MedKoo Cat#: 581614 | Name: Demoxytocin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

Demoxytocin
Demoxytocin
CAS#113-78-0

Theoretical Analysis

MedKoo Cat#: 581614

Name: Demoxytocin

CAS#: 113-78-0

Chemical Formula: C43H65N11O12S2

Exact Mass: 991.4256

Molecular Weight: 992.18

Elemental Analysis: C, 52.05; H, 6.60; N, 15.53; O, 19.35; S, 6.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Demoxytocin; Sandopart; Odeax; Sandopral; desaminooxytocin; deaminooxytocin。
IUPAC/Chemical Name
(S)-1-((4R,7S,10S,13S,16S)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-((S)-sec-butyl)-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)-N-((S)-1-((2-amino-2-oxoethyl)amino)-4-methyl-1-oxopentan-2-yl)pyrrolidine-2-carboxamide
InChi Key
GTYWGUNQAMYZPF-QPLNMOKZSA-N
InChi Code
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
SMILES Code
CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)CCSSC[C@H](NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCC(=O)N)NC1=O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 992.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Pliska V, Jutz G. Kinetics of oxytocin and deaminooxytocin displacement from the OXTR-receptor compartment in rat uterus ex vivo. Biochem Pharmacol. 2018 Feb;148:278-287. doi: 10.1016/j.bcp.2018.01.006. Epub 2018 Jan 5. PubMed PMID: 29309759. 2: Rousslang KW, Reid PJ, Holloway DM, Haynes DR, Dragavon J, Ross JB. Time-resolved phosphorescence of tyrosine, tyrosine analogs, and tyrosyl residues in oxytocin and small peptides. J Protein Chem. 2002 Nov;21(8):547-55. PubMed PMID: 12638657. 3: Chen L, Zoulíková I, Slaninová J, Barany G. Synthesis and pharmacology of novel analogues of oxytocin and deaminooxytocin: directed methods for the construction of disulfide and trisulfide bridges in peptides. J Med Chem. 1997 Mar 14;40(6):864-76. PubMed PMID: 9083475. 4: Chen L, Bauerová H, Slaninová J, Barany G. Syntheses and biological activities of parallel and antiparallel homo and hetero bis-cystine dimers of oxytocin and deamino-oxytocin. Pept Res. 1996 May-Jun;9(3):114-21. PubMed PMID: 8875590. 5: Liwo A, Tempczyk A, Ołdziej S, Shenderovich MD, Hruby VJ, Talluri S, Ciarkowski J, Kasprzykowski F, Lankiewicz L, Grzonka Z. Exploration of the conformational space of oxytocin and arginine-vasopressin using the electrostatically driven Monte Carlo and molecular dynamics methods. Biopolymers. 1996 Feb;38(2):157-75. PubMed PMID: 8589250. 6: de Groot AN, Hekster YA, Vree TB, van Dongen PW. Oxytocin and desamino-oxytocin tablets are not stable under simulated tropical conditions. J Clin Pharm Ther. 1995 Apr;20(2):115-9. PubMed PMID: 7650072. 7: Munson MC, Lebl M, Slaninová J, Barany G. Solid-phase synthesis and biological activity of the parallel dimer of deamino-oxytocin. Pept Res. 1993 May-Jun;6(3):155-9. PubMed PMID: 8318747. 8: Husain J, Blundell TL, Cooper S, Pitts JE, Tickle IJ, Wood SP, Hruby VJ, Buku A, Fischman AJ, Wyssbrod HR, et al. The conformation of deamino-oxytocin: X-ray analysis of the 'dry' and 'wet' forms. Philos Trans R Soc Lond B Biol Sci. 1990 Apr 27;327(1243):625-54. Erratum in: Philos Trans R Soc Lond Biol 1990 Jun 30;328(1251):239. PubMed PMID: 1972289. 9: Liwo A, Tempczyk A, Grzonka Z. Molecular mechanics calculations on deaminooxytocin and on deamino-arginine-vasopressin and its analogues. J Comput Aided Mol Des. 1989 Jan;2(4):281-309. PubMed PMID: 2715790. 10: Hauksson A, Akerlund M, Melin P. Uterine blood flow and myometrial activity at menstruation, and the action of vasopressin and a synthetic antagonist. Br J Obstet Gynaecol. 1988 Sep;95(9):898-904. PubMed PMID: 3191063. 11: Urry DW. On the development of the conformation of deamino oxytocin. Int J Pept Protein Res. 1987 Nov;30(5):701-3. PubMed PMID: 3436708. 12: Melin P, Trojnar J, Johansson B, Vilhardt H, Akerlund M. Synthetic antagonists of the myometrial response to vasopressin and oxytocin. J Endocrinol. 1986 Oct;111(1):125-31. PubMed PMID: 3783079. 13: Wood SP, Tickle IJ, Treharne AM, Pitts JE, Mascarenhas Y, Li JY, Husain J, Cooper S, Blundell TL, Hruby VJ, et al. Crystal structure analysis of deamino-oxytocin: conformational flexibility and receptor binding. Science. 1986 May 2;232(4750):633-6. PubMed PMID: 3008332. 14: Mehta AC. Buccal and oral drugs: induction of labour. Acta Chir Hung. 1986;27(3):157-63. PubMed PMID: 3469841. 15: Sørensen SS, Brocks V, Lenstrup C. Induction of labor and cervical ripening by intracervical prostaglandin E2. Obstet Gynecol. 1985 Jan;65(1):110-4. PubMed PMID: 3880877. 16: Westergaard JG, Lange AP, Pedersen GT, Secher NJ. Use of oral oxytocics for stimulation of labor in cases of premature rupture of the membranes at term. A randomized comparative study of prostaglandin E2 tablets and demoxytocin resoriblets. Acta Obstet Gynecol Scand. 1983;62(2):111-6. PubMed PMID: 6575576. 17: Westergaard JG, Lange AP, Pedersen GT, Secher NJ. Oral oxytocics for induction of labor. A randomized study of prostaglandin E2 tablets and demoxytocin resoriblets. Acta Obstet Gynecol Scand. 1983;62(2):103-10. PubMed PMID: 6575575. 18: Lange AP, Westergaard JG, Secher NJ, Pedersen GT. Labor induction with prostaglandins. Acta Obstet Gynecol Scand Suppl. 1983;113:177-85. PubMed PMID: 6574677. 19: Lange AP, Secher NJ, Westergaard JG, Skovgård I. Neonatal jaundice after labour induced or stimulated by prostaglandin E2 or oxytocin. Lancet. 1982 May 1;1(8279):991-4. PubMed PMID: 6122848. 20: Lykkesfeldt G, Osler M. Induction of labor with oral prostaglandin E2 and buccal demoxytocin without amniotomy. Acta Obstet Gynecol Scand. 1981;60(4):429-30. PubMed PMID: 7282312.