Details of the Drug

General Information of Drug (ID: DMXE76K)

Drug Name
Delamanid
Synonyms OPC-67683; Nitro-dihydroimidazo-oxazole derivatives (tuberculosis), Otsuka; 2-nitroimidazole derivatives (tuberculosis), Otsuka
Indication
Disease Entry ICD 11 Status REF
Multi-drug resistant tuberculosis MG52.00 Approved [1]
Mycobacterium infection 1B10-1B21 Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 534.5
Logarithm of the Partition Coefficient (xlogp) 5.6
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 11
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 135 mcg/L [3]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 10-14 days [3]
Bioavailability
The bioavailability of drug is 35%C60% [3]
Elimination
The drug is excreted primarily in the stool, with less than 5% excretion in the urine [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 30 - 38 hours [5]
Metabolism
The drug is metabolized via the albumin and to a lesser extent, CYP3A4 [5]
Vd
The volume of distribution (Vd) of drug is 2,100 L [5]
Chemical Identifiers
Formula
C25H25F3N4O6
IUPAC Name
(2R)-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]phenoxy]methyl]-3H-imidazo[2,1-b][1,3]oxazole
Canonical SMILES
C[C@@]1(CN2C=C(N=C2O1)[N+](=O)[O-])COC3=CC=C(C=C3)N4CCC(CC4)OC5=CC=C(C=C5)OC(F)(F)F
InChI
InChI=1S/C25H25F3N4O6/c1-24(15-31-14-22(32(33)34)29-23(31)38-24)16-35-18-4-2-17(3-5-18)30-12-10-20(11-13-30)36-19-6-8-21(9-7-19)37-25(26,27)28/h2-9,14,20H,10-13,15-16H2,1H3/t24-/m1/s1
InChIKey
XDAOLTSRNUSPPH-XMMPIXPASA-N
Cross-matching ID
PubChem CID
6480466
ChEBI ID
CHEBI:134742
CAS Number
681492-22-8
DrugBank ID
DB11637
TTD ID
D0S3NU
INTEDE ID
DR0432
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
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
Bacterial Cell membrane (Bact CM) TTXT4D5 NOUNIPROTAC Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Compassionate use of delamanid in adults and children for drug-resistant tuberculosis: 5-year update. Eur Respir J. 2021 May 20;57(5):2002483.
2 ClinicalTrials.gov (NCT01424670) Safety and Efficacy Trial of Delamanid for 6 Months in Patients With Multidrug Resistant Tuberculosis. U.S. National Institutes of Health.
3 Sasahara K, Shimokawa Y, Hirao Y, Koyama N, Kitano K, Shibata M, Umehara K: Pharmacokinetics and Metabolism of Delamanid, a Novel Anti-Tuberculosis Drug, in Animals and Humans: Importance of Albumin Metabolism In Vivo. Drug Metab Dispos. 2015 Aug;43(8):1267-76. doi: 10.1124/dmd.115.064527. Epub 2015 Jun 8.
4 Szumowski JD, Lynch JB: Profile of delamanid for the treatment of multidrug-resistant tuberculosis. Drug Des Devel Ther. 2015 Jan 29;9:677-82. doi: 10.2147/DDDT.S60923. eCollection 2015.
5 Deltyba, INN-Delamanid - European Medicines Agency - Europa EU
6 Pharmacokinetics and metabolism of delamanid, a novel anti-tuberculosis drug, in animals and humans: importance of albumin metabolism in vivo. Drug Metab Dispos. 2015 Aug;43(8):1267-76.