Delamanid - ≥99% , Mycobacterium tuberculosis H37Rv inhibitor, CAS No.681492-22-8, Mycobacterium tuberculosis H37Rv inhibitor

CAS: 681492-22-8 Cat. No.: D413211 Molecular Weight: 534.48 EC Number: 875-884-1

GRADE & PURITY ≥99%

Synonyms

NCGC00348214-01 | JKLYZOGJWVAIQS-UHFFFAOYSA-N | (R)-2-Methyl-6-nitro-2-((4-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl)phenoxy)methyl)-2,3-dihydroimidazo[2,1-b]oxazole | 1-(4-{[(2R)-2-methyl-6-nitro-2H,3H-imidazo[2,1-b][1,3]oxazol-2-yl]methoxy}phenyl)-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Delamanid (OPC-67683) is a new anti-tuberculosis drug with an excellent intracellular bactericidal activity and a high accumulation rate.

In vitro

Delamanid potently inhibits the synthesis of mycolic acid, a long-chain fatty acid of the M. tuberculosis (mycobacterium tuberculosis) cell wall. Delamanid at concentrations of less than 5 μM shows no inhibitory effects on the efflux ABC transporters P-gp, BCRP, and BSEP or on the hepatic or renal SLC transporters OATPs, OCTs, and OATs. Delamanid is not metabolized by NADPH-dependent reactions, including those catalyzed by CYP enzymes, in human or animal liver microsomes. Also, delamanid has no inhibitory effects on the metabolism of exogenous CYP substrate compounds by eight CYP isoforms (CYP1A2, CYP2A6, CYP2B6, CYP2C8/9, CYP2C19, CYP2D6, CYP2E1, and CYP3A), even at a concentration of 100 μmol/liter, well above the therapeutic concentration

In vivo

The water solubility of delamanid is poor and its absorption is increased more than two-fold by coadministration with food. The absolute bioavailability is unknown but estimated to be between 25% and 47%. delamanid is more than 99% protein bound, with a high volume of distribution (Vz/F of 2100 L) and a half-life of 30-38 hours. Delamanid is excreted primarily in the stool, with less than 5% excretion in the urine. It is thought to be primarily metabolized by albumin, with secondary contributions from P450 enzymes, primarily CYP3A4. Animal studies indicate that delamanid is excreted in breast milk.

Specifications

Synonyms

NCGC00348214-01 | JKLYZOGJWVAIQS-UHFFFAOYSA-N | (R)-2-Methyl-6-nitro-2-((4-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl)phenoxy)methyl)-2, 3-dihydroimidazo[2, 1-b]oxazole | 1-(4-{[(2R)-2-methyl-6-nitro-2H, 3H-imidazo[2, 1-b][1, 3]oxazol-2-yl]methoxy}phenyl)-

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Mycobacterium tuberculosis H37Rv inhibitor

Purity

≥99%

Product Properties

• ALogP: 5.6

Names and Identifiers

• Pubchem Sid: 504764251
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764251
• Canonical Smiles: CC1(CN2C=C(N=C2O1)[N+](=O)[O-])COC3=CC=C(C=C3)N4CCC(CC4)OC5=CC=C(C=C5)OC(F)(F)F
• 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
• InChIKey: XDAOLTSRNUSPPH-XMMPIXPASA-N
• 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
• Isomeric 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
• Molecular Weight: 534.48
• Reaxy-Rn: 12292766
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=12292766&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Piperidines
      • Subclass Phenylpiperidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Piperidines
• Subclass: Phenylpiperidines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpiperidines
• Alternative Parents: Aminophenyl ethers Aniline and substituted anilines Dialkylarylamines Nitroaromatic compounds Nitroimidazoles Phenoxy compounds Alkyl aryl ethers N-substituted imidazoles Imidolactams Heteroaromatic compounds Trihalomethanes Organic oxoazanium compounds Oxacyclic compounds Azacyclic compounds Propargyl-type 1,3-dipolar organic compounds Organic oxides Hydrocarbon derivatives Alkyl fluorides Organofluorides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenylpiperidine - Aminophenyl ether - Phenoxy compound - Nitroaromatic compound - Nitroimidazole - Phenol ether - Tertiary aliphatic/aromatic amine - Dialkylarylamine - Aniline or substituted anilines - Alkyl aryl ether - Monocyclic benzene moiety - N-substituted imidazole - Benzenoid - Imidolactam - Azole - Imidazole - Heteroaromatic compound - Organic nitro compound - Tertiary amine - Trihalomethane - C-nitro compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Azacycle - Oxacycle - Ether - Organic oxoazanium - Alkyl halide - Organofluoride - Organohalogen compound - Organic oxide - Organonitrogen compound - Organopnictogen compound - Alkyl fluoride - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Amine - Halomethane - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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CRHR1 Tclin Corticotropin releasing factor receptor 1 (2996 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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GCGR Tclin Glucagon receptor (2563 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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ESR2 Tclin Estrogen receptor beta (9272 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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ADRB3 Tclin Beta-3 adrenergic receptor (5850 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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EDNRB Tclin Endothelin receptor ET-B (1928 Activities)

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Associated Targets(non-human)

Mc4r Melanocortin receptor 4 (1205 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Ntsr1 Neurotensin receptor 1 (48 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Bdkrb1 Bradykinin B1 receptor (77 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Helicobacter pylori (3113 Activities)

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Salmonella typhimurium (15756 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Clostridioides difficile (2968 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Mycobacterium tuberculosis variant bovis (1746 Activities)

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Leishmania infantum (5912 Activities)

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Trypanosoma brucei (78846 Activities)

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Leishmania donovani (89745 Activities)

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Trypanosoma cruzi (99888 Activities)

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Mus musculus (284745 Activities)

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Vero (26788 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: insoluble in H2O; insoluble in EtOH; ≥24.9 mg/mL in DMSO
• Molecular Weight: 534.500 g/mol
• XLogP3: 5.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 534.173 Da
• Monoisotopic Mass: 534.173 Da
• Topological Polar Surface Area: 104.000 Ų
• Heavy Atom Count: 38
• Formal Charge: 0
• Complexity: 795.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Pusheng Xu, Yi Li, Bihan Xu, Dan Cao, Xu Dong, Yanghui Xiang, Xiuzhi Jiang, Xin Yuan, Yuwei Qiu, Ying Zhang.  (2025)  Novel mutations in the marR gene (MAB_2648c) modify nitroxoline activity in Mycobacterium abscessus.  ANTIMICROBIAL AGENTS AND CHEMOTHERAPY,  69  (5):   [PMID:40167421] [10.1128/aac.01744-24]