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Metopimazine-d6

CAT: 0804-HY-116578S-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-116578S-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Metopimazine-d6 (EXP999-d6; RP9965-d6) is the deuterium labeled Metopimazine. Metopimazine (EXP999; RP9965) is a phenothiazine, orally available, selective dopamine D2 receptor antagonist that does not penetrate the blood-brain barrier. Metopimazine blocks dopamine D2 receptors in the chemoreceptor trigger zone and the periphery, thereby inhibiting nausea and vomiting. Metopimazine is indicated for chemotherapy-induced nausea and vomiting, and has low central side effects due to its poor brain penetration. The use of metopimazine in acute gastroenteritis may have potential risks[1][2][3][4].
CAS Number
1215315-86-8
Product Name Alternative
EXP999-d6; RP9965-d6
UNSPSC
12352005
Target
Dopamine Receptor; Isotope-Labeled Compounds
Type
Isotope-Labeled Compounds
Related Pathways
GPCR/G Protein; Neuronal Signaling; Others
Field of Research
Neurological Disease
Solubility
10 mM in DMSO
Smiles
C(C(C(N1CCC(C(N)=O)CC1)([2H])[2H])([2H])[2H])(N2C=3C(SC=4C2=CC=CC4)=CC=C(S(C)(=O)=O)C3)([2H])[2H]
Molecular Formula
C22H21D6N3O3S2
Molecular Weight
451.64
References & Citations
[1]Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53 (2) :211-216.|[2]Victoire Roussel, et al. Estimating the excess of inappropriate prescriptions of anti-dopaminergic anti-emetics during acute gastroenteritis epidemics in France. Pharmacoepidemiol Drug Saf. 2013 Oct;22 (10) :1080-5.|[3]Mozgova O, et al. A new spectrophotometric method for the quantitative determination of Metopimazine based on the absorbance of its sulfoxide[J]. Chemical Papers, 2024, 78 (11) : 6585-6591.|[4]Jolliet P, et al. Evidence of lowest brain penetration of an antiemetic drug, metopimazine, compared to domperidone, metoclopramide and chlorpromazine, using an in vitro model of the blood-brain barrier. Pharmacol Res. 2007 Jul;56 (1) :11-7.
Shipping Conditions
Room temperature
Scientific Category
Isotope-Labeled Compounds
Clinical Information
No Development Reported
Isoform
D2 Receptor

Chemical Information

Metopimazine-d6
CAS Number1215315-86-8
PubChem CID46782361
IUPAC Name1-[1,1,2,2,3,3-hexadeuterio-3-(2-methylsulfonylphenothiazin-10-yl)propyl]piperidine-4-carboxamide
Molecular FormulaC22H27N3O3S2
Molecular Weight451.6
XLogP3.1
Topological Polar Surface Area117
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Heavy Atom Count30
Formal Charge0
Complexity703
SMILES
[2H]C([2H])(C([2H])([2H])N1CCC(CC1)C(=O)N)C([2H])([2H])N2C3=CC=CC=C3SC4=C2C=C(C=C4)S(=O)(=O)C
InChI
InChI=1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26)/i4D2,11D2,12D2
InChIKey
BQDBKDMTIJBJLA-NPUHHBJXSA-N
Chemical Structure
2D Structure
2D structure of Metopimazine-d6
CAS: 1215315-86-8
CID: 46782361
Formula: C22H27N3O3S2
MW: 451.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight451.6
XLogP33.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass451.18704455
Monoisotopic Mass451.18704455
Topological Polar Surface Area117 Ų
Heavy Atom Count30
Formal Charge0
Complexity703
Isotope Atom Count6
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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