clomipramine (CHEBI:47780)

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CHEBI:47780 - clomipramine

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ChEBI Name	clomipramine

ChEBI ID	CHEBI:47780

Definition	A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(dimethylamino)propyl group. One of the more sedating tricyclic antidepressants, it is used as the hydrochloride salt for the treatment of depression as well as obsessive-compulsive disorder and phobias.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:47359, CHEBI:3754

Supplier Information	ChemicalBook:CB5173107, eMolecules:1883437, ZINC000000020248

Download	Molfile XML SDF

more structures >>

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-1.2645 1.9758 -1.0802 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1386 4.1841 1.7583 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5051 3.2755 2.5809 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5936 1.9467 2.2043 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0248 1.5451 1.0032 C 0 0 0 0 0 0 0 0 0 0 0 0

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-0.9846 -0.6026 0.4087 C 0 0 0 0 0 0 0 0 0 0 0 0

3.2370 -0.3942 -1.4953 C 0 0 0 0 0 0 0 0 0 0 0 0

3.6573 1.4262 -3.0367 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7072 3.7728 0.5665 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.6288 2.4393 0.1954 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4428 -0.3054 0.2400 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8103 0.0711 -1.1956 C 0 0 0 0 0 0 0 0 0 0 0 0

4.8536 -0.6651 -3.2777 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1168 0.2293 0.5609 N 0 0 0 0 0 0 0 0 0 0 0 0

3.5905 -0.0327 -2.8755 N 0 0 0 0 0 0 0 0 0 0 0 0

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-3.9314 -3.0821 0.2849 H 0 0 0 0 0 0 0 0 0 0 0 0

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-0.5313 1.4080 -1.6535 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1985 5.2222 2.0500 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9376 3.6038 3.5146 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0997 1.2326 2.8358 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9293 0.0880 -0.8053 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2989 -1.4764 -1.3767 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4131 1.8313 -2.3640 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9202 1.6658 -4.0664 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6877 1.8627 -2.7981 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2093 4.4849 -0.0715 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4296 -1.3907 0.3400 H 0 0 0 0 0 0 0 0 0 0 0 0

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5 6 1 0 0 0 0

5 11 1 0 0 0 0

5 26 1 0 0 0 0

5 44 1 0 0 0 0

6 16 1 0 0 0 0

6 27 1 0 0 0 0

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7 28 1 0 0 0 0

8 9 4 0 0 0 0

8 29 1 0 0 0 0

9 10 4 0 0 0 0

9 30 1 0 0 0 0

10 16 4 0 0 0 0

10 20 1 0 0 0 0

11 12 4 0 0 0 0

12 20 1 0 0 0 0

13 18 1 0 0 0 0

13 21 1 0 0 0 0

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18 39 1 0 0 0 0

18 40 1 0 0 0 0

19 21 1 0 0 0 0

19 41 1 0 0 0 0

19 42 1 0 0 0 0

19 43 1 0 0 0 0

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reading 45 atoms

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Wikipedia	License
Clomipramine, sold under the brand name Anafranil among others, is a tricyclic antidepressant (TCA). It is used in the treatment of various conditions, most notably obsessive–compulsive disorder but also many other disorders, including hyperacusis, panic disorder, major depressive disorder, trichotillomania, body dysmorphic disorder and chronic pain. It has also been notably used to treat premature ejaculation and the cataplexy associated with narcolepsy. It may also address certain fundamental features surrounding narcolepsy besides cataplexy (especially hypnagogic and hypnopompic hallucinations). The evidence behind this, however, is less robust. As with other antidepressants (notably including selective serotonin reuptake inhibitors), it may paradoxically increase the risk of suicide in those under the age of 25, at least in the first few weeks of treatment. It is typically taken by mouth, although intravenous preparations are sometimes used. Common side effects include dry mouth, constipation, loss of appetite, sleepiness, weight gain, sexual dysfunction, and trouble urinating. Serious side effects include an increased risk of suicidal behavior in those under the age of 25, seizures, mania, and liver problems. If stopped suddenly, a withdrawal syndrome may occur with headaches, sweating, and dizziness. It is unclear if it is safe for use in pregnancy. Its mechanism of action is not entirely clear but is believed to involve increased levels of serotonin and norepinephrine. Clomipramine was discovered in 1964 by the Swiss drug manufacturer Ciba-Geigy. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.
Read full article at Wikipedia

Formula

C19H23ClN2

Net Charge

Average Mass

314.85210

Monoisotopic Mass

314.15498

InChI

InChI=1S/C19H23ClN2/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3

InChIKey

GDLIGKIOYRNHDA-UHFFFAOYSA-N

SMILES

CN(C)CCCN1c2ccccc2CCc2ccc(Cl)cc12

Roles Classification
Biological Role(s):	serotonin uptake inhibitor A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. serotonergic antagonist Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists. serotonergic drug EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of trypanothione-disulfide reductase (EC 1.8.1.12).

Application(s):	serotonin uptake inhibitor A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent. antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. serotonergic antagonist Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists. serotonergic drug

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	clomipramine (CHEBI:47780) has functional parent imipramine (CHEBI:47499) clomipramine (CHEBI:47780) has role anticoronaviral agent (CHEBI:149553) clomipramine (CHEBI:47780) has role antidepressant (CHEBI:35469) clomipramine (CHEBI:47780) has role EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor (CHEBI:77402) clomipramine (CHEBI:47780) has role serotonergic antagonist (CHEBI:48279) clomipramine (CHEBI:47780) has role serotonergic drug (CHEBI:48278) clomipramine (CHEBI:47780) has role serotonin uptake inhibitor (CHEBI:50949) clomipramine (CHEBI:47780) is a dibenzoazepine (CHEBI:47804) clomipramine (CHEBI:47780) is conjugate base of clomipramine(1+) (CHEBI:64209)

Incoming	clomipramine(1+) (CHEBI:64209) is conjugate acid of clomipramine (CHEBI:47780)

IUPAC Name

3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine

Synonyms	Sources
3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine	NIST Chemistry WebBook
3-(3-CHLORO-5H-DIBENZO[B,F]AZEPIN-5-YL)-N,N-DIMETHYLPROPAN-1-AMINE	PDBeChem
3-chloroimipramine	ChemIDplus
chlorimipramine	NIST Chemistry WebBook
Clomipramine	KEGG COMPOUND
G 34586	NIST Chemistry WebBook
monochlorimipramine	NIST Chemistry WebBook

Manual Xrefs	Databases
701	DrugCentral
C06918	KEGG COMPOUND
CH371799	Patent
Clomipramine	Wikipedia
CXX	PDBeChem
D07727	KEGG DRUG
DB01242	DrugBank
LSM-3171	LINCS
US3467650	Patent
View more database links

Registry Numbers	Types	Sources
1323477	Reaxys Registry Number	Reaxys
303-49-1	CAS Registry Number	KEGG COMPOUND
303-49-1	CAS Registry Number	ChemIDplus
303-49-1	CAS Registry Number	NIST Chemistry WebBook

Citations

Jones DC, Ariza A, Chow WH, Oza SL, Fairlamb AH (2010)
Comparative structural, kinetic and inhibitor studies of Trypanosoma brucei trypanothione reductase with T. cruzi.
Molecular and biochemical parasitology 169, 12-19 [PubMed:19747949]
[show Abstract]

Gillman PK (2007)
Tricyclic antidepressant pharmacology and therapeutic drug interactions updated.
British journal of pharmacology 151, 737-748 [PubMed:17471183]
[show Abstract]

Rivarola HW, Bustamante JM, Lo Presti S, Fernández AR, Enders JE, Gea S, Fretes R, Paglini-Oliva P (2005)
Trypanosoma cruzi: chemotherapeutic effects of clomipramine in mice infected with an isolate obtained from an endemic area.
Experimental parasitology 111, 80-86 [PubMed:16085036]
[show Abstract]

Ivey JL, Rosenberg DR (2002)
Clomipramine use in obsessive-compulsive disorder.
Expert review of neurotherapeutics 2, 783-790 [PubMed:19810911]
[show Abstract]

Pirola R, Mundo E, Bellodi L, Bareggi SR (2002)
Simultaneous determination of clomipramine and its desmethyl and hydroxy metabolites in plasma of patients by high-performance liquid chromatography after solid-phase extraction.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 772, 205-210 [PubMed:12007764]
[show Abstract]

Markianos M, Hatzimanolis J, Lykouras L, Christodoulou GN (2002)
Prolactin responses to acute clomipramine and haloperidol of male schizophrenic patients in a drug-free state and after treatment with clozapine or with olanzapine.
Schizophrenia research 56, 11-17 [PubMed:12084414]
[show Abstract]

Last Modified

23 April 2020

CHEBI:47780 - clomipramine

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