ArgipressinProduct ingredient for Vasopressin
- Name
- Argipressin
- Drug Entry
- Vasopressin
Vasopressin (arginine-vasopressin or antidiuretic hormone) is a nonapeptide primarily produced in the hypothalamus that exhibits diverse physiological functions related to diuresis, hemodynamic modulation, and behaviour.1,2,3,4,6 Vasopressin is very similar to oxytocin, differing in the third and eighth amino acids.7 Despite a wide variety of functions, exogenous vasopressin is primarily used to control blood pressure during systemic shock by increasing vasoconstriction and renal fluid reuptake by acting through V1 and V2 cellular receptors.6,7,8,10
The vasopressive effect of posterior pituitary gland extracts was noted in 1895, while vasopressin itself was not purified until 1951. It has been used for more than five decades for varying conditions, including variceal bleeding, diabetes insipidus, and, more recently, vasodilatory shock.7 It is currently marketed under the trademark VASOSTRICT® by PAR Pharmaceuticals.10
- Accession Number
- DBSALT002464
- Structure
Structure for Argipressin (DBSALT002464)
- Synonyms
- 8-Arginine-vasopressin / 8-L-Arginine vasopressin / 8-L-argininevasopressin / Arginine vasopressin / arginine-vasopressin / Argipresina / Argipressin / Argipressin tannate / Argipressine / Argipressinum / Vasopressin (arginine form)
- UNII
- Y4907O6MFD
- CAS Number
- 113-79-1
- Weight
- Average: 1084.24
Monoisotopic: 1083.437854941 - Chemical Formula
- C46H65N15O12S2
- InChI Key
- KBZOIRJILGZLEJ-LGYYRGKSSA-N
- InChI
- 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
- IUPAC Name
- (2S)-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
- SMILES
- N[C@H]1CSSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(N)=O
- External Links
- KEGG Drug
- D02983
- ChemSpider
- 559126
- BindingDB
- 50044777
- ChEBI
- 34543
- ChEMBL
- CHEMBL373742
- Wikipedia
- Vasopressin
- Predicted Properties
Property Value Source Water Solubility 0.128 mg/mL ALOGPS logP -1.6 ALOGPS logP -7.2 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 9.5 Chemaxon pKa (Strongest Basic) 11.8 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 16 Chemaxon Hydrogen Donor Count 15 Chemaxon Polar Surface Area 461.43 Å2 Chemaxon Rotatable Bond Count 19 Chemaxon Refractivity 282.89 m3·mol-1 Chemaxon Polarizability 105.73 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon