Identification
- Summary
Desmopressin is a synthetic analog of vasopressin used to reduce renal excretion of water in central diabetes insipidus and nocturia.
- Brand Names
- Ddavp, Nocdurna, Octostim
- Generic Name
- Desmopressin
- DrugBank Accession Number
- DB00035
- Background
Desmopressin (dDAVP), a synthetic analogue of 8-arginine vasopressin (ADH), is an antidiuretic peptide drug modified by deamination of 1-cysteine and substitution of 8-L-arginine by 8-D-arginine. ADH is an endogenous pituitary hormone that has a crucial role in the control of the water content in the body. Upon release from the stimulation of increased plasma osmolarity or decreased circulating blood volume, ADH mainly acts on the cells of the distal part of the nephron and the collecting tubules in the kidney 6. The hormone interacts with V1, V2 or V3 receptors with differing signal cascade systems.
Desmopressin displays enhanced antidiuretic potency, fewer pressor effects due to V2-selective actions, and a prolonged half-life and duration of action compared to endogenous ADH 2. It has been employed clinically since 1972 and is available in various formulations including intranasal solution, intravenous solution, oral tablet and oral lyophilisate 3. Desmopressin is indicated for the treatment of polyuric conditions including primary nocturnal enuresis, nocturia, and diabetes insipidus. It was also newly approved for the treatment of mild classical hemophilia and von Willebrand's disease for minor surgeries. The active ingredient in most formulations is desmopressin acetate. Nocdurna, or desmopressin acetate, was approved by the FDA on June 21st, 2018 for the treatment of nocturia due to nocturnal polyuria in adults. It is available as a sublingual tablet.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Desmopressin (DB00035)
- Weight
- Average: 1069.22
Monoisotopic: 1068.426955905 - Chemical Formula
- C46H64N14O12S2
- Synonyms
- 1-(3-mercaptopropionic acid)-8-D-arginine-vasopressin
- 1-deamino-8-D-arginine vasopressin
- 1-desamino-8-D-arginine vasopressin
- dDAVP
- Desmopresina
- Desmopressin
- Desmopressine
- Desmopressinum
Pharmacology
- Indication
Indicated for the treatment of nocturia due to nocturnal polyuria in adults who awaken at least 2 times per night to void (intranasal).
Indicated as antidiuretic replacement therapy in the management of central cranial diabetes insipidus and for management of the temporary polyuria and polydipsia following head trauma or surgery in the pituitary region (intranasal/parenteral).
Indicated for patients with hemophilia A with factor VIII coagulant activity levels greater than 5% or mild to moderate classic von Willebrand's Disease (Type I) with factor VIII levels greater than 5% during surgical procedures and postoperatively to maintain hemostasis (parenteral).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Bleeding •••••••••••• •••••••••• •••••••• Prevention of Bleeding •••••••••••• ••• •••••••••••• ••••••• •••••••• Treatment of Bleeding •••••••••••• Treatment of Bleeding •••••••••••• •••••••••• •••••••••• •••••••• Treatment of Bleeding •••••••••••• •••••••••• •••••••••• •••••••• - Contraindications & Blackbox Warnings
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By mimicking the actions of endogenous ADH, desmopressin acts as a selective agonist of V2 receptors expressed in the renal collecting duct (CD) to increase water re-absorption and reduce urine production. Desmopressin has been shown to be more potent than ADH in increasing plasma levels of factor VIII activity in patients with hemophilia and von Willebrand's disease Type I 8. Desmopressin demonstrates markedly diminished pressor activity. Desmopressin administered intranasally has an antidiuretic effect about one-tenth that of an equivalent dose administered by injection 7.
- Mechanism of action
Upon binding of desmopressin to V2 receptors in the basolateral membrane of the cells of the distal tubule and collecting ducts of the nephron, adenylyl cyclase is stimulated. The resulting intracellular cascades in the collecting duct lead to increased rate of insertion of water channels, called aquaporins, into the lumenal membrane and enhanced the permeability of the membrane to water 6.
Target Actions Organism AVasopressin V2 receptor agonistHumans AVasopressin V1a receptor Not Available Humans AVasopressin V1b receptor Not Available Humans - Absorption
Following nasal spray administration of 0.83 mcg and 1.66 mcg, median time to peak plasma concentrations (Tmax) was 0.25 and 0.75 hour, respectively Label. The peak plasma concentration was approximately 4.00 (± 3.85) pg/mL and 9.11 (± 6.90) pg/mL, respectively Label. The bioavailability of 1.5 mg/mL desmopressin administered by the intranasal route was between 3.3 and 4.1% 8.
The absolute bioavailability of orally administered desmopressin varies between 0.08% and 0.16% where the mean maximum plasma concentration is reached within 2 hours 9.
- Volume of distribution
The distribution volume of orally administered desmopressin is 0.2 – 0.32 l/kg 9. It is not reported to cross the blood-brain barrier.
- Protein binding
Following radioiodination (125I) in the N-terminal, the fraction of plasma protein binding of desmopressin was reported to be 17.3 ± 1.5% in a pharmacokinetic study involving healthy subjects 5.
- Metabolism
In vitro, in human liver microsome preparations, it has been shown that no significant amount of desmopressin is metabolised in the liver and thus human liver metabolism in vivo is not likely to occur 9.
- Route of elimination
Desmopressin is mainly excreted in the urine. About 65% of the amount of desmopressin absorbed after oral administration could be recovered in the urine within 24 hours 9.
- Half-life
Following an intranasal dose of 1.66 mcg of desmopressin, the median apparent terminal half-life was 2.8 hours Label. Terminal half-life significantly increased from 3 hours in normal healthy patients to 9 hours in patients with severe renal impairment Label. The oral terminal half life of desmopressin ranges from 2 to 3.11 hours 9.
- Clearance
Not Available
- Adverse Effects
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Intravenous TDLo in humans is reported to be 0.3 µg/kg/10M MSDS. Desmopressin is associated with hyponatremia in case of overdose, which may require temporary or permanent discontinuation of the therapy depending on severity. The effects of hyponatremia include seizure, altered mental status (confusion, drowsiness or continuing headache), cardiac arrhythmias and worsening edema. Other signs of overdose may include oliguria and rapid weight gain due to fluid retention Label. In case of overdose, reduce the dose or frequency of drug administration, or discontinue use if appropriate. Assessment of serum sodium and initiation of appropriate medical treatment is recommended.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Desmopressin may decrease the excretion rate of Abacavir which could result in a higher serum level. Acebutolol Desmopressin may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of hypertension, hyponatremia, and water intoxication can be increased when Aceclofenac is combined with Desmopressin. Acemetacin The risk or severity of hypertension, hyponatremia, and water intoxication can be increased when Acemetacin is combined with Desmopressin. Acetaminophen Desmopressin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Desmopressin acetate XB13HYU18U 62357-86-2 YNKFCNRZZPFMEX-XHPDKPNGSA-N Desmopressin acetate anhydrous 1K12647SFC 62288-83-9 MLSVJHOYXJGGTR-IFHOVBQLSA-N - Product Images
- International/Other Brands
- Adiuretin (Ferring) / DesmoMelt (Ferring)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bipazen Solution 4 mcg / mL Intramuscular; Intravenous; Subcutaneous Kvr Pharmaceuticals Inc. 2021-10-13 Not applicable Canada 
Ddavp Injection 4 ug/1mL Intravenous Ferring Pharmaceuticals Inc. 1984-05-01 Not applicable US 
Ddavp Tablet 0.1 mg/1 Oral sanofi-aventis U.S. LLC 1995-09-06 2016-09-30 US Ddavp Tablet 0.2 mg/1 Oral Ferring Pharmaceuticals Inc. 1995-09-06 Not applicable US Ddavp Solution 4 ug/1mL Intravenous sanofi-aventis U.S. LLC 1984-03-30 2017-10-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-desmopressin Tablet 0.2 mg Oral Apotex Corporation 2007-01-31 Not applicable Canada Apo-desmopressin Tablet 0.1 mg Oral Apotex Corporation 2007-01-31 Not applicable Canada Desmopressin Acetate Tablet 0.1 mg/1 Oral American Health Packaging 2012-11-06 2023-08-31 US 
Desmopressin Acetate Tablet 0.1 mg/1 Oral BluePoint Laboratories 2023-08-03 Not applicable US Desmopressin Acetate Injection, solution 4 ug/1mL Intravenous; Subcutaneous Athenex Pharmaceutical Division, Llc. 2020-11-30 Not applicable US
Categories
- ATC Codes
- H01BA02 — Desmopressin
- Drug Categories
- Agents that produce hypertension
- Amino Acids, Peptides, and Proteins
- Antidiuretic Agents
- Arginine Vasopressin
- Cardiovascular Agents
- Coagulants
- Drugs that are Mainly Renally Excreted
- Factor VIII Activator
- Hematologic Agents
- Hemostatics
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Increased Coagulation Factor VIII Activity
- Increased Coagulation Factor VIII Concentration
- Natriuretic Agents
- Nerve Tissue Proteins
- Neuropeptides
- Oligopeptides
- Peptide Hormones
- Peptides
- Pituitary
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormones
- Pituitary Hormones, Posterior
- Posterior Pituitary Lobe Hormones
- Proteins
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Vasopressin Analog
- Vasopressin and Analogues
- Vasopressins
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- ENR1LLB0FP
- CAS number
- 16679-58-6
- InChI Key
- NFLWUMRGJYTJIN-PNIOQBSNSA-N
- InChI
- InChI=1S/C46H64N14O12S2/c47-35(62)15-14-29-40(67)58-32(22-36(48)63)43(70)59-33(45(72)60-18-5-9-34(60)44(71)56-28(8-4-17-52-46(50)51)39(66)53-23-37(49)64)24-74-73-19-16-38(65)54-30(21-26-10-12-27(61)13-11-26)41(68)57-31(42(69)55-29)20-25-6-2-1-3-7-25/h1-3,6-7,10-13,28-34,61H,4-5,8-9,14-24H2,(H2,47,62)(H2,48,63)(H2,49,64)(H,53,66)(H,54,65)(H,55,69)(H,56,71)(H,57,68)(H,58,67)(H,59,70)(H4,50,51,52)/t28-,29+,30+,31+,32+,33+,34+/m1/s1
- IUPAC Name
- (2R)-2-{[(2S)-1-[(4R,7S,10S,13S,16S)-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
- NC(=O)CC[C@@H]1NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)CCSSC[C@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](CCCNC(N)=N)C(=O)NCC(N)=O
References
- Synthesis Reference
Krister Larsson, Thomas Mellbrand, Birgitta Mornstam, Jan Roschester, Jan-Ake Skoldback, "High purity desmopressin produced in large single batches." U.S. Patent US5674850, issued November, 1991.
US5674850- General References
- Leissinger C, Becton D, Cornell C Jr, Cox Gill J: High-dose DDAVP intranasal spray (Stimate) for the prevention and treatment of bleeding in patients with mild haemophilia A, mild or moderate type 1 von Willebrand disease and symptomatic carriers of haemophilia A. Haemophilia. 2001 May;7(3):258-66. [Article]
- Richardson DW, Robinson AG: Desmopressin. Ann Intern Med. 1985 Aug;103(2):228-39. [Article]
- Vande Walle J, Stockner M, Raes A, Norgaard JP: Desmopressin 30 years in clinical use: a safety review. Curr Drug Saf. 2007 Sep;2(3):232-8. [Article]
- Agerso H, Seiding Larsen L, Riis A, Lovgren U, Karlsson MO, Senderovitz T: Pharmacokinetics and renal excretion of desmopressin after intravenous administration to healthy subjects and renally impaired patients. Br J Clin Pharmacol. 2004 Oct;58(4):352-8. doi: 10.1111/j.1365-2125.2004.02175.x. [Article]
- Lundin S, Broeders A, Melin P: Pharmacokinetic properties of the tocolytic agent [Mpa1, D-Tyr(Et)2, Thr4, Orn8]-oxytocin (antocin) in healthy volunteers. Clin Endocrinol (Oxf). 1993 Sep;39(3):369-74. [Article]
- 32. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 399-400). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
- DDVAP Nasal Spray FDA Label [Link]
- Stimate (desmopressin acetate) nasal spray FDA Label [Link]
- UKPAR for Desmopressin acetate 100mcg and 200mcg Tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0014260
- KEGG Drug
- D00291
- KEGG Compound
- C06944
- ChemSpider
- 4470602
- BindingDB
- 50205308
- 3251
- ChEBI
- 4450
- ChEMBL
- CHEMBL1429
- Therapeutic Targets Database
- DNC000526
- PharmGKB
- PA449237
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Desmopressin
- FDA label
- Download (1.22 MB)
- MSDS
- Download (26.2 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Diagnostic Monosymptomatic Nocturnal Enuresis 1 4 Completed Prevention Blood Loss During Surgery / Hemorrhage / Postoperative Hemorrhages 1 4 Completed Prevention Kidney Failure 1 4 Completed Prevention Patients Undergoing Endoscopic Sinus Surgery 1 4 Completed Treatment Acquired Von Willebrand Disease Secondary to Severe Aortic Stenosis / Heye´s Syndrome / Severe Aortic Stenosis 1
Pharmacoeconomics
- Manufacturers
- Sanofi aventis us llc
- Bedford laboratories div ben venue laboratories inc
- Hospira inc
- Teva parenteral medicines inc
- Ferring pharmaceuticals inc
- Bausch and lomb pharmaceuticals inc
- Apotex inc richmond hill
- Csl behring llc
- Apotex inc etobicoke site
- Teva pharmaceuticals usa
- Watson laboratories inc
- Packagers
- Amerisource Health Services Corp.
- Apotex Inc.
- Arcola Laboratories
- Bachem Inc.
- Barr Pharmaceuticals
- Bausch & Lomb Inc.
- CSL Behring LLC
- Ferring Pharmaceuticals Inc.
- Hospira Inc.
- Kaiser Foundation Hospital
- Pharmacy Service Center
- Physicians Total Care Inc.
- Promex Medical Inc.
- Rechon Life Science AB
- Sanofi-Aventis Inc.
- Sicor Pharmaceuticals
- Sun Pharmaceutical Industries Ltd.
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Solution Intramuscular; Intravenous; Subcutaneous 4 mcg / mL Solution Intravenous 4 ug/1mL Spray Nasal 0.1 ug/1mL Liquid Intramuscular; Intravenous; Subcutaneous 4 mcg / mL Solution Nasal 0.1 mg / mL Aerosol, metered Nasal 10 mcg / act Solution Nasal 0.100 mg Solution Intravenous 4 mcg Solution Nasal; Respiratory (inhalation) 89 mcg Injection Intravenous 4 ug/1mL Injection Intravenous; Subcutaneous 4 ug/1mL Injection Intravenous; Subcutaneous 40 ug/10mL Injection, solution Intravenous; Subcutaneous 4 ug/1mL Injection, solution Intravenous; Subcutaneous 40 ug/10mL Powder Not applicable 1 g/1g Solution Nasal 0.1 mg/1mL Spray Nasal 0.1 mg/1mL Spray Nasal 10 ug/1 Spray Nasal 10 ug/0.1mL Tablet Oral 0.1 mg/1 Tablet Oral 0.2 mg/1 Tablet, orally disintegrating Sublingual 120 µg Tablet, orally disintegrating Sublingual 240 µg Tablet, orally disintegrating Sublingual 60 µg Spray, metered Nasal 10 mcg / act Tablet 120 MICROGRAMMI Tablet 240 MICROGRAMMI Tablet 60 MICROGRAMMI Spray Nasal 0.1 % Solution Sublingual 0.4 mg Solution Intrasinal; Nasal 0.1 mg Injection, solution Intravenous; Subcutaneous 40 mcg Injection, solution Parenteral 20 MCG/1ML Injection, solution Parenteral 4 MCG/0.5ML Solution Intramuscular; Intravenous; Subcutaneous 20 cg Solution Intramuscular; Intravenous; Subcutaneous 4 mcg Solution Intramuscular; Intravenous; Subcutaneous 400000 mcg Tablet, orally disintegrating Oral 120 cg Tablet, soluble Oral Solution Intrasinal; Nasal 10 mg Solution Intramuscular; Intravenous; Subcutaneous 4 cg Solution Intravenous; Subcutaneous 0.025 mg Solution Nasal 89 mcg Solution Parenteral 15.00 mcg Tablet Tablet Oral Tablet Oral 89 mcg Injection, solution Intramuscular; Intravenous 4 μg Solution Nasal Solution 100 mcg/1ml Injection, solution 4 mcg/1ml Spray Nasal 100 mcg/1ml Solution Nasal; Respiratory (inhalation) 0.089 mg Injection, solution Intramuscular; Intravenous 4 mcg/ml Injection Intramuscular; Intravenous; Subcutaneous 4 mcg/ml Injection Intravenous Tablet Oral 60 mcg Tablet Oral 120 mcg Powder Oral 120 cg Powder Oral 120 µg Powder Oral 240 µg Powder Oral 60 µg Spray Nasal 0.1 mg/ml Solution Nasal 0.1 mg/ml Tablet, orally disintegrating Sublingual 120 mcg Tablet, orally disintegrating Sublingual 240 mcg Tablet, orally disintegrating Sublingual 60 mcg Tablet, orally disintegrating Sublingual Tablet Oral 0.1 mg Tablet Oral 0.2 mg Tablet 100 mcg Tablet 200 mcg Injection, solution 4 MCG/ML Solution / drops Nasal 0.1 MG/ML Spray Nasal 50 MCG/ML Tablet 0.1 MG Tablet 0.2 MG Tablet 120 MCG Tablet 240 MCG Tablet 60 MCG Solution Nasal 0.09 mg Solution Oral Aerosol Nasal 89.000 mg Solution Parenteral 13.400 mcg Tablet Oral 178.000 mcg Tablet Sublingual 27.7 ug/1 Tablet Sublingual 55.3 ug/1 Tablet, orally disintegrating Sublingual 25 mcg Tablet, orally disintegrating Sublingual 50 mcg Powder Oral 25 mcg Powder Oral Powder Oral 50 mcg Spray, metered Nasal 0.83 ug/1 Spray, metered Nasal 1.66 ug/1 Tablet, orally disintegrating Sublingual 120 Mikrogramm Tablet, orally disintegrating Sublingual 240 Mikrogramm Tablet, orally disintegrating Sublingual 60 Mikrogramm Spray, metered Nasal 0.1 g / L Solution Parenteral 30.0 mcg Solution Intravenous; Subcutaneous 15 mcg Spray Nasal 1.5 mg/ml Solution Intravenous; Subcutaneous 15 µg/ml Injection, solution Intravenous; Subcutaneous Injection, solution Intravenous; Subcutaneous 15 mcg/ml Solution Intravenous; Subcutaneous 15 mcg / mL Spray Nasal 150 mcg / act Solution Nasal 89.00 mcg Spray Nasal Spray, metered Nasal 0.1 mg/ml Tablet Sublingual 120 mcg Tablet Sublingual 60 mcg Solution Intravenous 15.000 mcg Spray, metered Nasal 1.5 mg/1mL Solution / drops Nasal 100 mcg/1ml Injection, solution 15 mcg/1ml - Prices
Unit description Cost Unit Stimate 1.5 mg/ml nasal spray 334.2USD ml Ddavp 0.01% nasal spray 50.76USD ml Ddavp 4 mcg/ml ampul 43.27USD ml Desmopressin 0.1 mg/ml spray 39.6USD ml Ddavp 0.1 mg/ml Solution 21.26USD ml Octostim 150 mcg/dose Metered Dose Spray 17.39USD dose Ddavp 4 mcg/ml 11.33USD ml Desmopressin ac 4 mcg/ml amp 7.28USD ml Desmopressin ac 4 mcg/ml vial 7.08USD ml Ddavp 0.2 mg tablet 6.43USD tablet Ddavp 0.1 mg tablet 4.47USD tablet Desmopressin acetate 0.2 mg tablet 4.44USD tablet Desmopressin acetate 0.1 mg tablet 3.08USD tablet Ddavp 0.2 mg Tablet 2.98USD tablet Ddavp 10 mcg/dose Metered Dose Spray 2.13USD dose Apo-Desmopressin 0.2 mg Tablet 1.67USD tablet Novo-Desmopressin 0.2 mg Tablet 1.67USD tablet Pms-Desmopressin 0.2 mg Tablet 1.67USD tablet Ddavp 0.1 mg Tablet 1.49USD tablet Apo-Desmopressin 10 mcg/dose Metered Dose Spray 1.48USD dose Apo-Desmopressin 0.1 mg Tablet 0.83USD tablet Novo-Desmopressin 0.1 mg Tablet 0.83USD tablet Pms-Desmopressin 0.1 mg Tablet 0.83USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7022340 No 2006-04-04 2023-04-30 US US5500413 No 1996-03-19 2013-06-29 US CA2484724 No 2007-01-16 2023-05-07 Canada CA2486833 No 2005-08-02 2024-04-30 Canada US9539302 No 2017-01-10 2030-06-15 US US7799761 No 2010-09-21 2024-09-26 US US7405203 No 2008-07-29 2023-05-06 US US7579321 No 2009-08-25 2023-05-06 US US9919025 No 2018-03-20 2023-05-07 US US9220747 No 2015-12-29 2023-05-07 US US9504647 No 2016-11-29 2023-05-07 US US9974826 No 2018-05-22 2030-04-13 US US8802624 No 2014-08-12 2023-12-29 US US7560429 No 2009-07-14 2024-02-02 US US7947654 No 2011-05-24 2023-12-29 US US10137167 No 2018-11-27 2029-05-21 US US10307459 No 2019-06-04 2023-05-07 US US11020448 No 2021-06-01 2029-05-21 US US11419914 No 2010-06-15 2030-06-15 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.11 mg/mL ALOGPS logP -1 ALOGPS logP -6.1 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 9.5 Chemaxon pKa (Strongest Basic) 11.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 14 Chemaxon Polar Surface Area 435.41 Å2 Chemaxon Rotatable Bond Count 19 Chemaxon Refractivity 279.78 m3·mol-1 Chemaxon Polarizability 104.78 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 - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7979 Blood Brain Barrier - 0.8866 Caco-2 permeable - 0.7612 P-glycoprotein substrate Substrate 0.8242 P-glycoprotein inhibitor I Non-inhibitor 0.7864 P-glycoprotein inhibitor II Non-inhibitor 0.9237 Renal organic cation transporter Non-inhibitor 0.5915 CYP450 2C9 substrate Non-substrate 0.7833 CYP450 2D6 substrate Non-substrate 0.7901 CYP450 3A4 substrate Non-substrate 0.5497 CYP450 1A2 substrate Non-inhibitor 0.8383 CYP450 2C9 inhibitor Non-inhibitor 0.7906 CYP450 2D6 inhibitor Non-inhibitor 0.8735 CYP450 2C19 inhibitor Non-inhibitor 0.765 CYP450 3A4 inhibitor Non-inhibitor 0.7663 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9331 Ames test Non AMES toxic 0.6679 Carcinogenicity Non-carcinogens 0.8428 Biodegradation Not ready biodegradable 0.9445 Rat acute toxicity 2.7183 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.83 hERG inhibition (predictor II) Inhibitor 0.6036
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Vasopressin receptor activity
- Specific Function
- Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. Involved in renal water reabsorption.
- Gene Name
- AVPR2
- Uniprot ID
- P30518
- Uniprot Name
- Vasopressin V2 receptor
- Molecular Weight
- 40278.57 Da
References
- Del Tredici AL, Vanover KE, Knapp AE, Bertozzi SM, Nash NR, Burstein ES, Lameh J, Currier EA, Davis RE, Brann MR, Mohell N, Olsson R, Piu F: Identification of novel selective V2 receptor non-peptide agonists. Biochem Pharmacol. 2008 Oct 30;76(9):1134-41. doi: 10.1016/j.bcp.2008.08.004. Epub 2008 Aug 12. [Article]
- Slusarz MJ, Slusarz R, Ciarkowski J: Investigation of mechanism of desmopressin binding in vasopressin V2 receptor versus vasopressin V1a and oxytocin receptors: molecular dynamics simulation of the agonist-bound state in the membrane-aqueous system. Biopolymers. 2006 Apr 5;81(5):321-38. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Vasopressin receptor activity
- Specific Function
- Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl-inositol-calcium second messenger system. Has been involved in social behavi...
- Gene Name
- AVPR1A
- Uniprot ID
- P37288
- Uniprot Name
- Vasopressin V1a receptor
- Molecular Weight
- 46799.105 Da
References
- Loichot C, Cazaubon C, De Jong W, Helwig JJ, Nisato D, Imbs JL, Barthelmebs M: Nitric oxide, but not vasopressin V2 receptor-mediated vasodilation, modulates vasopressin-induced renal vasoconstriction in rats. Naunyn Schmiedebergs Arch Pharmacol. 2000 Mar;361(3):319-26. [Article]
- Mechaly I, Laurent F, Portet K, Serrano J, Cros G: Vasopressin V2 (SR121463A) and V1a (SR49059) receptor antagonists both inhibit desmopressin vasorelaxing activity. Eur J Pharmacol. 1999 Nov 3;383(3):287-90. [Article]
- Barthelmebs M, Krieger JP, Grima M, Nisato D, Imbs JL: Vascular effects of [Arg8]vasopressin in the isolated perfused rat kidney. Eur J Pharmacol. 1996 Oct 31;314(3):325-32. [Article]
- Pequeux C, Keegan BP, Hagelstein MT, Geenen V, Legros JJ, North WG: Oxytocin- and vasopressin-induced growth of human small-cell lung cancer is mediated by the mitogen-activated protein kinase pathway. Endocr Relat Cancer. 2004 Dec;11(4):871-85. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Vasopressin receptor activity
- Specific Function
- Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl-inositol-calcium second messenger system.
- Gene Name
- AVPR1B
- Uniprot ID
- P47901
- Uniprot Name
- Vasopressin V1b receptor
- Molecular Weight
- 46970.345 Da
References
- Pequeux C, Keegan BP, Hagelstein MT, Geenen V, Legros JJ, North WG: Oxytocin- and vasopressin-induced growth of human small-cell lung cancer is mediated by the mitogen-activated protein kinase pathway. Endocr Relat Cancer. 2004 Dec;11(4):871-85. [Article]
- Dinan TG, O'Brien S, Lavelle E, Scott LV: Further neuroendocrine evidence of enhanced vasopressin V3 receptor responses in melancholic depression. Psychol Med. 2004 Jan;34(1):169-72. [Article]
- Craighead M, Milne R, Campbell-Wan L, Watson L, Presland J, Thomson FJ, Marston HM, Macsweeney CP: Characterization of a novel and selective V1B receptor antagonist. Prog Brain Res. 2008;170:527-35. doi: 10.1016/S0079-6123(08)00440-8. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Kotnik P, Nielsen J, Kwon TH, Krzisnik C, Frokiaer J, Nielsen S: Altered expression of COX-1, COX-2, and mPGES in rats with nephrogenic and central diabetes insipidus. Am J Physiol Renal Physiol. 2005 May;288(5):F1053-68. Epub 2005 Jan 11. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Kotnik P, Nielsen J, Kwon TH, Krzisnik C, Frokiaer J, Nielsen S: Altered expression of COX-1, COX-2, and mPGES in rats with nephrogenic and central diabetes insipidus. Am J Physiol Renal Physiol. 2005 May;288(5):F1053-68. Epub 2005 Jan 11. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55