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Namespace Prefixes

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Statements

Subject Item
n2:DB00755
rdf:type
n3:Drug
n3:description
Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis. Tretinoin also represents the class of anticancer drugs called differentiating agents and is used in the treatment of acute promyelocytic leukemia (APL).
n3:dosage
n13:271B58D4-363D-11E5-9242-09173F13E4C5 n13:271B58E9-363D-11E5-9242-09173F13E4C5 n13:271B58EA-363D-11E5-9242-09173F13E4C5 n13:271B58EB-363D-11E5-9242-09173F13E4C5 n13:271B58D3-363D-11E5-9242-09173F13E4C5 n13:271B58DD-363D-11E5-9242-09173F13E4C5 n13:271B58D5-363D-11E5-9242-09173F13E4C5 n13:271B58D6-363D-11E5-9242-09173F13E4C5 n13:271B58D7-363D-11E5-9242-09173F13E4C5 n13:271B58D8-363D-11E5-9242-09173F13E4C5 n13:271B58DE-363D-11E5-9242-09173F13E4C5 n13:271B58DF-363D-11E5-9242-09173F13E4C5 n13:271B58E0-363D-11E5-9242-09173F13E4C5 n13:271B58E1-363D-11E5-9242-09173F13E4C5 n13:271B58D9-363D-11E5-9242-09173F13E4C5 n13:271B58DA-363D-11E5-9242-09173F13E4C5 n13:271B58DB-363D-11E5-9242-09173F13E4C5 n13:271B58DC-363D-11E5-9242-09173F13E4C5 n13:271B58E6-363D-11E5-9242-09173F13E4C5 n13:271B58E7-363D-11E5-9242-09173F13E4C5 n13:271B58E8-363D-11E5-9242-09173F13E4C5 n13:271B58E2-363D-11E5-9242-09173F13E4C5 n13:271B58E3-363D-11E5-9242-09173F13E4C5 n13:271B58E4-363D-11E5-9242-09173F13E4C5 n13:271B58E5-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Huang ME, Ye YC, Chen SR, Chai JR, Lu JX, Zhoa L, Gu LJ, Wang ZY: Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia. Blood. 1988 Aug;72(2):567-72. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/3165295 # Castaigne S, Chomienne C, Daniel MT, Ballerini P, Berger R, Fenaux P, Degos L: All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results. Blood. 1990 Nov 1;76(9):1704-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/2224119 # Sanz MA: Treatment of acute promyelocytic leukemia. Hematology Am Soc Hematol Educ Program. 2006;:147-55. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17124054 # Mao JT, Goldin JG, Dermand J, Ibrahim G, Brown MS, Emerick A, McNitt-Gray MF, Gjertson DW, Estrada F, Tashkin DP, Roth MD: A pilot study of all-trans-retinoic acid for the treatment of human emphysema. Am J Respir Crit Care Med. 2002 Mar 1;165(5):718-23. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11874821 # Roth MD, Connett JE, D'Armiento JM, Foronjy RF, Friedman PJ, Goldin JG, Louis TA, Mao JT, Muindi JR, O'Connor GT, Ramsdell JW, Ries AL, Scharf SM, Schluger NW, Sciurba FC, Skeans MA, Walter RE, Wendt CH, Wise RA: Feasibility of retinoids for the treatment of emphysema study. Chest. 2006 Nov;130(5):1334-45. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17099008
n3:group
approved investigational nutraceutical
n3:halfLife
0.5-2 hours
n3:indication
For the the induction of remission in patients with acute promyelocytic leukemia (APL), French-American-British (FAB) classification M3 (including the M3 variant); For the topical treatment of acne vulgaris, flat warts and other skin conditions (psoriasis, ichthyosis congenita, icthyosis vulgaris, lamellar icthyosis, keratosis palmaris et plantaris, epidermolytic hyperkeratosis, senile comedones, senile keratosis, keratosis follicularis (Darier's disease), and basal cell carcinomas.); For palliative therapy to improve fine wrinkling, mottled hyperpigmentation, roughness associated with photodamage.
n3:manufacturer
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owl:sameAs
n6:DB00755 n28:DB00755
dcterms:title
Tretinoin
adms:identifier
n15:5337 n16:DB00755 n18:15367 n20:D00094 n21:0062-0187-02 n22:C00777 n23:46504843 n24:PA451746 n25:444795 n31:Tretinoin
n3:mechanismOfAction
Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
n3:packager
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n3:patent
n30:5470567 n30:6353029
n3:synonym
Stieva-a AGN 100335 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl) beta-Retinoic acid Tretinoine (french) (einecs) All Trans Retinoic Acid Renova all-trans-Retinoic acid Eudyna trans-Retinoic acid Tretinoinum Tretin m (all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid All Trans-Retinoic Acid Retionic Acid Vitinoin Retin-a Tretinoina all-trans-Vitamin a1 acid Ro 1-5488 RETINOIC acid Trétinoïne Solage Vitamin A acid Acide retinoique (french) (dsl) Tretinoin Retisol-a all-trans-beta-Retinoic acid all-trans-Tretinoin Vesanoid all-trans-Vitamin a acid all-(e)-Retinoic acid ATRA
n8:hasAHFSCode
n9:84-16-00 n9:92-00-00
n3:mixture
n32:271B5870-363D-11E5-9242-09173F13E4C5 n32:271B586F-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
> 95%
n26:hasConcept
n27:M0021879
foaf:page
n11:tretinoin.html n17:tretinoin.htm
n3:IUPAC-Name
n4:271B58F0-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B58F6-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B58F5-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B58F2-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B58F3-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B58F4-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B58EE-363D-11E5-9242-09173F13E4C5 n4:271B5905-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B58EC-363D-11E5-9242-09173F13E4C5 n4:271B58EF-363D-11E5-9242-09173F13E4C5 n4:271B5907-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B58ED-363D-11E5-9242-09173F13E4C5
n8:hasATCCode
n19:D10AD01 n19:L01XX14
n3:H-Bond-Acceptor-Count
n4:271B58FC-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B58FD-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B58F7-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B58F8-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B58FA-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B58F9-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B58FB-363D-11E5-9242-09173F13E4C5
n3:absorption
1-31% (topical)
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
302-79-4
n3:category
n3:containedIn
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n3:Bioavailability
n4:271B5901-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5903-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5904-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5906-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5900-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B58FF-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5902-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B58F1-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B58FE-363D-11E5-9242-09173F13E4C5