Identification

Name
Vasopressin
Accession Number
DB00067
Description

Antidiuretic hormone, also known as vasopressin, is a nine amino acid peptide secreted from the posterior pituitary. Antidiuretic hormone binds to receptors in the distal or collecting tubules of the kidney and promotes reabsorbtion of water back into the circulation

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 2140.46
Monoisotopic: 2138.869561874
Chemical Formula
C92H130N28O24S4
Synonyms
  • Vasopressin, unspecified
  • Vasopressina

Pharmacology

Indication

For the treatment of enuresis, polyuria, diabetes insipidus, polydipsia and oesophageal varices with bleeding

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Vasopressin is an antidiuretic hormone indicated for the prevention and treatment of postoperative abdominal distention, in abdominal roentgenography to dispel interfering gas shadows, and in diabetes insipidus. Vasopressin can cause contraction of smooth muscle of the gastrointestinal tract and of all parts of the vascular bed, especially the capillaries, small arterioles and venules. It has less effect on the smooth musculature of the large veins. Vasopressin may also be used to control bleeding in some forms of von Willebrand disease and to treat extreme cases of bed wetting in children. It may also play a role in memory formation although the mechanism is unknown.

Mechanism of action

Vasopressin acts on three different receptors, vasopressin receptor V1a (which initiates vasoconstriction, liver gluconeogenesis, platelet aggregation and release of factor VIII), vasopressin receptor V1b (which mediates corticotrophin secretion from the pituitary) and vasopressin receptor V2 which controls free water reabsorption in the renal medullar. The binding of vasopressin to the V2 receptor activates adenylate cyclase which causes the release of aquaporin 2 channels into the cells lining the renal medullar duct. This allows water to be reabsorbed down an osmotic gradient so the urine is more concentrated.

TargetActionsOrganism
AVasopressin V2 receptor
agonist
Humans
AVasopressin V1a receptorNot AvailableHumans
AVasopressin V1b receptorNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

1%

Metabolism

The majority of a dose of vasopressin is metabolized and rapidly destroyed in the liver and kidneys.

Route of elimination
Not Available
Half-life

10-20 minutes

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
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.
DrugInteraction
ArdeparinThe therapeutic efficacy of Vasopressin can be decreased when used in combination with Ardeparin.
BemiparinThe therapeutic efficacy of Vasopressin can be decreased when used in combination with Bemiparin.
CarbamazepineThe risk or severity of water intoxication can be increased when Carbamazepine is combined with Vasopressin.
DalteparinThe therapeutic efficacy of Vasopressin can be decreased when used in combination with Dalteparin.
DanaparoidThe therapeutic efficacy of Vasopressin can be decreased when used in combination with Danaparoid.
EnoxaparinThe therapeutic efficacy of Vasopressin can be decreased when used in combination with Enoxaparin.
HeparinThe therapeutic efficacy of Vasopressin can be decreased when used in combination with Heparin.
LevothyroxineLevothyroxine may increase the vasoconstricting activities of Vasopressin.
LidocaineThe risk or severity of hypertension can be increased when Vasopressin is combined with Lidocaine.
LiothyronineLiothyronine may increase the vasoconstricting activities of Vasopressin.
Additional Data Available
  • Extended Description
    Extended Description
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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
  • Avoid alcohol.

Products

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Product Ingredients
IngredientUNIICASInChI Key
ArgipressinY4907O6MFD113-79-1KBZOIRJILGZLEJ-LGYYRGKSSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PitressinInjection20 [USP'U]/1mLIntramuscular; SubcutaneousCardinal Health2007-10-012016-05-31US flag
PitressinInjection20 [USP'U]/1mLIntramuscular; SubcutaneousPar Pharmaceutical2007-10-012016-06-30US flag
PitressinInjection, solution20 [USP'U]/1mLIntramuscular; SubcutaneousPhysicians Total Care, Inc.2011-05-172011-09-30US flag
Pitressin Inj 10 Unit/0.5mlLiquidIntramuscular; SubcutaneousParke Davis Division, Warner Lambert Canada Inc.1971-12-311997-08-25Canada flag
Pressyn ArLiquidIntramuscular; SubcutaneousFerring Pharmaceuticals2002-11-042017-03-10Canada flag
VasopressinInjection, solution20 [USP'U]/1mLIntramuscular; SubcutaneousAmerican Regent1992-10-012013-05-01US flag
VasopressinInjection, solution20 [USP'U]/1mLIntramuscular; SubcutaneousGeneral Injectables & Vaccines2010-08-012013-03-01US flag
VasopressinInjection, solution20 [USP'U]/1mLIntramuscularCardinal Health2011-10-172012-03-31US flag
VasopressinInjection, solution20 [USP'U]/1mLIntravenous; SubcutaneousPhysicians Total Care, Inc.2011-05-172013-01-15US flag
VasopressinInjection20 [USP'U]/1mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2018-11-17Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
PitressinVasopressin (20 [USP'U]/1mL)InjectionIntramuscular; SubcutaneousCardinal Health2007-10-012016-05-31US flag
PitressinVasopressin (20 [USP'U]/1mL)InjectionIntramuscular; SubcutaneousPar Pharmaceutical2007-10-012016-06-30US flag
PitressinVasopressin (20 [USP'U]/1mL)Injection, solutionIntramuscular; SubcutaneousPhysicians Total Care, Inc.2011-05-172011-09-30US flag
VasopressinArgipressin (20 [USP'U]/1mL)Injection, solutionIntramuscular; SubcutaneousAmerican Regent1992-10-012013-05-01US flag
VasopressinArgipressin (20 [USP'U]/1mL)Injection, solutionIntramuscular; SubcutaneousGeneral Injectables & Vaccines2010-08-012013-03-01US flag
VasopressinArgipressin (20 [USP'U]/1mL)Injection, solutionIntravenous; SubcutaneousPhysicians Total Care, Inc.2011-05-172013-01-15US flag
VasopressinArgipressin (20 [USP'U]/1mL)Injection, solutionIntramuscular; SubcutaneousAmerican Regent1996-08-152013-07-01US flag
VasopressinVasopressin (20 [USP'U]/1mL)Injection, solutionIntramuscular; SubcutaneousGeneral Injectables & Vaccines2013-12-17Not applicableUS flag
VasopressinArgipressin (20 [USP'U]/1mL)Injection, solutionIntravenous; SubcutaneousPhysicians Total Care, Inc.2007-01-022013-01-15US flag
VasopressinVasopressin (20 [USP'U]/1mL)Injection, solutionIntramuscularCardinal Health2011-10-172012-03-31US flag

Categories

Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
Y87Y826H08
CAS number
11000-17-2
InChI Key
JLTCWSBVQSZVLT-UHFFFAOYSA-N
InChI
InChI=1S/C46H65N15O12S2.C46H65N13O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25;47-17-5-4-9-29(40(65)52-22-38(51)63)54-45(70)35-10-6-18-59(35)46(71)34-24-73-72-23-28(48)39(64)55-31(20-26-11-13-27(60)14-12-26)43(68)56-32(19-25-7-2-1-3-8-25)42(67)53-30(15-16-36(49)61)41(66)57-33(21-37(50)62)44(69)58-34/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53);1-3,7-8,11-14,28-35,60H,4-6,9-10,15-24,47-48H2,(H2,49,61)(H2,50,62)(H2,51,63)(H,52,65)(H,53,67)(H,54,70)(H,55,64)(H,56,68)(H,57,66)(H,58,69)
IUPAC Name
2-({1-[19-amino-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)-N-(carbamoylmethyl)-5-[(diaminomethylidene)amino]pentanamide; 6-amino-2-({1-[19-amino-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)-N-(carbamoylmethyl)hexanamide
SMILES
NCCCCC(NC(=O)C1CCCN1C(=O)C1CSSCC(N)C(=O)NC(CC2=CC=C(O)C=C2)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(N)=O)C(=O)N1)C(=O)NCC(N)=O.NC1CSSCC(NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC2=CC=C(O)C=C2)NC1=O)C(=O)N1CCCC1C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O

References

Synthesis Reference

Nedumparambil A. Abraham, Hans U. Immer, Kazimir Sestanj, "Process for producing triglycyl-lysine vasopressin and intermediates therefor." U.S. Patent US4093610, issued June, 1963.

US4093610
General References
  1. Bielsky IF, Hu SB, Szegda KL, Westphal H, Young LJ: Profound impairment in social recognition and reduction in anxiety-like behavior in vasopressin V1a receptor knockout mice. Neuropsychopharmacology. 2004 Mar;29(3):483-93. [PubMed:14647484]
  2. Wersinger SR, Caldwell HK, Martinez L, Gold P, Hu SB, Young WS 3rd: Vasopressin 1a receptor knockout mice have a subtle olfactory deficit but normal aggression. Genes Brain Behav. 2007 Aug;6(6):540-51. Epub 2006 Nov 3. [PubMed:17083331]
  3. Lolait SJ, Stewart LQ, Jessop DS, Young WS 3rd, O'Carroll AM: The hypothalamic-pituitary-adrenal axis response to stress in mice lacking functional vasopressin V1b receptors. Endocrinology. 2007 Feb;148(2):849-56. Epub 2006 Nov 22. [PubMed:17122081]
  4. Wersinger SR, Kelliher KR, Zufall F, Lolait SJ, O'Carroll AM, Young WS 3rd: Social motivation is reduced in vasopressin 1b receptor null mice despite normal performance in an olfactory discrimination task. Horm Behav. 2004 Dec;46(5):638-45. [PubMed:15555506]
  5. Kanwar S, Woodman RC, Poon MC, Murohara T, Lefer AM, Davenpeck KL, Kubes P: Desmopressin induces endothelial P-selectin expression and leukocyte rolling in postcapillary venules. Blood. 1995 Oct 1;86(7):2760-6. [PubMed:7545469]
KEGG Drug
D00101
KEGG Compound
C00840
PubChem Substance
46505933
ChemSpider
10152658
RxNav
11149
ChEMBL
CHEMBL373742
Therapeutic Targets Database
DAP000018
PharmGKB
PA451858
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Vasopressin
AHFS Codes
  • 68:28.00 — Pituitary
MSDS
Download (143 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceEndotoxaemia1
4CompletedPreventionHemorrhage1
4CompletedPreventionRenal Failure1
4CompletedTreatmentBlood Loss During Vaginal Hysterectomy1
4CompletedTreatmentBlood Loss,Surgical1
4CompletedTreatmentCardiac Arrest (CA)1
4Not Yet RecruitingPreventionAcute Kidney Injury (AKI) / End Stage Liver Diseases / Liver Cirrhosis / Liver Transplant; Complications1
4RecruitingPreventionAcute Kidney Injury (AKI)1
4RecruitingTreatmentShock1
4Unknown StatusTreatmentCardiac Arrest (CA)1

Pharmacoeconomics

Manufacturers
  • Parke davis div warner lambert co
Packagers
  • American Regent
  • APP Pharmaceuticals
  • APPD
  • A-S Medication Solutions LLC
  • Cardinal Health
  • JHP Pharmaceuticals LLC
  • Luitpold Pharmaceuticals Inc.
  • Monarch Pharmacy
  • PD-Rx Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
SolutionIntramuscular; Subcutaneous20 IU
Injection, solution, concentrateIntravenous40 I.E./2ml
Injection, solution20 mg/1mL
InjectionIntramuscular; Subcutaneous20 [USP'U]/1mL
Injection, solutionIntramuscular; Subcutaneous20 [USP'U]/1mL
LiquidIntramuscular; Subcutaneous
SolutionIntravenous20 IU
InjectionIntravenous20 IU/mL
Injection, solutionIntramuscular20 [USP'U]/1mL
Injection, solutionIntravenous; Subcutaneous20 [USP'U]/1mL
LiquidIntramuscular; Nasal; Subcutaneous
SolutionIntramuscular; Subcutaneous
InjectionIntravenous20 [USP'U]/1mL
InjectionIntravenous40 [USP'U]/100mL
InjectionIntravenous60 [USP'U]/100mL
Prices
Unit descriptionCostUnit
Pitressin 20 unit/ml vial7.68USD ml
Vasopressin 10 unit/0.5 ml vial2.88USD vial
Vasopressin 20 unit/ml vial1.86USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9687526No2017-06-272035-01-30US flag
US9375478No2016-06-282035-01-30US flag
US9744209No2017-08-292035-01-30US flag
US9744239No2017-08-292035-01-30US flag
US9750785No2017-09-052035-01-30US flag
US9937223No2018-04-102035-01-30US flag
US10010575No2015-01-302035-01-30US flag
US9925233No2015-01-302035-01-30US flag
US9974827No2015-01-302035-01-30US flag
US9968649No2015-01-302035-01-30US flag
US9962422No2015-01-302035-01-30US flag
US9925234No2015-01-302035-01-30US flag
US9981006No2015-01-302035-01-30US flag
US9919026No2015-01-302035-01-30US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

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

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.124 mg/mLALOGPS
logP-1.4ALOGPS
logP-7.2ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.65ChemAxon
pKa (Strongest Basic)11.5ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area463.93 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity272.59 m3·mol-1ChemAxon
Polarizability108.29 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
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
  1. Boson WL, Della Manna T, Damiani D, Miranda DM, Gadelha MR, Liberman B, Correa H, Romano-Silva MA, Friedman E, Silva FF, Ribeiro PA, De Marco L: Novel vasopressin type 2 (AVPR2) gene mutations in Brazilian nephrogenic diabetes insipidus patients. Genet Test. 2006 Fall;10(3):157-62. [PubMed:17020465]
  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. Bouley R, Hawthorn G, Russo LM, Lin HY, Ausiello DA, Brown D: Aquaporin 2 (AQP2) and vasopressin type 2 receptor (V2R) endocytosis in kidney epithelial cells: AQP2 is located in 'endocytosis-resistant' membrane domains after vasopressin treatment. Biol Cell. 2006 Apr;98(4):215-32. [PubMed:16563128]
  4. Yi X, Bouley R, Lin HY, Bechoua S, Sun TX, Del Re E, Shioda T, Raychowdhury MK, Lu HA, Abou-Samra AB, Brown D, Ausiello DA: Alix (AIP1) is a vasopressin receptor (V2R)-interacting protein that increases lysosomal degradation of the V2R. Am J Physiol Renal Physiol. 2007 May;292(5):F1303-13. Epub 2007 Feb 6. [PubMed:17287200]
  5. 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
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
  1. Hiroyama M, Wang S, Aoyagi T, Oikawa R, Sanbe A, Takeo S, Tanoue A: Vasopressin promotes cardiomyocyte hypertrophy via the vasopressin V1A receptor in neonatal mice. Eur J Pharmacol. 2007 Mar 22;559(2-3):89-97. Epub 2006 Dec 29. [PubMed:17275806]
  2. Liedman R, Grant L, Igidbashian S, James I, McLeod A, Skillern L, Akerlund M: Intrauterine pressure, ischemia markers, and experienced pain during administration of a vasopressin V1a receptor antagonist in spontaneous and vasopressin-induced dysmenorrhea. Acta Obstet Gynecol Scand. 2006;85(2):207-11. [PubMed:16532916]
  3. Adikesavan NV, Mahmood SS, Stanley N, Xu Z, Wu N, Thibonnier M, Shoham M: A C-terminal segment of the V1R vasopressin receptor is unstructured in the crystal structure of its chimera with the maltose-binding protein. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Apr 1;61(Pt 4):341-5. Epub 2005 Mar 24. [PubMed:16511036]
  4. Hammock EA, Lim MM, Nair HP, Young LJ: Association of vasopressin 1a receptor levels with a regulatory microsatellite and behavior. Genes Brain Behav. 2005 Jul;4(5):289-301. [PubMed:16011575]
  5. Aoyagi T, Birumachi J, Hiroyama M, Fujiwara Y, Sanbe A, Yamauchi J, Tanoue A: Alteration of glucose homeostasis in V1a vasopressin receptor-deficient mice. Endocrinology. 2007 May;148(5):2075-84. Epub 2007 Feb 15. [PubMed:17303660]
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
  1. Young WS, Li J, Wersinger SR, Palkovits M: The vasopressin 1b receptor is prominent in the hippocampal area CA2 where it is unaffected by restraint stress or adrenalectomy. Neuroscience. 2006 Dec 28;143(4):1031-9. Epub 2006 Oct 4. [PubMed:17027167]
  2. Volpi S, Liu Y, Aguilera G: Vasopressin increases GAGA binding activity to the V1b receptor promoter through transactivation of the MAP kinase pathway. J Mol Endocrinol. 2006 Jun;36(3):581-90. [PubMed:16720725]
  3. Wersinger SR, Caldwell HK, Christiansen M, Young WS 3rd: Disruption of the vasopressin 1b receptor gene impairs the attack component of aggressive behavior in mice. Genes Brain Behav. 2007 Oct;6(7):653-60. Epub 2006 Dec 20. [PubMed:17284170]
  4. Slusarz MJ, Gieldon A, Slusarz R, Ciarkowski J: Analysis of interactions responsible for vasopressin binding to human neurohypophyseal hormone receptors-molecular dynamics study of the activated receptor-vasopressin-G(alpha) systems. J Pept Sci. 2006 Mar;12(3):180-9. [PubMed:16114100]
  5. Jurkevich A, Berghman LR, Cornett LE, Kuenzel WJ: Characterization and immunohistochemical visualization of the vasotocin VT2 receptor in the pituitary gland of the chicken, Gallus gallus. Gen Comp Endocrinol. 2005 Aug;143(1):82-91. Epub 2005 Mar 23. [PubMed:15993108]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Madon J, Hagenbuch B, Landmann L, Meier PJ, Stieger B: Transport function and hepatocellular localization of mrp6 in rat liver. Mol Pharmacol. 2000 Mar;57(3):634-41. [PubMed:10692506]

Drug created on June 13, 2005 07:24 / Updated on October 31, 2020 10:29

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