REA

RETINOIC ACID

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is present as a standalone ligand in 22 entries

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Chemical Component Summary
Name	RETINOIC ACID
Identifiers	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Formula	C₂₀ H₂₈ O₂
Molecular Weight	300.435
Type	NON-POLYMER
Isomeric SMILES	CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
InChI	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+
InChIKey	SHGAZHPCJJPHSC-YCNIQYBTSA-N

Chemical Details
Formal Charge	0
Atom Count	50
Chiral Atom Count	0
Bond Count	50
Aromatic Bond Count	0

Drug Info: DrugBank

DrugBank ID	DB00755
Name	Tretinoin
Groups	approved investigational nutraceutical
Description	Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of [vitamin A] (retinol).[A257474] It is an oxidation product in the physiological pathway of vitamin A metabolism.[A257689] In human circulation, tretinoin is normally found at very low concentrations, approximately 4 to 14 nmol/L.[A257689] Tretinoin exhibits anti-inflammatory, antineoplastic, antioxidant, and free radical-scavenging activities.[A257689] It has been used in dermatology for many years to treat various skin conditions ranging from acne to wrinkles [A257474,A258185] and activates nuclear receptors to regulate epithelial cell growth and differentiation.[A257474,A257629,A257609] Tretinoin is given orally to treat acute promyelocytic leukemia [L45349] and topically to treat skin conditions such as acne.[L45389,L34869,L45384]
Synonyms	all trans Retinoic acid beta-Retinoic acid Acide retinoique 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL) Vitamin A acid all trans-Retinoic acid Retinoic acid all-trans-beta-Retinoic acid all-trans-Retinoic acid all-trans-Vitamin A1 acid Tretinoina Tretinoin ATRA Trétinoïne trans-Retinoic acid all-trans-Tretinoin Retionic acid Tretinoinum all-(E)-Retinoic acid all-trans-Vitamin A acid (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid Tretin M
Brand Names	Clindamycin 1% / Niacinamide 4% / Spironolactone 2% / Tretinoin 0.025% Obagi TRETIN-X Cream 0.05% Dapsone 6% / Niacinamide 2% / Tretinoin 0.025% Dermapak Plus Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% / Tretinoin 0.025% Hydrocortisone 0.5% / Hydroquinone 8% / Tretinoin 0.05% Hydroquinone 6% /tretinoin 0.05% Veltin Vitinoin - Crm 0.025% Clindamycin 1% / Niacinamide 4% / Tretinoin 0.05% TRETIN-X Gel 0.025% Hydroquinone 4% / Tretinoin 0.025% Imiquimod 5% / Tretinoin 0.025% Stie Vaa Sol 0.05% Clindamycin 1% / Sodium Sulfacetamide Monohydrate 5% / Tretinoin 0.025% Tretinoin Cream Twyneo Dexamethasone Sodium Phosphate 0.1% / Finasteride 0.1% / Minoxidil 5% / Tretinoin 0.025% Tretinopak Refissa Retin-A MICRO Rejuva-A Biacna Topical Gel Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025% Clindamycin Phosphate and Tretinoin Clindamycin Phosphate and Tretinion Hydroquinone 8% / Tretinoin 0.025%. Stieva-A Benzoyl Peroxide 2.5%, Clindamycin Phosphate 1%, Niacinamide 2% / Tretinoin 0.05% Stieva-A Gel Stievamycin Mild Desoximetasone 0.05% / Hydroquinone 6% / Tretinoin 0.05% Retin-A Hydrocortisone 0.5% / Hydroquinone 8% / Tretinoin 0.025% Clindamycin Phosphate 1.2% and Tretinoin 0.025% 011218 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025% Niacinamide 4% / Tretinoin 0.1% Niacinamide 4% / Tretinoin 0.05% Hydrocortisone 0.5% / Hydroquinone 6% / Tretinoin 0.05% Solage Stievamycin Regular Clindamycin 1% / Niacinamide 4% / Tretinoin 0.025% Benzoyl Peroxide 5% / Niacinamide 2% / Tretinoin 0.025% Hyaluronic Acid Sodium Salt 0.5% / Niacinamide 4% / Tretinoin 0.025% Tretinoin Gel Atralin 141017 Hydrocortisone 0.5% / Hydroquinone 6% / Tretinoin 0.025% Hyaluronic Acid Sodium Salt 0.5% / Niacinamide 4% / Tretinoin 0.1% Hydroquinone 4% / Tretinoin 0.025% / Triamcinolone Acetonide 0.025% Hydroquinone 5% / Tretinoin 0.025% / Triamcinolone Acetonide 0.025% Hydroquinone 6% / Tretinoin 0.05% / Triamcinolone 0.025% 141060 Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025% Clindamycin Phosphate and Tretinoin Gel 1.2%/0.025% Minoxidil 7% / Progesterone 0.1% / Tretinoin 0.025% Solagé Tretin.x Tri-luma Dermawerx Zmt Pak Tretinoin Gel Microsphere Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.05% Tretin-X Fluocinolone Acetonide 0.01% / Minoxidil 5% / Tretinoin 0.025% Renova Niacinamide 2% / Spironolactone 5% / Tretinoin 0.05% Vitamin A Acid 0.01% Cream Stieva-A Solution 011010 Niacinamide 4% / Tretinoin 0.025% Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.1% Tretinoin (Emollient) Triderma Benzoyl Peroxide 5% / Clindamycin1% / Niacinamide 2% / Tretinoin 0.025% Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Tretinoin 0.05% Hyaluronic Acid Sodium Salt 0.5% / Hydroquinone 4% / Tretinoin 0.05% 011013 Niacinamide 4% / Tretinoin 0.025% Dr. Throwers Pbc No. 1 Vesanoid Vitinoin - Crm 0.05% 141016 Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025% Vitamin A Acid 0.025% Cream Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025% Tretinoin Stieva-A Cream Niacinamide 4% / Tretinoin 0.025% TRETIN-X Cream 0.025% Stievaa Gel 0.01% Refissa Tretinoin (Emollient) Vitamin A Acid 0.1% Cream Avita Derma Lightening Ascorbyl Palmitate 2% / Hyaluronic Acid Sodium Salt 0.2% / Niacinamide 5% / Tretinoin 0.025% TRETIN-X Cream 0.1% Minoxidil 7% / Tretinoin 0.025% Retisol-A Imiquimod 5% / Salicylic Acid 30% / Tretinoin 0.1% Vitinoin Gel - 0.025% Vitamin A Acid 0.05% Cream Vitinoin - Crm 0.1% Dr. Throwers Hydrotet 141061 Hydrocortisone 0.5% / Hydroquinone 8% / Tretinoin 0.025% Hydrocortisone 0.5% / Hydroquinone 6% / Tretinoin 0.025% OLIVIA QUIDO FIRM and FADE II Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% / Tretinoin 0.05% Hydroquinone 8% / Tretinoin 0.025% 011021 Niacinamide 4% / Tretinoin 0.05% Stievamycin Forte Ziana OLIVIA QUIDO FIRM and FADE I Dapsone 8.5% / Niacinamide 2% / Tretinoin 0.025% Hydrocortisone 1% / Hydroquinone 8% / Tretinoin 0.05% TretinX Jamp Tretinoin Altreno Benzoyl Peroxide 2.5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.025% 011220 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.05% 011020 Niacinamide 4% / Tretinoin 0.05% Minoxidil 5% / Progesterone 0.1% / Tretinoin 0.025% TRETIN-X Gel 0.01% Vitamin A Acid Finasteride 0.1% / Minoxidil 7% / Tretinoin 0.025% Hyaluronic Acid Sodium Salt 0.5% / Niacinamide 4% / Tretinoin 0.05% Cenovia
Indication	Oral tretinoin is indicated for induction of remission in adults and pediatric patients one year of age and older with acute promyelocytic leukemia (APL), characterized by the presence of t(15;17) translocation or presence of PML/RARα gene expression and who are refractory to or who have relapsed from anthracycline chemotherapy or for whom anthracycline-based chemotherapy is contraindicated.[L45349] Topical tretinoin is also indicated alone [L45389] or in combination with [benzoyl peroxide] [L34869] or [clindamycin] [L45384] for the treatment of acne vulgaris. It is also used in prescription and over-the-counter for treating various skin conditions such as melasma,[L45394] hyperpigmentation,[A257474] and photoaging [A258180] alone or in combination with other drugs.
Categories	Agents that produce hypertension Alkenes Anti-Acne Preparations Anti-Acne Preparations for Topical Use Antineoplastic Agents Antineoplastic and Immunomodulating Agents Biological Factors Cardiotoxic antineoplastic agents Carotenoids Cell Stimulants and Proliferants Cyclohexanes Cyclohexenes Cycloparaffins Cytochrome P-450 CYP2A6 Substrates Cytochrome P-450 CYP2B6 Substrates Cytochrome P-450 CYP2C18 Substrates Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2E1 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Substrates Dermatologicals Diterpenes Hydrocarbons, Acyclic Hypotensive Agents Immunosuppressive Agents Keratolytic Agents Pigments, Biological Polyenes Retinoids Retinoids for cancer treatment Retinoids for Topical Use in Acne Terpenes UGT2B7 substrates Vitamin A Vitamins Vitamins (Fat Soluble)
ATC-Code	L01XF01 D10AD51 D10AD01
CAS number	302-79-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Retinoic acid receptor alpha	MASNSSSCPTPGGGHLNGYPVPPYAFFFPPMLGGLSPPGALTTLQHQLPV...	unknown	agonist
Retinoic acid receptor beta	MTTSGHACPVPAVNGHMTHYPATPYPLLFPPVIGGLSLPPLHGLHGHPPP...	unknown	agonist
Retinoic acid receptor gamma	MATNKERLFAAGALGPGSGYPGAGFPFAFPGALRGSPPFEMLSPSFRGLG...	unknown	agonist
Retinoic acid receptor RXR-alpha	MDTKHFLPLDFSTQVNSSLTSPTGRGSMAAPSLHPSLGPGIGSPGQLHSP...	unknown	agonist
Retinoic acid receptor RXR-beta	MSWAARPPFLPQRHAAGQCGPVGVRKEMHCGVASRWRRRRPWLDPAAAAA...	unknown	agonist
Retinoic acid receptor RXR-gamma	MYGNYSHFMKFPAGYGGSPGHTGSTSMSPSAALSTGKPMDSHPSYTDTPV...	unknown	agonist
Cellular retinoic acid-binding protein 1	MPNFAGTWKMRSSENFDELLKALGVNAMLRKVAVAAASKPHVEIRQDGDQ...	unknown	binder
Retinoic acid receptor responder protein 1	MQPRRQRLPAPWSGPRGPRPTAPLLALLLLLAPVAAPAGSGDPDDPGQPQ...	unknown	agonist
Retinal dehydrogenase 1	MSSSGTPDLPVLLTDLKIQYTKIFINNEWHDSVSGKKFPVFNPATEEELC...	unknown	substrate
Retinal dehydrogenase 2	MTSSKIEMPGEVKADPAALMASLHLLPSPTPNLEIKYTKIFINNEWQNSE...	unknown	substrate
Retinoic acid-induced protein 3	MATTVPDGCRNGLKSKYYRLCDKAEAWGIVLETVATAGVVTSVAFMLTLP...	unknown	regulator
Lipocalin-1	MKPLLLAVSLGLIAALQAHHLLASDEEIQDVSGTWYLKAMTVDREFPEMN...	unknown	binder
Odorant-binding protein 2a	MKTLFLGVTLGLAAALSFTLEEEDITGTWYVKAMVVDKDFPEDRRPRKVS...	unknown	binder
Retinol-binding protein 4	MKWVWALLLLAALGSGRAERDCRVSSFRVKENFDKARFSGTWYAMAKKDP...	unknown	binder
[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 4, mitochondrial	MKAARFVLRSAGSLNGAGLVPREVEHFSRYSPSPLSMKQLLDFGSENACE...	unknown	upregulator
Carcinoembryonic antigen	MESPSAPPHRWCIPWQRLLLTGEGRTTWERVGGGSWGLLGRTGL	unknown	downregulator
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	substrate
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 2A6	MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...	unknown	substrate
Cytochrome P450 2C18	MDPAVALVLCLSCLFLLSLWRQSSGRGRLPSGPTPLPIIGNILQLDVKDM...	unknown	substrate
Cytochrome P450 1A1	MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...	unknown	substrate
Cytochrome P450 4A11	MSVSVLSPSRLLGDVSGILQAASLLILLLLLIKAVQLYLHRQWLLKALQQ...	unknown	substrate
UDP-glucuronosyltransferase 2B7	MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...	unknown	substrate
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	substrate
Cytochrome P450 26A1	MGLPALLASALCTFVLPLLLFLAAIKLWDLYCVSGRDRSCALPLPPGTMG...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Cellular retinoic acid-binding protein 1	MPNFAGTWKMRSSENFDELLKALGVNAMLRKVAVAAASKPHVEIRQDGDQ...	unknown	substrate
Cellular retinoic acid-binding protein 2	MPNFSGNWKIIRSENFEELLKVLGVNVMLRKIAVAAASKPAVEIKQEGDT...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682