Citizendia

Oxytocin
Systematic (IUPAC) name
3-(19-amino-13-sec-butyl-7-

(carboxymethyl)-4-(2-(1-(carboxymethylamino)-5- guanidino-1-oxopentan-2-ylcarbamoyl) pyrrolidine-1-carbonyl)-16-(4-hydroxybenzyl)- 6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17- pentaazacycloicosan-10-yl)propanoic acid

Identifiers
CAS number50-56-6
ATC codeH01BB02
PubChem439302
DrugBankBTD00016
Chemical data
FormulaC43H66N12O12S2 
Mol. mass1007. 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 They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 19 g/mol
Pharmacokinetic data
Bioavailabilitynil
Protein binding30%
Metabolismhepatic oxytocinases
Half life1-6 min
ExcretionBiliary and renal
Therapeutic considerations
Pregnancy cat.

A(AU)

Legal status

POM(UK) -only(US)

RoutesIntranasal, IV, IM
oxytocin, prepro- (neurophysin I)
Identifiers
SymbolOXT
Alt. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of A drug's efficiency may be affected by the degree to which it binds to the proteins within Blood plasma. Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The kidneys are complicated organs that have numerous biological roles 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 For a topic outline on this subject see List of basic Australia topics. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom, the UK or Britain,is a Sovereign state located A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained The United States of America —commonly referred to as the In Pharmacology and Toxicology, a route Nasal sprays, or nasal mists, are used for the nasal delivery of a drug or drugs generally to alleviate cold or Allergy symptoms such as Nasal congestion Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. Intramuscular injection is the injection of a substance directly into a Muscle. SymbolsOT
Entrez5020
HUGO8528
OMIM167050
RefSeqNM_000915
UniProtP01178
Other data
LocusChr. 20 p13

Oxytocin (IPA: /ˌɔk. The Entrez Global Query Cross-Database Search System is a powerful Federated search engine or Web portal that allows users to search many discrete Health sciences The Human Genome Organisation (HUGO is an organization involved in the Human Genome Project, a project about mapping the human genome The Mendelian Inheritance in Man project is a Database that catalogues all the known Diseases with a genetic component, and—when possible—links them The National Center for Biotechnology Information ( NCBI) is part of the United States National Library of Medicine (NLM a branch of the National Institutes Swiss-Prot is a manually curated Biological database of Protein sequences In the fields of Genetics and Evolutionary computation, a locus (plural loci) is a fixed position on a Chromosome such as the position of a Chromosome 20 is one of the 23 pairs of Chromosomes in Humans People normally have two copies of this chromosome The International Phonetic Alphabet (IPA is a system of phonetic notation based on the Latin alphabet, devised by the International Phonetic sɪ. ˈtoʊ. sɪn/) (Greek, "quick birth") is a mammalian hormone that also acts as a neurotransmitter in the brain. Mammals ( class Mammalia) are a class of Vertebrate Animals characterized by the presence of Sweat glands, including sweat glands Hormones (from Greek ὁρμή - "impetus" are chemicals released by cells that affect cells in other parts of the body See Chemical synapse for an introduction to concepts and terminology used in this article The brain is the center of the Nervous system in animals All Vertebrates and the majority of Invertebrates have a brain

It best known for its roles in female reproduction: it is released in large amounts after distension of the cervix and vagina during labor, and after stimulation of the nipples, facilitating birth and breastfeeding, respectively. The cervix (from Latin "neck" is the lower narrow portion of the Uterus where it joins with the top end of the Vagina. The vagina (from Latin, literally " Sheath " or " Scabbard " is a fibromuscular tubular tract leading from the Uterus In its most general form a nipple is a Structure from which a fluid emanates Childbirth (also called labour, birth, partus or parturition) is the culmination of a Human Pregnancy or Breastfeeding is the feeding of an Infant or young Child with Breast milk directly from human Breasts, not from a Baby bottle or other Recent studies have begun to investigate oxytocin's role in various behaviors, including social recognition and bonding, anxiety, and maternal behaviors.

Contents

Synthesis, storage and release

Oxytocin is made in magnocellular neurosecretory cells in the supraoptic nucleus and paraventricular nucleus of the hypothalamus and is released into the blood from the posterior lobe of the pituitary gland. Magnocellular neurosecretory cells are large cells within the Supraoptic nucleus and Paraventricular nucleus of the Hypothalamus. The supraoptic nucleus ( SON) is a nucleus of Magnocellular neurosecretory cells in the Hypothalamus of the mammalian brain The paraventricular nucleus (PVN is an aggregation of neurons in the Hypothalamus which produces many Hormones. The hypothalamus links the Nervous system to the Endocrine system via the Pituitary gland (hypophysis The posterior pituitary (or neurohypophysis) comprises the Posterior lobe of the Pituitary gland and is part of the Endocrine system. The pituitary gland, or hypophysis, is an Endocrine gland about the size of a Pea. Oxytocin is also made by some neurons in the paraventricular nucleus that project to other parts of the brain and to the spinal cord.

In the pituitary gland, oxytocin is packaged in large, dense-core vesicles, where it is bound to neurophysin I as shown in the inset of the figure; neurophysin is a large peptide fragment of the larger precursor protein molecule from which oxytocin is derived by enzymatic cleavage. The pituitary gland, or hypophysis, is an Endocrine gland about the size of a Pea. Neurophysin I is a carrier Protein with a size of 10 K Da and containing 90 to 97 Aminoacids that transports neurohypophysial Hormones along Peptides (from the Greek πεπτίδια, "small digestibles" are short Polymers formed from the linking in a defined order of α- Amino Proteins are large Organic compounds made of Amino acids arranged in a linear chain and joined together by Peptide bonds between the Carboxyl Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins

Secretion of oxytocin from the neurosecretory nerve endings is regulated by the electrical activity of the oxytocin cells in the hypothalamus. These cells generate action potentials that propagate down axons to the nerve endings in the pituitary; the endings contain large numbers of oxytocin-containing vesicles, which are released by exocytosis when the nerve terminals are depolarised. In Neurophysiology, the action potential is a self-regenerating Wave of Electrochemical activity that allows Nerve cells to carry a signal An axon or nerve fiber is a long slender projectionof a nerve cell or Neuron, that conducts electrical impulses away from the neuron's Cell Exocytosis (ek-soh-sy-TOH-sis Greek: Έξω - external and κύτος - cell is the durable process by which a cell directs secretory vesicles out of the Cell

Oxytocin is also synthesized by corpora lutea of several species, including ruminants and primates. The corpus luteum ( Latin for "yellow body" (plural corpora lutea) is a temporary Endocrine structure in mammals involved in production of Along with estrogen, it is involved in inducing the endometrial synthesis of Prostaglandin-F2alpha to cause regression of the corpus luteum.

Structure and relation to vasopressin

Oxytocin is a peptide of nine amino acids (a nonapeptide). Peptides (from the Greek πεπτίδια, "small digestibles" are short Polymers formed from the linking in a defined order of α- Amino In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this The sequence is cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine (CYIQNCPLG). Not to be confused with Cystine, its oxidized dimer Cysteine (abbreviated as Cys or C) is an α- Amino acid with Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 20 Amino acids that are used by cells to synthesize Isoleucine (abbreviated as Ile or I) is an α- Amino acid with the Chemical formula HO2CCH(NH2CH(CH3CH2CH3 Glutamine (abbreviated as Gln or Q; the abbreviation Glx or Z represents either glutamate or Glutamic acid) is one of the 20 Asparagine (abbreviated as Asn or N; Asx or B represent either asparagine or Aspartic acid) is one of the 20 most common natural Not to be confused with Cystine, its oxidized dimer Cysteine (abbreviated as Cys or C) is an α- Amino acid with Proline (abbreviated as Pro or P) is an α- Amino acid, one of the twenty DNA -encoded amino acids Leucine (abbreviated as Leu or L) is an α- Amino acid with the Chemical formula HO2CCH(NH2CH2CH(CH32 Glycine (abbreviated as Gly or G) is the Organic compound with the formula NH2CH2COOH The cysteine residues form a sulfur bridge. In Chemistry, a disulfide bond is a single Covalent bond derived from the coupling of Thiol groups Oxytocin has a molecular mass of 1007 daltons. The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one The unified atomic mass unit ( u) or Dalton ( Da) or sometimes universal mass unit, is an unit of Mass used to express One international unit (IU) of oxytocin is the equivalent of about 2 micrograms of pure peptide. In Pharmacology, the International Unit is a unit of measurement for the amount of a substance based on measured Biological activity or effect In the Metric system, a microgram is 1/1000000 of a Gram (1 × 10-6 or 1/1000 of a milligram is one of the smallest units of weight/mass commonly used

Oxytocin structure. Inset shows oxytocin bound to neurophysin
Oxytocin structure. Inset shows oxytocin bound to neurophysin

The structure of oxytocin is very similar to that of vasopressin (cysteine - tyrosine - phenylalanine - glutamine - asparagine - cysteine - proline - arginine - glycine), also a nonapeptide with a sulfur bridge, whose sequence differs from oxytocin by 2 amino acids. Arginine vasopressin ( AVP) also known as vasopressin, argipressin or antidiuretic hormone ( ADH) is a Hormone found in Not to be confused with Cystine, its oxidized dimer Cysteine (abbreviated as Cys or C) is an α- Amino acid with Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 20 Amino acids that are used by cells to synthesize Phe redirects here For the BitTorrent feature see PHE. For the constellation see Phoenix (constellation. Glutamine (abbreviated as Gln or Q; the abbreviation Glx or Z represents either glutamate or Glutamic acid) is one of the 20 Asparagine (abbreviated as Asn or N; Asx or B represent either asparagine or Aspartic acid) is one of the 20 most common natural Not to be confused with Cystine, its oxidized dimer Cysteine (abbreviated as Cys or C) is an α- Amino acid with Proline (abbreviated as Pro or P) is an α- Amino acid, one of the twenty DNA -encoded amino acids Arginine (abbreviated as Arg or R) is an α- Amino acid. The L-form is one of the 20 most common natural amino acids Glycine (abbreviated as Gly or G) is the Organic compound with the formula NH2CH2COOH Peptides (from the Greek πεπτίδια, "small digestibles" are short Polymers formed from the linking in a defined order of α- Amino A table showing the sequences of members of the vasopressin/oxytocin superfamily and the species expressing them is present in the vasopressin article. Arginine vasopressin ( AVP) also known as vasopressin, argipressin or antidiuretic hormone ( ADH) is a Hormone found in Oxytocin and vasopressin were isolated and synthesized by Vincent du Vigneaud in 1953, work for which he received the Nobel Prize in Chemistry in 1955. Vincent du Vigneaud ( May 18, 1901 &ndash December 11, 1978) was an American Biochemist. The Nobel Prize in Chemistry (Nobelpriset i kemi is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of Chemistry.

Oxytocin and vasopressin are the only known hormones released by the human posterior pituitary gland to act at a distance. However, oxytocin neurons make other peptides, including corticotropin-releasing hormone (CRH) and dynorphin, for example, that act locally. Corticotropin-releasing hormone ( CRH) originally named corticotropin-releasing factor ( CRF) and also called corticoliberin, is a Polypeptide Dynorphins are a class of Opioid peptides that arise from the precursor Protein prodynorphin The magnocellular neurons that make oxytocin are adjacent to magnocellular neurons that make vasopressin, and are similar in many respects.

Actions

Oxytocin has peripheral (hormonal) actions, and also has actions in the brain. The actions of oxytocin are mediated by specific, high affinity oxytocin receptors. The oxytocin receptor is a G-protein-coupled receptor which requires Mg2+ and cholesterol. G protein-coupled receptors ( GPCRs) also known as seven transmembrane domain receptors, 7TM receptors, heptahelical receptors, and Magnesium (mægˈniːziəm is a Chemical element with the symbol Mg, Atomic number 12 Atomic weight 24 Cholesterol is a Lipid found in the Cell membranes and transported in the Blood plasma of all Animals It is an essential component of mammalian It belongs to the rhodopsin-type (class I) group of G-protein-coupled receptors. Rhodopsin, also known as visual purple, is a Pigment of the Retina that is responsible for both the formation of the Photoreceptor cells and the

Peripheral (hormonal) actions

The peripheral actions of oxytocin mainly reflect secretion from the pituitary gland. (See oxytocin receptor for more detail on its action. Oxytocin receptors function as inducers of uterine contractions and milk ejection )

Actions of oxytocin within the brain

Oxytocin secreted from the pituitary gland cannot re-enter the brain because of the blood-brain barrier. The blood-brain barrier (BBB is a metabolic or cellular structure in the Central nervous system (CNS that restricts the passage of various chemical substances and microscopic Instead, the behavioral effects of oxytocin are thought to reflect release from centrally projecting oxytocin neurons, different from those that project to the pituitary gland. Oxytocin receptors are expressed by neurons in many parts of the brain and spinal cord, including the amygdala, ventromedial hypothalamus, septum and brainstem. The la amygdalae ( Latin, also la corpus amygdaloideum, singular la amygdala, from Greek el αμυγδαλή grc-Latn amygdalē, 'almond' The ventromedial nucleus (sometimes referred to as the ventromedial hypothalamus) is a nucleus of the Hypothalamus. A septum ( Latin: something that encloses; plural Septa) is a partition separating two cavities or spaces The brain stem (or brainstem) is the lower part of the Brain, adjoining and structurally continuous with the Spinal cord.

Drug forms

Synthetic oxytocin is sold as medication under the trade names Pitocin and Syntocinon and also as generic oxytocin. Medication, also referred to as medicine, can be loosely defined as any substance intended for use in the diagnosis cure mitigation treatment or prevention of disease A generic drug (generic drugs short generics is a drug which is produced and distributed without Patent protection Oxytocin is destroyed in the gastrointestinal tract, and therefore must be administered by injection or as nasal spray. Nasal sprays, or nasal mists, are used for the nasal delivery of a drug or drugs generally to alleviate cold or Allergy symptoms such as Nasal congestion Oxytocin has a half-life of typically about three minutes in the blood. Half-Life (computer-game page here It's already listed in the disambiguation page Oxytocin given intravenously does not enter the brain in significant quantities - it is excluded from the brain by the blood-brain barrier. Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. The blood-brain barrier (BBB is a metabolic or cellular structure in the Central nervous system (CNS that restricts the passage of various chemical substances and microscopic There is no evidence for significant CNS entry of oxytocin by nasal spray. Oxytocin nasal sprays have been used to stimulate breastfeeding but the efficacy of this approach is doubtful[22].

Injected oxytocin analogues are used to induce labor and support labor in case of non-progression of parturition. It has largely replaced ergotamine as the principal agent to increase uterine tone in acute postpartum haemorrhage. Ergotamine is an Ergopeptine and part of the Ergot family of Alkaloids it is structurally and biochemically closely related to Ergoline. Obstetrical hemorrhage refers to heavy bleeding during Pregnancy, labor, or the Puerperium. Oxytocin is also used in veterinary medicine to facilitate birth and to increase milk production. Veterinary medicine the application of medical, diagnostic, and therapeutic principles to companion, domestic, exotic, wildlife The tocolytic agent atosiban (Tractocile) acts as an antagonist of oxytocin receptors; this drug is registered in many countries to suppress premature labour between 24 and 33 weeks of gestation. Tocolytics are medications used to suppress Premature labor (from the Greek tokos, Childbirth, and lytic, capable of dissolving Atosiban ( Tractocile or Antocin, RWJ 22164 is an inhibitor of the hormones Oxytocin and Vasopressin. A receptor antagonist is a type of receptor ligand or Drug that does not provoke a biological response itself upon binding to a receptor, but blocks It has fewer side-effects than drugs previously used for this purpose (ritodrine, salbutamol and terbutaline). Ritodrine hydrochloride (trade name Yutopar) is a Tocolytic Drug, used to stop Premature labor. Salbutamol ( INN) or albuterol ( USAN) is a short-acting β2-adrenergic receptor agonist used for the relief of Bronchospasm Terbutaline ( Trade names Brethine, Bricanyl, or Brethaire) is a β2-adrenergic receptor agonist, used as a fast-acting

Some have suggested that the trust-inducing property of oxytocin might help those who suffer from social anxieties, while others have noted the potential for abuse with confidence tricks. Social Phobia Social anxiety is a term used to describe an experience of Anxiety ( Emotional discomfort Fear, apprehension or Worry A confidence trick or confidence game (also known as a bunko, con, flim flam, gaffle, grift, scam, scheme [23]

Potential adverse reactions

Oxytocin is relatively safe when used at recommended doses. Potential side effects include:

Evolution

Virtually all vertebrates have an oxytocin-like nonapeptide hormone that supports reproductive functions and a vasopressin-like nonapeptide hormone involved in water regulation. Vertebrates are members of the Subphylum Vertebrata, Chordates with backbones or spinal columns The grouping sometimes includes Peptides (from the Greek πεπτίδια, "small digestibles" are short Polymers formed from the linking in a defined order of α- Amino The two genes are always located close to each other (less than 15,000 bases apart) on the same chromosome and are transcribed in opposite directions. A chromosome is an organized structure of DNA and Protein that is found in cells. It is thought that the two genes resulted from a gene duplication event; the ancestral gene is estimated to be about 500 million years old and is found in cyclostomes (modern members of the Agnatha). Gene duplication (or chromosomal duplication) is any duplication of a region of DNA that contains a Gene; it may occur as an error in Homologous Agnatha ( Greek, "no jaws" is a Paraphyletic superclass of jawless fish in the phylum Chordata, subphylum Vertebrata [9]

References

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External links

The Boston Globe (and Boston Sunday Globe) is the most widely circulated daily Newspaper in Boston and in New England,

Dictionary

oxytocin

-noun

  1. (biochemistry) A hormone that stimulates contractions during labour/labor, and then the production of milk.
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