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.

Structure

Similar Structures

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

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

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Ddavp	Tablet	0.1 mg/1	Oral	Ferring Pharmaceuticals Inc.	1995-09-06	Not applicable
Ddavp	Tablet	0.2 mg/1	Oral	Sanofi Aventis	1995-09-06	2018-10-24
Ddavp	Injection	4 ug/1mL	Intravenous	Ferring Pharmaceuticals Inc.	1984-03-30	Not applicable
Ddavp	Spray	0.1 ug/1mL	Nasal	Ferring Pharmaceuticals Inc.	1978-02-21	Not applicable
Ddavp	Tablet	0.1 mg/1	Oral	Sanofi Aventis	1995-09-06	2018-10-24
Ddavp	Injection	4 ug/1mL	Intravenous	Ferring Pharmaceuticals Inc.	1984-03-30	Not applicable
Ddavp	Spray	0.1 mg/1mL	Nasal	Ferring Pharmaceuticals Inc.	1978-02-21	Not applicable
Ddavp	Solution	0.1 mg/1mL	Nasal	Sanofi Aventis	1978-02-21	2018-10-11
Ddavp	Solution	4 ug/1mL	Intravenous	Physicians Total Care, Inc.	1984-03-30	2010-06-30
Ddavp	Tablet	0.2 mg/1	Oral	Ferring Pharmaceuticals Inc.	1995-09-06	Not applicable

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Application Number

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Product Code

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Desmopressin Acetate	Tablet	0.2 mg/1	Oral	Mylan Institutional	2007-12-26	2017-11-30
Desmopressin Acetate	Tablet	0.2 mg/1	Oral	Glenmark Pharmaceuticals Inc.,Usa	2015-05-28	Not applicable
Desmopressin Acetate	Tablet	0.2 mg/1	Oral	Apotex Corporation	2006-03-07	Not applicable
Desmopressin Acetate	Tablet	0.1 mg/1	Oral	Impax Generics	2006-01-27	2019-08-31
Desmopressin Acetate	Solution	0.1 mg/1mL	Nasal	Bauch & Lomb Incorporated	1999-01-25	Not applicable
Desmopressin Acetate	Tablet	0.1 mg/1	Oral	Actavis Pharma, Inc.	2011-08-15	Not applicable
Desmopressin Acetate	Spray	0.1 mg/1mL	Nasal	Cadila Healthcare Limited	2018-02-01	Not applicable
Desmopressin Acetate	Tablet	0.2 mg/1	Oral	bryant ranch prepack	2011-08-15	Not applicable
Desmopressin Acetate	Spray	10 ug/0.1mL	Nasal	Prasco, Laboratories	2014-01-01	Not applicable
Desmopressin Acetate	Tablet	0.2 mg/1	Oral	BluePoint Laboratories	2014-02-27	Not applicable

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Application Number

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Product Code

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International/Other Brands

Adiuretin (Ferring) / DesmoMelt (Ferring)

Categories

UNII

ENR1LLB0FP

CAS number

16679-58-6

Weight

Average: 1069.22
Monoisotopic: 1068.426955905

Chemical Formula

C₄₆H₆₄N₁₄O₁₂S₂

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

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).

Associated Conditions

Pharmacodynamics

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	agonist	Humans
AVasopressin V1a receptor	Not Available	Humans
AVasopressin V1b receptor	Not Available	Humans

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Adverse Effects

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Contraindications

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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

Toxicity

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.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

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
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1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	The risk or severity of hypertension can be increased when Desmopressin is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazole	The risk or severity of hypertension can be increased when Desmopressin is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of hypertension can be increased when Desmopressin is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of hypertension can be increased when Desmopressin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of hypertension can be increased when Desmopressin is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The risk or severity of hypertension can be increased when Desmopressin is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of hypertension can be increased when Desmopressin is combined with 5-methoxy-N,N-dimethyltryptamine.
Abacavir	Desmopressin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abediterol	The risk or severity of hypertension can be increased when Desmopressin is combined with Abediterol.
Acarbose	Desmopressin may decrease the excretion rate of Acarbose which could result in a higher serum level.

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Extended Description

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Severity

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Action

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Food Interactions

Not Available

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. [PubMed:11380629]
Richardson DW, Robinson AG: Desmopressin. Ann Intern Med. 1985 Aug;103(2):228-39. [PubMed:3893256]
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. [PubMed:18690973]
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. [PubMed:15373927]
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. [PubMed:8222299]
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
ChEBI: 4450
ChEMBL: CHEMBL1429
Therapeutic Targets Database: DNC000526
PharmGKB: PA449237
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Desmopressin

ATC Codes

H01BA02 — Desmopressin

AHFS Codes

68:28.00 — Pituitary

FDA label

Download (1.22 MB)

MSDS

Download (26.2 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Not Yet Recruiting	Treatment	Castrate Resistance Prostate Cancer	1
1	Completed	Not Available	Healthy Volunteers	1
1	Completed	Diagnostic	Hemophilia A	1
1	Completed	Treatment	Bleeding / Dyspnea / Tachycardia	1
1	Completed	Treatment	High Blood Pressure (Hypertension)	1
1	Recruiting	Treatment	Cerebrovascular Stroke / Intracranial Arteriosclerosis / Large-Artery Atherosclerosis (Embolus/Thrombosis)	1
2	Completed	Not Available	Breast Cancer	1
2	Completed	Other	Colorectal Cancers / Rectal hemorrhage	1
2	Completed	Treatment	Cerebral Hemorrhage	1
2	Completed	Treatment	Nocturia	4
2	Completed	Treatment	Urinary Bladder, Overactive	1
2	Recruiting	Treatment	Stroke, Acute	1
2	Terminated	Treatment	Nocturia	1
2	Unknown Status	Treatment	Postoperative Ecchymosis	1
2, 3	Terminated	Treatment	Leptospirosis	1
2, 3	Terminated	Treatment	Nocturia	1
3	Completed	Treatment	Central Diabetes Insipidus	1
3	Completed	Treatment	Nocturia	9
3	Completed	Treatment	Nocturnal Enuresis	2
3	Completed	Treatment	Primary Nocturnal Enuresis	1
3	Recruiting	Treatment	Nocturnal Enuresis / Sickle Cell Anemia	1
3	Terminated	Treatment	Nocturia / Obstructive Sleep Apnoea (OSA)	1
3	Unknown Status	Treatment	Pain / Renal Colic	1
4	Active Not Recruiting	Prevention	C.Surgical Procedure; Cardiac / Disorders, Blood Coagulation	1
4	Completed	Diagnostic	Monosymptomatic Nocturnal Enuresis	1
4	Completed	Prevention	Blood Loss,Surgical / Hemorrhage / Postoperative Hemorrhages	1
4	Completed	Prevention	Patients Undergoing Endoscopic Sinus Surgery	1
4	Completed	Prevention	Renal Failure	1
4	Completed	Treatment	Acquired Von Willebrand Disease Secondary to Severe Aortic Stenosis / Heye´s Syndrome / Severe Aortic Stenosis	1
4	Completed	Treatment	Enuresis / Polyuria	1
4	Completed	Treatment	Hemophilia A	1
4	Completed	Treatment	Monosymptomatic Nocturnal Enuresis	1
4	Completed	Treatment	Nocturia	1
4	Completed	Treatment	Nocturnal Enuresis	1
4	Completed	Treatment	Nocturnal Polyuria	1
4	Completed	Treatment	Primary Nocturnal Enuresis	1
4	Recruiting	Treatment	Children With Mild Hemophilia A / Mild Haemophilia A Without Inhibitor	1
4	Recruiting	Treatment	Enuresis, Nocturnal	1
4	Terminated	Treatment	Hemorrhage / Postoperative Blood Loss	1
4	Terminated	Treatment	Parkinson's Disease (PD)	1
4	Unknown Status	Treatment	Hypothermia Induced Impairment of Primary Haemostasis	1
4	Unknown Status	Treatment	Nocturia	1
4	Unknown Status	Treatment	Nocturnal Enuresis	1
4	Withdrawn	Other	Kidney Damage	1
Not Available	Completed	Not Available	Determine if Sweat [Na+] is Regulated by the V2R / Electrolyte imbalance / Hypernatremia / Hyponatremia	1
Not Available	Completed	Not Available	Head Injury Trauma Blunt	1
Not Available	Completed	Not Available	Nocturia Associated With Nocturnal Polyuria	1
Not Available	Completed	Not Available	Platelets Dysfunction	1
Not Available	Completed	Basic Science	Gender Difference in V2 Receptor Function in Response to dDAVP Infusion / Nocturia / Nocturnal Enuresis	1
Not Available	Completed	Prevention	Blood Platelet Disorders / Disorders, Blood Coagulation / Hematologic Diseases / Hypermenorrhea / Von Willebrand 's disease Type 1	1
Not Available	Completed	Screening	Diabetes Insipidus / Diabetes Insipidus, Neurohypophyseal	1
Not Available	Completed	Treatment	Coagulation Disorders / Liver Cirrhosis	1
Not Available	Completed	Treatment	Desmopressin / Hemodilution / Mild Hypothermia / NSAIDs / Platelets Dysfunction	1
Not Available	Completed	Treatment	Renal Colic	1
Not Available	Not Yet Recruiting	Treatment	Monosymptomatic Nocturnal Enuresis	1
Not Available	Recruiting	Not Available	Nocturia	1
Not Available	Unknown Status	Not Available	Acquired Haemophilia	1
Not Available	Unknown Status	Screening	Diabetes Insipidus	1
Not Available	Unknown Status	Treatment	Idiopathic Scoliosis	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	Nasal	0.1 mg/1mL
Spray	Nasal	0.1 ug/1mL
Spray	Nasal	0.1 mg/1mL
Tablet	Oral	0.1 mg/1
Tablet	Oral	0.2 mg/1
Liquid	Intramuscular; Intravenous; Subcutaneous
Tablet, orally disintegrating	Sublingual
Solution	Nasal
Aerosol, metered	Nasal
Tablet	Oral
Injection	Intravenous	4 ug/1mL
Injection, solution	Intravenous; Subcutaneous	4 ug/1mL
Injection, solution	Intravenous; Subcutaneous	40 ug/10mL
Powder	Not applicable	1 g/1g
Solution	Intravenous	4 ug/1mL
Spray	Nasal	10 ug/1
Spray	Nasal	10 ug/0.1mL
Spray, metered	Nasal
Tablet	Sublingual	27.7 ug/1
Tablet	Sublingual	55.3 ug/1
Tablet, orally disintegrating	Sublingual	25 mcg
Tablet, orally disintegrating	Sublingual	50 mcg
Spray, metered	Nasal	0.83 ug/1
Spray, metered	Nasal	1.66 ug/1
Liquid	Intravenous; Subcutaneous
Spray	Nasal
Spray, metered	Nasal	1.5 mg/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)
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US7022340	No	2006-04-04	2023-04-30
US5500413	No	1996-03-19	2013-06-29
CA2484724	No	2007-01-16	2023-05-07
CA2486833	No	2005-08-02	2024-04-30
US9539302	No	2017-01-10	2030-06-15
US7799761	No	2010-09-21	2024-09-26
US7405203	No	2008-07-29	2023-05-06
US7579321	No	2009-08-25	2023-05-06
US9919025	No	2018-03-20	2023-05-07
US9220747	No	2015-12-29	2023-05-07
US9504647	No	2016-11-29	2023-05-07
US9974826	No	2018-05-22	2030-04-13
US8802624	No	2014-08-12	2023-12-29
US7560429	No	2009-07-14	2024-02-02
US7947654	No	2011-05-24	2023-12-29
US10137167	No	2018-11-27	2029-05-21
US10307459	No	2019-06-04	2023-05-07

Additional Data Available

Filed On

The date on which a patent was filed with the relevant government.

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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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST): Not Available
Spectra: Not Available

Taxonomy

Classification: Not classified

Targets

Details1. Vasopressin V2 receptor

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. [PubMed:18761325]
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. [PubMed:16333859]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Details2. Vasopressin V1a receptor

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. [PubMed:10731046]
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. [PubMed:10594321]
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. [PubMed:8957254]
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. [PubMed:15613460]

Details3. Vasopressin V1b receptor

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. [PubMed:15613460]
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. [PubMed:14971638]
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. [PubMed:18655906]

Enzymes

Details1. Prostaglandin G/H synthase 1

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. [PubMed:15644490]

Details2. Prostaglandin G/H synthase 2

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. [PubMed:15644490]

Drug created on June 13, 2005 07:24 / Updated on January 23, 2020 17:07

Desmopressin

Identification

Structure for Desmopressin (DB00035)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References

Enzymes

References

References