: 20 Sex: M Population Size: 1 Sources: Page: p.2 |
Tremor | Disc. AE | 10794.4 ug 2 times / day multiple, oral Overdose Dose: 10794.4 ug, 2 times / day Route: oral Route: multiple Dose: 10794.4 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Fatigue Age Group: 20 Sex: M Population Size: 1 Sources: Page: p.2 |
Anxiety | severe Disc. AE |
10794.4 ug 2 times / day multiple, oral Overdose Dose: 10794.4 ug, 2 times / day Route: oral Route: multiple Dose: 10794.4 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Fatigue Age Group: 20 Sex: M Population Size: 1 Sources: Page: p.2 |
Abdominal pain | Disc. AE | 15000 ug 2 times / day multiple, oral Overdose Dose: 15000 ug, 2 times / day Route: oral Route: multiple Dose: 15000 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Hypothyroidism Age Group: 30 Sex: F Population Size: 1 Sources: Page: p.2 |
Confusion | Disc. AE | 15000 ug 2 times / day multiple, oral Overdose Dose: 15000 ug, 2 times / day Route: oral Route: multiple Dose: 15000 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Hypothyroidism Age Group: 30 Sex: F Population Size: 1 Sources: Page: p.2 |
Diplopia | Disc. AE | 15000 ug 2 times / day multiple, oral Overdose Dose: 15000 ug, 2 times / day Route: oral Route: multiple Dose: 15000 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Hypothyroidism Age Group: 30 Sex: F Population Size: 1 Sources: Page: p.2 |
Disorientation | Disc. AE | 15000 ug 2 times / day multiple, oral Overdose Dose: 15000 ug, 2 times / day Route: oral Route: multiple Dose: 15000 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Hypothyroidism Age Group: 30 Sex: F Population Size: 1 Sources: Page: p.2 |
Nausea | Disc. AE | 15000 ug 2 times / day multiple, oral Overdose Dose: 15000 ug, 2 times / day Route: oral Route: multiple Dose: 15000 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Hypothyroidism Age Group: 30 Sex: F Population Size: 1 Sources: Page: p.2 |
Vomiting | Disc. AE | 15000 ug 2 times / day multiple, oral Overdose Dose: 15000 ug, 2 times / day Route: oral Route: multiple Dose: 15000 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Hypothyroidism Age Group: 30 Sex: F Population Size: 1 Sources: Page: p.2 |
Headache | severe Disc. AE |
15000 ug 2 times / day multiple, oral Overdose Dose: 15000 ug, 2 times / day Route: oral Route: multiple Dose: 15000 ug, 2 times / day Sources: Page: p.2 |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Hypothyroidism Age Group: 30 Sex: F Population Size: 1 Sources: Page: p.2 |
Loose stools | 100% DLT |
50 ug 2 times / day multiple, oral Highest studied dose Dose: 50 ug, 2 times / day Route: oral Route: multiple Dose: 50 ug, 2 times / day Sources: Page: p.3 |
unhealthy, 39 ± 6.2 n = 2 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 39 ± 6.2 Sex: M+F Population Size: 2 Sources: Page: p.3 |
Anxiety | 50% DLT |
50 ug 2 times / day multiple, oral Highest studied dose Dose: 50 ug, 2 times / day Route: oral Route: multiple Dose: 50 ug, 2 times / day Sources: Page: p.3 |
unhealthy, 39 ± 6.2 n = 2 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 39 ± 6.2 Sex: M+F Population Size: 2 Sources: Page: p.3 |
Tachycardia | 50% DLT |
50 ug 2 times / day multiple, oral Highest studied dose Dose: 50 ug, 2 times / day Route: oral Route: multiple Dose: 50 ug, 2 times / day Sources: Page: p.3 |
unhealthy, 39 ± 6.2 n = 2 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 39 ± 6.2 Sex: M+F Population Size: 2 Sources: Page: p.3 |
PubMed
Title | Date | PubMed |
---|---|---|
The relationship between the serum leptin concentrations of thyrotoxic patients during treatment and their total fat mass is different from that of normal subjects. | 1998 Nov |
|
Spatio-temporal expression of TSH beta and FSH beta genes in normally metamorphosing, metamorphosed, and metamorphosis-arrested Hynobius retardatus. | 2000 Sep |
|
Expression and regulation of osteopontin and connective tissue growth factor transcripts in rat anterior pituitary. | 2001 Apr |
|
Habituation of thermal sensations, skin temperatures, and norepinephrine in men exposed to cold air. | 2001 Apr |
|
Variable effects of goitrogens in inducing precocious metamorphosis in sea lampreys (Petromyzon marinus). | 2001 Apr 15 |
|
Side-effects of iodized oil administration in patients with simple goiter. | 2001 Feb |
|
Seasonality in plasma thyroxine in the desert tortoise, Gopherus agassizii. | 2001 Feb |
|
Regular moderate intensity physical activity and blood concentrations of endogenous anabolic hormones and thyroid hormones in aging men. | 2001 Feb |
|
Engineering a potential antagonist of human thyrotropin and thyroid-stimulating antibody. | 2001 Feb 16 |
|
Relationships between plasma levels of organochlorines, retinol and thyroid hormones from polar bears (Ursus maritimus) at Svalbard. | 2001 Feb 23 |
|
Inhibition of T3 production in levothyroxine-treated female mice by the root extract of Convolvulus pluricaulis. | 2001 Jan |
|
Influence of selenium supplements on the post-traumatic alterations of the thyroid axis: a placebo-controlled trial. | 2001 Jan |
|
Effect of cold exposure on energy balance and liver respiratory capacity in post-weaning rats fed a high-fat diet. | 2001 Jan |
|
Influence of a high ambient temperature on lipid metabolism in the growing pig. | 2001 Jan |
|
Endocrine relationships of Meishan and White composite females after weaning and during the luteal phase of the estrous cycle. | 2001 Jan |
|
Thyroid hormones regulate lipid peroxidation and antioxidant enzyme activities in Anabas testudineus (Bloch). | 2001 Jan |
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Effects of different activity and inactivity paradigms on myosin heavy chain gene expression in striated muscle. | 2001 Jan |
|
Thyroid hormone stimulates acetyl-coA carboxylase-alpha transcription in hepatocytes by modulating the composition of nuclear receptor complexes bound to a thyroid hormone response element. | 2001 Jan 12 |
|
Triiodothyronine downregulates the periportal expression of alpha class glutathione S-transferase in rat liver. | 2001 Jan 5 |
|
Hormone binding by protein disulfide isomerase, a high capacity hormone reservoir of the endoplasmic reticulum. | 2001 Jan 5 |
|
Androgen-Dependent transcriptional regulation of the prostate-specific antigen gene by thyroid hormone 3,5,3'-L-triiodothyronine. | 2001 Jan-Feb |
|
Effects of caloric restriction on skeletal muscle mitochondrial proton leak in aging rats. | 2001 Mar |
|
Characterization of hepatic low-K(m) outer-ring deiodination in red drum (Sciaenops ocellatus). | 2001 Mar |
|
Transcriptional repression by thyroid hormone receptors. A role for receptor homodimers in the recruitment of SMRT corepressor. | 2001 May 18 |
|
Slower skeletal muscle phenotypes are critical for constitutive expression of Hsp70 in overloaded rat plantaris muscle. | 2006 Mar |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1606687
The relative affinity of the rat synaptosomes for various T3 analogs was measured by incubating [3H]T3 with increasing amounts of T3, D-T3, T4, TRIAC and rT3, The results were expressed as the molar ratio of the concentrations of T3 or analog needed to decreaseby 50% the binding of [3H]T3.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:08:15 GMT 2023
by
admin
on
Fri Dec 15 15:08:15 GMT 2023
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Record UNII |
GCA9VV7D2N
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1553
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FDA ORPHAN DRUG |
46090
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WHO-VATC |
QH03AA02
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FDA ORPHAN DRUG |
523216
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WHO-ATC |
H03AA02
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Code System | Code | Type | Description | ||
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GCA9VV7D2N
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80774
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18258
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SUB02931MIG
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GCA9VV7D2N
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100000089973
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m6835
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1368019
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C2581
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CHEMBL1544
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142448
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200-223-5
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DBSALT000321
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DTXSID8047505
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23666110
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758175
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6484
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55-06-1
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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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 |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |