Details of the Drug

General Information of Drug (ID: DM4W8RE)

Drug Name
MELAGATRAN
Synonyms
Melagatran; 159776-70-2; UNII-2A9QP32MD4; Melagatran [INN]; 2A9QP32MD4; CHEBI:43966; MELAGATRAN (ASTRA-ZENECA); C22H31N5O4; Melagatran (INN); N-((R)-(((2S)-2-((-p-Amidobenzyl)carbamoyl)-1-azetidinyl)carbonyl)cyclohexylmethyl)glycine; [((1R)-2-{(2S)-2-[({4-[AMINO(IMINO)METHYL]BENZYL}AMINO)CARBONYL]AZETIDINYL}-1-CYCLOHEXYL-2-OXOETHYL)AMINO]ACETIC ACID; MEL; H-319/68; N-((R)-(((2S)-2-((p-Amidinobenzyl)carbamoyl)-1-azetidinyl)carbonyl)cyclohexylmethyl)glycine
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 429.5
Logarithm of the Partition Coefficient (xlogp) -1
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 2.1719 micromolar/kg/day [1]
Chemical Identifiers
Formula
C22H31N5O4
IUPAC Name
2-[[(1R)-2-[(2S)-2-[(4-carbamimidoylphenyl)methylcarbamoyl]azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino]acetic acid
Canonical SMILES
C1CCC(CC1)[C@H](C(=O)N2CC[C@H]2C(=O)NCC3=CC=C(C=C3)C(=N)N)NCC(=O)O
InChI
InChI=1S/C22H31N5O4/c23-20(24)16-8-6-14(7-9-16)12-26-21(30)17-10-11-27(17)22(31)19(25-13-18(28)29)15-4-2-1-3-5-15/h6-9,15,17,19,25H,1-5,10-13H2,(H3,23,24)(H,26,30)(H,28,29)/t17-,19+/m0/s1
InChIKey
DKWNMCUOEDMMIN-PKOBYXMFSA-N
Cross-matching ID
PubChem CID
183797
ChEBI ID
CHEBI:43966
CAS Number
159776-70-2
DrugBank ID
DB13616
TTD ID
D01MUU
VARIDT ID
DR00946

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cationic trypsinogen (PRSS1) TT2WR1T TRY1_HUMAN Inhibitor [2]
Coagulation factor IIa (F2) TT6L509 THRB_HUMAN Inhibitor [3]
Coagulation factor Xa (F10) TTCIHJA FA10_HUMAN Inhibitor [2]
Plasminogen (PLG) TTP86E2 PLMN_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
P-glycoprotein 1 (ABCB1) DTP P-GP 7.23E-01 -8.20E-02 -3.22E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
2 Orally active thrombin inhibitors. Part 1: optimization of the P1-moiety. Bioorg Med Chem Lett. 2006 May 15;16(10):2641-7.
3 Orally active thrombin inhibitors. Part 2: optimization of the P2-moiety. Bioorg Med Chem Lett. 2006 May 15;16(10):2648-53.
4 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.