Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H21NO2S |
Molecular Weight | 351.462 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)C1=CC=C(N=C1)C#CC2=CC3=C(SCCC3(C)C)C=C2
InChI
InChIKey=OGQICQVSFDPSEI-UHFFFAOYSA-N
InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
DescriptionSources: https://www.drugbank.ca/drugs/DB00799https://www.ncbi.nlm.nih.gov/pubmed/26937021 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdfCurator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf
Sources: https://www.drugbank.ca/drugs/DB00799https://www.ncbi.nlm.nih.gov/pubmed/26937021 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf
Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf
Tazarotene a novel acetylenic retinoid is known to be effective in the topical treatment of psoriasis and acne. Tazarotene is rapidly and completely metabolized to its active metabolite tazarotenic acid. The exact mechanism of action of tazarotenic acid in the treatment of psoriasis and acne is not clearly defined. However, it is thought that the selective interaction of tazarotenic acid with the retinoic acid receptor (RAR) family (RARα, RARβ, and RARγ) and the subsequent induction of both positive and negative gene regulatory effects may be involved.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2003 |
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Target ID: CHEMBL2055 |
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Target ID: CHEMBL2008 |
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Target ID: CHEMBL2003 |
40.0 nM [EC50] | ||
Target ID: CHEMBL2008 Sources: http://www.drugbank.ca/drugs/DB00799 |
0.8 nM [EC50] | ||
Target ID: CHEMBL2055 |
63.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | TAZORAC Approved UseTAZORAC® (tazarotene) Gel 0.05% and 0.1% are indicated for the topical treatment of patients with stable
plaque psoriasis of up to 20% body surface area involvement.
TAZORAC® (tazarotene) Gel 0.1% is also indicated for the topical treatment of patients with facial acne vulgaris of mild to moderate severity. Launch Date9.700992E11 |
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Primary | TAZORAC Approved UseTAZORAC® (tazarotene) Gel 0.05% and 0.1% are indicated for the topical treatment of patients with stable
plaque psoriasis of up to 20% body surface area involvement.
TAZORAC® (tazarotene) Gel 0.1% is also indicated for the topical treatment of patients with facial acne
vulgaris of mild to moderate severity. Launch Date9.700992E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.44 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31641413 |
5 mg single, topical dose: 5 mg route of administration: Topical experiment type: SINGLE co-administered: |
TAZAROTENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
105.72 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31641413 |
5 mg single, topical dose: 5 mg route of administration: Topical experiment type: SINGLE co-administered: |
TAZAROTENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
33.6 mg 1 times / day multiple, oral Highest studied dose Dose: 33.6 mg, 1 times / day Route: oral Route: multiple Dose: 33.6 mg, 1 times / day Sources: Page: p.812 |
unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: Page: p.812 |
DLT: Hypercalcaemia, Hypertriglyceridaemia... Dose limiting toxicities: Hypercalcaemia (grade 3, 17%) Sources: Page: p.812Hypertriglyceridaemia (grade 4, 17%) |
25.2 mg 1 times / day multiple, oral MTD Dose: 25.2 mg, 1 times / day Route: oral Route: multiple Dose: 25.2 mg, 1 times / day Sources: Page: p.812 |
unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: Page: p.812 |
DLT: Musculoskeletal pain... Dose limiting toxicities: Musculoskeletal pain (grade 3, 17%) Sources: Page: p.812 |
0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
Disc. AE: Disorder fetal, Skin irritation... AEs leading to discontinuation/dose reduction: Disorder fetal Sources: Page: p.1Skin irritation Pruritus Burning skin Skin red Skin peeling Photosensitivity Sunburn |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypercalcaemia | grade 3, 17% DLT |
33.6 mg 1 times / day multiple, oral Highest studied dose Dose: 33.6 mg, 1 times / day Route: oral Route: multiple Dose: 33.6 mg, 1 times / day Sources: Page: p.812 |
unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: Page: p.812 |
Hypertriglyceridaemia | grade 4, 17% DLT |
33.6 mg 1 times / day multiple, oral Highest studied dose Dose: 33.6 mg, 1 times / day Route: oral Route: multiple Dose: 33.6 mg, 1 times / day Sources: Page: p.812 |
unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: Page: p.812 |
Musculoskeletal pain | grade 3, 17% DLT |
25.2 mg 1 times / day multiple, oral MTD Dose: 25.2 mg, 1 times / day Route: oral Route: multiple Dose: 25.2 mg, 1 times / day Sources: Page: p.812 |
unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: Page: p.812 |
Burning skin | Disc. AE | 0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
Disorder fetal | Disc. AE | 0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
Photosensitivity | Disc. AE | 0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
Pruritus | Disc. AE | 0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
Skin irritation | Disc. AE | 0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
Skin peeling | Disc. AE | 0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
Skin red | Disc. AE | 0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
Sunburn | Disc. AE | 0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plaque psoriasis|Acne vulgaris Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
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Management of scalp psoriasis: guidelines for corticosteroid use in combination treatment. | 2001 |
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Efficacy and tolerability of once-daily tazarotene 0.1% gel versus once-daily tretinoin 0.025% gel in the treatment of facial acne vulgaris: a randomized trial. | 2001 Jun |
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Retinoids for the treatment of psoriasis: outlook for the future. | 2001 May |
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1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects. | 2001 May |
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Tazarotene 0.1% gel in the treatment of fingernail psoriasis: a double-blind, randomized, vehicle-controlled study. | 2001 Nov |
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Treatment of psoriasis. Part 1. Topical therapy and phototherapy. | 2001 Oct |
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Developments in topical retinoid therapy for acne. | 2001 Sep |
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Retinoids--which dermatological indications will benefit in the near future? | 2001 Sep-Oct |
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The modern age of acne therapy: a review of current treatment options. | 2001 Sep-Oct |
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Practical management of psoriasis in the elderly: epidemiology, clinical aspects, quality of life, patient education and treatment options. | 2002 |
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Treatment of cutaneous T cell lymphoma: current status and future directions. | 2002 |
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Successful treatment of acne vulgaris using a new method: results of a randomized vehicle-controlled trial of short-contact therapy with 0.1% tazarotene gel. | 2002 Apr |
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Is TIG1 a new tumor suppressor in prostate cancer? | 2002 Apr 3 |
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Treatment of warty dyskeratoma with tazarotenic acid. | 2002 Feb |
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Refining retinoids with heteroatoms. | 2002 Jun |
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Combination of calcipotriene (Dovonex) ointment and tazarotene (Tazorac) gel versus clobetasol ointment in the treatment of plaque psoriasis: a pilot study. | 2002 Jun |
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Tazarotene (tazorac) for acne. | 2002 Jun 10 |
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Topical tazarotene therapy for psoriasis, acne vulgaris, and photoaging. | 2002 Mar |
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A clinical evaluation of tazarotene 0.1% gel, with and without a high- or mid-high-potency corticosteroid, in patients with stable plaque psoriasis. | 2002 Mar-Apr |
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Drug interactions in psoriasis: the pros and cons of combining topical psoriasis therapies. | 2002 May-Jun |
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[Immunosuppresive agents, retinoids and new trends in the therapy of psoriasis]. | 2002 Nov |
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Oral lichen planus: a preliminary clinical study on treatment with tazarotene. | 2002 Nov |
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Questionable techniques for evaluating photodamage. | 2002 Nov |
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Efficacy of 0.1% tazarotene cream for the treatment of photodamage: a 12-month multicenter, randomized trial. | 2002 Nov |
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[Psoriatic onycho-pachydermo- periostitis]. | 2002 Oct |
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Treating keratosis pilaris. | 2002 Sep |
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Retrospective analysis of the treatment of psoriasis of the palms and soles. | 2003 |
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Treatment of occupational koilonychia with tazarotene gel. | 2003 |
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Optimizing treatment with topical tazarotene. | 2003 |
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The rationale for using a topical retinoid for inflammatory acne. | 2003 |
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Wrinkles. | 2003 Dec |
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The efficacy of topical tazarotene monotherapy and combination therapies in psoriasis. | 2003 Dec |
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Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23. | 2003 Dec 18 |
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Tazarotene-induced gene 3 is suppressed in basal cell carcinomas and reversed in vivo by tazarotene application. | 2003 Oct |
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A phase 1 study of tazarotene in adults with advanced cancer. | 2003 Sep 1 |
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Spotlight on adapalene in acne vulgaris. | 2004 |
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Tazarotene does not affect the pharmacokinetics and efficacy of a norethindrone/ethinylestradiol oral contraceptive. | 2004 |
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Adapalene: a review of its use in the treatment of acne vulgaris. | 2004 |
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Tazarotene 0.1% cream for the treatment of photodamage. | 2004 Apr |
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The p73 gene is an anti-tumoral target of the RARbeta/gamma-selective retinoid tazarotene. | 2004 Dec |
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Histological effects of tazarotene 0.1% cream vs. vehicle on photodamaged skin: a 6-month, multicentre, double-blind, randomized, vehicle-controlled study in patients with photodamaged facial skin. | 2004 Dec |
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A retinoic acid receptor beta/gamma-selective prodrug (tazarotene) plus a retinoid X receptor ligand induces extracellular signal-regulated kinase activation, retinoblastoma hypophosphorylation, G0 arrest, and cell differentiation. | 2004 Dec |
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Treatment of lentigo maligna with tazarotene 0.1% gel. | 2004 Jan |
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Questions & answers. Of all the treatments that promise to improve the appearance of aging skin, which ones have been medically proven to actually work? | 2004 Jul |
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Topical tazarotene chemoprevention reduces Basal cell carcinoma number and size in Ptch1+/- mice exposed to ultraviolet or ionizing radiation. | 2004 Jul 1 |
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Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene. | 2004 Jul-Aug |
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Current management strategies for cutaneous T-cell lymphoma. | 2004 May-Jun |
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Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma. | 2004 Nov 1 |
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Topical retinoids in the management of acne: the best path to clear results. | 2004 Oct |
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Comparison of topical retinoids in the treatment of acne. | 2004 Sep-Oct |
Patents
Sample Use Guides
For psoriasis: It is recommended that treatment start with TAZORAC (Tazarotene) 0.05% Gel, with strength increased to 0.1% if tolerated and medically indicated. Apply TAZORAC® Gel once a day, in the evening, to psoriatic lesions, using enough (2 mg/cm2) to cover only the lesion with a thin film to no more than 20% of body surface area. If a bath or shower is taken prior to application, the skin should be dry before applying the gel. If
emollients are used, they should be applied at least an hour before application of TAZORAC® Gel.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18483315
Tazarotene treatment caused a dose-dependent reduction in cell proliferation in BCC cell line ASZ001 cells (the strongest effect on cell proliferation was at 10 umol/L)
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000007700
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N0000007700
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N0000007700
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WHO-ATC |
D05AX05
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WHO-VATC |
QD05AX05
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NCI_THESAURUS |
C804
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NDF-RT |
N0000007700
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EU-Orphan Drug |
EU/3/06/423
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NDF-RT |
N0000175607
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N0000007700
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C086827
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5381
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118292-40-3
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32184
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83947
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DB00799
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TAZAROTENE
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M10488
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81BDR9Y8PS
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CHEMBL1657
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Tazarotene
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2571
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6952
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7328
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C29487
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ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
SUBSTANCE RECORD