Amitriptyline
Systematic (IUPAC) name
3-(10,11-dihydro-5H-dibenzo[[a,d]] cycloheptene-5-ylidene)-N, N-dimethyl-1-propanamine
Identifiers
CAS number	549-18-8
ATC code	N06AA09
PubChem	2160
DrugBank	APRD00227
Chemical data
Formula	C20H23N
Mol. mass	277.403 g/mol
Pharmacokinetic data
Bioavailability	40%
Metabolism	Hepatic
Half life	12-24 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	D(US) Image File history File links Download high-resolution version (1100x1195, 57 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Tricyclic antidepressant Amitriptyline ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
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Routes	Oral

Amitriptyline (or Amitryptyline) hydrochloride (sold as Elavil, Tryptanol, Endep, Elatrol, Tryptizol, Trepiline, Laroxyl) is a tricyclic antidepressant drug. It is a white, odorless (but tastes like licorice), crystalline compound which is freely soluble in water; it is usually dispensed in tablet form. In terms of its mechanism of action, amitriptyline inhibits serotonin and noradrenaline reuptake almost equally. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Chemical structure of the tricyclic antidepressant amitriptyline. ... It has been suggested that Blockbuster drug be merged into this article or section. ... Species Glycyrrhiza acanthocarpa Glycyrrhiza aspera Glycyrrhiza astragalina Glycyrrhiza bucharica Glycyrrhiza echinata Glycyrrhiza eurycarpa Glycyrrhiza foetida Glycyrrhiza glabra Glycyrrhiza iconica Glycyrrhiza korshinskyi Glycyrrhiza lepidota Glycyrrhiza pallidiflora Glycyrrhiza triphylla Glycyrrhiza uralensis Glycyrrhiza yunnanensis Ref: ILDIS Version 6. ... Crystal (disambiguation) Insulin crystals A crystal is a solid in which the constituent atoms, molecules, or ions are packed in a regularly ordered, repeating pattern extending in all three spatial dimensions. ... Wikipedia does not yet have an article with this exact name. ... Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ... Norepinephrine, known as noradrenaline outside the USA, is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ...

Uses

Approved

Amitriptyline is approved for the treatment of endogenous depression and involutional melancholia (depression of late life, which is no longer seen as a disease in its own right.) Adult typical dosages are 75 to 200 mg daily, with half this initially for elderly or adolescents. Clinical depression (also called major depressive disorder, or unipolar depression when compared to bipolar disorder) is a state of intense sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ... Involutional melancholia or involutional depression is a traditional name for a psychiatric disorder affecting mainly elderly or late middle aged people, usually accompanied with paranoia. ...

It may also be used to treat nocturnal enuresis (bed wetting). Children between the ages of 7 to 10 years having a dose of 10 to 20 mg, older children 25 to 50 mg at night. It should be gradually withdrawn at the end of the course, which overall should be of no more than 3 months.^[1] Bedwetting (or enuresis) is involuntary urination while asleep in bed. ...

In some European countries it is also approved as prophylaxis for patients with frequent migraines (usually 25 to 75 mg).

Unapproved/Off-Label/Investigational

Amitriptyline may be prescribed for other conditions such as insomnia, migraine, rebound headache, chronic pain, postherpetic neuralgia (persistent pain following a shingles attack), fibromyalgia, vulvodynia, interstitial cystitis, irritable bowel syndrome, diabetic peripheral neuropathy, neurological pain, and painful paresthesias related to multiple sclerosis and as a preventative (prophylaxis) for patients with frequent migraines. It is also used in small (10 mg) doses to act as a painkiller and ease the effects of Carpal Tunnel Syndrome. Typically lower dosages are required for pain modification of 10 to 50 mg daily.^[1] This article is about the sleeping disorder. ... Rebound headaches, also known as medication overuse headaches, occur when pain medications (analgesics) are taken too frequently to relieve headache. ... Chronic pain was originally defined as pain that has lasted 6 months or longer. ... Postherpetic neuralgia (PHN) is a painful condition caused by the varicella zoster virus in a dermatomal distribution (the area governed by a particular sensory nerve) after an attack of herpes zoster (HZ) (commonly known as shingles), usually manifesting after the vesicles have crusted over and begun to heal. ... Herpes zoster, colloquially known as shingles, is the reactivation of varicella zoster virus, leading to a crop of painful blisters over the area of a dermatome. ... Fibromyalgia (FM or FMS) is a chronic syndrome (constellation of signs and symptoms) characterized by diffuse or specific muscle, joint, or bone pain, fatigue, and a wide range of other symptoms. ... Vulvodynia refers to a disorder of vulvar pain, burning, and discomfort that interferes with the quality of life. ... Interstitial cystitis (commonly abbreviated to IC) is a urinary bladder disease of unknown cause characterised by urinary frequency (as often as every 10 minutes), urgency, pressure and/or pain in the bladder and/or pelvis. ... Diabetic neuropathies are neuropathic disorders that are associated with diabetes mellitus. ... Neurology is a branch of medicine dealing with disorders of the central and peripheral nervous systems. ... Paresthesia or paraesthesia (in British English) is a sensation of tingling, pricking, or numbness of a persons skin with no apparent long-term physical effect, more generally known as the feeling of pins and needles or of a limb being asleep. // Transient paresthesia is the temporary sensation of tingling... For other uses of painkiller, see painkiller (disambiguation) An analgesic (colloquially known as painkiller) is any member of the diverse group of drugs used to relieve pain. ... This article is about the medical condition. ...

Amitriptyline in very small doses (5 mg a day) is also sometimes prescribed to help ease the symptoms of chronic fatigue syndrome. It is thought to help combat symptoms of insomnia primarily, in addition to other selected symptoms of the affliction. Chronic fatigue syndrome (CFS), also known as Myalgic Encephalomyelitis (ME), Post-Viral Fatigue Syndrome (PVFS), and various other names, is a syndrome (or group of syndromes) of unknown and possibly multiple etiologies, affecting the central nervous system (CNS) and possibly the immune system as well as other organs. ...

A randomized controlled trial published in June 2005 found that amitriptyline was effective in functional dyspepsia refractory to famotidine and mosapride combination therapy.^[2] A randomized controlled trial (RCT) is a form of clinical trial, or scientific procedure used in the testing of the efficacy of medicines or medical procedures. ... Dyspepsia is a constant pain in the stomach. ... Famotidine is a histamine H2-receptor antagonist that inhibits stomach acid production, and is commonly used in the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD). ... In contemporary usage, the expression combination therapy most often refers to the simultaneous administration of two or more medications to treat a single disease, but the expression is also used when other types of therapy are used at the same time. ...

Side effects

Common side effects of using amitriptyline are weight loss or gain, drowsiness, nervousness, and dizziness insomnia. Some rare side effects include tinnitus, hypotension, mania, psychosis, anticholinergic effects, heart block, arrhythmias, extrapyramidal symptoms, depression, and hepatic toxicity. An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Tinnitus (IPA pronunciation: or ,[1] from the Latin word for ringing[2]) is the perception of sound in the human ear in the absence of corresponding external sound(s). ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... Mania is a severe medical condition characterized by extremely elevated mood, energy, and thought patterns. ... Psychosis is a generic psychiatric term for a mental state often described as involving a loss of contact with reality. Stedmans Medical Dictionary defines psychosis as a severe mental disorder, with or without organic damage, characterized by derangement of personality and loss of contact with reality and causing deterioration... An anticholinergic agent is a member of a class of pharmaceutical compounds which serve to reduce the effects mediated by acetylcholine in the central nervous system and peripheral nervous system. ... A heart block is a disease in the electrical system of the heart. ... A cardiac arrhythmia, also called cardiac dysrhythmia, is a disturbance in the regular rhythm of the heartbeat. ... In human anatomy, the extrapyramidal system is a neural network located in the brain that is part of the motor system involved in the coordination of movement. ... Look up depression in Wiktionary, the free dictionary. ... The liver is an organ in vertebrates including humans. ... // Toxic and Intoxicated redirect here – toxic has other uses, which can be found at Toxicity (disambiguation); for the state of being intoxicated by alcohol see Drunkenness. ...

Overdose: The symptoms and the treatment of an overdose are largely the same as for the other tricyclic antidepressants.

Further information: Tricyclic antidepressant#Overdose

Chemical structure of the tricyclic antidepressant amitriptyline. ...

Footnotes

Otherwise known as the doctors prescribing Bible the British National Formulary (BNF) contains a wide spectrum of information on prescribing and pharmacology, among others indications, side effects and costs of the prescription of all medication drugs available on the National Health Service. ...

References

• PubChem Substance Summary: Amitriptyline National Center for Biotechnology Information.
• TREPILINE®-10 TABLETS; TREPILINE®-25 TABLETS South African Electronic Package Inserts. 12 May 1978. Revised February 2004.
• SAROTEN® RETARD 25 mg Capsules; SAROTEN® RETARD 50 mg Capsules South African Electronic Package Inserts. December 1987. Updated May 2000.
• AMITRIP® Amitriptyline hydrochloride 10 mg, 25 mg and 50 mg Capsules Medsafe NZ Physician Data Sheet. November 2004.