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T1850000

Tretinoin

European Pharmacopoeia (EP) Reference Standard

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Synonym(s):
Retinoic acid, ATRA, Tretinoin, Vitamin A acid, all-trans-Retinoic acid
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
302-79-4
Molecular Weight:
300.44
Beilstein:
2057223
MDL number:
MFCD00001551
PubChem Substance ID:
329826691
NACRES:
NA.24

biological source

synthetic

grade

pharmaceutical primary standard

Agency

EP

API family

tretinoin

form

solid

manufacturer/tradename

EDQM

technique(s)

gas chromatography (GC): suitable
liquid chromatography (LC): suitable

mp

180-181 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)C(C)(C)CCC1

InChI

1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

InChI key

SHGAZHPCJJPHSC-YCNIQYBTSA-N

Gene Information

human ... RARA(5914) , RARB(5915) , RARG(5916)

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General description

This product is provided as delivered and specified by the issuing pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the authority of the issuing pharmacopoeia. For further information and support please go to the website of the issuing pharmacopoeia.

Tretinoin is a medication used to treat a variety of skin conditions such as photodamaged skin, acne, etc. It is used as an anti-aging product and also as an oral treatment for leukemia.

Application

This European Pharmacopoeia reference standard is intended for use only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

all−trans−Retinoic acid (ATRA) is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). The bound RAR and RXR act as transcription factors that regulate the growth and differentiation of both normal and malignant cells. Cytochromes P450 (CYPs) catalyze the 4-hydroxylation of ATRA. Retinoic acid primes embryonic stem cells to become neurons.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - Skin Irrit. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Tretinoin: The Active Retinoid Medication Used for Treatment of Acne Fast and Effectively (2019)
Bogdan Jakiela et al.
American journal of respiratory cell and molecular biology, 51(2), 229-241 (2014-03-05)
Human rhinoviruses (RVs) are a major cause of exacerbations in asthma and other chronic airway diseases. A characteristic feature of asthmatic epithelium is goblet cell metaplasia and mucus hypersecretion. Bronchial epithelium is also an important source of lipid mediators, including
Michael D Griswold et al.
Biology of reproduction, 86(2), 35-35 (2011-11-15)
The requirement for vitamin A in reproduction and development was first determined from studies of nutritional deficiencies. Subsequent research has shown that embryonic development and both male and female reproduction are modulated by retinoic acid (RA), the active form of
Rie Saba et al.
Developmental biology, 389(2), 173-181 (2014-03-01)
Germ cell sex is defined by factors derived from somatic cells. CYP26B1 is known to be a male sex-promoting factor that inactivates retinoic acid (RA) in somatic cells. In CYP26B1-null XY gonads, germ cells are exposed to a higher level
Joel Villalobos et al.
Investigative ophthalmology & visual science, 54(5), 3751-3762 (2013-04-25)
The safety of chronic implantation of a retinal prosthesis in the suprachoroidal space has not been established. This study aimed to determine the safety of a wide-field suprachoroidal electrode array following chronic implantation using histopathologic techniques and electroretinography. A platinum
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