Details of the Drug

General Information of Drug (ID: DMJCF1O)

Drug Name
Maralixibat
Synonyms
Lopixibat; UNII-UYB6UOF69L; Maralixibat [USAN]; 716313-53-0; UYB6UOF69L; CHEMBL363392; Maralixibat (USAN); Lopixibat cation; CHEMBL17879; 1-(4-((4-((4R,5R)-3,3-dibutyl-7-(dimethylamino)-4-hydroxy-1,1-dioxido-2,3,4,5-tetrahydrobenzo[b]thiepin-5-yl)phenoxy)methyl)benzyl)-1,4-diazabicyclo[2.2.2]octan-1-ium; LUM001 CATION; LUM-001 CATION; SCHEMBL10013954; BDBM50140282; 4-Aza-1-azoniabicyclo(2.2.2)octane, 1-((4-((4-((4R,5R)-3,3-dibutyl-7-(dimethylamino)-2,3,4,5-tetrahydro-4-hydroxy-1,1-dioxido-1-benzothiepin-5-yl)phenoxy)methyl)phenyl)methyl)-; D10951; Q27291331; (4R,5R)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2H-1$l^{6}-benzothiepin-4-ol; 1-{4-[4-((4R,5R)-3,3-Dibutyl-7-dimethylamino-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1H-1lambda*6*-benzo[b]thiepin-5-yl)-phenoxymethyl]-benzyl}-4-aza-1-azonia-bicyclo[2.2.2]octane; chloride
Indication
Disease Entry ICD 11 Status REF
Pruritus EC90 Approved [1]
Progressive familial intrahepatic cholestasis 5C58.03 Phase 3 [2]
Alagille syndrome LB20.0Y Phase 2 [3]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 675
Logarithm of the Partition Coefficient (xlogp) 7.1
Rotatable Bond Count (rotbonds) 13
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 3.43 +/- 2.13 mcgh/L [4]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 1.65 +/- 1.10 mcg/L [4]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 0.75 h [4]
Elimination
A 5 mg radiolabelled dose of maralixibat is 73% eliminated in feces and 0.066% eliminated in urine [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.6 hours [4]
Chemical Identifiers
Formula
C40H56N3O4S+
IUPAC Name
(4R,5R)-5-[4-[[4-(4-aza-1-azoniabicyclo[2.2.2]octan-1-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2H-1lambda6-benzothiepin-4-ol
Canonical SMILES
CCCCC1(CS(=O)(=O)C2=C(C=C(C=C2)N(C)C)[C@H]([C@H]1O)C3=CC=C(C=C3)OCC4=CC=C(C=C4)C[N+]56CCN(CC5)CC6)CCCC
InChI
InChI=1S/C40H56N3O4S/c1-5-7-19-40(20-8-6-2)30-48(45,46)37-18-15-34(41(3)4)27-36(37)38(39(40)44)33-13-16-35(17-14-33)47-29-32-11-9-31(10-12-32)28-43-24-21-42(22-25-43)23-26-43/h9-18,27,38-39,44H,5-8,19-26,28-30H2,1-4H3/q+1/t38-,39-/m1/s1
InChIKey
STPKWKPURVSAJF-LJEWAXOPSA-N
Cross-matching ID
PubChem CID
9831643
CAS Number
716313-53-0
DrugBank ID
DB16226
TTD ID
DZB84T
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Ileal sodium/bile acid cotransporter (SLC10A2) TTPI1M5 NTCP2_HUMAN Inhibitor [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Pruritus
ICD Disease Classification EC90
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Ileal sodium/bile acid cotransporter (SLC10A2) DTT SLC10A2 2.54E-01 -0.06 -0.17
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2023. Application Number: 214662.
2 ClinicalTrials.gov (NCT04185363) An Extension Study of Maralixibat in Patients With Progressive Familial Intrahepatic Cholestasis (PFIC). U.S. National Institutes of Health.
3 ClinicalTrials.gov (NCT04729751) A Study to Evaluate the Safety and Tolerability of Maralixibat in Infant Participants With Cholestatic Liver Diseases Including Progressive Familial Intrahepatic Cholestasis (PFIC) and Alagille Syndrome (ALGS). (RISE). U.S. National Institutes of Health.
4 FDA Approved Drug Products: Livmarli (Marilixibat) Oral Solution
5 Ileal bile acid transporter inhibition as an anticholestatic therapeutic target in biliary atresia and other cholestatic disorders. Hepatol Int. 2020 Sep;14(5):677-689.