TP0

Amitriptyline

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is present as a standalone ligand in 3 entries

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Chemical Component Summary
Name	Amitriptyline
Synonyms	3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine
Identifiers	n/a
Formula	C₂₀ H₂₃ N
Molecular Weight	277.403
Type	NON-POLYMER
Isomeric SMILES	CN(C)CCC=C1c2ccccc2CCc3c1cccc3
InChI	InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
InChIKey	KRMDCWKBEZIMAB-UHFFFAOYSA-N

Chemical Details
Formal Charge	0
Atom Count	44
Chiral Atom Count	0
Bond Count	46
Aromatic Bond Count	12

Drug Info: DrugBank

DrugBank ID	DB00321
Name	Amitriptyline
Groups	approved
Description	Amitriptyline is a tricyclic antidepressant that has been used to treat depression for decades. ELAVIL, a previously approved branded product of amitriptyline, was first approved by the FDA in 1961.[A259342] Amitriptyline has been investigated in the treatment of pain-related conditions, attributed to its analgesic properties.[A174661]
Synonyms	Amitriptyline pamoate 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine Amitriptyline hydrochloride Amitriptylin 10,11-dihydro-5-(γ-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene 5-(γ-dimethylaminopropylidene)-5H-dibenzo[a,d][1,4]cycloheptadiene Amitriptilina 5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene Amitriptylinum 10,11-dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-Δ5,γ-propylamine Amitriptyline 5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptatriene 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amine
Brand Names	PMS-levazine 4/25 Tab Amitriptyline Hydrochloride Etrafon A Tab PMS-levazine 3/15 Tab Ag-amitriptyline Mar-amitriptyline Equipto - Amitriptyline External Cream Compounding Kit Perphenazine and Amitriptyline Hydrochloride Amitriptyline Ipg-amitriptyline Jamp-amitriptyline Tablets Sentravil PM-25 Elavil Pamoate Syr 10mg/5ml Amitriptyline Hydrochloride Tablets USP Bio-amitriptyline Elavil Limbitrol Elavil 25 mg Apo Peram Tab 3-15 PMS-amitriptyline Amitriptyline HCl Tab 50mg Amitriptyline 25 Tab Triavil Tab Priva-amitriptyline Jamp-amitriptyline Amitriptyline 10 Tab Dom-amitriptyline Novo-triptyn Tab 10mg Amitriptyline-25 Novo-triptyn Tab 50mg Amitriptyline hydrochloride Amitriptyline Tablets B.p 25mg Elavil Tablet 10mg Amitriptyline HCl Tab 25mg Etrafon 2 10 Amitriptyline hcl Amitriptyline-50 Elavil Tablet 75mg Levate Apo Peram Tab 2-25 PMS-levazine 2/25 Tab Amitriptyline HCL Chlordiazepoxide and Amitriptyline HCl Limbitrol DS Etrafon F Tab Novo-triptyn Tab 25mg Zyvodol Elavil Tablet 50mg Amitriptyline HCl Proavil Tab Amitriptyline-10 Apo-amitriptyline Chlordiazepoxide and Amitriptyline Hydrochloride Elavil Plus Tab Etrafon D Tab Nu-amitriptyline Tablets Teva-amitriptyline Elavil Tablet 25mg
Indication	This drug in indicated for the following conditions [FDA label]: Major depressive disorder in adults [L46357] Management of neuropathic pain in adults Prophylactic treatment of chronic tension-type headache (CTTH) in adults Prophylactic treatment of migraine in adults Treatment of nocturnal enuresis in children aged 6 years and above when organic pathology, including spina bifida and related disorders, have been excluded and no response has been achieved to all other non-drug and drug treatments, including antispasmodics and vasopressin-related products. This product should only be prescribed by a healthcare professional with expertise in the management of persistent enuresis [FDA label] Off-label uses: irritable bowel syndrome, sleep disorders, diabetic neuropathy, agitation, fibromyalgia, and insomnia
Categories	Adrenergic alpha-1 Receptor Antagonists Adrenergic alpha-Antagonists Adrenergic Antagonists Adrenergic Uptake Inhibitors Agents producing tachycardia Agents that produce hypertension Agents that reduce seizure threshold Analgesics Analgesics, Non-Narcotic Anticholinergic Agents Antidepressive Agents Antidepressive Agents Indicated for Depression Antidepressive Agents, Tricyclic Central Nervous System Agents Central Nervous System Depressants Combined Inhibitors of Serotonin/Norepinephrine Reuptake Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2B6 Substrates Cytochrome P-450 CYP2B6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 inhibitors (strength unknown) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (moderate) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs that are Mainly Renally Excreted Histamine Antagonists Histamine H1 Antagonists Membrane Transport Modulators Moderate Risk QTc-Prolonging Agents Muscarinic Antagonists Narrow Therapeutic Index Drugs Neurotoxic agents Neurotransmitter Agents Neurotransmitter Uptake Inhibitors Non-Selective Monoamine Reuptake Inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Psychotropic Drugs QTc Prolonging Agents Sensory System Agents Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Serotonin 5-HT2 Receptor Antagonists Serotonin 5-HT2A Receptor Antagonists Serotonin 5-HT2C Receptor Antagonists Serotonin Agents Serotonin Modulators Serotonin Receptor Antagonists Tertiary amine tricyclic antidepressants Tricyclics and Other Norepinephrine-reuptake Inhibitors UGT1A1 Inhibitors UGT1A4 substrates
ATC-Code	N06AA09 N06CA01
CAS number	50-48-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Sodium-dependent noradrenaline transporter	MLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRD...	unknown	inhibitor
Sodium-dependent serotonin transporter	METTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...	unknown	inhibitor
5-hydroxytryptamine receptor 2A	MDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...	unknown	antagonist
5-hydroxytryptamine receptor 1A	MDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...	unknown	inhibitor,inducer
Delta-type opioid receptor	MEPAPSAGAELQPPLFANASDAYPSACPSAGANASGPPGARSASSLALAI...	unknown	agonist
Kappa-type opioid receptor	MDSPIQIFRGEPGPTCAPSACLPPNSSAWFPGWAEPDSNGSAGSEDAQLE...	unknown	agonist
High affinity nerve growth factor receptor	MLRGGRRGQLGWHSWAAGPGSLLAWLILASAGAAPCPDACCPHGSSGLRC...	unknown	agonist,activator
BDNF/NT-3 growth factors receptor	MSSWIRWHGPAMARLWGFCWLVVGFWRAAFACPTSCKCSASRIWCSDPSP...	unknown	agonist
Alpha-1A adrenergic receptor	MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...	unknown	antagonist,inhibitor
Alpha-1D adrenergic receptor	MTFRDLLSVSFEGPRPDSSAGGSSAGGGGGSAGGAAPSEGPAVGGVPGGA...	unknown	antagonist
Alpha-2A adrenergic receptor	MGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...	unknown	antagonist,agonist
Histamine H1 receptor	MSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLY...	unknown	antagonist
Potassium voltage-gated channel subfamily KQT member 2	MVQKSRNGGVYPGPSGEKKLKVGFVGLDPGAPDSTRDGALLIAGSEAPKR...	unknown	inhibitor
Potassium voltage-gated channel subfamily A member 1	MTVMSGENVDEASAAPGHPQDGSYPRQADHDDHECCERVVINISGLRFET...	unknown	inhibitor
Histamine H2 receptor	MAPNGTASSFCLDSTACKITITVVLAVLILITVAGNVVVCLAVGLNRRLR...	unknown	blocker
Histamine H4 receptor	MPDTNSTINLSLSTRVTLAFFMSLVAFAIMLGNALVILAFVVDKNLRHRS...	unknown	binder
Sigma non-opioid intracellular receptor 1	MQWAVGRRWAWAALLLAVAAVLTQVVWLWLGTQSFVFQREEIAQLARQYA...	unknown	agonist
5-hydroxytryptamine receptor 2C	MVNLRNAVHSFLVHLIGLLVWQCDISVSPVAAIVTDIFNTSDGGRFKFPD...	unknown	antagonist
Alpha-1B adrenergic receptor	MNPDLDTGHNTSAPAHWGELKNANFTGPNQTSSNSTLPQLDITRAISVGL...	unknown	antagonist
5-hydroxytryptamine receptor 7	MMDVNSSGRPDLYGHLRSFLLPEVGRGLPDLSPDGGADPVAGSWAPHLLS...	unknown	antagonist
5-hydroxytryptamine receptor 1D	MSPLNQSAEGLPQEASNRSLNATETSEAWDPRTLQALKISLAVVLSVITL...	unknown	binder
Mu-type opioid receptor	MDSSAAPTNASNCTDALAYSSCSPAPSPGSWVNLSHLDGNLSDPCGPNRT...	unknown	binder
5-hydroxytryptamine receptor 1B	MEEPGAQCAPPPPAGSETWVPQANLSSAPSQNCSAKDYIYQDSISLPWKV...	unknown	binder
5-hydroxytryptamine receptor 6	MVPEPGPTANSTPAWGAGPPSAPGGSGWVAAALCVVIALTAAANSLLIAL...	unknown	antagonist
Potassium voltage-gated channel subfamily KQT member 3	MGLKARRAAGAAGGGGDGGGGGGGAANPAGGDAAAAGDEERKVGLAPGDV...	unknown	inhibitor
5-hydroxytryptamine receptor 1C	MVNLGNAVRSLLMHLIGLLVWQFDISISPVAAIVTDTFNSSDGGRLFQFP...	unknown	antagonist
Muscarinic acetylcholine receptor	MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...	unknown	ligand
HERG human cardiac K+ channel	MPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...	unknown	blocker
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate,inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	substrate
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate,inhibitor
UDP-glucuronosyltransferase 2B10	MALKWTTVLLIQLSFYFSSGSCGKVLVWAAEYSLWMNMKTILKELVQRGH...	unknown	substrate,inhibitor
UDP-glucuronosyltransferase 1-4	MARGLQVPLPRLATGLLLLLSVQPWAESGKVLVVPTDGSPWLSMREALRE...	unknown	substrate
Glutathione S-transferases (Cytosolic)	MAEKPKLHYFNARGRMESTRWLLAAAGVEFEEKFIKSAEDLDKLRNDGYL...	unknown	inhibitor
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	binder
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	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