delavirdine

CHEBI:119573 ·resolve ·ANTIVIRAL ·EXACT SEEDED

The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:35358
Label unavailable CHEBI:38207
Label unavailable CHEBI:46844
Label unavailable CHEBI:46921

Chemical structure

Computed structure properties
Molecular formula	C22H28N6O3S
Charge	0
Average mass	456.572 Da
Monoisotopic mass	456.19436 Da
Source	ChEBI
InChIKey	WHBIGIKBNXZKFE-UHFFFAOYSA-N

SMILES

CC(C)Nc1cccnc1N1CCN(C(=O)c2cc3cc(NS(C)(=O)=O)ccc3n2)CC1

InChI

InChI=1S/C22H28N6O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20/h4-8,13-15,24-26H,9-12H2,1-3H3

Also called

N-[2-({4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl}carbonyl)-1H-indol-5-yl]methanesulfonamide (EXACT_SYNONYM)— chebi
(N-[2-[4-[3-(1-methylethylamino)pyridin-2-yl]piperazin-1-yl]carbonyl-1H-indol-5-yl] methanesulfonamide) (EXACT_SYNONYM)— chebi
1-(3-((1-methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulfonyl)amino)-1H-indol-2-yl)carbonyl)piperazine (EXACT_SYNONYM)— chebi
2-(4-(5-methanesulfonamido-1H-indol-2-ylcarbonyl)-1-piperazinyl)-N-(1-methylethyl)-3-pyridinamine (EXACT_SYNONYM)— chebi
Delavirdine (EXACT_SYNONYM)— chebi
N-(2-(1-(3-(isopropylamino)pyridin-2-yl)piperazine-4-carbonyl)-1H-indol-5-yl)methanesulfonamide (EXACT_SYNONYM)— chebi
N-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yl}-methanesulfonamide (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antiviral drug CHEBI:36044
HIV-1 reverse transcriptase inhibitor CHEBI:53756

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:119573`	delavirdine	`antibioticmech:chebi-10f5984ad7`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Gag-Pol polyprotein [588-1027,K690N]/[588-1147,K690N] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Human immunodeficiency virus 1 NCBITaxon:11676

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	625 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 3490` `assay 457_1` `monomer 1944`	`PMID:10514285`

Organism-specific examples
Protein	Gene	Organism	Entry
Gag-Pol polyprotein `UniProtKB:P04585` BindingDB target chain 1	—	Human immunodeficiency virus 1 `NCBITaxon:11676`	REVIEWED

PMID:10514285 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Gag-Pol polyprotein [588-1027,P823L]/[588-1147,P823L] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Human immunodeficiency virus 1 NCBITaxon:11676

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	18000 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 3262` `assay 402_1` `monomer 1944`	`PMID:8809165`

Organism-specific examples
Protein	Gene	Organism	Entry
Gag-Pol polyprotein `UniProtKB:P04585` BindingDB target chain 1	—	Human immunodeficiency virus 1 `NCBITaxon:11676`	REVIEWED

PMID:8809165 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Gag-Pol polyprotein [588-1027]/[588-1147] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Human immunodeficiency virus 1 NCBITaxon:11676

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	260 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 2135` `assay 402_1` `monomer 1944`	`PMID:8809165`
IC50	1100 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 2808` `assay 427_1` `monomer 1944`	`PMID:7684450`
IC50	1100 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 2952` `assay 5_1` `monomer 1944`	`PMID:10698447`
IC50	1.3 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 3474` `assay 457_1` `monomer 1944`	`PMID:10514285`
IC50	422 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 3664` `assay 467_1` `monomer 1944`	`PMID:10821714`

Organism-specific examples
Protein	Gene	Organism	Entry
Gag-Pol polyprotein `UniProtKB:P04585` BindingDB target chain 1	—	Human immunodeficiency virus 1 `NCBITaxon:11676`	REVIEWED

PMID:8809165 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:7684450 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:10698447 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:10514285 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:10821714 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Gag-Pol polyprotein [588-1127,Y768C]/[588-1147,Y768C] VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Human immunodeficiency virus 1 NCBITaxon:11676

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	8320 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 3277` `assay 402_1` `monomer 1944`	`PMID:8809165`
IC50	114 nM	HIV-1 RT Assay The IC50 of reverse transcriptase is the concentration that inhibits 50% of recombinant HIV-1 RT RNA-directed DNA polymerase activity in vitro.	`RSID 3482` `assay 457_1` `monomer 1944`	`PMID:10514285`

Organism-specific examples
Protein	Gene	Organism	Entry
Gag-Pol polyprotein `UniProtKB:P04585` BindingDB target chain 1	—	Human immunodeficiency virus 1 `NCBITaxon:11676`	REVIEWED

PMID:8809165 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:10514285 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

Causal graphs

Evidence-backed mechanism graphs: how the compound reaches its target, what the target does, and how the effect propagates to growth inhibition or death.

Delavirdine inhibits HIV-1 reverse transcriptase MECHANISTIC

Delavirdine inhibits HIV-1 reverse transcriptase RNA-directed DNA polymerase activity, blocking the viral DNA synthesis step required for HIV-1 reverse transcription.

Nodes — delavirdine_hiv1_reverse_transcriptase_inhibition
Node	Label	Type	Grounding
`delavirdine`	delavirdine	COMPOUND	`CHEBI:119573`
`hiv1_reverse_transcriptase`	HIV-1 reverse transcriptase Examples: Gag-Pol polyprotein (gag-pol) `UniProtKB:P04585`, Human immunodeficiency virus type 1 group M subtype B (isolate HXB2) `NCBITaxon:11706` REVIEWED — HIV-1 Gag-Pol precursor encoding the p66/p51 reverse transcriptase heterodimer bound at the non-nucleoside inhibitor pocket by delavirdine (U-90152) (PMID:1726658; PMID:10602683, PDB 1KLM; HXB2 reference isolate context).	GENE_OR_PROTEIN	REVIEWED_LABEL_ONLY
`rna_directed_dna_polymerase_activity`	RNA-directed DNA polymerase activity	MOLECULAR_FUNCTION	GO:0003964
`hiv1_reverse_transcription`	HIV-1 reverse transcription	BIOLOGICAL_PROCESS	REVIEWED_LABEL_ONLY

Edges — delavirdine_hiv1_reverse_transcriptase_inhibition
Subject	Predicate	Object	Evidence
`delavirdine`	inhibits	`hiv1_reverse_transcriptase`	PMID:8809165 (BindingDB-curated HIV-1 reverse transcriptase IC50 measurements in this record support direct inhibition by delavirdine.) PMID:10514285 (BindingDB-curated assays in this record measured delavirdine inhibition of wild-type and mutant HIV-1 reverse transcriptases.)
`hiv1_reverse_transcriptase`	enables	`rna_directed_dna_polymerase_activity`	PMID:1377403 (The first HIV-1 reverse transcriptase-inhibitor crystal structure supports reverse transcriptase as a viral DNA polymerase drug target.)
`rna_directed_dna_polymerase_activity`	is required for	`hiv1_reverse_transcription`	PMID:1377403 (HIV-1 reverse transcriptase structural work connects the drug target to the viral DNA polymerase activity required during reverse transcription.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_CAUSAL_GRAPH 2026-09-04 · codex · LLM-assisted
Added a PMID-supported causal graph for delavirdine inhibition of HIV-1 reverse transcriptase.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated HIV-1 HXB2 Gag-Pol polyprotein (P04585) UniProtKB protein example on the delavirdine_hiv1_reverse_transcriptase_inhibition hiv1_reverse_transcriptase causal graph node.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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