| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 25mg |
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| Other Sizes |
| Targets |
Oxytocin antiparallel dimer targets the same receptors as native oxytocin, including the oxytocin receptor (OTR) and the vasopressin receptors (V1a, V1b, V2), due to the conserved structural homology between oxytocin and vasopressin. Dimerization in the antiparallel configuration significantly alters the three-dimensional structure and reduces receptor binding affinity. The dimer exhibits oxytocin-like and vasopressin-like activity, but with much lower potency compared to native oxytocin, and is considered less toxic than the native hormone.
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| ln Vitro |
The dicystine dimers of oxytocin and deaminated oxytocin, whether homogeneous or heterogeneous, have biological activity ranging from 0.2% to 6% of oxytocin [1].
In vitro, the biological activity of oxytocin antiparallel dimer is significantly reduced compared to native oxytocin. Studies of oxytocin and deamino-oxytocin dimers (both parallel and antiparallel, homo and hetero bis-cystine dimers) show biological activities ranging from 0.2% to 6% of native oxytocin. The antiparallel dimer retains partial oxytocin- and vasopressin-like activity, but is less potent than the native monomer. It may act as a weak partial agonist or antagonist depending on the specific assay and receptor system. |
| ln Vivo |
Rats respond less acutely to oxytocin dimer (intravenous injection; single dose) than to oxytocin (LD50=43 mg/kg vs. 25 mg/kg) [2].
In vivo, oxytocin antiparallel dimer exhibits reduced biological activity and is less toxic than native oxytocin. The specific effects in animal models (e.g., uterine contraction, milk ejection, vasopressor response) are not as potent as oxytocin. The reduced activity is consistent with its lower binding affinity and altered structure due to the antiparallel disulfide configuration. Historical bioassays have likely used anesthetized rat models to compare the activity of oxytocin dimers to native oxytocin. |
| Enzyme Assay |
Cell-free receptor binding assays for oxytocin dimers use membrane preparations from cells expressing recombinant oxytocin receptors (e.g., HEK293-OTR). The antiparallel dimer is incubated with radiolabeled [3H]-oxytocin in binding buffer at 25degC for 60-120 minutes. Bound and free radioligand are separated by filtration through GF/B filters, and radioactivity is counted by scintillation. The dimer shows reduced binding affinity compared to native oxytocin, consistent with its lower biological activity.
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| Cell Assay |
Cell-based functional assays for oxytocin dimers: cells expressing oxytocin receptors (e.g., HEK293-OTR) are seeded in 96-well plates. For calcium flux assays, cells are loaded with calcium-sensitive dye (e.g., Fluo-4) and treated with antiparallel dimer or native oxytocin (0.1-1000 nM). Changes in intracellular calcium are measured using a fluorescence plate reader. The dimer produces reduced maximal response (lower Emax) and/or reduced potency (higher EC50) compared to native oxytocin (estimated 0.2-6% activity).
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| Animal Protocol |
In vivo animal studies for oxytocin dimers are not typically performed for quality control purposes. Historical studies may have used the standard rat uterine contraction or milk ejection bioassay. Anesthetized rats (often diethylstilbestrol-primed) are used, and the test compound is administered intravenously. Uterine contractions are measured via a transducer, and the response is compared to a standard oxytocin dose-response curve. The antiparallel dimer shows significantly reduced activity (0.2-6%) compared to native oxytocin in these models.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies of oxytocin antiparallel dimer are limited. As a peptide dimer with molecular weight ~2014 Da, it would be expected to have low oral bioavailability due to gastrointestinal degradation and a short plasma half-life due to proteolysis. The antiparallel disulfide configuration may slightly alter stability compared to the parallel dimer. This compound is not intended for therapeutic use, so PK properties are not a primary research focus.
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| Toxicity/Toxicokinetics |
Oxytocin antiparallel dimer is reported to be less toxic than native oxytocin. The reduced toxicity is consistent with its lower biological activity (0.2-6% of oxytocin). Specific toxicological data are not publicly available for this impurity standard. For oxytocin itself, toxicity is primarily an extension of its pharmacological effects: uterine hyperstimulation (leading to fetal distress or uterine rupture), hyponatremia with water retention, and rarely anaphylaxis. Dimerization reduces these risks by attenuating receptor activation.
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| References |
[1]. Chen L, et al. Syntheses and biological activities of parallel and antiparallel homo and hetero bis-cystine dimers of oxytocin and deamino-oxytocin. Pept Res. 1996;9(3):114-121.
[2]. Berde B, et al. Some pharmacological properties of oxytocin-dimers (α+ β)[J]. Experientia, 1971, 27: 1304-1305. |
| Additional Infomation |
Oxytocin antiparallel dimer (also known as beta-Oxytocin dimer or Oxytocin EP Impurity B) is not a drug and has no clinical indications. It is a research-grade peptide impurity reference standard used for oxytocin analysis in pharmaceutical quality control, stability studies, and impurity profiling of oxytocin drug products. Oxytocin is a mammalian neurohypophysial hormone used clinically to induce or augment labor, control postpartum hemorrhage, and facilitate milk ejection. This dimer is an analytical standard only and is not for human use. Typically supplied as a lyophilized powder.
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| Molecular Formula |
C86H132N24O24S4
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|---|---|
| Molecular Weight |
2014.37469387054
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| Exact Mass |
2012.872
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| CAS # |
20054-93-7
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| Related CAS # |
Oxytocin antiparallel dimer TFA
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| PubChem CID |
168008728
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
-5.1
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| Hydrogen Bond Donor Count |
24
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| Hydrogen Bond Acceptor Count |
30
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| Rotatable Bond Count |
34
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| Heavy Atom Count |
138
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| Complexity |
4000
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| Defined Atom Stereocenter Count |
15
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| SMILES |
CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)NC(C(=O)N[C@H](C(=O)NC(C(=O)N[C@H](C(=O)NC(CSSC[C@@H](C(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N)[C@@H](C)CC)CC4=CC=C(C=C4)O)N)C(=O)N5CCC[C@H]5C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
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| InChi Key |
SBLVMJOXVMBHCL-HPNMVLHHSA-N
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| InChi Code |
InChI=1S/C86H132N24O24S4/c1-9-43(7)69-83(131)97-51(23-25-63(89)113)75(123)101-57(33-65(91)115)77(125)105-59(85(133)109-27-11-13-61(109)81(129)103-53(29-41(3)4)73(121)95-35-67(93)117)39-138-136-38-50(88)72(120)100-56(32-46-17-21-48(112)22-18-46)80(128)108-70(44(8)10-2)84(132)98-52(24-26-64(90)114)76(124)102-58(34-66(92)116)78(126)106-60(40-137-135-37-49(87)71(119)99-55(79(127)107-69)31-45-15-19-47(111)20-16-45)86(134)110-28-12-14-62(110)82(130)104-54(30-42(5)6)74(122)96-36-68(94)118/h15-22,41-44,49-62,69-70,111-112H,9-14,23-40,87-88H2,1-8H3,(H2,89,113)(H2,90,114)(H2,91,115)(H2,92,116)(H2,93,117)(H2,94,118)(H,95,121)(H,96,122)(H,97,131)(H,98,132)(H,99,119)(H,100,120)(H,101,123)(H,102,124)(H,103,129)(H,104,130)(H,105,125)(H,106,126)(H,107,127)(H,108,128)/t43-,44-,49-,50-,51-,52?,53-,54-,55-,56?,57-,58-,59-,60?,61-,62-,69-,70-/m0/s1
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| Chemical Name |
(2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(7S,13S,19R,24R,27S,30S,33S,36S,39R)-19,39-diamino-7,27-bis(2-amino-2-oxoethyl)-24-[(2S)-2-[[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]-10,30-bis(3-amino-3-oxopropyl)-13,33-bis[(2S)-butan-2-yl]-16,36-bis[(4-hydroxyphenyl)methyl]-6,9,12,15,18,26,29,32,35,38-decaoxo-1,2,21,22-tetrathia-5,8,11,14,17,25,28,31,34,37-decazacyclotetracontane-4-carbonyl]pyrrolidine-2-carboxamide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.4964 mL | 2.4822 mL | 4.9643 mL | |
| 5 mM | 0.0993 mL | 0.4964 mL | 0.9929 mL | |
| 10 mM | 0.0496 mL | 0.2482 mL | 0.4964 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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