Details
Stereochemistry | ACHIRAL |
Molecular Formula | C28H28O3 |
Molecular Weight | 412.5212 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COc1ccc(cc1C23CC4CC(CC(C4)C2)C3)-c5ccc6cc(ccc6c5)C(=O)O
InChI
InChIKey=LZCDAPDGXCYOEH-UHFFFAOYSA-N
InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)
Molecular Formula | C28H28O3 |
Molecular Weight | 412.5212 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Adapalene is a topical retinoid primarily used in the treatment of acne and is used (off-label) to treat keratosis pilaris as well as other skin conditions. Galderma currently markets it under the trade names Differin in some countries, and Adaferin in India. Adapalene acts on retinoid receptors. Biochemical and pharmacological profile studies have demonstrated that adapalene is a modulator of cellular differentiation, keratinization, and inflammatory processes all of which represent important features in the pathology of acne vulgaris. Mechanistically, adapalene binds to specific retinoic acid nuclear receptors but does not bind to the cytosolic receptor protein. Although the exact mode of action of adapalene is unknown, it is suggested that topical adapalene normalizes the differentiation of follicular epithelial cells resulting in decreased microcomedone formation.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2003 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10651997 |
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Target ID: CHEMBL2008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10651997 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DIFFERIN Approved UseAdapalene gel, 0.1% is indicated for the topical treatment of acne vulgaris. Launch Date8.3350081E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.04 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10898827 |
6.8 mg 1 times / day multiple, topical dose: 6.8 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
ADAPALENE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.1 % 1 times / day multiple, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1364 |
unhealthy, 12–26 n = 87 Health Status: unhealthy Condition: Acne Age Group: 12–26 Sex: M+F Population Size: 87 Sources: Page: p.1364 |
Disc. AE: Irritation skin... AEs leading to discontinuation/dose reduction: Irritation skin (severe, 9.2%) Sources: Page: p.1364 |
0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: Page: p.59 |
unhealthy, 45 - 65 n = 40 Health Status: unhealthy Condition: Cutaneous photoaging Age Group: 45 - 65 Sex: F Population Size: 40 Sources: Page: p.59 |
Disc. AE: Irritation skin... AEs leading to discontinuation/dose reduction: Irritation skin (severe, 7.5%) Sources: Page: p.59 |
0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
Disc. AE: Erythema, Scales... AEs leading to discontinuation/dose reduction: Erythema Sources: Page: p.1Scales Application site dryness Stinging |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Irritation skin | severe, 9.2% Disc. AE |
0.1 % 1 times / day multiple, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: Page: p.1364 |
unhealthy, 12–26 n = 87 Health Status: unhealthy Condition: Acne Age Group: 12–26 Sex: M+F Population Size: 87 Sources: Page: p.1364 |
Irritation skin | severe, 7.5% Disc. AE |
0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: Page: p.59 |
unhealthy, 45 - 65 n = 40 Health Status: unhealthy Condition: Cutaneous photoaging Age Group: 45 - 65 Sex: F Population Size: 40 Sources: Page: p.59 |
Application site dryness | Disc. AE | 0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
Erythema | Disc. AE | 0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
Scales | Disc. AE | 0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
Stinging | Disc. AE | 0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
The role of specific retinoid receptors in sebocyte growth and differentiation in culture. | 2000 Feb |
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Adapalene biochemistry and the evolution of a new topical retinoid for treatment of acne. | 2001 |
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Comparison of the cumulative irritation potential of adapalene gel and cream with that of erythromycin/tretinoin solution and gel and erythromycin/isotretinoin gel. | 2001 Feb |
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Are 2 combined antimicrobial mechanisms better than 1 for the treatment of acne vulgaris? Clinical and antimicrobial results of a topical combination product containing 1% clindamycin and 5% benzoyl peroxide. Introduction. | 2001 Feb |
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Acral Darier's disease successfully treated with adapalene. | 2001 Jan-Feb |
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Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents. | 2001 Jul |
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Comparison of treatment of acne vulgaris with alternate-day applications of tazarotene 0.1% gel and once-daily applications of adapalene 0.1% gel: a randomized trial. | 2001 Jun |
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Synthesis, high-performance liquid chromatography-nuclear magnetic resonance characterization and pharmacokinetics in mice of CD271 glucuronide. | 2001 Jun 5 |
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Adapalene gel 0.1% for topical treatment of acne vulgaris in African patients. | 2001 Oct |
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Adapalene gel 0.1% is effective and well tolerated in acne patients in a dermatology practice setting. | 2001 Oct |
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Polarized light photography and videomicroscopy greatly enhance the capability of estimating the therapeuic response to a topical retinoid (adapalene) in acne vulgaris. | 2001 Oct |
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The modern age of acne therapy: a review of current treatment options. | 2001 Sep-Oct |
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Perioral dermatitis successfully treated with topical adapalene. | 2002 Mar |
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Comparison of the effects of tretinoin, adapalene and collagenase in an experimental model of wound healing. | 2002 Mar-Apr |
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Prospective study of depressive symptoms and quality of life in acne vulgaris patients treated with isotretinoin compared to antibiotic and topical therapy. | 2002 Nov |
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Topical adapalene gel 0.1% vs. isotretinoin gel 0.05% in the treatment of acne vulgaris: a randomized open-label clinical trial. | 2002 Sep |
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Current concepts of the pathogenesis of acne: implications for drug treatment. | 2003 |
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Optimizing treatment with topical tazarotene. | 2003 |
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Management of acne. | 2003 Jan |
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Assessment of adapalene gel for the treatment of actinic keratoses and lentigines: a randomized trial. | 2003 Jul |
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13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? | 2003 Mar 28 |
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Retinoids: fascinating up-and-coming scenario. | 2003 May |
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The synthetic retinoid adapalene inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. | 2003 Nov 10 |
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Clinical review: topical retinoids. | 2003 Oct |
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Cumulative irritancy comparison of adapalene gel 0.1% versus other retinoid products when applied in combination with topical antimicrobial agents. | 2003 Sep |
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Is combined oral and topical therapy better than oral therapy alone in patients with moderate to moderately severe acne vulgaris? A comparison of the efficacy and safety of lymecycline plus adapalene gel 0.1%, versus lymecycline plus gel vehicle. | 2003 Sep |
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Efficacy and tolerability of combined topical treatment of acne vulgaris with adapalene and clindamycin: a multicenter, randomized, investigator-blinded study. | 2003 Sep |
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A review of the use of combination therapies for the treatment of acne vulgaris. | 2003 Sep |
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Adapalene: a review of its use in the treatment of acne vulgaris. | 2004 |
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A successful maintenance approach in inflammatory acne with adapalene gel 0.1% after an initial treatment in combination with clindamycin topical solution 1% or after monotherapy with clindamycin topical solution 1%. | 2004 Dec |
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Topical tretinoin or adapalene in acne vulgaris: an overview. | 2004 Jul |
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Topical agents used in the management of hyperpigmentation. | 2004 Jun-Jul |
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Drugs. Adapalene. | 2005 Apr 26-May 2 |
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Topical retinoids in inflammatory acne: a retrospective, investigator-blinded, vehicle-controlled, photographic assessment. | 2005 Feb |
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Fox fordyce disease in a prepubertal girl. | 2005 Jan-Feb |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Benzoyl peroxide, adapalene, and their combination in the treatment of acne vulgaris. | 2005 Mar |
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Adapalene vs. metronidazole gel for the treatment of rosacea. | 2005 Mar |
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Milia en plaque. | 2005 Mar |
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Prescribing patterns for topical retinoids within NAMCS data. | 2005 Mar-Apr |
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Tazarotene cream versus adapalene cream in the treatment of facial acne vulgaris: a multicenter, double-blind, randomized, parallel-group study. | 2005 Mar-Apr |
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Mechanism-based treatment of acne vulgaris: the value of combination therapy. | 2005 May-Jun |
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The MORE trial: effectiveness of adapalene gel 0.1% in real-world dermatology practices. | 2006 Jul |
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The results of the MORE trial: overview. | 2006 Jul |
Sample Use Guides
Cream should be applied to affected areas of the skin, once daily at nighttime.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17518990
Explants of normal human skin and explants of acne patients were incubated with adapalene (10(-7) or 10(-6) M) for 24 h. Evaluation of epidermal expression by immunohistochemistry showed a decreased expression of TLR-2 and IL-10 in explants of normal skin and explants of acne with adapalene. On the contrary, adapalene increased CD1d expression in explants of acne patients. Thus, adapalene can modulate the epidermal immune system by increasing the CD1d expression and by decreasing the IL-10 expression by keratinocytes.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:11:53 UTC 2021
by
admin
on
Fri Jun 25 21:11:53 UTC 2021
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Record UNII |
1L4806J2QF
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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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WHO-VATC |
QD10AD53
Created by
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NDF-RT |
N0000175607
Created by
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NDF-RT |
N0000007700
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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NCI_THESAURUS |
C804
Created by
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NDF-RT |
N0000007700
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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WHO-ATC |
D10AD03
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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NDF-RT |
N0000007700
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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NDF-RT |
N0000007700
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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WHO-VATC |
QD10AD03
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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WHO-ATC |
D10AD53
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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NDF-RT |
N0000007700
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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Code System | Code | Type | Description | ||
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ADAPALENE
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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SUB05261MIG
Created by
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PRIMARY | |||
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CHEMBL1265
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6675
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PRIMARY | |||
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DB00210
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C063610
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PRIMARY | |||
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M1408
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PRIMARY | Merck Index | ||
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C28989
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60223
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87
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1L4806J2QF
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1011709
Created by
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106685-40-9
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5429
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60164
Created by
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Adapalene
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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106685-40-9
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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PRIMARY |
Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
correction factor: for the calculation of content, multiply the peak area of impurity A by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
correction factor: for the calculation of content, multiply the peak area of impurity C by 7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
correction factor: for the calculation of content, multiply the peak area of impurity D by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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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 |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |