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    Oxytocin molecular structure

    Oxytocin Stats & Data

    Pitocin Syntocinon
    NPS DataHub
    MW1007.2
    FormulaC43H66N12O12S2
    CAS50-56-6
    IUPAC1-({(4''R'',7''S'',10''S'',13''S'',16''S'',19''R'')-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-(4-hydroxybenzyl)-13-[(1''S'')-1-methylpropyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-L-prolyl-L-leucylglycinamide
    SMILESCCC(C)C1NC(=O)C(NC(=O)C(N)CSSCC(NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC1=O)C(=O)N1CCCC1C(=O)NC(CC(C)C)C(=O)NCC(N)=O)Cc1ccc(O)cc1
    InChIKeyXNOPRXBHLZRZKH-DSZYJQQASA-N
    Chemical Class Opioid
    Psychoactive Class Depressant

    Pharmacology

    DrugBank
    State Liquid

    Description

    Sir Henry H. Dale first identified oxytocin and its uterine contractile properties in 1906. Like all other neurohypophysial hormones, oxytocin is composed of nine amino acids with a disulfide bridge between the Cys 1 and 6 residues. In the mid-1950s, synthetic oxytocin was successfully synthesized by a biochemist named Vincent du Vigneaud; he was later recognized with a Nobel prize for his work. Oxytocin continues to be an important tool in modern obstetrics to induce labor when indicated and to manage postpartum hemorrhage. It is estimated that labor induction with oxytocin is used in almost 10% of deliveries globally. It should be noted that there are risks associated with oxytocin intervention during childbirth. Oxytocin should be used judiciously only when necessary and by experienced healthcare practitioners. Although most commonly linked to labor and delivery, oxytocin actually has broad peripheral and central effects. It plays an important role in pair bonding, social cognition and functioning, and even fear conditioning. Oxytocin also serves a role in metabolic homeostasis and cardiovascular regulation.

    Mechanism of Action

    Oxytocin plays a vital role in labour and delivery. The hormone is produced in the hypothalamus and is secreted from the paraventricular nucleus to the posterior pituitary where it is stored. It is then released in pulses during childbirth to induce uterine contractions. The concentration of oxytocin receptors on the myometrium increases significantly during pregnancy and reaches a peak in early labor. Activation of oxytocin receptors on the myometrium triggers a downstream cascade that leads to increased intracellular calcium in uterine myofibrils which strengthens and increases the frequency of uterine contractions. In humans, most hormones are regulated by negative feedback; however, oxytocin is one of the few that is regulated by positive feedback. The head of the fetus pushing on the cervix signals the release of oxytocin from the posterior pituitary of the mother. Oxytocin then travels to the uterus where it stimulates uterine contractions. The elicited uterine contractions will then stimulate the release of increasing amounts of oxytocin. This positive feedback loop will continue until parturition.

    Pharmacodynamics

    Oxytocin is a nonapeptide, pleiotropic hormone that exerts important physiological effects. It is most well known to stimulate parturition and lactation, but also has important physiological influences on metabolic and cardiovascular functions, sexual and maternal behaviour, pair bonding, social cognition, and fear conditioning. It is worth noting that oxytocin receptors are not limited to the reproductive system but can be found in many peripheral tissues and in central nervous system structures including the brain stem and amygdala.

    Metabolism

    Oxytocin is rapidly removed from the plasma by the liver and kidney. The enzyme oxytocinase is largely responsible for the metabolism and regulation of oxytocin levels in pregnancy and only a small percentage of the neurohormone is excreted in the urine unchanged. Oxytocinase activity increases throughout pregnancy and peaks in the plasma, placenta and uterus near term. The placenta is a key source of oxytocinase during gestation and produces increasing amounts of the enzyme in response to increasing levels of oxytocin produced by the mother. Oxytocinase activity is also expressed in mammary glands, heart, kidney, and the small intestine. Lower levels of activity can be found in the brain, spleen, liver, skeletal muscle, testes, and colon. The level of oxytocin degradation is negligible in non-pregnant women, men, and cord blood.

    Absorption

    Oxytocin is administered parenterally and is fully bioavailable. It takes approximately 40 minutes for oxytocin to reach steady-state concentrations in the plasma after parenteral administration.

    Toxicity

    Administration of supratherapeutic doses of exogenous oxytocin can lead to myocardial ischemia, tachycardia, and arrhythmias. High doses can also lead to uterine spasms, hypertonicity, or rupture. Oxytocin has antidiuretic properties, thus, high daily doses (as a single dose or administered slowly over 24 hours) may lead to extreme water intoxication resulting in maternal seizures, coma, and even death. The risk of antidiuresis and water intoxication in the mother appears to be greater when fluids are given orally.

    Indication

    Administration of exogenous oxytocin is indicated in the antepartum period to initiate or improve uterine contractions for vaginal delivery in situations where there is fetal or maternal concern. For example, It may be used to induce labor in cases of Rh sensitization, maternal diabetes, preeclampsia at or near term, and when delivery is indicated due to prematurely ruptured membranes. Importantly, oxytocin is not approved or indicated for elective induction of labor. Oxytocin may be used to reinforce labor in select cases of uterine inertia and as adjunctive therapy in the management of incomplete or inevitable abortion. In the postpartum period, oxytocin may be used to induced contractions in the 3rd stage of labor and to control postpartum bleeding or hemorrhage.

    Half-life

    The plasma half-life of oxytocin ranges from 1-6 minutes. The half-life is decreased in late pregnancy and during lactation.

    Elimination

    The enzyme oxytocinase is largely responsible for the metabolism and regulation of oxytocin levels in pregnancy; only a small percentage of the neurohormone is excreted in the urine unchanged.

    Clearance

    In a study that observed 10 women who were given oxytocin to induce labor, the mean metabolic clearance rate was 7.87 mL/min.

    Effect Profile

    Curated + 8 Reports
    Opioid 5.1

    Strong euphoria with moderate itching/nausea, mild sedation

    Euphoria / Warmth×3
    9
    Analgesia×2
    0
    Sedation / Relaxation×1
    5
    Itching / Nausea×1
    6

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 1d Half tolerance 21d Baseline ~35d

    Experience Report Analysis

    Erowid
    8 Reports
    2010–2018 Date Range
    8 With Age Data
    2 Effects Detected

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Effect Analysis

    Erowid

    Effects aggregated from 8 experience reports (8 Erowid)

    8 Reports
    2 Effects Detected
    2 Positive
    0 Adverse
    0 Neutral

    Effect Sentiment Distribution

    Confidence Distribution

    Positive Effects 2

    Euphoria 37.5% 70%
    Empathy 37.5% 70%

    Adverse Effects 0

    Real-World Dose Distribution

    62K Doses

    From 6 individual dose entries

    Form / Preparation

    Most common forms and preparations reported

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