Identification

Name
Desmopressin
Accession Number
DB00035  (BTD00112, BTD00061, BIOD00112, BIOD00061)
Type
Small Molecule
Groups
Approved
Description

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
Thumb
Synonyms
  • 1-(3-mercaptopropionic acid)-8-D-arginine-vasopressin
  • 1-deamino-8-D-arginine vasopressin
  • 1-desamino-8-D-arginine vasopressin
  • dDAVP
  • Desmopresina
  • Desmopressine
  • Desmopressinum
Product Ingredients
IngredientUNIICASInChI Key
Desmopressin acetateXB13HYU18U62357-86-2YNKFCNRZZPFMEX-XHPDKPNGSA-N
Desmopressin acetate anhydrous1K12647SFC62288-83-9MLSVJHOYXJGGTR-IFHOVBQLSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DdavpSolution4 ug/1mLIntravenousPhysicians Total Care, Inc.1984-03-302010-06-30Us
DdavpSpray0.1 ug/1mLNasalFerring Pharmaceuticals Inc.1978-02-21Not applicableUs
DdavpTablet0.1 mg/1OralSanofi Aventis1995-09-062018-10-24Us
DdavpInjection4 ug/1mLIntravenousFerring Pharmaceuticals Inc.1984-03-30Not applicableUs
DdavpSolution4 ug/1mLIntravenousSanofi Aventis1984-03-302018-08-08Us
DdavpTablet0.2 mg/1OralFerring Pharmaceuticals1995-09-06Not applicableUs
DdavpSpray0.1 mg/1mLNasalFerring Pharmaceuticals Inc.1978-02-21Not applicableUs
DdavpSolution0.1 mg/1mLNasalSanofi Aventis1978-02-212018-10-11Us
DdavpTablet0.1 mg/1OralFerring Pharmaceuticals1995-09-06Not applicableUs
DdavpTablet0.2 mg/1OralSanofi Aventis1995-09-062018-10-24Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desmopressin AcetateTablet0.1 mg/1OralImpax Generics2006-01-27Not applicableUs
Desmopressin AcetateTablet0.2 mg/1OralTeva2006-01-272017-12-31Us00093 7317 01 nlmimage10 02360120
Desmopressin AcetateSpray10 ug/0.1mLNasalPrasco, Laboratories2014-01-01Not applicableUs
Desmopressin AcetateTablet0.2 mg/1OralWatson Pharmaceuticals2011-01-142013-05-31Us0591 222620180907 15195 1pvcfe2
Desmopressin AcetateTablet0.1 mg/1OralApotex Corporation2006-03-07Not applicableUs
Desmopressin AcetateInjection, solution4 ug/1mLIntravenous; SubcutaneousSun Pharmaceutical Industries, Inc.2013-01-30Not applicableUs
Desmopressin acetateInjection4 ug/1mLIntravenousTeva Parenteral Medicines, Inc.1997-11-01Not applicableUs
Desmopressin AcetateTablet0.2 mg/1OralPhysicians Total Care, Inc.2007-07-19Not applicableUs54868 112920180907 15195 1piprr9
Desmopressin AcetateTablet0.2 mg/1OralAmerincan Health Packaging2010-01-122012-11-30Us
Desmopressin AcetateTablet0.2 mg/1OralGlenmark Pharmaceuticals Inc.,Usa2015-05-28Not applicableUs
International/Other Brands
Adiuretin (Ferring) / DesmoMelt (Ferring) / Minirin / Stimate
Categories
UNII
ENR1LLB0FP
CAS number
16679-58-6
Weight
Average: 1069.217
Monoisotopic: 1068.426954962
Chemical Formula
C46H64N14O12S2
InChI Key
NFLWUMRGJYTJIN-NXBWRCJVSA-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-/m0/s1
IUPAC Name
(2S)-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].

TargetActionsOrganism
AVasopressin V2 receptor
agonist
Human
AVasopressin V1a receptorNot AvailableHuman
AVasopressin V1b receptorNot AvailableHuman
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
DrugInteraction
AbacavirDesmopressin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseDesmopressin may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacThe risk or severity of hypertension, hyponatremia, and water intoxication can be increased when Aceclofenac is combined with Desmopressin.
AcemetacinThe risk or severity of hypertension, hyponatremia, and water intoxication can be increased when Acemetacin is combined with Desmopressin.
AcetaminophenDesmopressin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetylsalicylic acidThe risk or severity of hypertension, hyponatremia, and water intoxication can be increased when Acetylsalicylic acid is combined with Desmopressin.
AclidiniumDesmopressin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineDesmopressin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Desmopressin which could result in a higher serum level.
AdefovirAdefovir may decrease the excretion rate of Desmopressin which could result in a higher serum level.
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
  1. 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]
  2. Richardson DW, Robinson AG: Desmopressin. Ann Intern Med. 1985 Aug;103(2):228-39. [PubMed:3893256]
  3. 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]
  4. 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]
  5. 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]
  6. 32. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 399-400). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  7. DDVAP Nasal Spray FDA Label [Link]
  8. Stimate (desmopressin acetate) nasal spray FDA Label [Link]
  9. UKPAR for Desmopressin acetate 100mcg and 200mcg Tablets [Link]
External Links
Human Metabolome Database
HMDB0014260
KEGG Drug
D00291
KEGG Compound
C06944
ChemSpider
10481973
BindingDB
50205291
ChEBI
4450
ChEMBL
CHEMBL376685
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
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedDiagnosticHemophilia A1
1CompletedTreatmentDyspnea / Haemorrhage / Tachycardia1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
2CompletedNot AvailableCancer, Breast1
2CompletedOtherColorectal Cancers / Rectal haemorrhage1
2CompletedTreatmentIntracerebral Hemorrhage1
2CompletedTreatmentNocturia1
2Not Yet RecruitingTreatmentStroke, Acute1
2RecruitingTreatmentNocturia1
2TerminatedTreatmentNocturia1
2Unknown StatusTreatmentPostoperative Ecchymosis1
2, 3TerminatedTreatmentLeptospirosis1
2, 3TerminatedTreatmentNocturia1
3CompletedTreatmentCentral Diabetes Insipidus1
3CompletedTreatmentNocturia7
3CompletedTreatmentNocturnal Enuresis2
3CompletedTreatmentPrimary Nocturnal Enuresis1
3RecruitingTreatmentNocturnal Enuresis / Sickle Cell Disorders1
3TerminatedTreatmentNocturia / Obstructive Sleep Apnoea (OSA)1
3Unknown StatusTreatmentPain NOS / Renal Colic1
4Active Not RecruitingPreventionC.Surgical Procedure; Cardiac / Disorders, Blood Coagulation1
4CompletedPreventionBlood Loss,Surgical / Hemorrhage / Postoperative Hemorrhages1
4CompletedPreventionPatients Undergoing Endoscopic Sinus Surgery1
4CompletedPreventionRenal Failure1
4CompletedTreatmentAcquired Von Willebrand Disease Secondary to Severe Aortic Stenosis / Heye´s Syndrome / Severe Aortic Stenosis1
4CompletedTreatmentEnuresis / Polyuria1
4CompletedTreatmentNocturia1
4CompletedTreatmentNocturnal Polyuria1
4CompletedTreatmentPrimary Nocturnal Enuresis1
4Not Yet RecruitingOtherKidney Damage1
4RecruitingDiagnosticMonosymptomatic Nocturnal Enuresis1
4RecruitingTreatmentChildren With Mild Hemophilia A / Mild Haemophilia A Without Inhibitor1
4RecruitingTreatmentEnuresis, Nocturnal1
4TerminatedTreatmentHemorrhage / Postoperative Blood Loss1
4TerminatedTreatmentParkinson's Disease (PD)1
4Unknown StatusTreatmentHypothermia Induced Impairment of Primary Haemostasis1
4Unknown StatusTreatmentNocturia1
4Unknown StatusTreatmentNocturnal Enuresis1
Not AvailableCompletedNot AvailableHead Injury Trauma Blunt1
Not AvailableCompletedNot AvailableNocturia Associated With Nocturnal Polyuria1
Not AvailableCompletedNot AvailablePlatelets Dysfunction1
Not AvailableCompletedBasic ScienceGender Difference in V2 Receptor Function in Response to dDAVP Infusion / Nocturia / Nocturnal Enuresis1
Not AvailableCompletedPreventionBlood Platelet Disorders / Disorders, Blood Coagulation / Hematologic Diseases / Hypermenorrhea / Von Willebrand 's disease Type 11
Not AvailableCompletedScreeningDiabetes Insipidus / Diabetes Insipidus, Neurohypophyseal1
Not AvailableCompletedTreatmentCoagulation Disorders / Liver Cirrhosis1
Not AvailableCompletedTreatmentDesmopressin / Hemodilution / Mild Hypothermia / NSAIDs / Platelets Dysfunction1
Not AvailableCompletedTreatmentRenal Colic1
Not AvailableRecruitingNot AvailableNocturia1
Not AvailableUnknown StatusNot AvailableAcquired Haemophilia1
Not AvailableUnknown StatusScreeningDiabetes Insipidus1
Not AvailableUnknown StatusTreatmentIdiopathic Scoliosis1

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
FormRouteStrength
SolutionNasal0.1 mg/1mL
SprayNasal0.1 ug/1mL
TabletOral0.1 mg/1
TabletOral0.2 mg/1
LiquidIntramuscular; Intravenous; Subcutaneous4 mcg
Tablet, orally disintegratingSublingual120 mcg
Tablet, orally disintegratingSublingual240 mcg
Tablet, orally disintegratingSublingual60 mcg
SolutionNasal0.1 mg
Aerosol, meteredNasal10 mcg
TabletOral0.1 mg
TabletOral0.2 mg
InjectionIntravenous4 ug/1mL
Injection, solutionIntravenous; Subcutaneous4 ug/1mL
Injection, solutionIntravenous; Subcutaneous40 ug/10mL
SolutionIntravenous4 ug/1mL
SprayNasal0.1 mg/1mL
SprayNasal10 ug/1
SprayNasal10 ug/0.1mL
Spray, meteredNasal10 mcg
TabletSublingual27.7 ug/1
TabletSublingual55.3 ug/1
Tablet, orally disintegratingSublingual25 mcg
Tablet, orally disintegratingSublingual50 mcg
Spray, meteredNasal0.83 ug/1
Spray, meteredNasal1.66 ug/1
LiquidIntravenous; Subcutaneous15 mcg
SprayNasal150 mcg
Spray, meteredNasal1.5 mg/1mL
Prices
Unit descriptionCostUnit
Stimate 1.5 mg/ml nasal spray334.2USD ml
Ddavp 0.01% nasal spray50.76USD ml
Ddavp 4 mcg/ml ampul43.27USD ml
Desmopressin 0.1 mg/ml spray39.6USD ml
Ddavp 0.1 mg/ml Solution21.26USD ml
Octostim 150 mcg/dose Metered Dose Spray17.39USD dose
Ddavp 4 mcg/ml11.33USD ml
Desmopressin ac 4 mcg/ml amp7.28USD ml
Desmopressin ac 4 mcg/ml vial7.08USD ml
Ddavp 0.2 mg tablet6.43USD tablet
Ddavp 0.1 mg tablet4.47USD tablet
Desmopressin acetate 0.2 mg tablet4.44USD tablet
Desmopressin acetate 0.1 mg tablet3.08USD tablet
Ddavp 0.2 mg Tablet2.98USD tablet
Ddavp 10 mcg/dose Metered Dose Spray2.13USD dose
Apo-Desmopressin 0.2 mg Tablet1.67USD tablet
Novo-Desmopressin 0.2 mg Tablet1.67USD tablet
Pms-Desmopressin 0.2 mg Tablet1.67USD tablet
Ddavp 0.1 mg Tablet1.49USD tablet
Apo-Desmopressin 10 mcg/dose Metered Dose Spray1.48USD dose
Apo-Desmopressin 0.1 mg Tablet0.83USD tablet
Novo-Desmopressin 0.1 mg Tablet0.83USD tablet
Pms-Desmopressin 0.1 mg Tablet0.83USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7022340No2003-04-302023-04-30Us
US5500413No1993-06-292013-06-29Us
CA2484724No2007-01-162023-05-07Canada
CA2486833No2005-08-022024-04-30Canada
US9539302No2010-06-152030-06-15Us
US7799761No2004-09-262024-09-26Us
US7405203No2003-05-062023-05-06Us
US7579321No2003-05-062023-05-06Us
US9919025No2003-05-072023-05-07Us
US9220747No2003-05-072023-05-07Us
US9504647No2003-05-072023-05-07Us
US9974826No2010-04-132030-04-13Us
US8802624No2003-12-292023-12-29Us
US7560429No2004-02-022024-02-02Us
US7947654No2003-12-292023-12-29Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 mg/mLALOGPS
logP-1ALOGPS
logP-6.1ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)11.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area435.41 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity279.78 m3·mol-1ChemAxon
Polarizability104.7 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7979
Blood Brain Barrier-0.8866
Caco-2 permeable-0.7612
P-glycoprotein substrateSubstrate0.8242
P-glycoprotein inhibitor INon-inhibitor0.7864
P-glycoprotein inhibitor IINon-inhibitor0.9237
Renal organic cation transporterNon-inhibitor0.5915
CYP450 2C9 substrateNon-substrate0.7833
CYP450 2D6 substrateNon-substrate0.7901
CYP450 3A4 substrateNon-substrate0.5497
CYP450 1A2 substrateNon-inhibitor0.8383
CYP450 2C9 inhibitorNon-inhibitor0.7906
CYP450 2D6 inhibitorNon-inhibitor0.8735
CYP450 2C19 inhibitorNon-inhibitor0.765
CYP450 3A4 inhibitorNon-inhibitor0.7663
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9331
Ames testNon AMES toxic0.6679
CarcinogenicityNon-carcinogens0.8428
BiodegradationNot ready biodegradable0.9445
Rat acute toxicity2.7183 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.83
hERG inhibition (predictor II)Inhibitor0.6036
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Cyclic peptides / Arginine and derivatives / Proline and derivatives / N-acyl-alpha amino acids and derivatives / Macrolactams / Alpha amino acid amides / Pyrrolidinecarboxamides / N-acylpyrrolidines / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives
show 14 more
Substituents
Alpha-oligopeptide / Cyclic alpha peptide / Arginine or derivatives / N-acyl-alpha amino acid or derivatives / Proline or derivatives / Macrolactam / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / N-acylpyrrolidine
show 30 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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
  1. 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]
  2. 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]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
Kind
Protein
Organism
Human
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
  1. 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]
  2. 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]
  3. 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

Kind
Protein
Organism
Human
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
  1. 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]
Kind
Protein
Organism
Human
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
  1. 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 November 12, 2018 07:11