Tretinoin | CAS#302-79-4 | retinoic acid receptor

MedKoo Cat#: 100890 | Name: Tretinoin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tretinoin is a naturally-occurring acid of retinol. Tretinoin binds to and activates retinoic acid receptors (RARs), thereby inducing changes in gene expression that lead to cell differentiation, decreased cell proliferation, and inhibition of tumorigenesis. This agent also inhibits telomerase, resulting in telomere shortening and eventual apoptosis of some tumor cell types. The oral form of tretinoin has teratogenic and embryotoxic properties.

Chemical Structure

Tretinoin

CAS#302-79-4

Theoretical Analysis

MedKoo Cat#: 100890

Name: Tretinoin

CAS#: 302-79-4

Chemical Formula: C20H28O2

Exact Mass: 300.2089

Molecular Weight: 300.43

Elemental Analysis: C, 79.96; H, 9.39; O, 10.65

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
200mg	USD 450.00	2 Weeks
500mg	USD 750.00	2 Weeks
1g	USD 1,250.00	2 Weeks

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Synonym

alltrans retinoic acid; alltrans vitamin A acid; betaretinoic acid; retinoic acid; TRA; trans retinoic acid; trans vitamin A acid; tretinoinum; Vitamin A Acid. US brand names: Aberel; Aknoten; Avita; Renova; RetinA; RetinA MICRO; Vesanoid. Foreign brand names: Airol; Cordes Vas; Dermairol; EpiAberel; Eudyna; RetisolA; StievaA; StievaA Forte; Vitinoin; ; Abbreviation: ATRA ; Acronyms: ATRA; TRA. Code name: Ro 5488.

IUPAC/Chemical Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

InChi Key

SHGAZHPCJJPHSC-YCNIQYBTSA-N

InChi Code

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+

SMILES Code

O=C(O)/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

More Info

Mechanism of Action Tretinoin is a metabolite of Vitamin A that binds with high affinity to specific retinoic acid receptors located in both the cytosol and nucleus, but cutaneous levels of tretinoin in excess of physiologic concentrations occur following application of a tretinoin-containing topical drug product. Although tretinoin activates three members of the retinoid acid (RAR) nuclear receptors (RAR α, RAR β, and RAR γ) which act to modify gene expression, subsequent protein synthesis, and epithelial cell growth and differentiation, it has not been established whether the clinical effects of tretinoin are mediated through activation of retinoic acid receptors, other mechanisms, or both. Although the exact mode of action of tretinoin is unknown, current evidence suggests that topical tretinoin decreases cohesiveness of follicular epithelial cells with decreased microcomedo formation. Additionally, tretinoin stimulates mitotic activity and increased turnover of follicular epithelial cells causing extrusion of the comedones. Medicinal Applications Medicinal Applications Dermatology: Tretinoin is most commonly used as a form of acne treatment. It was the first retinoid developed for this type of topical use. Tretinoin is the best studied retinoid in the treatment of photoaging. It is used by some as a hair loss treatment and also a component of many commercial products that are advertised as being able to slow skin aging or remove wrinkles. Topical tretinoin is also used to treat and reduce the appearance of stretch marks by increasing collagen production in the dermis. From: http://en.wikipedia.org/wiki/Tretinoin . Dermatology: Tretinoin is most commonly used as a form of acne treatment. It was the first retinoid developed for this type of topical use. Tretinoin is the best studied retinoid in the treatment of photoaging. It is used by some as a hair loss treatment and also a component of many commercial products that are advertised as being able to slow skin aging or remove wrinkles. Topical tretinoin is also used to treat and reduce the appearance of stretch marks by increasing collagen production in the dermis. From: http://en.wikipedia.org/wiki/Tretinoin . Leukemia: in addition, tretinoin (marketed as Vesanoid) is also used to treat at least one form of cancer (acute promyelocytic leukemia (APL), also called acute myeloid leukemia subtype M3), usually together with other drugs, by causing the immature blood cells to differentiate (i.e. mature). The pathology of the leukemia is due to the highly proliferative immature cells; retinoic acid drives these cells to develop into functional cells, which helps to alleviate the disease. It is usually prescribed for 15 days every 3 months at about 8-10 10mg capsules per day. From http://en.wikipedia.org/wiki/Tretinoin. Leukemia: in addition, tretinoin (marketed as Vesanoid) is also used to treat at least one form of cancer (acute promyelocytic leukemia (APL), also called acute myeloid leukemia subtype M3), usually together with other drugs, by causing the immature blood cells to differentiate (i.e. mature). The pathology of the leukemia is due to the highly proliferative immature cells; retinoic acid drives these cells to develop into functional cells, which helps to alleviate the disease. It is usually prescribed for 15 days every 3 months at about 8-10 10mg capsules per day. From http://en.wikipedia.org/wiki/Tretinoin.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 300.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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