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Tretinoin
Systematic (IUPAC) name
3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl) -nona-2,4,6,8-tetraenoic acid
Identifiers
CAS number 302-79-4
ATC code D10AD01 L01XX14
PubChem 5538
DrugBank APRD00362
Chemical data
Formula C20H28O2 
Mol. mass 300. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 4412 g/mol
Physical data
Melt. point 180 °C (356 °F)
Pharmacokinetic data
Bioavailability  ?
Protein binding > 95%
Metabolism  ?
Half life 0. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of A drug's efficiency may be affected by the degree to which it binds to the proteins within Blood plasma. Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity 5-2 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat.

X
Legal status

Prescription Only (S4)(AU)
Routes Topical, oral

Tretinoin is the acid form of vitamin A and so also known as all-trans retinoic acid or ATRA. Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. For a topic outline on this subject see List of basic Australia topics. In Pharmacology and Toxicology, a route Vitamin A refers to a family of similarly shaped molecules the Retinoids. It is a drug commonly used to treat acne vulgaris and keratosis pilaris. Acne vulgaris (commonly called acne) is a Skin disease caused by changes in the Pilosebaceous units (skin structures consisting of a Hair follicle Keratosis pilaris (KP also follicular keratosis is a very common genetic follicular condition that is manifested by the appearance of rough bumps on the skin It is available as a cream or gel (brand names Renova, Retin-A). It is also used to treat acute promyelocytic leukemia (APML) which is sold for this indication by Roche under the brand name Vesanoid. Acute promyelocytic leukemia is a subtype of Acute myelogenous leukemia (AML a Cancer of the Blood and Bone marrow.

Contents

Uses

Dermatology

Tretinoin is most commonly used as a form of acne treatment. [1] It was the first retinoid developed for this type of topical use. The retinoids are a class of Chemical compounds that are related chemically to Vitamin A. Tretinoin is the best studied retinoid in the treatment of photoaging. [2] 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. [3] Topical tretinoin is also used to treat and reduce the appearance of stretch marks by increasing collagen production in the dermis. In Medicine, a topical Medication is applied to body surfaces such as the Skin or Mucous membranes for example the Vagina " Striae " is also a general term referring to thin narrow grooves or channels or a thin line or band especially if several of them are parallel or close together Collagen is the main Protein of Connective tissue in Animals and the most abundant protein in Mammals making up about 50% of the whole-body protein The dermis is a layer of Skin beneath the epidermis that consists of Connective tissue, and cushions the body from stress and strain [4]

Leukemia

In addition, tretinoin (marketed as Vesanoid) is also used to treat at least one form of cancer (acute promyelocytic leukemia (APML), also called acute myeloid leukemia subtype M3), usually together with other drugs, by causing the immature blood cells to differentiate (i. Acute promyelocytic leukemia is a subtype of Acute myelogenous leukemia (AML a Cancer of the Blood and Bone marrow. Acute myeloid leukemia ( AML) also known as acute myelogenous leukemia, is a Cancer of the Myeloid line of White blood cells characterized e. mature) and die. [5][6] 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 over 3 months at about 8 capsules per day.

Clinical pharmacology

Although the exact mode of action of tretinoin is unknown, current evidence suggests that topical tretinoin decreases cohesiveness of follicular epithelial cells with decreased blackhead formation. In biology and medicine epithelium is a tissue composed of cells that line the cavities and surfaces of structures throughout the body A blackhead (medically known as an open comedo, plural comedones) is a yellowish or blackish bump or plug on the skin Additionally, tretinoin stimulates mitotic activity and increased turnover of follicular epithelial cells causing extrusion of the blackheads (comedones). Mitosis is the process in which a Eukaryotic cell separates the Chromosomes in its Cell nucleus, into two identical sets in two daughter nuclei In biology and medicine epithelium is a tissue composed of cells that line the cavities and surfaces of structures throughout the body A blackhead (medically known as an open comedo, plural comedones) is a yellowish or blackish bump or plug on the skin

Its success in treating acute promyelocytic leukemia was a major breakthrough in the treatment of this type of leukemia. [7] It works in APML because the majority of cases involve a chromosomal translocation of chromosomes 15 and 17, which causes genetic fusion of the retinoic acid receptor (RAR) gene to the promyelocytic leukemia (PML) gene. A chromosome is an organized structure of DNA and Protein that is found in cells. This fusion PML-RAR protein is responsible for preventing immature myeloid cells from differentiating into more mature cells. The term myeloid suggests an origin in the Bone marrow or Spinal cord, or a resemblance to the marrow or spinal cord This block in differentiation is thought to cause leukemia. ATRA acts on PML-RAR to lift this block, causing the immature promyelocytes to differentiate to normal mature blood cells. A promyelocyte (or progranulocyte) is a Granulocyte precursor developing from the Myeloblast and developing into the Myelocyte.

Side effects

In dermatological use

When used, dryness of the affected skin may occur. More sensitive patients may also experience redness, scaling, itching, and burning. A gradual increase in the frequency and amount of tretinoin application is best, as this allows one's skin to adequately adjust to the drug. Patients should be careful to follow their physician's recommendations when beginning a round of treatment.

This product increases the risk of extreme sunburn; care should be taken (shade, sunscreen, etc. Sunscreen (also known as sunblock or suntan lotion) is a Lotion, spray or other Topical product that absorbs or reflects the Sun 's ) to protect treated skin from overexposure to ultraviolet light.

Because usage of tretinoin may cause thinning of the skin, it is strongly recommended that patients who are using the drug abstain from hair removal waxing. The wax will, when removed, pull off the top level of epithelium (skin) with it, leaving a red, inflamed, sore, and unattractive mark for several days. Tweezing or threading (epilation) is a viable option for hair removal while using tretinoin. Threading is an ancient method of hair removal which originated in India spread to the Middle and Far East, and is now gaining popularity in Western countries The recommended timeframe to wait for a waxing treatment after using tretinoin varies from source to source; anywhere from 5 days to 3 months have been reported. Patients should consult with their aesthetician and dermatologist to discuss the best hair removal options during or after tretinoin use.

In leukemia use

There is a unique complication of retinoic acid syndrome in patients with acute promyelocytic leukemia. Retinoic acid syndrome (RAS is a potentially life threatening complication seen in patients with Acute promyelocytic leukemia (APML who are treated with all-trans retinoic This is associated with the development of dyspnea, fever, weight gain, peripheral edema and is treated with dexamethasone. The etiology of retinoic acid syndrome has been attributed to capillary leak syndrome from cytokine release from the differentiating promyelocytes. Capillary leak syndrome (sometimes systemic capillary leak syndrome or Clarkson syndrome) is a rare Medical condition where the number and size of the

Teratogenicity

It is a teratogen, and therefore can cause birth defects and tests have shown increases in foetal skull abnormalities in rats. Teratology stems from the Greek ( Genitive) meaning monster, or marvel and, meaning word, speech. Women who are or may be pregnant, or who are seeking to become pregnant, are therefore warned against using it. [8] This teratogenic effect is caused by the interference of the exogenous retinoic acid with endogenous retinoic acid signaling, which plays a role in patterning the developing embryo. Retinol (Afaxin, the animal form of Vitamin A, is a fat-soluble vitamin important in vision and Bone growth However the risks of topical tretinoin to the unborn child seems to be limited. [9]

Research uses

A study published by the European Respiratory Journal in 2002 suggested that tretinoin can reverse the effects of emphysema in mice by returning elasticity (and regenerating lung tissue through gene mediation) to the alveoli. [10] Studies suggested that this might form a promising treatment in human emphysema patients,[11] A newer follow-up study done in 2006 found inconclusive results("no definitive clinical benefits") using Vitamin A (retinoic acid) in treatment of emphysema in humans and stated that further research is needed to reach conclusions on this treatment. [12]

See also

Footnotes

  1. ^ MedlinePlus Drug Information: Tretinoin
  2. ^ Stefanaki C, Stratigos A, Katsambas A (Jun 2005). More than half of men are affected by Male pattern baldness by age 50 and baldness treatments are estimated to be a US $1 billion per year industry Hypervitaminosis A refers to the effects of excessive Vitamin A (specifically retinoid intake "Topical retinoids in the treatment of photoaging". J Cosmet Dermatol 4(2): 130-4. PMID 17166212.  
  3. ^ Retin-A, Tretinoin as a hair loss treatment
  4. ^ Stretch marks - treatment. NHS Direct - Health encyclopaedia. NHS Direct Online (2007-06-27). Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1358 - Republic of Dubrovnik is founded 1709 - Peter the Great defeats Charles XII of Sweden Retrieved on 2007-06-28. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1098 - Fighters of the First Crusade defeat Kerbogha of Mosul.
  5. ^ Huang M, Ye Y, Chen S, Chai J, Lu J, Zhoa L, Gu L, Wang Z (1988). "Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia" (PDF). Blood 72 (2): 567-72. PMID 3165295.   - Abstract
  6. ^ Castaigne S, Chomienne C, Daniel M, Ballerini P, Berger R, Fenaux P, Degos L (1990). "All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results" (PDF). Blood 76 (9): 1704-9. PMID 2224119.  
  7. ^ Sanz M (2006). "Treatment of acute promyelocytic leukemia". Hematology Am Soc Hematol Educ Program: 147-55. PMID 17124054.  
  8. ^ Tretinoin facts and comparsions at Drugs.com
  9. ^ Loureiro KD, Kao KK, Jones KL, Alvarado S, Chavez C, Dick L, Felix R, Johnson D, Chambers CD (Jul 2005). "Minor malformations characteristic of the retinoic acid embryopathy and other birth outcomes in children of women exposed to topical tretinoin during early pregnancy". Am J Med Genet A 136(2): 117-21. PMID 15940677.  
  10. ^ "Vitamin may cure smoking disease", BBC News, December 22, 2003. Events 1790 - The Turkish fortress of Izmail is stormed and captured by Suvorov and his Russian armies Year 2003 ( MMIII) was a Common year starting on Wednesday of the Gregorian calendar. Retrieved on 2006-11-18. Year 2006 ( MMVI) was a Common year starting on Sunday of the Gregorian calendar. Events 326 - The old St Peter's Basilica is consecrated 1302 - Pope Boniface VIII issues the Papal bull  
  11. ^ Mao J, Goldin J, Dermand J, Ibrahim G, Brown M, Emerick A, McNitt-Gray M, Gjertson D, Estrada F, Tashkin D, Roth M (2002). "A pilot study of all-trans-retinoic acid for the treatment of human emphysema". Am J Respir Crit Care Med 165 (5): 718-23. PMID 11874821.  
  12. ^ Roth M, Connett J, D'Armiento J, Foronjy R, Friedman P, Goldin J, Louis T, Mao J, Muindi J, O'Connor G, Ramsdell J, Ries A, Scharf S, Schluger N, Sciurba F, Skeans M, Walter R, Wendt C, Wise R (2006). "Feasibility of retinoids for the treatment of emphysema study". Chest 130 (5): 1334-45. PMID 17099008.  

External links

Dictionary

tretinoin

-noun

  1. (organic chemistry, pharmacology) Acid form of vitamin A commonly used to treat acne vulgaris and keratosis pilaris.
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