Vasopressin
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MedKoo CAT#: 329883

CAS#: 11000-17-2

Description: Vasopressin, also named antidiuretic hormone (ADH), arginine vasopressin (AVP) or argipressin, is a hormone synthesized as a peptide prohormone in neurons in the hypothalamus, and is converted to AVP. It then travels down the axon of that cell, which terminates in the posterior pituitary, and is released from vesicles into the circulation in response to extracellular fluid hypertonicity (hyperosmolality). AVP has two primary functions. First, it increases the amount of solute-free water reabsorbed back into the circulation from the filtrate in the kidney tubules of the nephrons. Second, AVP constricts arterioles, which increases peripheral vascular resistance and raises arterial blood pressure.


Price and Availability

Size
Price

25mg
USD 525
Size
Price

100mg
USD 1650
Size
Price

Vasopressin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 329883
Name: Vasopressin
CAS#: 11000-17-2
Chemical Formula: C46H65N15O12S2
Exact Mass: 1083.4379
Molecular Weight: 1084.239
Elemental Analysis: C, 50.96; H, 6.04; N, 19.38; O, 17.71; S, 5.91


Synonym: Vasopressin; antidiuretic hormone (ADH); arginine vasopressin (AVP) ; argipressin; H-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 (Disulfide Bridge Cys1-Cys6)

IUPAC/Chemical Name: (S)-N-((S)-1-((2-amino-2-oxoethyl)amino)-5-guanidino-1-oxopentan-2-yl)-1-((4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide

InChi Key: KBZOIRJILGZLEJ-LGYYRGKSSA-N

InChi Code: InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1

SMILES Code: O=C([C@@H](N)CSSC[C@H](NC1=O)C(N2[C@H](C(N[C@H](C(NCC(N)=O)=O)CCCNC(N)=N)=O)CCC2)=O)N[C@H](C(N[C@H](C(N[C@H](C(N[C@H]1CC(N)=O)=O)CCC(N)=O)=O)CC3=CC=CC=C3)=O)CC4=CC=C(O)C=C4


Technical Data

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 water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in water

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Vasopressin regulates the tonicity of body fluids. It is released from the posterior pituitary in response to hypertonicity and causes the kidneys to reabsorb solute-free water and return it to the circulation from the tubules of the nephron, thus returning the tonicity of the body fluids toward normal. An incidental consequence of this renal reabsorption of water is concentrated urine and reduced urine volume. AVP released in high concentrations may also raise blood pressure by inducing moderate vasoconstriction.

AVP also may have a variety of neurological effects on the brain. It may influence pair-bonding in voles. The high-density distributions of vasopressin receptor AVPr1a in prairie vole ventral forebrain regions have been shown to facilitate and coordinate reward circuits during partner preference formation, critical for pair bond formation.

A very similar substance, lysine vasopressin (LVP) or lypressin, has the same function in pigs and is used in human AVP deficiency.


References

1: Gizowski C, Trudel E, Bourque CW. Central and peripheral roles of vasopressin in the circadian defense of body hydration. Best Pract Res Clin Endocrinol Metab. 2017 Dec;31(6):535-546. doi: 10.1016/j.beem.2017.11.001. Epub 2017 Nov 13. Review. PubMed PMID: 29224666.

2: Terranova JI, Ferris CF, Albers HE. Sex Differences in the Regulation of Offensive Aggression and Dominance by Arginine-Vasopressin. Front Endocrinol (Lausanne). 2017 Nov 14;8:308. doi: 10.3389/fendo.2017.00308. eCollection 2017. Review. PubMed PMID: 29184535; PubMed Central PMCID: PMC5694440.

3: Ishikawa SE. Is Exaggerated Release of Arginine Vasopressin an Endocrine Disorder? Pathophysiology and Treatment. J Clin Med. 2017 Oct 31;6(11). pii: E102. doi: 10.3390/jcm6110102. Review. PubMed PMID: 29088071; PubMed Central PMCID: PMC5704119.

4: Caldwell HK, Aulino EA, Rodriguez KM, Witchey SK, Yaw AM. Social Context, Stress, Neuropsychiatric Disorders, and the Vasopressin 1b Receptor. Front Neurosci. 2017 Oct 16;11:567. doi: 10.3389/fnins.2017.00567. eCollection 2017. Review. PubMed PMID: 29085277; PubMed Central PMCID: PMC5650633.

5: Phelps SM, Okhovat M, Berrio A. Individual Differences in Social Behavior and Cortical Vasopressin Receptor: Genetics, Epigenetics, and Evolution. Front Neurosci. 2017 Oct 4;11:537. doi: 10.3389/fnins.2017.00537. eCollection 2017. Review. PubMed PMID: 29085274; PubMed Central PMCID: PMC5649215.

6: Song Z, Albers HE. Cross-talk among oxytocin and arginine-vasopressin receptors: Relevance for basic and clinical studies of the brain and periphery. Front Neuroendocrinol. 2017 Oct 18. pii: S0091-3022(17)30064-X. doi: 10.1016/j.yfrne.2017.10.004. [Epub ahead of print] Review. PubMed PMID: 29054552.

7: Clark WF, Devuyst O, Roussel R. The vasopressin system: new insights for patients with kidney diseases: Epidemiological evidence and therapeutic perspectives. J Intern Med. 2017 Oct;282(4):310-321. doi: 10.1111/joim.12654. Epub 2017 Sep 14. Review. PubMed PMID: 28905441.

8: Rondon-Berrios H, Berl T. Vasopressin Receptor Antagonists in Hyponatremia: Uses and Misuses. Front Med (Lausanne). 2017 Aug 21;4:141. doi: 10.3389/fmed.2017.00141. eCollection 2017. Review. PubMed PMID: 28879182; PubMed Central PMCID: PMC5573438.

9: Zhang Q, Liu B, Zhao L, Qi Z, Shao H, An L, Li C. Efficacy of vasopressin-epinephrine compared to epinephrine alone for out of hospital cardiac arrest patients: A systematic review and meta-analysis. Am J Emerg Med. 2017 Oct;35(10):1555-1560. doi: 10.1016/j.ajem.2017.07.040. Epub 2017 Jul 18. Review. PubMed PMID: 28754320.

10: Vinod P, Krishnappa V, Chauvin AM, Khare A, Raina R. Cardiorenal Syndrome: Role of Arginine Vasopressin and Vaptans in Heart Failure. Cardiol Res. 2017 Jun;8(3):87-95. doi: 10.14740/cr553w. Epub 2017 Jun 30. Review. PubMed PMID: 28725324; PubMed Central PMCID: PMC5505291.

11: Nakamura K, Velho G, Bouby N. Vasopressin and metabolic disorders: translation from experimental models to clinical use. J Intern Med. 2017 Oct;282(4):298-309. doi: 10.1111/joim.12649. Epub 2017 Sep 7. Review. PubMed PMID: 28688111.

12: Patisaul HB. Endocrine Disruption of Vasopressin Systems and Related Behaviors. Front Endocrinol (Lausanne). 2017 Jun 19;8:134. doi: 10.3389/fendo.2017.00134. eCollection 2017. Review. PubMed PMID: 28674520; PubMed Central PMCID: PMC5475378.

13: Bankir L, Bichet DG, Morgenthaler NG. Vasopressin: physiology, assessment and osmosensation. J Intern Med. 2017 Oct;282(4):284-297. doi: 10.1111/joim.12645. Epub 2017 Jul 26. Review. PubMed PMID: 28649750.

14: Flahault A, Couvineau P, Alvear-Perez R, Iturrioz X, Llorens-Cortes C. Role of the Vasopressin/Apelin Balance and Potential Use of Metabolically Stable Apelin Analogs in Water Metabolism Disorders. Front Endocrinol (Lausanne). 2017 May 31;8:120. doi: 10.3389/fendo.2017.00120. eCollection 2017. Review. PubMed PMID: 28620355; PubMed Central PMCID: PMC5450005.

15: Park KS, Yoo KY. Role of vasopressin in current anesthetic practice. Korean J Anesthesiol. 2017 Jun;70(3):245-257. doi: 10.4097/kjae.2017.70.3.245. Epub 2017 May 26. Review. PubMed PMID: 28580075; PubMed Central PMCID: PMC5453886.

16: Bachmann S, Mutig K. Regulation of renal Na-(K)-Cl cotransporters by vasopressin. Pflugers Arch. 2017 Aug;469(7-8):889-897. doi: 10.1007/s00424-017-2002-2. Epub 2017 Jun 2. Review. PubMed PMID: 28577072.

17: Prager-Khoutorsky M, Choe KY, Levi DI, Bourque CW. Role of Vasopressin in Rat Models of Salt-Dependent Hypertension. Curr Hypertens Rep. 2017 May;19(5):42. doi: 10.1007/s11906-017-0741-2. Review. PubMed PMID: 28451854.

18: Johnson ZV, Young LJ. Oxytocin and vasopressin neural networks: Implications for social behavioral diversity and translational neuroscience. Neurosci Biobehav Rev. 2017 May;76(Pt A):87-98. doi: 10.1016/j.neubiorev.2017.01.034. Review. PubMed PMID: 28434591; PubMed Central PMCID: PMC5407410.

19: Vishram-Nielsen JK, Gustafsson F. Vasopressin and Vasopressin Antagonists in Heart Failure. Handb Exp Pharmacol. 2017;243:307-328. doi: 10.1007/164_2017_28. Review. PubMed PMID: 28432473.

20: Saad AF, Maybauer MO. The role of vasopressin and the vasopressin type V1a receptor agonist selepressin in septic shock. J Crit Care. 2017 Aug;40:41-45. doi: 10.1016/j.jcrc.2017.03.008. Epub 2017 Mar 15. Review. PubMed PMID: 28319910.