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106685-40-9 Usage

Brand name

Differin (Galderma).

Uses

Retinoic acid analogs. Adapalene is an agonist of RARβ, and RARγ receptor. Adapalene inhibits cell proliferation and inducing apoptosis in colorectal cancer cells in vitro. Adapalene gel is an effective medication for treatment of acne.

Biological Activity

Retinoic acid analog that is a RAR β and RAR γ agonist (AC 50 values are 2.2, 9.3, 22 and > 1000 nM for RAR β , RAR γ , RAR α and RXR α receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cell in vitro . Displays comedolytic activity.

Pharmacokinetics

The transdermal absorption rate of adapalene is very low. In clinical trials, the adapalene level of skin acne areas subject to long-term treatment is undetectable. Appling C14 labeled adapalene for rats (intravenous, intraperitoneal injection, oral and dermal medication), rabbits (intravenous oral and dermal administration), respectively, clarified the distribution of radioactivity among various tissues. Also, liver, spleen adrenal and ovarian have the highest level. Adapalene is mainly metabolized through demethylation, hydroxylation and binding reactions of oxygen 1 and metabolism in vivo and mainly excreted through bile.
[Interaction] No interaction between the product and other skin drugs has been reported. But we should not use other retinoids or other drugs with similar mechanism of action. Adapalene has stable chemical structure, and is not easily to break down in the air and sunlight. A wide range of animal and human studies found no phototoxicity and photosensitivity. However, it is not clear whether it is safe to take it when animal and humans are subject to repeated exposure to sunlight or ultraviolet. Avoid excessive sunshine and UV radiation when use this product. Adapalene has a very low level of transdermal absorption, making it impossible to interact with the systematic medication drugs. No evidence was found that the effect of birth control pills, antibiotics and other oral medications are affected by the using Duff Man for treating skin disease.
Duff Man may have a slight local stimulation. Being treated together with the peeling agent, agent or contraction irritating substances can cause additional irritation. Therefore, use other skin medication early in the morning such as erythromycin (concentrations ≤4%), clindamycin phosphate (1%) aqueous solution or benzoyl peroxide gel (concentration ≤10%); Use Duff Man gel at night so that you can avoid drug co-degradation or accumulation of stimulation effect.
[Adverse reactions] During the first 2-4 weeks of treatment, the most common adverse reactions are erythema, dryness, scaling, itching, burning or tingling. The extent is mostly mild to moderate. Less frequent adverse reactions include: sunburn, skin irritation, burning and stinging skin discomfort. Rarely adverse reactions include: redness of acne, dermatitis and contact dermatitis, eye swelling, conjunctivitis, redness, itching, skin discoloration, rashes and eczema. Reduce the amount of drugs applied or totally withdrawal when serious adverse reactions happen.

Naphthoic acid derivative

Adapalene, a new class of drugs Naphthoic acid derivatives, was developed by France Galdeama Laboratories Company. It first entered into market in June 1996, under the trade name "Differin", mainly used for relieving inflammatory skin lesions, adjusting differentiation of hair follicles, gland epithelial cells, and also acne treatment.

Uses

Retinoid selective for retinoic acid receptor (RAR) subtypes ?and . Antiacne

Definition

ChEBI: A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.

Uses

inhibits serotonin and noradrenaline reuptake antidepressant antimigraine therapeutic

Uses

Acnetreatment

Adapalene acid drug safety compared with other topical Vitamin A

The effect of traditional topical Vitamin A acid drugs (RA) on the treatment of acne vulgaris is indeed very good, but the irritating side effects limit its use. RA causes local irritation because of its unstable structure and poor receptor selectivity caused by series of weak divalent bond chains in its molecular structure. Studies have shown that RA can be degraded by a number of factors: exposure to sunlight within 24 h, 60.0%~80.0% of baseline concentration RA degradation, and if use an oxidizing agent such as benzoyl peroxide the same time when apply RA, 80% of RA would be degraded within 4 h, and all RA disappear within 24 h. In order to find a more stable molecule with similar effect as RA but much smaller side effect, people developed a naphthoic acid derivative-adapalene. Adapalene has small irritation effect due to: 1. Molecularly stable: The unstable divalent bond chains in RA are replaced by the aromatic ring of naphthoic acid, making it stable in the light and oxidants without degradation even in 72 h. 2. Highly selective receptor binding: after entering the cell, RA first bound to cytoplasmic vitamin A acid bound protein (CRABP), and has no selectivity when binds to nuclear receptor RARα, β, γ. Adapalene does not bind CRABP, but selectively binds to specific amino acids sequences of the binding site in nuclear receptor RAR-β and RAR-γ receptor, then binds to RXR, further binds to specific DNA sites, regulating transcription machinery, protein synthesis, and cell proliferation and differentiation. Therefore, it is highly specific and has a small side effect. 3. Low cellular toxicity: Study found that effects of different vitamin A acid on keratinocyte cell cytotoxicity are also different. Adapalene molecule is neutral, has low cytotoxicity to keratinocytes compared with the long-chain organic acids, Vitamin A acid. 4. Adapalene has a clear anti-inflammatory effect. However, this kind of effect for other Vitamin A acid is not still clear.
In short, adapalene, a third generation vitamin A drugs, not only have a stronger effect on regulation of epidermal cell differentiation, inhibit proliferation of hair follicle keratinocytes and keratinocytes, inhibition sebaceous cell proliferation, dissolved angle plug acne, etc than all-trans vitamin A acid drugs, but also has a strong anti-inflammatory effect. Because of its unique stability, its efficacy and tolerability is much higher than other Vitamin A acid drugs.

Uses

anesthetic

Uses

Retinoid selective for retinoic acid receptor (RAR) subtypes β and γ. Antiacne.

Pharmacological effects

Adapalene is a retinoid compounds, and is proven to have anti-inflammatory properties in both in vivo and in vitro models of inflammation. It has stable chemical structure, and is not easily to break down in the air and the light. It shares the same mode of action with retinoic acid, bounding to specific retinoic acid nuclear receptors except that adapalene doesn’t bound to the cytoplasmic protein binding receptor. It has been proven to treat acne and affect acne vulgaris and differentiation in skin drug tests established by mouse animal model. Its mechanism of action is reducing the formation of micro-acne through leading the normal differentiation of hair follicle cells. In the standard anti-inflammatory assay both in vivo and in vitro, adapalene has a better effect than retinoic acid. It can inhibit the chemotaxis reaction of human polymorphonuclear leukocytes and also inhibit the metabolism of polymorphonuclear cell through inhibition the formation of anti-inflammatory mediators via oxidation reaction of arachidonic acid, thus relieving inflammatory response by the cell-mediated response. It is useful in the treatment of routine skin with acne, pimples and pustules as the main performance. It can also be used for the treatment of the acne presented in face, chest and back.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Chemical Properties

White Crystalline Solid
InChI:InChI=1/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)

106685-40-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (Y0001119)  Adapalene for peak identification  European Pharmacopoeia (EP) Reference Standard 106685-40-9 Y0001119 1,880.19CNY Detail
Sigma-Aldrich (Y0001121)  Adapalene  European Pharmacopoeia (EP) Reference Standard 106685-40-9 Y0001121 1,880.19CNY Detail
Sigma-Aldrich (PHR1388)  Adapalene  pharmaceutical secondary standard; traceable to USP and PhEur 106685-40-9 PHR1388-500MG 952.15CNY Detail
TCI America (A2549)  Adapalene  >98.0%(HPLC)(T) 106685-40-9 1g 1,990.00CNY Detail
TCI America (A2549)  Adapalene  >98.0%(HPLC)(T) 106685-40-9 200mg 730.00CNY Detail

106685-40-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name adapalene

1.2 Other means of identification

Product number -
Other names 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106685-40-9 SDS

106685-40-9Synthetic route

tert-butyl 6-(3-(1-adamantyl)-4-anisyl)-2-naphthoate

tert-butyl 6-(3-(1-adamantyl)-4-anisyl)-2-naphthoate

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 22h;100%
3-(1-adamantyl)-4-methoxyphenylboronic acid
459423-32-6

3-(1-adamantyl)-4-methoxyphenylboronic acid

6-bromo-2-naphthoic acid
5773-80-8

6-bromo-2-naphthoic acid

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium carbonate; palladium 10% on activated carbon In tetrahydrofuran; water for 8h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 1h; Product distribution / selectivity;
99%
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium hydroxide; 5%-palladium/activated carbon In tetrahydrofuran; water at 55℃; for 2h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃; pH=6 - 7; Product distribution / selectivity;
99%
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium carbonate; palladium diacetate; CyJohnPhos In tetrahydrofuran; water for 2 - 4h; Suzuki Coupling; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 1h; Product distribution / selectivity;
94.8%
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester
106685-41-0

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide
Stage #2: With hydrogenchloride In water Product distribution / selectivity;
97%
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide
Stage #2: With hydrogenchloride In water Product distribution / selectivity;
96%
With water; sodium hydroxide In propylene glycol89%
6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid sodium salt

6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid sodium salt

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran; water at 60 - 70℃; Heating / reflux;95%
With hydrogenchloride In water pH=3 - 4; Product distribution / selectivity;80%
(6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)methanol
106685-54-5

(6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)methanol

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 24h;94%
6-bromo-2-naphthoic acid
5773-80-8

6-bromo-2-naphthoic acid

3-adamantyl-4-methoxyphenyltriethoxysilane

3-adamantyl-4-methoxyphenyltriethoxysilane

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Inert atmosphere;93%
6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoic acid potassium salt

6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoic acid potassium salt

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 40℃; for 1.5h;89.29%
With hydrogenchloride In 1,4-dioxane; methanol; water
With hydrogenchloride In water Product distribution / selectivity;
ethyl 6 (3-adamantyl-4-methoxyphenyl)-2-naphthoate
951645-46-8

ethyl 6 (3-adamantyl-4-methoxyphenyl)-2-naphthoate

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: ethyl 6 (3-adamantyl-4-methoxyphenyl)-2-naphthoate With sodium hydroxide In tetrahydrofuran; ethanol at 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol for 1h; Reflux;
70%
carbon dioxide
124-38-9

carbon dioxide

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-bromonaphthalene With tert.-butyl lithium; sodium hydride In tetrahydrofuran; pentane at -60 - 20℃; for 0.666667h;
Stage #2: carbon dioxide In tetrahydrofuran; pentane at -60 - 20℃; for 1.5h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; pentane for 0.166667h; Product distribution / selectivity;
41%
Stage #1: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-bromonaphthalene With n-butyllithium; sodium hydride In tetrahydrofuran; hexane at -40 - 20℃; for 0.666667h;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -40 - 20℃; for 1.5h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 0.166667h; Product distribution / selectivity;
30%
4-bromo-phenol
106-41-2

4-bromo-phenol

p-bromo-anisole (?)

p-bromo-anisole (?)

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature
2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h
3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane
4: 81 percent / 2 N NaOH / methanol / 8 h / Heating
View Scheme
1-adamanthanol
768-95-6

1-adamanthanol

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature
2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h
3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane
4: 81 percent / 2 N NaOH / methanol / 8 h / Heating
View Scheme
Multi-step reaction with 5 steps
1: sulfuric acid; acetic acid / 48 h / 20 °C
2: potassium carbonate / acetone / 8 h / Reflux
3: magnesium / tetrahydrofuran / 1 h / 40 °C
4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C
5: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C
2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux
3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux
3.2: 1.25 h / Heating / reflux
3.3: 2.17 h
4.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux
5.1: hydrogenchloride / water / pH 3 - 4
View Scheme
Multi-step reaction with 5 steps
1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C
2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux
3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux
3.2: 1.25 h / Heating / reflux
3.3: 2.17 h
4.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux
5.1: hydrogenchloride / water
View Scheme
2-(1-adamantyl)-4-bromophenol
104224-68-2

2-(1-adamantyl)-4-bromophenol

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h
2: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane
3: 81 percent / 2 N NaOH / methanol / 8 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 8 h / Reflux
2: magnesium / tetrahydrofuran / 1 h / 40 °C
3: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C
4: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C
1.2: 80 - 100 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C
2.2: 1.5 h / 20 °C
3.1: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux
2.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux
2.2: 1.25 h / Heating / reflux
2.3: 2.17 h
3.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux
4.1: hydrogenchloride / water / pH 3 - 4
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux
2.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux
2.2: 1.25 h / Heating / reflux
2.3: 2.17 h
3.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux
4.1: hydrogenchloride / water
View Scheme
2-(1-adamantyl)-4-bromoanisole
104224-63-7

2-(1-adamantyl)-4-bromoanisole

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane
2: 81 percent / 2 N NaOH / methanol / 8 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: magnesium / tetrahydrofuran / 1 h / 40 °C
2: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C
3: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: n-butyllithium
2: 21 h / Flow reactor
3: sodium hydroxide; water / propylene glycol
View Scheme
3-adamantyl-4-methoxyphenyl potassium trifluoroborate

3-adamantyl-4-methoxyphenyl potassium trifluoroborate

methyl 6-bromo-2-naphthoate
33626-98-1

methyl 6-bromo-2-naphthoate

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: 3-adamantyl-4-methoxyphenyl potassium trifluoroborate; methyl 6-bromo-2-naphthoate With potassium hydroxide; 5%-palladium/activated carbon In tetrahydrofuran; water for 10.25h; Suzuki Miyaura coupling; Heating / reflux;
Stage #2: With hydrogenchloride; water
3-(1-adamantyl)-4-methoxyphenylboronic acid
459423-32-6

3-(1-adamantyl)-4-methoxyphenylboronic acid

methyl 6-bromo-2-naphthoate
33626-98-1

methyl 6-bromo-2-naphthoate

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
3-(1-adamantyl)-4-methoxybenzene magnesium bromide
1036766-54-7

3-(1-adamantyl)-4-methoxybenzene magnesium bromide

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C
2: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
6-(4-methoxyphenyl)-2-naphthoic acid

6-(4-methoxyphenyl)-2-naphthoic acid

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere
2.1: sulfuric acid / chloroform / 20 °C
3.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C
3.2: 1 h / Reflux
View Scheme
ethyl 6-(4-methoxyphenyl)-2-naphthoate
1334137-82-4

ethyl 6-(4-methoxyphenyl)-2-naphthoate

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid / chloroform / 20 °C
2.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C
2.2: 1 h / Reflux
View Scheme
4-bromo-phenol
106-41-2

4-bromo-phenol

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sulfuric acid; acetic acid / 48 h / 20 °C
2: potassium carbonate / acetone / 8 h / Reflux
3: magnesium / tetrahydrofuran / 1 h / 40 °C
4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C
5: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C
2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux
3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux
3.2: 1.25 h / Heating / reflux
3.3: 2.17 h
4.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux
5.1: hydrogenchloride / water / pH 3 - 4
View Scheme
Multi-step reaction with 5 steps
1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C
2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux
3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux
3.2: 1.25 h / Heating / reflux
3.3: 2.17 h
4.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux
5.1: hydrogenchloride / water
View Scheme
6-bromo-2-naphthoic acid
5773-80-8

6-bromo-2-naphthoic acid

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: palladium 10% on activated carbon; sodium carbonate / methanol; water / 78 °C / Inert atmosphere
2.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere
3.1: sulfuric acid / chloroform / 20 °C
4.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C
4.2: 1 h / Reflux
View Scheme
methyl 6-bromo-2-naphthoate
33626-98-1

methyl 6-bromo-2-naphthoate

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium hydroxide / methanol / 8 h / 50 °C
2.1: palladium 10% on activated carbon; sodium carbonate / methanol; water / 78 °C / Inert atmosphere
3.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere
4.1: sulfuric acid / chloroform / 20 °C
5.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C
5.2: 1 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C
1.2: 80 - 100 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C
2.2: 1.5 h / 20 °C
3.1: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
Poloxamer124

Poloxamer124

sodium docusate
577-11-7

sodium docusate

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
In glycerol
In glycerol
In glycerol
6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester
106685-43-2

6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C
1.2: 1.5 h / 20 °C
2.1: sodium hydroxide / methanol / 8 h / Reflux
View Scheme
2-methoxycarbonyl-6-naphthol p-toluenesulfonate

2-methoxycarbonyl-6-naphthol p-toluenesulfonate

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere
2: sulfuric acid / chloroform / 20 °C
3: sodium hydroxide / tetrahydrofuran; water / 6 h / Reflux
View Scheme
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

adapalene
106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere
2: sulfuric acid / chloroform / 20 °C
3: sodium hydroxide / tetrahydrofuran; water / 6 h / Reflux
View Scheme
ethanamine hydrochloride
557-66-4

ethanamine hydrochloride

adapalene
106685-40-9

adapalene

ethylamide of 6-[3-(1-adamantyl)-4-methoxyphenyl]2-naphthoic acid
106685-55-6

ethylamide of 6-[3-(1-adamantyl)-4-methoxyphenyl]2-naphthoic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;100%
adapalene
106685-40-9

adapalene

(6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)methanol
106685-54-5

(6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)methanol

Conditions
ConditionsYield
Stage #1: adapalene With borane-THF In tetrahydrofuran at 0 - 20℃; for 3h;
Stage #2: With water In tetrahydrofuran
98%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 3h;98%
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 2h;79%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
Ν,Ο-dimethylhydroxylamine hydrochloride

Ν,Ο-dimethylhydroxylamine hydrochloride

adapalene
106685-40-9

adapalene

6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-N-methoxy-N-methyl-2-naphthamide

6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-N-methoxy-N-methyl-2-naphthamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;98%
adapalene
106685-40-9

adapalene

6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoyl fluoride

6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoyl fluoride

Conditions
ConditionsYield
With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique;95%
5-methyloxazole-2-carboxylic acid ethyl ester
33123-68-1

5-methyloxazole-2-carboxylic acid ethyl ester

adapalene
106685-40-9

adapalene

ethyl 2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-5-methyloxazole-4-carboxylate

ethyl 2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-5-methyloxazole-4-carboxylate

Conditions
ConditionsYield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;92%
2-((trifluoromethyl)thio)isoindoline-1,3-dione
719-98-2

2-((trifluoromethyl)thio)isoindoline-1,3-dione

adapalene
106685-40-9

adapalene

C29H27F3O2S

C29H27F3O2S

Conditions
ConditionsYield
With iron(III) chloride; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h; chemoselective reaction;91%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

adapalene
106685-40-9

adapalene

1,3-dioxoisoindolin-2-yl 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate

1,3-dioxoisoindolin-2-yl 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 2h; Schlenk technique; Inert atmosphere;90%
With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 3h; Inert atmosphere;21%
benzoxazole
273-53-0

benzoxazole

adapalene
106685-40-9

adapalene

C34H31NO2

C34H31NO2

Conditions
ConditionsYield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;87%
1-Methylbenzimidazole
1632-83-3

1-Methylbenzimidazole

adapalene
106685-40-9

adapalene

2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-1-methyl-1H-benzo[d]imidazole

2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-1-methyl-1H-benzo[d]imidazole

Conditions
ConditionsYield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;85%
phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

adapalene
106685-40-9

adapalene

diethyl (6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)phosphonate

diethyl (6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)phosphonate

Conditions
ConditionsYield
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Inert atmosphere; Schlenk technique;83%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;72%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane for 18h; Inert atmosphere; Schlenk technique; Heating;72%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

adapalene
106685-40-9

adapalene

2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-1-methyl-1H-imidazole

2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-1-methyl-1H-imidazole

Conditions
ConditionsYield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;81%
N,N-Dimethylacrylamide
2680-03-7

N,N-Dimethylacrylamide

adapalene
106685-40-9

adapalene

(E)-3-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-N,N-dimethylacrylamide

(E)-3-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-N,N-dimethylacrylamide

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; 2,2-dimethylpropanoic anhydride; bis[2-(diphenylphosphino)phenyl] ether; sodium chloride In tetrahydrofuran at 150℃; for 10h; Heck Reaction; Schlenk technique; Inert atmosphere;80%
adapalene
106685-40-9

adapalene

ethanethiol
75-08-1

ethanethiol

adapalene S-ethyl thioester

adapalene S-ethyl thioester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h; Inert atmosphere;79.3%
adapalene
106685-40-9

adapalene

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester
106685-41-0

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran; methanol at 0 - 20℃; for 1h;79%
2,2,2,-trichloroethoxycarbonyl azide

2,2,2,-trichloroethoxycarbonyl azide

adapalene
106685-40-9

adapalene

2,2,2-trichloroethyl (6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)carbamate

2,2,2-trichloroethyl (6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)carbamate

Conditions
ConditionsYield
With dmap; copper diacetate In dimethyl sulfoxide at 100℃; for 6h; Schlenk technique; Sealed tube; Inert atmosphere;77%
N-(2-methylbenzoyl)-8-aminoquinoline
1182669-71-1

N-(2-methylbenzoyl)-8-aminoquinoline

adapalene
106685-40-9

adapalene

2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-6-methyl-N-(quinolin-8-yl)benzamide

2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-6-methyl-N-(quinolin-8-yl)benzamide

Conditions
ConditionsYield
With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; fluoro-N,N,N′,N′-bis(tetramethylene)formamidinium hexafluorophosphate In 1,4-dioxane at 140℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Molecular sieve;76%
adapalene
106685-40-9

adapalene

6-(3-((3R,5R,7R)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthaldehyde-formyl-d1

6-(3-((3R,5R,7R)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthaldehyde-formyl-d1

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 2,4,6-Triisopropylthiophenol; water-d2; triphenylphosphine In dichloromethane at 20℃; for 36h; Inert atmosphere; Irradiation; Schlenk technique; Sealed tube;73%
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 2,4,6-Triisopropylthiophenol; water-d2; triphenylphosphine In dichloromethane at 20℃; for 36h; Irradiation; Inert atmosphere; Sealed tube;73%
Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

adapalene
106685-40-9

adapalene

(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)diphenylphosphine oxide

(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)diphenylphosphine oxide

Conditions
ConditionsYield
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 115℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;68%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 115℃; for 18h; Inert atmosphere; Schlenk technique;68%
2-phenyl-1,3,4-oxadiazole
825-56-9

2-phenyl-1,3,4-oxadiazole

adapalene
106685-40-9

adapalene

2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-5-phenyl-1,3,4-oxadiazole

2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-5-phenyl-1,3,4-oxadiazole

Conditions
ConditionsYield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;68%
3,3,3-trifluoro-2-phenylpropene
384-64-5

3,3,3-trifluoro-2-phenylpropene

adapalene
106685-40-9

adapalene

1-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-4,4-difluoro-3-phenylbut-3-en-1-one

1-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-4,4-difluoro-3-phenylbut-3-en-1-one

Conditions
ConditionsYield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 48h; Molecular sieve; Inert atmosphere; Sealed tube; Irradiation;67%
adapalene
106685-40-9

adapalene

carbonic acid 1,1-dimethyl-3-phenyl-prop-2-ynyl ester methyl ester
371256-80-3

carbonic acid 1,1-dimethyl-3-phenyl-prop-2-ynyl ester methyl ester

C39H40O3

C39H40O3

Conditions
ConditionsYield
With potassium phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In N,N-dimethyl acetamide at 110℃; regiospecific reaction;51%

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