IXX

3-(5H-DIBENZO[B,F]AZEPIN-5-YL)-N,N-DIMETHYLPROPAN-1-AMINE

Created:	2007-06-07
Last modified:	2020-09-28

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3 entries where IXX is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	45
Chiral Atom Count	0
Bond Count	47
Aromatic Bond Count	12

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Chemical Component Summary
Name	3-(5H-DIBENZO[B,F]AZEPIN-5-YL)-N,N-DIMETHYLPROPAN-1-AMINE
Synonyms	5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenz[b,f]azepine; 10,11-Dehydroimipramine; Depramine
Systematic Name (OpenEye OEToolkits)	3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethyl-propan-1-amine
Formula	C₁₉ H₂₄ N₂
Molecular Weight	280.407
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	c1cc3c(cc1)CCc2c(cccc2)N3CCCN(C)C
SMILES	CACTVS	3.341	CN(C)CCCN1c2ccccc2CCc3ccccc13
SMILES	OpenEye OEToolkits	1.5.0	CN(C)CCCN1c2ccccc2CCc3c1cccc3
Canonical SMILES	CACTVS	3.341	CN(C)CCCN1c2ccccc2CCc3ccccc13
Canonical SMILES	OpenEye OEToolkits	1.5.0	CN(C)CCCN1c2ccccc2CCc3c1cccc3
InChI	InChI	1.03	InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
InChIKey	InChI	1.03	BCGWQEUPMDMJNV-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB00458
Name	Imipramine
Groups	approved
Description	Imipramine, the prototypical tricyclic antidepressant (TCA), is a dibenzazepine-derivative TCA. TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, imipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, imipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as imipramine and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also block histamine H<sub>1</sub> receptors, α<sub>1</sub>-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively [A6584]. Imipramine has less sedative and anticholinergic effects than the tertiary amine TCAs, amitriptyline and clomipramine. Imipramine may be used to treat depression and nocturnal enuresis in children [FDA Label]. Unlabeled indications include chronic and neuropathic pain (including diabetic neuropathy), panic disorder, attention-deficit/hyperactivity disorder (ADHD), and post-traumatic stress disorder (PTSD) [L1349,L1348,A31900,L1351,L1352,L1353,A31904].
Synonyms	Imipramine Imipramine pamoate N-(γ-dimethylaminopropyl)iminodibenzyl N-(gamma-Dimethylaminopropyl)iminodibenzyl Imipramine hydrochloride 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine Imizine Imipramin 10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine Imipraminum Imipramina
Brand Names	Novo-pramine Tab 50mg Imipramine Tab 25mg PMS Imipramine Tab 50mg Tofranil 75mg Imipramine Hydrochloride Tablets 50mg Tofranil 25mg Imipramine 50 Tab 50mg Imipramine Hydrochloride Tablets 25mg Novo-pramine Tab 10mg Imipramine Novo-pramine Tab 25mg Impril Tofranil-PM PMS Imipramine Tab 25mg Imipramine Hydrochloride Tofranil 50mg Tofranil PMS Imipramine Tab 10mg Imipramine hydrochloride Imipramine 25tab Tofranil 10mg Apo-imipramine Imipramine Pamoate Imipramine 10tab
Indication	For the relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older [FDA Label]. May also be used off-label to manage panic disorders with or without agoraphobia, as a second line agent for ADHD in children and adolescents, to manage bulimia nervosa, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, for the treatment of acute stress disorder and posttraumatic stress disorder, and for symptomatic treatment of postherpetic neuralgia and painful diabetic neuropathy [L1349,L1348,A31900,L1351,L1352,L1353,A31904].
Categories	Adrenergic Agents 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 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 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (moderate) Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) 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 CYP2C18 Substrates Cytochrome P-450 CYP2C18 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 inhibitors (strength unknown) Cytochrome P-450 CYP2C19 Inhibitors (strong) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dibenzazepines Drugs that are Mainly Renally Excreted Heterocyclic Compounds, Fused-Ring Histamine Antagonists Histamine H1 Antagonists Hypotensive Agents Membrane Transport Modulators Moderate Risk QTc-Prolonging Agents Muscarinic Antagonists Narrow Therapeutic Index Drugs Nervous System Neurotoxic agents Neurotransmitter Agents Neurotransmitter Uptake Inhibitors Non-Selective Monoamine Reuptake Inhibitors OCT2 Inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Psychoanaleptics Psychotropic Drugs QTc Prolonging 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
ATC-Code	N06AA02
CAS number	50-49-7

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
Histamine H1 receptor	MSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLY...	unknown	antagonist
Alpha-1A adrenergic receptor	MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...	unknown	antagonist
Alpha-1D adrenergic receptor	MTFRDLLSVSFEGPRPDSSAGGSSAGGGGGSAGGAAPSEGPAVGGVPGGA...	unknown	antagonist
Muscarinic acetylcholine receptor M1	MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...	unknown	antagonist
Muscarinic acetylcholine receptor M2	MNNSTNSSNNSLALTSPYKTFEVVFIVLVAGSLSLVTIIGNILVMVSIKV...	unknown	antagonist
Muscarinic acetylcholine receptor M3	MTLHNNSTTSPLFPNISSSWIHSPSDAGLPPGTVTHFGSYNVSRAAGNFS...	unknown	antagonist
Muscarinic acetylcholine receptor M4	MANFTPVNGSSGNQSVRLVTSSSHNRYETVEMVFIATVTGSLSLVTVVGN...	unknown	antagonist
Muscarinic acetylcholine receptor M5	MEGDSYHNATTVNGTPVNHQPLERHRLWEVITIAAVTAVVSLITIVGNVL...	unknown	antagonist
Potassium voltage-gated channel subfamily D member 2	MAAGVAAWLPFARAAAIGWMPVASGPMPAPPRQERKRTQDALIVLNVSGT...	unknown	inhibitor
Potassium voltage-gated channel subfamily D member 3	MAAGVAAWLPFARAAAIGWMPVANCPMPLAPADKNKRQDELIVLNVSGRR...	unknown	inhibitor
5-hydroxytryptamine receptor 2C	MVNLRNAVHSFLVHLIGLLVWQCDISVSPVAAIVTDIFNTSDGGRFKFPD...	unknown	antagonist,binder
Alpha-1B adrenergic receptor	MNPDLDTGHNTSAPAHWGELKNANFTGPNQTSSNSTLPQLDITRAISVGL...	unknown	antagonist
5-hydroxytryptamine receptor 7	MMDVNSSGRPDLYGHLRSFLLPEVGRGLPDLSPDGGADPVAGSWAPHLLS...	unknown	antagonist
D(1) dopamine receptor	MRTLNTSAMDGTGLVVERDFSVRILTACFLSLLILSTLLGNTLVCAAVIR...	unknown	binder
Dopamine D2 receptor	MDPLNLSWYDDDLERQNWSRPFNGSDGKADRPHYNYYATLLTLLIAVIVF...	unknown	binder
Potassium voltage-gated channel subfamily H member 2	MPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...	unknown	inhibitor
Sodium-dependent dopamine transporter	MSKSKCSVGLMSSVVAPAKEPNAVGPKEVELILVKEQNGVQLTSSTLTNP...	unknown	inhibitor
5-hydroxytryptamine receptor 1A	MDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...	unknown	activator
5-hydroxytryptamine receptor 6	MVPEPGPTANSTPAWGAGPPSAPGGSGWVAAALCVVIALTAAANSLLIAL...	unknown	binder
Potassium voltage-gated channel subfamily H member 1	MTMAGGRRGLVAPQNTFLENIVRRSNDTNFVLGNAQIVDWPIVYSNDGFC...	unknown
Alpha-1-acid glycoprotein 2	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDRITGKWFYIASAF...	unknown
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate,inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate,inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	substrate
Cytochrome P450 2C18	MDPAVALVLCLSCLFLLSLWRQSSGRGRLPSGPTPLPIIGNILQLDVKDM...	unknown	substrate
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	inhibitor
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	inhibitor
Solute carrier family 22 member 3	MPSFDEALQRVGEFGRFQRRVFLLLCLTGVTFAFLFVGVVFLGTQPDHYW...	unknown	inhibitor
Solute carrier family 22 member 4	MRDYDEVIAFLGEWGPFQRLIFFLLSASIIPNGFNGMSVVFLAGTPEHRC...	unknown	inhibitor
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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