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Chemistry

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Also known as: Unii-s276568koy, Gadopiclenol [usan], S276568koy, Elucirem, P03277, Who 10744
Molecular Formula
C35H54GdN7O15
Molecular Weight
970.1  g/mol
InChI Key
GNRQMLROZPOLDG-UHFFFAOYSA-K
FDA UNII
S276568KOY

Gadopiclenol
Gadopiclenol is a gadolinium-based paramagnetic contrast agent, with potential imaging enhancing activity upon magnetic resonance imaging (MRI). Upon administration of gadopiclenol and placement in a magnetic field, this agent produces a large magnetic moment and creates a large local magnetic field, which can enhance the relaxation rate of nearby protons. This change in proton relaxation dynamics, increases the MRI signal intensity of tissues in which this agent has accumulated; therefore, contrast and visualization of those tissues is enhanced compared to unenhanced MRI.
1 2D Structure

Gadopiclenol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[3,9-bis[1-carboxylato-4-(2,3-dihydroxypropylamino)-4-oxobutyl]-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]-5-(2,3-dihydroxypropylamino)-5-oxopentanoate;gadolinium(3+)
2.1.2 InChI
InChI=1S/C35H57N7O15.Gd/c43-19-24(46)14-36-30(49)7-4-27(33(52)53)40-10-12-41(28(34(54)55)5-8-31(50)37-15-25(47)20-44)17-22-2-1-3-23(39-22)18-42(13-11-40)29(35(56)57)6-9-32(51)38-16-26(48)21-45;/h1-3,24-29,43-48H,4-21H2,(H,36,49)(H,37,50)(H,38,51)(H,52,53)(H,54,55)(H,56,57);/q;+3/p-3
2.1.3 InChI Key
GNRQMLROZPOLDG-UHFFFAOYSA-K
2.1.4 Canonical SMILES
C1CN(CC2=NC(=CC=C2)CN(CCN1C(CCC(=O)NCC(CO)O)C(=O)[O-])C(CCC(=O)NCC(CO)O)C(=O)[O-])C(CCC(=O)NCC(CO)O)C(=O)[O-].[Gd+3]
2.2 Other Identifiers
2.2.1 UNII
S276568KOY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3,6,9,15-tetraazabicyclo(9.3.1)pentadeca-1(15),11,13-triene-3,6,9-triacetic Acid, Alpha, Alpha', Alpha''-tris(3-((2,3-dihydroxypropyl)amino)-3-oxopropyl)-, Gadolinium Salt (1:1)

2. Gadolinium 2,2',2''-(3,6,9,15-tetraazabicyclo(9.3.1)pentadeca-1(15),11,13-triene-3,6,9-triyl)tris(5-((2,3-dihydroxypropyl)amino)-5-oxopentanoate)

2.3.2 Depositor-Supplied Synonyms

1. Unii-s276568koy

2. Gadopiclenol [usan]

3. S276568koy

4. Elucirem

5. P03277

6. Who 10744

7. 933983-75-6

8. P-03277

9. (alpha3,alpha6,alpha9-tris(3-((2,3-dihydroxypropyl)amino)-3-oxopropyl)-3,6,9,15-tetraazabicyclo(9.3.1)pentadeca-1(15),11,13-triene-3,6,9-triacetato(3-)-kappan3,kappan6,kappan9,kappan15,kappao3,kappao6,kappao9)gadolinium

10. 2-[3,9-bis[1-carboxylato-4-(2,3-dihydroxypropylamino)-4-oxobutyl]-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]-5-(2,3-dihydroxypropylamino)-5-oxopentanoate;gadolinium(3+)

11. Gadopiclenolum

12. Vueway

13. Gadopiclenol [inn]

14. Schembl21682611

15. Gbca P03277

16. P 03277

17. Gadolinium-based Magnetic Resonance Contrast Agent P03277

18. (.alpha.3,.alpha.6,.alpha.9-tris(3-((2,3-dihydroxypropyl)amino)-3-oxopropyl)-3,6,9,15-tetraazabicyclo(9.3.1)pentadeca-1(15),11,13-triene-3,6,9-triacetato(3-)-.kappa.n3,.kappa.n6,.kappa.n9,.kappa.n15,.kappa.o3,.kappa.o6,.kappa.o9)gadolinium

19. Gadolinium, (.alpha.3, .alpha.6, .alpha.9-tris(3-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-3-oxopropyl)-3,6,9,15-tetraazabicyclo(9.3.1)pentadeca-1(15),11,13-triene-3,6,9-triacetato(3-)-.kappa.n3, .kappa.n6, .kappa.n9, .kappa.n15, .kappa.o3, .kappa.o6, .kappa.o9)

20. Gadolinium, (alpha3, Alpha6, Alpha9-tris(3-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-3-oxopropyl)-3,6,9,15-tetraazabicyclo(9.3.1)pentadeca-1(15),11,13-triene-3,6,9-triacetato(3-)-kappan3, Kappan6, Kappan9, Kappan15, Kappao3, Kappao6, Kappao9)

2.4 Create Date
2007-07-23
3 Chemical and Physical Properties
Molecular Weight 970.1 g/mol
Molecular Formula C35H54GdN7O15
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count19
Rotatable Bond Count21
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area352
Heavy Atom Count58
Formal Charge0
Complexity1200
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count6
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Indication

Gadopiclenol is indicated in adult and pediatric patients aged 2 years and older for use with magnetic resonance imaging (MRI) to detect and visualize lesions with abnormal vascularity in the central nervous system (brain, spine, and associated tissues) and the body (head and neck, thorax, abdomen, pelvis, and musculoskeletal system).


Detection and visualization of disorders or lesions with suspected abnormal vascularity in various body regions for diagnostic purposes


Detection and visualisation of areas with disruption of the blood brain barrier and/or abnormal vascularity for diagnostic purposes


5 Pharmacology and Biochemistry
5.1 ATC Code

V - Various

V08 - Contrast media

V08C - Magnetic resonance imaging contrast media

V08CA - Paramagnetic contrast media

V08CA12 - Gadopiclenol


5.2 Absorption, Distribution and Excretion

Absorption

At a dose range between 0.025 mmol/kg and 0.3 mmol/kg (0.5 times to 6 times the recommended dosage), the Cmax and AUCinf of gadopiclenol increases in a dose-proportional manner. At the recommended dose, gadopiclenol has a Cmax of 525 g/mL and an AUCinf of 569 gh/mL. A study that evaluated the pharmacokinetic parameters of gadopiclenol in healthy subjects and patients with brain lesions did not detect significant differences between the two groups.


Route of Elimination

Gadopiclenol is mainly excreted in urine by glomerular filtration. Within 48 hours after administration, approximately 98% of the gadopiclenol dose was recovered in urine.


Volume of Distribution

At steady state, the mean volume of distribution of gadopiclenol is 13 L.


Clearance

Gadopiclenol has a total body clearance of 100 mL/min and a renal clearance of 81 mL/min.


5.3 Metabolism/Metabolites

Gadopiclenol is not metabolized and is eliminated unchanged.


5.4 Biological Half-Life

Gadopiclenol has a mean elimination half-life of is 1.5 hours.


5.5 Mechanism of Action

Gadopiclenol is a macrocyclic non-ionic complex of gadolinium and a paramagnetic molecule that develops a magnetic moment when placed in a magnetic field. The magnetic moment alters the relaxation rates of water protons in its vicinity in the body. Its use in magnetic resonance imaging (MRI) allows to selectively increase contrast in tissues where gadopiclenol accumulates.


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