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]
ATC Code
J04AK06: Delamanid
J04AK: Other drugs for treatment of tuberculosis
J04A: DRUGS FOR TREATMENT OF TUBERCULOSIS
J04: ANTIMYCOBACTERIALS
J: ANTIINFECTIVES FOR SYSTEMIC USE
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
CHEMBL218650
CAS Number
681492-22-8
UNII
8OOT6M1PC7
DrugBank ID
DB11637
TTD ID
D0S3NU
INTEDE ID
DR0432
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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.