Ornipressin

Ornipressin (omithine-8-vasopressin, POR-8) is the most commonly used vasopressin analogue in Germany, Switzerland, New Zealand and Australia. While it has minimal antidiuretic activity whilst maintaining equipotent vasoconstrictor activity as the natural hormone, vasoprssin.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: 10-101-40

CAS No:3397-23-7

Synonyms/Alias:ORNIPRESSIN;Ornipressine;Ornipresina;Orpressin;3397-23-7;POR 8;Ornipressin [INN];Ornipressina;Ornipressinum;Ornithine Vasopressin;8-Ornithinevasopressin;8-L-Ornithinevasopressin;Orn(8)-vasopressin;POR 8 Sandoz;(Orn8) Vasopressin;POR-8;Ornipressina [DCIT];Ornipresina [INN-Spanish];Ornipressine [INN-French];Ornipressinum [INN-Latin];UNII-1KTH6N080W;Vasopressin, 8-L-ornithine-;1KTH6N080W;ORNIPRESSIN [MI];EINECS 222-253-8;ORNIPRESSIN [MART.];ORNIPRESSIN [WHO-DD];(2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-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-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;CHEMBL1819440;Ornipressin (INN);Ornipressin Diacetate Salt;Ornipresina (INN-Spanish);Ornipressine (INN-French);Ornipressinum (INN-Latin);ORNIPRESSIN (MART.);(2S)-N-[(2S)-5-Amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,10S,13R,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;CYS-TYR-PHE-GLN-ASN-CYS-PRO-ORN-GLY-NH2 (1-6 DISULFIDE);CYS-TYR-PHE-GLN-ASN-CYS-PRO-ORN-GLY-NH2 (1-6 DISULPHIDE);POR 8 Sandoz (TN);(2S)-N-((2S)-5-amino-1-((2-amino-2-oxoethyl)amino)-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-hydroxyphenyl)methyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide;Vasopressin, Ornithine;Ornithine 8 Vasopressin;Ornithine-8-Vasopressin;SCHEMBL296322;H01BA05;CHEBI:136020;MUNMIGOEDGHVLE-LGYYRGKSSA-N;HY-P0083;BDBM50350865;AKOS030529555;CS-5839;DB13464;NCGC00509864-02;DA-56485;NS00049980;Q3038432;(S)-N-((S)-5-amino-1-((2-amino-2-oxoethyl)amino)-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;222-253-8;

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M.F/Formula
C45H63N13O12S2
M.W/Mr.
1042.2
Sequence
One Letter Code:CYFQNCPXG
Three Letter Code:H-Cys(1)-Tyr-Phe-Gln-Asn-Cys(1)-Pro-Orn-Gly-NH2
Labeling Target
Gonadotropin-releasing hormone (GNRH) Receptor
Application
Ornipressin is a vasoconstrictor, haemostatic and renal agent.
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Biological Activity
Ornipressin is a potent vasoconstrictor, hemostatic and renal agent.
Areas of Interest
Cardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
Functions
Peptide binding
Source#
Synthetic
Long-term Storage Conditions
Soluble in DMSO, not in water
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.
Short-term Storage Conditions
Dry, dark and at 0 - 4 °C
Solubility
-20 °C
Organism
Human
InChI
InChI=1S/C45H63N13O12S2/c46-16-4-8-28(39(64)51-21-37(50)62)53-44(69)34-9-5-17-58(34)45(70)33-23-72-71-22-27(47)38(63)54-30(19-25-10-12-26(59)13-11-25)42(67)55-31(18-24-6-2-1-3-7-24)41(66)52-29(14-15-35(48)60)40(65)56-32(20-36(49)61)43(68)57-33/h1-3,6-7,10-13,27-34,59H,4-5,8-9,14-23,46-47H2,(H2,48,60)(H2,49,61)(H2,50,62)(H,51,64)(H,52,66)(H,53,69)(H,54,63)(H,55,67)(H,56,65)(H,57,68)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
InChI Key
MUNMIGOEDGHVLE-LGYYRGKSSA-N
BoilingPoint
N/A
ShelfLife
>2 years if stored properly
References

We sought to evaluate the efficacy and side effect profile of a small dose of ornipressin, a vasopressin agonist specific for the V1 receptor, administered to reverse the hypotension associated with combined general/epidural anesthesia. A total of 60 patients undergoing intestinal surgery were studied. After the induction of anesthesia, 7-8 mL of bupivacaine 0.5% with 2 microg/kg clonidine and 0.05 microg/kg sufentanil after an infusion of 5 mL of bupivacaine 0.06% with 0.5 microg x kg(-1) x h(-1) clonidine and 0.1 microg/h of sufentanil were administered by an epidural catheter placed at T7-8 vertebral interspace. When 20% reduction of baseline arterial blood pressure developed, patients were randomly assigned to receive, in a double-blinded design, dopamine started at 2 microg x kg(-1) x min(-1), norepinephrine started at 0.04 microg x kg(-1) x min(-1), or ornipressin started at 1 IU/h. Fifteen patients presenting without hypotension were used as control subjects. Beside routine monitoring, S-T segment analysis, arterial lactacidemia, and gastric tonometry were performed. Ornipressin restored arterial blood pressure after 8 +/- 2 vs 7 +/- 3 min in the norepinephrine group and 11 +/- 3 min in the dopamine group (P < 0.05). This effect was achieved with 2 IU/h of ornipressin in most of the patients (11 of 15). Ornipressin did not induce any modification of the S-T segment; however, it significantly increased intracellular gastric PCO(2) (P < 0.05), indicating splanchnic vasoconstriction.

De Kock, M., Laterre, P. F., Andruetto, P., Vanderessen, L., Dekrom, S., Vanderick, B., & Lavand'homme, P. (2000). Ornipressin (Por 8): an efficient alternative to counteract hypotension during combined general/epidural anesthesia. Anesthesia & Analgesia, 90(6), 1301-1307.

Melting Point
N/A

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