Aviptadil Acetate

Aviptadil, also known as vasoactive intestinal polypeptide (VIP), is a 28 amino acid neuropeptide that belongs to the glucagon-growth hormone-releasing factor secretion superfamily. Aviptadil acts as a potent systemic vasodilator and bronchodilator. It inhibits the proliferation of vascular and bronchial smooth muscle cells and decreases platelet aggregation. These biological effects are mediated by specific VIP receptors.

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Aviptadil Acetate(CAS 40077-57-4)

CAT No: 10-101-43

CAS No: 40077-57-4

Synonyms/Alias: VIP; Vasoactive Intestinal Polypeptide; invicorp; Aviptadil

Chemical Name: 4-[[1-[[1-[[1-[[1-[[1-[[1-[[1-[[1-[[1-[[1-[[1-[[6-amino-1-[[5-amino-1-[[1-[[1-[[1-[[6-amino-1-[[6-amino-1-[[1-[[1-[[4-amino-1-[[1-[[1-[[1-[(1,4-diamino-1,4-dioxobutan-2-yl)amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-[[2-[[2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-oxobutanoic acid

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC147H238N44O42S
M.W/Mr.3325.87
SequenceHSDAVFTDNYTRLRKQMAVKKYLNSILN
Labeling TargetPeptides
ApplicationAviptadil exerts potent anti-inflammatory and immunomodulatory effects and is used in the treatment of erectile dysfunction.
AppearanceSolid powder
Purity>98% (or refer to the Certificate of Analysis)
Areas of InterestCardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
TargetSARS-CoV
Source#Synthetic
Long-term Storage ConditionsSoluble in DMSO, not in water
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
InChIInChI=1S/C147H239N43O42S2/c1-71(2)55-97(175-120(207)77(12)165-130(217)105(65-112(201)202)181-140(227)107(68-191)185-121(208)87(151)62-84-67-160-70-163-84)133(220)179-102(59-81-29-19-18-20-30-81)137(224)189-117(80(15)195)145(232)184-106(66-113(203)204)139(226)190-116(79(14)194)144(231)183-103(61-83-38-42-86(197)43-39-83)138(225)188-115(78(13)193)143(230)173-92(35-28-52-162-147(158)159)127(214)176-98(56-72(3)4)131(218)170-91(34-27-51-161-146(156)157)125(212)167-89(32-22-25-49-149)124(211)171-93(44-45-109(152)198)128(215)172-94(46-53-233-16)122(209)164-76(11)119(206)166-95(47-54-234-17)129(216)169-88(31-21-24-48-148)123(210)168-90(33-23-26-50-150)126(213)178-101(60-82-36-40-85(196)41-37-82)135(222)177-99(57-73(5)6)134(221)180-104(64-111(154)200)136(223)186-108(69-192)141(228)187-114(75(9)10)142(229)182-100(58-74(7)8)132(219)174-96(118(155)205)63-110(153)199/h18-20,29-30,36-43,67,70-80,87-108,114-117,191-197H,21-28,31-35,44-66,68-69,148-151H2,1-17H3,(H2,152,198)(H2,153,199)(H2,154,200)(H2,155,205)(H,160,163)(H,164,209)(H,165,217)(H,166,206)(H,167,212)(H,168,210)(H,169,216)(H,170,218)(H,171,211)(H,172,215)(H,173,230)(H,174,219)(H,175,207)(H,176,214)(H,177,222)(H,178,213)(H,179,220)(H,180,221)(H,181,227)(H,182,229)(H,183,231)(H,184,232)(H,185,208)(H,186,223)(H,187,228)(H,188,225)(H,189,224)(H,190,226)(H,201,202)(H,203,204)(H4,156,157,161)(H4,158,159,162)
InChI KeyUGKBLTCXYMBLJU-UHFFFAOYSA-N
Canonical SMILESCC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)NC(C(C)O)C(=O)NC(CC(=O)O)C(=O)NC(C(C)O)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(C(C)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CCC(=O)N)C(=O)NC(CCSC)C(=O)NC(C)C(=O)NC(CCSC)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CC3=CC=C(C=C3)O)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)N)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(CC4=CNC=N4)N
BoilingPointN/A
ShelfLife>2 years if stored properly
References

Vasoactive Intestinal Peptide (VIP) is a neuropeptide, expressed by lymphoid as well as neural cells, which has diverse effects on the cellular mediators of inflammation and immunity and is also a potent neurotransmitter. VIP seems to have a major role in the homeostasis of the respiratory system, while several studies, including clinical trials, suggest that VIP-inhaled agonists could be used in respiratory therapeutics.

Mathioudakis A G, Chatzimavridou-Grigoriadou V, Evangelopoulou E, et al. Vasoactive intestinal peptide inhaled agonists: potential role in respiratory therapeutics[J]. Hippokratia, 2013, 17(1): 12.

Pulmonary hypertension (PH) leads to an increased right ventricular workload, cardiac failure and death. In idiopathic pulmonary arterial hypertension (PAH) the vasodilating vasoactive intestinal peptide (aviptadil) is deficient. The aim of the present study was to test the acute effects on haemodynamics and blood gases, and the safety, of a single dose of inhaled aviptadil in chronic PH. A total of 20 patients with PH (PAH in nine, PH in lung disease in eight and chronic thromboembolic PH in three) inhaled a single 100-microg dose of aviptadil during right-heart catheterisation. Haemodynamics and blood gases were measured. Aviptadil aerosol caused a small and temporary but significant selective pulmonary vasodilation, an improved stroke volume and mixed venous oxygen saturation. Overall, six patients experienced a pulmonary vascular resistance reduction of >20%. In patients with significant lung disease, aviptadil tended to improve oxygenation. The pulmonary vasodilating effect of aviptadil aerosol was modest and short-lived, did not cause any side-effects and led to a reduced workload of the right ventricle without affecting systemic blood pressure. Aviptadil inhalation tended to improve oxygenation in patients with significant lung disease. Further studies are needed to evaluate the full therapeutic potential of aviptadil aerosol, including higher doses and chronic treatment.

Leuchte H H, Baezner C, Baumgartner R A, et al. Inhalation of vasoactive intestinal peptide in pulmonary hypertension[J]. European Respiratory Journal, 2008, 32(5): 1289-1294.

Melting PointN/A

1. Implications of ligand-receptor binding kinetics on GLP-1R signalling

2. Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line

3. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function

4. Novel Peptide-Based PD1 Immunomodulators Demonstrate Efficacy in Infectious Disease Vaccines and Therapeutics

5. Extended exenatide administration enhances lipid metabolism and exacerbates pancreatic injury in mice on a high fat, high carbohydrate diet

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