REA

RETINOIC ACID

Created:	1999-07-08
Last modified:	2016-10-18

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22 entries where REA is found as a standalone ligand

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

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Chemical Component Summary
Name	RETINOIC ACID
Systematic Name (OpenEye OEToolkits)	(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

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	C1(CCCC(=C1\C=C\C(=C\C=C\C(=C\C(=O)O)C)C)C)(C)C
SMILES	CACTVS	3.385	CC1=C(C=CC(C)=CC=CC(C)=CC(O)=O)C(C)(C)CCC1
SMILES	OpenEye OEToolkits	1.7.6	CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
Canonical SMILES	CACTVS	3.385	CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)C(C)(C)CCC1
Canonical SMILES	OpenEye OEToolkits	1.7.6	CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
InChI	InChI	1.03	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	InChI	1.03	SHGAZHPCJJPHSC-YCNIQYBTSA-N

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-Vitamin A acid ATRA all-trans-beta-Retinoic acid (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid Vitamin A acid Tretin M all trans-Retinoic acid beta-Retinoic acid Tretinoina Acide retinoique all-(E)-Retinoic acid Retionic acid 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL) Tretinoinum Trétinoïne all-trans-Vitamin A1 acid trans-Retinoic acid Tretinoin all-trans-Tretinoin Retinoic acid all trans Retinoic acid all-trans-Retinoic acid
Brand Names	Vitinoin - Crm 0.025% Stievamycin Mild Clindamycin 1% / Niacinamide 4% / Tretinoin 0.025% Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025% Benzoyl Peroxide 2.5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.025% Derma Lightening Avita 141017 Hydrocortisone 0.5% / Hydroquinone 6% / Tretinoin 0.025% TretinX Tretinopak OLIVIA QUIDO FIRM and FADE I Niacinamide 4% / Tretinoin 0.1% Tretinoin (Emollient) Retin-A MICRO Hydrocortisone 0.5% / Hydroquinone 8% / Tretinoin 0.025% Vitamin A Acid 0.025% Cream Clindamycin Phosphate and Tretinoin Gel 1.2%/0.025% Imiquimod 5% / Tretinoin 0.025% TRETIN-X Cream 0.1% Vitamin A Acid 0.05% Cream Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Tretinoin 0.05% Fluocinolone Acetonide 0.01% / Minoxidil 5% / Tretinoin 0.025% Hyaluronic Acid Sodium Salt 0.5% / Hydroquinone 4% / Tretinoin 0.05% Stieva-A Gel Hydrocortisone 0.5% / Hydroquinone 6% / Tretinoin 0.05% Vitamin A Acid 0.1% Cream Vitinoin Gel - 0.025% Clindamycin 1% / Niacinamide 4% / Tretinoin 0.05% Dapsone 8.5% / Niacinamide 2% / Tretinoin 0.025% Desoximetasone 0.05% / Hydroquinone 6% / Tretinoin 0.05% Vitinoin - Crm 0.05% Hydrocortisone 0.5% / Hydroquinone 6% / Tretinoin 0.025% Minoxidil 7% / Progesterone 0.1% / Tretinoin 0.025% Solage Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.05% 141016 Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025% Hydroquinone 4% / Tretinoin 0.025% / Triamcinolone Acetonide 0.025% Renova Clindamycin Phosphate and Tretinion Niacinamide 4% / Tretinoin 0.025% Twyneo Refissa Stievamycin Regular Triderma Hydrocortisone 1% / Hydroquinone 8% / Tretinoin 0.05% Retisol-A Tretinoin Gel Microsphere Refissa Tretinoin (Emollient) Stieva-A Cream 011020 Niacinamide 4% / Tretinoin 0.05% Benzoyl Peroxide 5% / Niacinamide 2% / Tretinoin 0.025% Ascorbyl Palmitate 2% / Hyaluronic Acid Sodium Salt 0.2% / Niacinamide 5% / Tretinoin 0.025% Hyaluronic Acid Sodium Salt 0.5% / Niacinamide 4% / Tretinoin 0.05% Dexamethasone Sodium Phosphate 0.1% / Finasteride 0.1% / Minoxidil 5% / Tretinoin 0.025% Biacna Topical Gel Benzoyl Peroxide 5% / Clindamycin1% / Niacinamide 2% / Tretinoin 0.025% Hyaluronic Acid Sodium Salt 0.5% / Niacinamide 4% / Tretinoin 0.1% Imiquimod 5% / Salicylic Acid 30% / Tretinoin 0.1% Tretin-X Finasteride 0.1% / Minoxidil 7% / Tretinoin 0.025% TRETIN-X Gel 0.025% Niacinamide 4% / Tretinoin 0.05% Hydroquinone 6% /tretinoin 0.05% Vitamin A Acid 0.01% Cream 011010 Niacinamide 4% / Tretinoin 0.025% 141061 Hydrocortisone 0.5% / Hydroquinone 8% / Tretinoin 0.025% Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% / Tretinoin 0.05% Vitamin A Acid 011021 Niacinamide 4% / Tretinoin 0.05% Stie Vaa Sol 0.05% Tretinoin Cream Cenovia 011218 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025% TRETIN-X Cream 0.05% Tretinoin Clindamycin 1% / Sodium Sulfacetamide Monohydrate 5% / Tretinoin 0.025% Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.1% 011013 Niacinamide 4% / Tretinoin 0.025% TRETIN-X Cream 0.025% Stievaa Gel 0.01% Dr. Throwers Pbc No. 1 Hydrocortisone 0.5% / Hydroquinone 8% / Tretinoin 0.05% Obagi Stieva-A Stieva-A Solution 011220 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.05% TRETIN-X Gel 0.01% Benzoyl Peroxide 2.5%, Clindamycin Phosphate 1%, Niacinamide 2% / Tretinoin 0.05% Hydroquinone 4% / Tretinoin 0.025% Stievamycin Forte Vitinoin - Crm 0.1% Dermapak Plus Rejuva-A 141060 Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025% Altreno Atralin Veltin Hydroquinone 6% / Tretinoin 0.05% / Triamcinolone 0.025% Tretinoin Gel Hyaluronic Acid Sodium Salt 0.5% / Niacinamide 4% / Tretinoin 0.025% Minoxidil 5% / Progesterone 0.1% / Tretinoin 0.025% Clindamycin Phosphate 1.2% and Tretinoin 0.025% Clindamycin Phosphate and Tretinoin Dermawerx Zmt Pak Tretin.x Hydroquinone 8% / Tretinoin 0.025% Dapsone 6% / Niacinamide 2% / Tretinoin 0.025% Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% / Tretinoin 0.025% Hydroquinone 5% / Tretinoin 0.025% / Triamcinolone Acetonide 0.025% Vesanoid Dr. Throwers Hydrotet Jamp Tretinoin Tri-luma Ziana Hydroquinone 8% / Tretinoin 0.025%. Niacinamide 2% / Spironolactone 5% / Tretinoin 0.05% Retin-A OLIVIA QUIDO FIRM and FADE II Solagé Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025% Clindamycin 1% / Niacinamide 4% / Spironolactone 2% / Tretinoin 0.025% Minoxidil 7% / Tretinoin 0.025%
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