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Gadopiclenol

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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 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 Formula	C₃₅H₅₄GdN₇O₁₅
Molecular Weight	970.1 g/mol
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	21
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	352
Heavy Atom Count	58
Formal Charge	0
Complexity	1200
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	6
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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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