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Felypressin

IUPAC name 1-[19-Amino-13,16-dibenzyl-10-(2-carbamoyl-ethyl)-7-carbamoylmethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaaza-cycloeicosane-4-carbonyl]-pyrrolidine-2-carboxylic acid [5-amino-1-(carbamoylmethyl-carbamoyl)-pentyl]-amide
Identifiers
CAS number	56-59-7^Y
PubChem	5956
ChemSpider	16736539^Y
UNII	17N2918V6G^Y
DrugBank	DB00093
ChEBI	CHEBI:60564^Y
ChEMBL	CHEMBL1697764^N
Jmol-3D images	Image 1
SMILES NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@H]4NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H](N)CSSC4)CC(N)=O
InChI InChI=1S/C46H65N13O11S2/c47-18-8-7-14-29(40(64)52-23-38(51)62)54-45(69)35-15-9-19-59(35)46(70)34-25-72-71-24-28(48)39(63)55-31(20-26-10-3-1-4-11-26)43(67)56-32(21-27-12-5-2-6-13-27)42(66)53-30(16-17-36(49)60)41(65)57-33(22-37(50)61)44(68)58-34/h1-6,10-13,28-35H,7-9,14-25,47-48H2,(H2,49,60)(H2,50,61)(H2,51,62)(H,52,64)(H,53,66)(H,54,69)(H,55,63)(H,56,67)(H,57,65)(H,58,68)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1^Y Key: SFKQVVDKFKYTNA-DZCXQCEKSA-N^Y InChI=1/C46H65N13O11S2/c47-18-8-7-14-29(40(64)52-23-38(51)62)54-45(69)35-15-9-19-59(35)46(70)34-25-72-71-24-28(48)39(63)55-31(20-26-10-3-1-4-11-26)43(67)56-32(21-27-12-5-2-6-13-27)42(66)53-30(16-17-36(49)60)41(65)57-33(22-37(50)61)44(68)58-34/h1-6,10-13,28-35H,7-9,14-25,47-48H2,(H2,49,60)(H2,50,61)(H2,51,62)(H,52,64)(H,53,66)(H,54,69)(H,55,63)(H,56,67)(H,57,65)(H,58,68)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1 Key: SFKQVVDKFKYTNA-DZCXQCEKBI
Properties
Molecular formula	C₄₆H₆₅N₁₃O₁₁S₂
Molar mass	1040.22 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Felypressin is a non-catecholamine vasoconstrictor that is chemically related to vasopressin, the posterior pituitary hormone. It is added to some local anaesthetics such as prilocaine in a concentration of 0.03 IU/ml. Felypressin is a Vasopressin 1 agonist, and will thus have effects at all Arginine vasopressin receptor 1As. It will, however, have its main physiological effects on vascular SMC's due to the form in which it is administered.

V1 receptors are found in various sites around the body. The major points include the CNS, Liver, Anterior Pituitary, Muscle (both vascular and non-vascular smooth muscle), and Platelets (CLAMP).

Another example of a V1 agonist is terlipressin - which is used in oesophageal varices.

References [edit]

"Vasopressin analogues and treatments", Prof Buckingham, Imperial College School of Medicine (ICSM) - adapted by JHPatel

Hypothalamic-pituitary hormones and analogues (H01)

Hypothalamic

GNRH	Agonists: Gonadorelin Nafarelin Histrelin Antagonists: Cetrorelix Ganirelix

Somatostatin	Agonists: Lanreotide Octreotide Pasireotide Vapreotide

Anterior pituitary

ACTH	Agonists: Corticotropin Cosyntropin Tetracosactide

GH	Agonists: IGF-1 (Mecasermin/Mecasermin rinfabate) Sermorelin Somatrem Antagonists: Pegvisomant

TSH	Agonists: Thyrotropin

Posterior pituitary

Oxytocin	Agonists: Carbetocin Demoxytocin Antagonists: Atosiban

Vasopressin	Agonists: Argipressin Desmopressin Felypressin Lypressin Ornipressin Terlipressin Antagonists: Conivaptan Demeclocycline Lixivaptan Mozavaptan Nelivaptan Relcovaptan Satavaptan Tolvaptan

M: END

anat/phys/devp/horm

noco (d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

Neuropeptidergics

Cholecystokinin

CCK_A	Agonists: Cholecystokinin CCK-4 Antagonists: Asperlicin Proglumide Lorglumide Devazepide Dexloxiglumide

CCK_B	Agonists: Cholecystokinin CCK-4 Gastrin Antagonists: Proglumide CI-988

CRH

CRF₁	Agonists: Corticotropin releasing hormone Antagonists: Antalarmin CP-154,526 Pexacerfont

CRF₂	Agonists: Corticotropin releasing hormone

Galanin

GAL₁	Agonists: Galanin Galanin-like peptide Galmic Galnon

GAL₂	Agonists: Galanin Galanin-like peptide Galmic Galnon

GAL₃	Agonists: Galanin Galmic Galnon

Ghrelin

GnRH

MCH

MCH₁	Agonists: Melanin concentrating hormone Antagonists: ATC-0175 GW-803,430 NGD-4715 SNAP-7941 SNAP-94847

MCH₂	Agonists: Melanin concentrating hormone

Melanocortin

MC₁	Agonists: alpha-MSH Afamelanotide BMS-470,539 Bremelanotide Melanotan II Antagonists: Agouti signalling peptide

MC₂	Agonists: ACTH Cosyntropin Tetracosactide

MC₃	Agonists: alpha-MSH Bremelanotide Melanotan II

MC₄	Agonists: alpha-MSH Bremelanotide Melanotan II PF-00446687 THIQ Antagonists: Agouti-related peptide

MC₅	Agonists: alpha-MSH Melanotan II

Neuropeptide S

Agonists: Neuropeptide S
Antagonists: SHA-68

Neuropeptide Y

Y₁	Agonists: Neuropeptide Y Peptide YY Antagonists: BIBP-3226

Y₂	Agonists: Neuropeptide Y Peptide YY Antagonists: BIIE-0246

Y₄	Agonists: Neuropeptide Y Pancreatic polypeptide Peptide YY Antagonists: UR-AK49

Y₅	Agonists: Neuropeptide Y Peptide YY Antagonists: Lu AA-33810

Neurotensin

NTS₁	Agonists: Neurotensin Neuromedin N Antagonists: SR-48692 SR-142,948

NTS₂	Agonists: Neurotensin Antagonists: Levocabastine SR-142,948

Orexin

OX₁	Agonists: Orexin-A Antagonists: Almorexant SB-334,867 SB-408,124 SB-649,868 Suvorexant

OX₂	Agonists: Orexin-A Antagonists: Almorexant SB-649,868 Suvorexant TCS-OX2-29

Oxytocin

Tachykinin

NK₁	Agonists: Substance P Antagonists: Aprepitant Befetupitant Casopitant CI-1021 CP-96,345 CP-99,994 CP-122,721 Dapitant Ezlopitant FK-888 Fosaprepitant GR-203,040 GW-597,599 HSP-117 L-733,060 L-741,671 L-743,310 L-758,298 Lanepitant LY-306,740 Maropitant Netupitant NKP-608 Nolpitantium Orvepitant RP-67,580 SDZ NKT 343 Vestipitant Vofopitant

NK₂	Agonists: Neurokinin A Antagonists: GR-159,897 Ibodutant Saredutant

NK₃	Agonists: Neurokinin B Antagonists: Osanetant Talnetant

Vasopressin

V_1A	Agonists: Desmopressin Felypressin Ornipressin Terlipressin Vasopressin Antagonists: Conivaptan Demeclocycline Relcovaptan

V_1B	Agonists: Felypressin Ornipressin Terlipressin Vasopressin Antagonists: Demeclocycline Nelivaptan

V₂	Agonists: Desmopressin Ornipressin Vasopressin Antagonists: Conivaptan Demeclocycline Lixivaptan Mozavaptan Satavaptan Tolvaptan

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Felypressin

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