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Oxytocin
Identification
- Name
- Oxytocin
- Accession Number
- DB00107
- Description
Synthetic 9 residue cyclic peptide. The hormone is prepared synthetically to avoid possible contamination with vasopressin (ADH) and other small polypeptides with biologic activity.
- Type
- Biotech
- Groups
- Approved, Vet approved
- Biologic Classification
- Protein Based Therapies
Hormones - Protein Structure
- Protein Chemical Formula
- C43H66N12O12S2
- Protein Average Weight
- 1007.187 Da
- Sequences
>DB00107 sequence CYIQNCPLG
Download FASTA Format- Synonyms
- Oxitocina
- Oxytocin
Pharmacology
- Indication
Used for labor induction, augmentation of labor, postpartum abbreviation of third stage of labor, postpartum control of uterine bleeding, termination of pregnancy and for the evaluation of fetal respiratory capability. Oxytocin cannot be used for elective induction of labor, there must be a clear medical requirement.
- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Indirectly stimulates contraction of uterine smooth muscle by increasing the sodium permeability of uterine myofibrils. Increases contraction amplitude and frequency, which tends to decrease cervical activity, produce dilation and effacement of the cervix, and transiently impede uterine blood flow; contractions produced by oxytocin at term are similar to those occurring during spontaneous labor. High estrogen concentrations lower the threshold for uterine response to oxytocin. Uterine response increases with the duration of pregnancy and is greater in labor than when not in labor; only very large doses elicit contractions in early pregnancy. Contracts myoepithelial cells surrounding the alveoli of the breasts, forcing milk from the alveoli into the larger ducts and facilitating milk ejection. Minimal antidiuretic activity relative to vasopressin; water intoxication possible at high doses and/or excessive electrolyte-free fluid.
- Mechanism of action
Uterine motility depends on the formation of the contractile protein actomyosin under the influence of the Ca2+-dependent phosphorylating enzyme myosin light-chain kinase. Oxytocin promotes contractions by increasing the intracellular Ca2+, which in turn activates myosin's light chain kinase.. Oxytocin has specific receptors in the muscle lining of the uterus and the receptor concentration increases greatly during pregnancy, reaching a maximum in early labor at term.
Target Actions Organism AOxytocin receptor agonistHumans UOxytocin-neurophysin 1 binderHumans - Absorption
Uterine response after IV administration is immediate and subsides after 1 hour. Uterine contractions occur 3-5mins after IM administration and decreases within 2-3 hours. When 100-200milliunits is administered IV, contractions of the myoepithelial tissue surrounding the alveoli of the breasts occur within minutes and last for about 20 mins.
- Volume of distribution
Distributes throughout the extracellular fluid and crosses the placenta. It is probable that it also distributes into milk in small amounts.
- Protein binding
30%
- Metabolism
Oxytocin is rapidly metabolized in the liver and also in the plasma by oxytocinases. It is also metabolized to a smaller degree by the mammary glands.
- Route of elimination
Biliary and renal (excreted unchanged in the urine)
- Half-life
1-6 min, this is decreased in late pregnancy and during lactation.
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Oxytocin can produce a severe water intoxication due to its antidiuretic effect. Prolonged IV infusions of more 40milliunits/min are usually the cause. Severe water intoxication with convulsions, coma, and death can occur. Some neonatal seizures have also been reported. Consider potential for water intoxication, particularly when administered by IV infusion and patient is receiving oral fluids. Uterine effects: High doses or hypersensitivity to oxytocin may cause uterine hypertonicity, spasm, tetanic contraction, or rupture of the uterus. There have also been reported allergic and anaphylactic reactions to oxytocin but they were rarely fatal.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAcebutolol The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Acebutolol. Acrivastine The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Ajmaline. Alfuzosin The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Alfuzosin. Alimemazine The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Alimemazine. Amantadine The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Amantadine. Amifampridine The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Amifampridine. Amiodarone The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Amiodarone. Amisulpride The risk or severity of QTc prolongation can be increased when Oxytocin is combined with Amisulpride. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataOxytocin Injection, solution 30 [USP'U]/500mL Intravenous Cantrell Drug Company 2011-10-20 Not applicable US 
Oxytocin Injection, solution 30 [USP'U]/500mL Intravenous Cantrell Drug Company 2011-10-20 Not applicable US Oxytocin Injection, solution 20 [USP'U]/1000mL Intravenous Cantrell Drug Company 2011-10-20 2017-12-06 US Oxytocin Injection, solution 10 [USP'U]/1mL Intramuscular; Intravenous Fresenius Kabi USA, LLC 2000-08-10 Not applicable US Oxytocin Injection, solution 10 [USP'U]/500mL Intravenous Cantrell Drug Company 2011-10-20 2012-11-09 US Oxytocin Injection, solution 30 [USP'U]/1000mL Intravenous Cantrell Drug Company 2016-03-18 Not applicable US Oxytocin Injection 10 [USP'U]/1mL Intramuscular; Intravenous Hikma Pharmaceuticals USA Inc. 1980-04-29 Not applicable US Oxytocin Injection 10 [USP'U]/1mL Intramuscular; Intravenous Baxter Laboratories 1990-09-30 2013-02-27 US Oxytocin Injection, solution 2 [USP'U]/100mL Intravenous Cantrell Drug Company 2011-10-20 Not applicable US Oxytocin Injection, solution 10 [USP'U]/1mL Intramuscular; Intravenous Cardinal Health 2000-08-10 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataOxytocin Injection 10 [USP'U]/1mL Intravenous Teva Parenteral Medicines, Inc. 2008-01-24 2011-04-30 US Oxytocin Injection 10 [USP'U]/1mL Intramuscular; Intravenous West-Ward Pharmaceuticals Corp 2013-02-13 Not applicable US Oxytocin Injection 10 [USP'U]/1mL Intramuscular; Intravenous West-Ward Pharmaceuticals Corp 2013-02-13 Not applicable US Oxytocin Injection 10 [iU]/1mL Intravenous Par Pharmaceutical 2012-06-01 2015-07-13 US Oxytocin Injection 10 [USP'U]/1mL Intramuscular; Intravenous Hikma Farmaceutica 2009-08-01 2014-10-01 US Oxytocin Injection, solution 10 [USP'U]/1mL Intramuscular; Intravenous Sagent Pharmaceuticals 2018-04-01 2018-07-19 US Oxytocin Injection 100 [USP'U]/10mL Intravenous Teva Parenteral Medicines, Inc. 2008-01-24 2011-02-28 US Oxytocin Injection 10 [iU]/1mL Intravenous Par Pharmaceutical 2012-06-01 2015-04-30 US Oxytocin Injection 100 [USP'U]/10mL Intramuscular; Intravascular Hikma Farmaceutica 2009-08-01 2014-10-01 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bakumokon 5% Minoxidil Oxytocin (0.01 mg/100mg) + Dutasteride (0.1 mg/100mg) + Minoxidil (5 mg/100mg) Liquid Topical DS LABORATORIES, INC. 2015-02-09 2017-10-19 US Bakumokon 7% Minoxidil Sulfate Oxytocin (0.01 mg/100mg) + Dutasteride (0.1 mg/100mg) + Minoxidil sulfate (7 mg/100mg) Liquid Topical DS LABORATORIES, INC. 2015-02-09 2017-10-11 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Oxytocin Oxytocin (10 [USP'U]/500mL) Injection, solution Intravenous Cantrell Drug Company 2011-10-20 2012-11-12 US Oxytocin Oxytocin (20 [USP'U]/1000mL) Injection, solution Intravenous Cantrell Drug Company 2011-10-20 2015-01-14 US Oxytocin Oxytocin (30 [USP'U]/500mL) Injection, solution Intravenous Cantrell Drug Company 2011-07-01 Not applicable US Oxytocin Oxytocin (30 [USP'U]/500mL) Injection, solution Intravenous Cantrell Drug Company 2011-10-20 Not applicable US Oxytocin Oxytocin (10 [USP'U]/1000mL) Injection, solution Intravenous Cantrell Drug Company 2012-07-30 Not applicable US Oxytocin Oxytocin (20 [USP'U]/500mL) Injection, solution Intravenous Cantrell Drug Company 2016-03-18 Not applicable US Oxytocin Oxytocin (30 [USP'U]/500mL) Injection, solution Intravenous Cantrell Drug Company 2011-10-20 Not applicable US Oxytocin Oxytocin (2 [USP'U]/100mL) Injection, solution Intravenous Cantrell Drug Company 2011-10-20 Not applicable US Oxytocin Oxytocin (10 [USP'U]/500mL) Injection, solution Intravenous Cantrell Drug Company 2011-10-20 2012-11-09 US Oxytocin Oxytocin (30 [USP'U]/1000mL) Injection, solution Intravenous Cantrell Drug Company 2016-03-18 Not applicable US
Categories
- ATC Codes
- G02AC01 — Methylergometrine and oxytocin
- G02AC — Ergot alkaloids and oxytocin incl. analogues, in combination
- G02A — UTEROTONICS
- G02 — OTHER GYNECOLOGICALS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Genito Urinary System and Sex Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Increased Uterine Smooth Muscle Contraction or Tone
- Oxytocin and Analogues
- Oxytocin, analogs & derivatives
- Oxytocin, antagonists & inhibitors
- Peptide Hormones
- Peptides
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormones
- Pituitary Hormones, Posterior
- Posterior Pituitary Lobe Hormones
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Reproductive Control Agents
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Uterotonic agents
- Chemical TaxonomyProvided by Classyfire
- Description
- Not Available
- Kingdom
- Organic Compounds
- Super Class
- Organic Acids
- Class
- Carboxylic Acids and Derivatives
- Sub Class
- Amino Acids, Peptides, and Analogues
- Direct Parent
- Peptides
- Alternative Parents
- Not Available
- Substituents
- Not Available
- Molecular Framework
- Not Available
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 1JQS135EYN
- CAS number
- 50-56-6
References
- Synthesis Reference
Kerstin Uvnas-Moberg, Thomas Lundeberg, "Use of substances having oxytocin activity for preparation of medicaments for wound healing." U.S. Patent US6262021, issued August, 1988.
US6262021- General References
- Kosfeld M, Heinrichs M, Zak PJ, Fischbacher U, Fehr E: Oxytocin increases trust in humans. Nature. 2005 Jun 2;435(7042):673-6. [PubMed:15931222]
- Takayanagi Y, Yoshida M, Bielsky IF, Ross HE, Kawamata M, Onaka T, Yanagisawa T, Kimura T, Matzuk MM, Young LJ, Nishimori K: Pervasive social deficits, but normal parturition, in oxytocin receptor-deficient mice. Proc Natl Acad Sci U S A. 2005 Nov 1;102(44):16096-101. Epub 2005 Oct 25. [PubMed:16249339]
- Carmichael MS, Humbert R, Dixen J, Palmisano G, Greenleaf W, Davidson JM: Plasma oxytocin increases in the human sexual response. J Clin Endocrinol Metab. 1987 Jan;64(1):27-31. [PubMed:3782434]
- Paquin J, Danalache BA, Jankowski M, McCann SM, Gutkowska J: Oxytocin induces differentiation of P19 embryonic stem cells to cardiomyocytes. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9550-5. Epub 2002 Jul 1. [PubMed:12093924]
- Jankowski M, Danalache B, Wang D, Bhat P, Hajjar F, Marcinkiewicz M, Paquin J, McCann SM, Gutkowska J: Oxytocin in cardiac ontogeny. Proc Natl Acad Sci U S A. 2004 Aug 31;101(35):13074-9. Epub 2004 Aug 17. [PubMed:15316117]
- External Links
- KEGG Drug
- D00089
- KEGG Compound
- C00746
- PubChem Substance
- 46506775
- 7824
- ChEMBL
- CHEMBL395429
- Therapeutic Targets Database
- DAP001156
- PharmGKB
- PA450760
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Oxytocin
- AHFS Codes
- 76:00.00 — Oxytocics
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Diagnostic Hyperbilirubinemia in neonates 1 4 Active Not Recruiting Treatment Healthy Volunteers 1 4 Completed Not Available Anxiety Disorders / Post Traumatic Stress Disorder (PTSD) / Reconsolidation 1 4 Completed Basic Science Health 1 4 Completed Basic Science Nicotine Dependence / Tobacco Smoking Behavior 1 4 Completed Basic Science Pain, Chronic 2 4 Completed Basic Science Social Behavior 1 4 Completed Other BMI >30 kg/m2 / Induction of Labour / Oxytocin 1 4 Completed Prevention Adverse Reaction to Oxytocin 1 4 Completed Prevention Blood Loss / Postpartum Haemorrhage (PPH) 1
Pharmacoeconomics
- Manufacturers
- App pharmaceuticals llc
- Baxter healthcare corp anesthesia critical care
- Teva parenteral medicines inc
- Abbott laboratories pharmaceutical products div
- Jhp pharmaceuticals llc
- Novartis pharmaceuticals corp
- Packagers
- APP Pharmaceuticals
- BAM Biotech
- Baxter International Inc.
- Bimeda Inc.
- Cardinal Health
- Central Admixture Pharmacy Services
- Gallipot
- Gland Pharma Ltd.
- Hikma Pharmaceuticals
- JHP Pharmaceuticals LLC
- Monarch Pharmacy
- MWI Veterinary Supply Co.
- Osburn Drug Co.
- PD-Rx Pharmaceuticals Inc.
- Pharmakon
- Pharmedium
- Teva Pharmaceutical Industries Ltd.
- Vedco Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Liquid Topical Injection, solution Intramuscular; Intravenous 5 iu/ml Solution Intravenous 10 IU Solution Intramuscular; Intravenous 10 IU Injection Injection Intramuscular; Intravascular 100 [USP'U]/10mL Injection Intravenous 10 [USP'U]/1mL Injection Intravenous 10 [iU]/1mL Injection Intravenous 100 [USP'U]/10mL Injection, solution Intramuscular; Intravenous 10 [USP'U]/1mL Injection, solution Intravenous 10 [USP'U]/1000mL Injection, solution Intravenous 10 [USP'U]/500mL Injection, solution Intravenous 2 [USP'U]/100mL Injection, solution Intravenous 20 [USP'U]/500mL Injection, solution Intravenous 20 [USP'U]/1000mL Injection, solution Intravenous 30 [USP'U]/1000mL Injection, solution Intravenous 30 [USP'U]/500mL Liquid Intramuscular; Intravenous Solution Intramuscular; Intravenous Injection Intramuscular; Intravenous 10 [USP'U]/1mL Injection Intravenous 10 Injection, solution Intramuscular; Intravenous 5 i.u./ml Injection, solution Intramuscular; Intravenous 10 [iU]/1mL Injection, solution Parenteral 5 U.I./ML Solution Intramuscular; Intravenous 5 IU - Prices
Unit description Cost Unit Oxytocin powder 1762.25USD g Oxytocin 10 unit/ml vial 9.84USD vial Pitocin 10 unit/ml vial 1.6USD ml Oxytocin-lr 40 unit/500 ml 0.09USD ml Oxytocin-d5w-lr 40 unit/500 ml 0.07USD ml Oxytocin-d5lr 30 unit/500 ml 0.06USD ml Oxytocin-lr 20 unit/500 ml 0.06USD ml Oxytocin-d5w-lr 15 unit/500 ml 0.05USD ml Oxytocin-d5w-lr 20 unit/500 ml 0.05USD ml Oxytocin-lr 10 unit/500 ml 0.05USD ml Oxytocin-d5-1/4ns 15 unit/250 0.04USD ml Oxytocin-d5w 40 unit/1000 ml 0.04USD ml Oxytocin-d5w-lr 10 unit/500 ml 0.04USD ml Oxytocin-d5w 20 unit/1000 ml 0.03USD ml Oxytocin-d5w 30 unit/1000 ml 0.03USD ml Oxytocin-lr 30 unit/500 ml 0.03USD ml Oxytocin-ns 30 unit/1000 ml 0.03USD ml Oxytocin-d5w 10 unit/1000 ml 0.02USD ml Oxytocin-lr 5 unit/500 ml 0.02USD ml Oxytocin-ns 40 unit/1000 ml 0.02USD ml Oxytocin-d5-1/2ns 10 unit/1000 0.01USD ml Oxytocin-d5-1/2ns 20 unit/1000 0.01USD ml Oxytocin-d5-1/2ns 30 unit/1000 0.01USD ml Oxytocin-d5-ns 20 unit/1000 ml 0.01USD ml Oxytocin-ns 10 unit/1000 ml 0.01USD ml Oxytocin-ns 20 unit/1000 ml 0.01USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source hydrophobicity -2.7 Not Available isoelectric point 5.51 Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Vasopressin receptor activity
- Specific Function
- Receptor for oxytocin. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system.
- Gene Name
- OXTR
- Uniprot ID
- P30559
- Uniprot Name
- Oxytocin receptor
- Molecular Weight
- 42770.99 Da
References
- Spyranti Z, Fragiadaki M, Magafa V, Borovickova L, Spyroulias GA, Cordopatis P, Slaninova J: In position 7 L- and D-Tic-substituted oxytocin and deamino oxytocin: NMR study and conformational insights. Amino Acids. 2010 Jul;39(2):539-48. doi: 10.1007/s00726-009-0470-1. Epub 2010 Jan 27. [PubMed:20108008]
- Frantz MC, Rodrigo J, Boudier L, Durroux T, Mouillac B, Hibert M: Subtlety of the structure-affinity and structure-efficacy relationships around a nonpeptide oxytocin receptor agonist. J Med Chem. 2010 Feb 25;53(4):1546-62. doi: 10.1021/jm901084f. [PubMed:20104850]
- Gimpl G, Reitz J, Brauer S, Trossen C: Oxytocin receptors: ligand binding, signalling and cholesterol dependence. Prog Brain Res. 2008;170:193-204. doi: 10.1016/S0079-6123(08)00417-2. [PubMed:18655883]
- Ahn TG, Han SJ, Cho YS, An TH, Pak SC, Flouret G: In vivo activity of the potent oxytocin antagonist on uterine activity in the rat. In Vivo. 2004 Nov-Dec;18(6):763-6. [PubMed:15646817]
- Furman DJ, Chen MC, Gotlib IH: Variant in oxytocin receptor gene is associated with amygdala volume. Psychoneuroendocrinology. 2011 Jul;36(6):891-7. doi: 10.1016/j.psyneuen.2010.12.004. Epub 2011 Jan 3. [PubMed:21208749]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Not Available
- Specific Function
- Neurophysin 1 specifically binds oxytocin.Oxytocin causes contraction of the smooth muscle of the uterus and of the mammary gland.
- Gene Name
- OXT
- Uniprot ID
- P01178
- Uniprot Name
- Oxytocin-neurophysin 1
- Molecular Weight
- 12721.51 Da
References
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Land H, Grez M, Ruppert S, Schmale H, Rehbein M, Richter D, Schutz G: Deduced amino acid sequence from the bovine oxytocin-neurophysin I precursor cDNA. Nature. 1983 Mar 24-30;302(5906):342-4. [PubMed:6687626]
- Rao VV, Loffler C, Battey J, Hansmann I: The human gene for oxytocin-neurophysin I (OXT) is physically mapped to chromosome 20p13 by in situ hybridization. Cytogenet Cell Genet. 1992;61(4):271-3. [PubMed:1486803]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Serine-type peptidase activity
- Specific Function
- Cleaves peptide bonds on the C-terminal side of prolyl residues within peptides that are up to approximately 30 amino acids long.
- Gene Name
- PREP
- Uniprot ID
- P48147
- Uniprot Name
- Prolyl endopeptidase
- Molecular Weight
- 80698.945 Da
References
- Irazusta J, Silveira PF, Gil J, Varona A, Casis L: Effects of hydrosaline treatments on prolyl endopeptidase activity in rat tissues. Regul Pept. 2001 Sep 15;101(1-3):141-7. [PubMed:11495689]
- Bausback HH, Ward PE: Vascular, post proline cleaving enzyme: metabolism of vasoactive peptides. Adv Exp Med Biol. 1986;198 Pt A:397-404. [PubMed:3544718]
- Yoshimoto T, Nishimura T, Kita T, Tsuru D: Post-proline cleaving enzyme (prolyl endopeptidase) from bovine brain. J Biochem. 1983 Oct;94(4):1179-90. [PubMed:6361010]
Drug created on June 13, 2005 07:24 / Updated on September 17, 2020 23:29
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