Oxytocin (medication)

Not to be confused with Oxycontin.

Oxytocin (medication)
Clinical data
Pronunciation/ˌɒksɪˈtoʊsɪn/
Trade namesPitocin, Syntocinon, Viatocinon, others
AHFS/Drugs.comMonograph
MedlinePlusa682685
License data
Pregnancy
category
  • AU: A
Routes of
administration		Intranasal, intravenous, intramuscular
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver and elsewhere (via oxytocinases)
Elimination half-life1–6 min (IV)
~2 h (intranasal)[4][5]
ExcretionBile duct and kidney
Identifiers
IUPAC name
  • 1-({(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-(4-hydroxybenzyl)-13-[(1S)-1-methylpropyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-L-prolyl-L-leucylglycinamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC43H66N12O12S2
Molar mass1007.19 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O
InChI
  • InChI=1S/C43H66N12O12S2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1 Y
  • Key:XNOPRXBHLZRZKH-DSZYJQQASA-N Y
  (verify)

Synthetic oxytocin, sold under the brand name Pitocin among others, is a medication made from the peptide oxytocin.[6][7] As a medication, it is used to cause contraction of the uterus to start labor, increase the speed of labor, and to stop bleeding following delivery.[6] For this purpose, it is given by injection either into a muscle or into a vein.[6]

Oxytocin is also available in intranasal spray form for psychiatric, endocrine and weight management use as a supplement. Intranasal oxytocin works on a different pathway than injected oxytocin, primarily along the olfactory nerve crossing the blood–brain barrier to the olfactory lobe in the brain, where dense magnocellular oxytocin neurons receive the nerve impulse quickly.

The natural occurrence of oxytocin was discovered in 1906.[8][9] It is on the World Health Organization's List of Essential Medicines.[10]

  1. ^ "Syntocinon 10 IU/ml Concentrate for Solution for Infusion". (emc). 25 October 2023. Retrieved 14 January 2024.
  2. ^ "Pitocin- oxytocin injection". DailyMed. 10 January 2008. Retrieved 14 January 2024.
  3. ^ "Oxytocin injection, solution". DailyMed. 16 October 2023. Retrieved 14 January 2024.
  4. ^ Cite error: The named reference pmid22436536 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference pmid22467107 was invoked but never defined (see the help page).
  6. ^ a b c "Oxytocin". The American Society of Health-System Pharmacists. Archived from the original on 20 May 2015. Retrieved 1 June 2015.
  7. ^ The Oxford Handbook of Prosocial Behavior. Oxford University Press. 2015. p. 354. ISBN 978-0-19-539981-3. Archived from the original on 1 August 2017.
  8. ^ Hurlemann R, Grinevich V (2018). Behavioral Pharmacology of Neuropeptides: Oxytocin. Springer. p. 37. ISBN 978-3-319-63739-6.
  9. ^ Cite error: The named reference pmid16992821 was invoked but never defined (see the help page).
  10. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
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