Demoxytocin

Demoxytocin
Clinical data
Other namesODA-914;
1-mercaptopropionate-
oxytoxin
Routes of
administration		Buccal
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 2-[(1-{[13-(butan-2-yl)-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}pyrrolidin-2-yl)formamido]-N-(carbamoylmethyl)-4-methylpentanamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.003.668 Edit this at Wikidata
Chemical and physical data
FormulaC43H65N11O12S2
Molar mass992.18 g·mol−1
3D model (JSmol)
  • CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@H](C(=O)N1)Cc2ccc(cc2)O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
  • InChI=1S/C43H65N11O12S2/c1-5-23(4)36-42(65)49-26(12-13-32(44)56)38(61)50-29(19-33(45)57)39(62)52-30(21-68-67-16-14-35(59)48-28(40(63)53-36)18-24-8-10-25(55)11-9-24)43(66)54-15-6-7-31(54)41(64)51-27(17-22(2)3)37(60)47-20-34(46)58/h8-11,22-23,26-31,36,55H,5-7,12-21H2,1-4H3,(H2,44,56)(H2,45,57)(H2,46,58)(H,47,60)(H,48,59)(H,49,65)(H,50,61)(H,51,64)(H,52,62)(H,53,63)/t23-,26-,27-,28-,29-,30-,31-,36-/m0/s1 ☒N
  • Key:GTYWGUNQAMYZPF-QPLNMOKZSA-N ☒N

Demoxytocin (INN) (brand names Sandopart, Odeax, Sandopral), also known as desaminooxytocin or deaminooxytocin, as well as 1-(3-mercaptopropanoic acid)oxytocin ([Mpa1]OT), is an oxytocic peptide drug that is used to induce labor,[1] promote lactation,[2] and to prevent and treat puerperal (postpartum) mastitis (breast inflammation).[3] Demoxytocin is a synthetic analogue of oxytocin and has similar activities,[4] but is more potent and has a longer half-life in comparison.[2][1] Unlike oxytocin, which is given via intravenous injection, demoxytocin is administered as a buccal tablet formulation.[2][5]

The drug was first synthesized in 1960 and was introduced into clinical practice in 1971 by Sandoz.[6][7] It is marketed in several European countries, including Italy, Czech Republic, and Poland.[8][6][2] It has the amino acid sequence Mpa-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 (Mpa = β-mercaptopropionic acid),[1] and is an analogue of oxytocin wherein the leading cysteine is replaced with β-mercaptopropionic acid.[1]

  1. ^ a b c d Bladon C (3 April 2002). "Modifications of Endogenous Peptides and Proteins". Pharmaceutical Chemistry: Therapeutic Aspects of Biomacromolecules. John Wiley & Sons. pp. 61–. ISBN 978-0-471-49637-3.
  2. ^ a b c d Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 93–. ISBN 978-94-011-4439-1.
  3. ^ Sternadel Z, Gerkowicz J (May 1979). "[Use of deaminooxytocin (Sandopart) in the prevention and treatment of puerperal mastitis]". Ginekologia Polska (in Polish). 50 (5): 413–416. PMID 468056.
  4. ^ van Boxtel CJ (6 August 2008). "Hormones and Hormone Antagonists". In van Boxtel CJ, Santoso B, Edwards IR (eds.). Drug Benefits and Risks: International Textbook of Clinical Pharmacology (2nd ed.). IOS Press. pp. 389–. ISBN 978-1-60750-345-3.
  5. ^ Thiery M (22 October 2013). "Stimulation of uterine activity". In Eskes TK, Finster M (eds.). Drug Therapy During Pregnancy. Elsevier. pp. 185–. ISBN 978-1-4831-6298-0.
  6. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 349–. ISBN 978-1-4757-2085-3.
  7. ^ Gross E, Meienhofer J (10 May 2014). "The Peptide Bond". In Gross E, Meienhofer J (eds.). Major Methods of Peptide Bond Formation: The Peptides Analysis, Synthesis, Biology. Elsevier. pp. 53–. ISBN 978-1-4832-1796-3.
  8. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 301–. ISBN 978-3-88763-075-1.