Demoxytocin
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Demoxytocin

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Demoxytocin, a heterodetic cyclic peptide, is the synthetic analog of the peptide hormone oxytocin with prolonged activity.

Category
Peptide Inhibitors
Catalog number
BAT-015399
CAS number
113-78-0
Molecular Formula
C43H65N11O12S2
Molecular Weight
992.18
Demoxytocin
IUPAC Name
(2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(4R,7S,10S,13S,16S)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide
Synonyms
dOT; (Deamino-Cys1)-Oxytocin; 3-Mercaptopropionyl-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 (Disulfide bridge: Cys1-Cys6); deamino-Cys(1)-Tyr-Ile-Gln-Asn-Cys(1)-Pro-Leu-Gly-NH2; deamino-cysteinyl-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparagyl-L-cysteinyl-L-prolyl-L-leucyl-glycinamide (1->6)-disulfide; Sandopart; desaminooxytocin; Demossitocina; 1-(3-Mercaptopropionic acid)-oxytocin
Appearance
White Powder
Purity
≥90%
Density
1.263±0.06 g/cm3 (Predicted)
Boiling Point
1518.8±65.0°C (Predicted)
Sequence
deamino-CYIQNCPLG-NH2 (Disulfide bridge: Cys1-Cys6)
Storage
Store at -20°C
Solubility
Soluble in Acetic Acid
InChI
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
InChI Key
GTYWGUNQAMYZPF-QPLNMOKZSA-N
Canonical SMILES
CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
1. Induction of labor and cervical ripening by intracervical prostaglandin E2
C Lenstrup, S S Sørensen, V Brocks Obstet Gynecol . 1985 Jan;65(1):110-4.
A randomized double-blind trial was conducted over 48 hours comparing the effectiveness of prostaglandin E2 gel administered intracervically with that of demoxytocin buccal tablets for induction of labor in 103 patients with unripe cervical status (Bishop score 5 or less). A statistically significant difference was found in success frequency between the two groups, both on the first day (54.7 and 34.0%, respectively) and on the second day (82.0 and 61.9%, respectively; P less than .05). Without being matched, variables influencing the course of labor in the two groups were comparable. There was no statistically significant difference in the induction-delivery interval between the two groups during the first and second days of the trial. In both the prostaglandin E2 and the demoxytocin groups, patients who had not gone into labor during the first day showed a statistically significant increment in the Bishop score on the morning of the second day (2.4 and 1.3, respectively; P less than .01). The frequency of instrumental deliveries and cesarean section was the same in both groups; neither hypertonic uterine contractions nor side effects were observed in any patient. It is concluded that prostaglandin E2 gel administered intracervically is particularly well suited for the induction of labor in patients with unripe cervical status because of its combined contraction-inducing and cervical-ripening properties.
2. A comparative study of labor induced by oral prostaglandin E2 and buccal tablets of demoxytocin
M Ulstein, S N Eikhom, N Sagen Int J Gynaecol Obstet . 1979 Nov-Dec;17(3):243-5. doi: 10.1002/j.1879-3479.1979.tb00158.x.
A comparative study of the efficacy of oral prostaglandin E2 and buccal tablets of demoxytocin for induction of labor in overdue pregnancies was made in groups of randomly selected patients. Labor was successfully induced in 95.7% of the women in the prostaglandin group and 92.1% of the women in the demoxytocin group. Although the operative delivery rate was low in both groups, it was significantly higher for the demoxytocin group. A low rate of perinatal distress was recorded and there were no serious side effects in either group. The time from start of induction until delivery, as well as the time from amniotomy until delivery, were compared for primiparae and multiparae separately. No significant differences were found. The blood loss during the third stage of labor was lower in the prostaglandin group. We find oral induction of labor in overdue pregnancies effective, safe and convenient.
3. 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
A P Lange, J G Westergaard, G T Pedersen, N J Secher Acta Obstet Gynecol Scand . 1983;62(2):111-6. doi: 10.3109/00016348309155773.
The efficacy of oral PGE2 tablets and buccal demoxytocin (resoriblets) for the induction of labor in cases of premature rupture of the membranes (PROM) after the 37th week of gestation has been evaluated in a prospective, randomized investigation of 193 women. PGE2 tablets (Prostin) were given to 109 parturients and demoxytocin resoriblets (Sandopart) to 84. The former were given in increasing doses from an initial 0.5 mg to a maximum of 1.5 mg every hour. The demoxytocin was administered at a constant dosage of 50 I.U. every 30 min. The treatment was unsuccessful in 10 of the women treated with PGE2 tablets and in 19 women receiving demoxytocin resoriblets. In addition, the treatment had to be discontinued in 5 women in the PGE2 group due to gastrointestinal side effects. This gives a total success rate of 86.3% for treatment with PGE2 against 77.4% in respect of demoxytocin. This difference is not significant. No difference was observed between the two treatment groups as regards: the stimulation-delivery interval, duration of the various stages of labor, efficacy in primiparae and multiparae, efficacy in patients with a high/low Bishop score. A significantly higher frequency of gastro-intestinal side effects was seen in those treated with PGE2 (21.7%) as compared with demoxytocin (3.6%). The frequency of surgical intervention was 17% in the PGE2 group and 10% in the demoxytocin group. In 4 cases where the stimulation was successful, cesarean section was carried out for reasons unrelated to the drug therapy. Despite the fact that demoxytocin treatment results in fewer side effects than PGE2, the efficacy of the drug is not superior. Based on experience from previous investigations carried out in this department, where intravenous oxytocin was found to be clearly better than oral PGE2 for the induction of labor in cases of PROM, intravenous oxytocin will remain the method of choice due to the shorter period of treatment, which must take priority.
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